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Pet Friendly Holiday Rentals in Manchester-by-the-Sea

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    52 Matching Rentals in the Manchester-by-the-Sea AreaView all 182 rentals
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    Manchester-by-the-Sea
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Manchester-by-the-Sea
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    The following rentals are within 15 kilometres of Manchester-by-the-Sea.
    GULLY POINT AT THE SEAWARD EXUDES CLASSIC COASTAL CHARM1 / 18
    (2)Excellent
    Rockport
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    One Bedroom Loft Apartment B at Cedar Hill Farm B & B1 / 6
    (1)Excellent
    Essex
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Private Garden
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 September 2017
    This was our first stay in a B&B, it did not disappoint! It was very clean, cozy and conveniently located to the town of Essex. Appreciated the breakfast choices, especially...
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    About this property
    We can now offer Apartment B to our options at Cedar Hill Farm B & B. This apartment is identical to Apt. A also located in our lower barn. The bedroom is on second floor with open to living area and cathedral ceiling. 8 Foot sliders open to open pastures, woods and meadows. Guests can enjoy...
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    Essex, Cape Ann 01929
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Rockport
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Ocean Views
    • Terrace
    • Waterfront
    • Washer
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Seaward offers a spectacular setting and charming accommodations. Loblolly Cove, offers accommodations for up to 4 people. One bedroom has a queen sized bed, while the rather spacious living room has accommodations for two more. At Loblolly Cove, you will enjoy a deck with ocean views and...
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    Rockport, Cape Ann 01966
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    NEW!  STUNNING STUDIO w/Scenic Harbor View1 / 19
    (3)Very good
    Gloucester
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Balcony
    • DVD Player
    • Air Conditioning
    • Secure Parking
    • Grill
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 November 2017
    Lovely apartment, with bonus deck for enjoying a BBQ & wine. Views of the working harbor can be enjoyed right from the bed (which is super-comfy!). Well equipped kitchen, all...
    Reviewed 24 November 2017
    One of the best vacations I've had in years. The owners were charming and attentive but also respectful of my privacy, which is important to me as a writer. The deck was a...
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    About this property
    Nestled on a hillside overlooking Gloucester's scenic harbor... enjoy magical sunsets, dining al fresco, twinkling harbor lights, and warm summer winds from the deck of this romantic getaway. This property is best described as a “studio plus”, featuring 3 separate rooms (400 sq. ft.): Bedroom with...
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    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Dragonfly1 / 7
    (2)Excellent
    Gloucester
    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Wi-Fi
    • Outdoor Dining Area
    • Secure Parking
    • Grill
    • Private Garden
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 September 2016
    A big, comfortable home, surrounded by woods, a short walk to the ocean, and a short ride to downtown Gloucester or Rocky Neck. A beautiful, well appointed place. Home for a...
    Reviewed 31 August 2016
    The Dragonfly is a great place to stay for a big group! It is a beautiful home, with so much character and is clearly well loved by Patricia, the owner. It is even better than...
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    About this property
    Spacious home located two blocks from Atlantic Ocean and close to wedding venues including Elks, Cruiseport, & Anninsquam Yacht Club. 7 day minimum stay Sat. To Sat in July & August. Large modern fully equipped kitchen with double oven, 5 burner Viking cooktop, dishwasher, washer, dryer. Three...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 11
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    Hillside Ocean View 2BR with Private Beach Access1 / 43
    (1)Excellent
    Ipswich
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
    • Cable/satellite TV
    • Wi-Fi
    • Balcony
    • Washer
    • Grill
    • Patio
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Thank you Mark for your hospitality, the cottage was a wonderful experience to show grandchildren what growing up in Ipswich is all about. The thoughtful amenenities...
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    About this property
    Set upon Great Neck hill, this antique winterized cottage has a great ambiance and a nice view of the water where the Atlantic meets the mouth of Ipswich River. Spacious and fun for families and small groups, you can walk right down to Pavilion Beach within 10 minutes and access to famed private...
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    Ipswich, Massachusetts 01938
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Gloucester
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Waterfront
    • Washer
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gloucester Waterfront Waterfront Vacation House with Dock Direct riverfront home with dock overlooking Annisquam River, Lobster Cove, Wingaersheek Beach, and out towards Ipswich Bay. Open living spaces with endless views of both the river and marshland. This is true waterfront living! So...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Salem
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    My recently renovated spacious apartment can accommodate 8 people. It is close to all of the major attractions in Salem, including Salem's historical district, the Salem Witch museum, the waterfront, Salem State University, and Salem hospital. You will be a short (~5 minute) drive from the beach....
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    Salem, Massachusetts 01970
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    LOVER'S COVE AT THE SEAWARD WITH OCEAN VIEWS & SEASIDE PATH TO BEACH &TOWN1 / 19
    (1)Excellent
    Rockport
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Grill
    • Ocean Views
    • Waterfront
    • Wi-Fi
    • Balcony
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    Our third Year at The Seaward, Nancy is a fantastic host, always. We love the apartment, and it always feels like we are at home. The weather was beautiful as always and the...
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    About this property
    This newly renovated ocean view apartment at the Seaward exudes classic coastal charm. Here you will fully relax while listening to the ocean waves. Lover’s Cove features exposed brick walls, newly conditioned hardwood floors and a king bed. This seaside apartment makes for our most spacious...
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    Rockport, Cape Ann 01966
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Ipswich
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Balcony
    • Housekeeping Included
    • Terrace
    • Secure Parking
    • Private Garden
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    August 28 thru LABOR DAY, which is Sept 5. 9 DAYS FOR PRICE OF 7!!! in idyllic Island of Little Neck. Check out lower prices in beautiful month of September. Surrounded by water views. Perfect for children. Private beach for Little Neck. A stones throw to Cranes beach and castle. This is a gated...
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    Location Information
    Ipswich, Massachusetts 01938
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Rockport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious seaside apartment offers 2 bedrooms, 2 bathrooms, and living room/kitchen with a sunny ocean view dining/game area within a bay window. At over 800 square feet it is our largest accommodation. You’ll enjoy Gap Cove’s seaside charm, with amenities including free WIFI, DVD player,...
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    Location Information
    Rockport, Cape Ann 01966
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Rockport
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Air Conditioning
    • Parking
    • Waterfront
    • Wi-Fi
    • Ocean Views
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spruce Cottage at The Seaward offers a spectacular ocean view setting and charming accommodations. Spruce Cottage, is a quaint and cozy two bedroom cottage with ocean views & fireplace. It has a private queen bed in one room and two twin beds in the other. The living room has a kitchenette and...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Ipswich
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Porch
    • Waterfront
    • Parking
    • Washer
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    High-lights of Scandinavian design throughout the house will give a sense of tranquility as the breezes pass through a nice old-fashioned screen porch. Two large long tables for dining inside or out help to bring friends and family together. The kitchen, dining and porch space are the focus of this...
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    Ipswich, Massachusetts 01938
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    The Forsythia Apt1 / 5
    (4)Excellent
    Salem
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Private Garden
    • Balcony
    • Wi-Fi
    • Terrace
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    The location of the apartment was terrific. Barbara was a very nice host. She was very good about communicating with us when we needed. She was also very accommodating.
    Reviewed 3 November 2017
    Very nice and clean. Great location. Close to the mall, downtown and the shops. Short walk to Pickering wharf. Barbara is a wonderful hostess. I would definitely stay again.
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    About this property
    Beautiful hardwood floors in the living room, study and bedroom. Walk to cafes, restaurants and the sea. Minutes to bus and commuter rail. In the heart of the city! Modest unit but cozy and convenient. Rustic in a good way. Comes with towels, bed-linens and toiletries. There is a microwave,...
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    Salem, Massachusetts 01970
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Waterfront Woodsy 3BR Cottage1 / 12
    (1)Excellent
    Gloucester
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Private Garden
    • Waterfront
    • Parking
    • Wi-Fi
    • Ocean Views
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 August 2017
    Our family of 4 (plus two standard poodles) thoroughly enjoyed our stay at this charming spot in the Lanesville section of Gloucester. The sunsets are spectacular, it's very...
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    About this property
    Imagine yourself walking across the lawn to the ocean, sweetly lapping the rocks. You take off your sandals and put your feet into the cool water. Second thought, jump right in! Great space for activities; near beaches, restaurants, galleries. The Space This cottage has been hosting travelers and...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Marblehead
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
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    • Washer
    • Parking
    • Patio
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on Marblehead Neck, just a short walk to the harbour, you'll find all you need to enjoy a luxurious stay in this grand New England home. All the comforts you need are provided in a clean and functional home. Top quality outfitting for everything. I'll personally make sure you have all you...
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    Marblehead, Massachusetts 01945
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    Rockport
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Grill
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This charming vacation rental home is situated just 300 yards from Whale Cove. Walk just 1 mile to a sandy beach or into the village of Rockport with its shops, restaurants, galleries and a world class Performance Center. Choose to cook your lobsters in the large, updated eat-in kitchen, which is...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    Marblehead
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Harbor views; Private deck; Private entrance; Fireplace Generous 1 bedroom Beautifully renovated antique gem in the heart of the Historic District. Gas fireplace; Full kitchen; washer/dryer; Completely renovated and comfortably furnished to make you feel right at home. Period charm and...
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    Marblehead, Massachusetts 01945
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Gloucester
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Direct waterfront on picturesque Goose Cove, this vacation home provides endless delights, both inside and out. This sunny and welcoming home is situated at the water's edge of the cove and offers three large bedrooms and 3 full baths as well as a lovely eat-in kitchen, formal dining and living...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Ipswich
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A great vacation starts with a unique destination and a space that suits your needs. This great little cottage promises a unique experience because of it's ambiance and location. A great old-fashioned cottage that is updated for convenience. It overlooks the Little Neck inlet with a great view of...
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    Ipswich, Massachusetts 01938
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Rockport
    6 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
    About this property
    This inviting family vacation home has bountiful space and is located in the highly desirable area of 'The Avenues' at the northern end of Rockport. Boasting 6 bedrooms, 3.5 baths and the ability to comfortably sleep 10 people, this is a house for the extended family to enjoy. This area of Rockport...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 10
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    Rockport
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Internet Access
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    Pet friendly
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    Smoking allowed
    About this property
    Quaint cozy pre-Revolutionary house with priceless view of picturesque Rockport village and Atlantic Ocean. Located on quiet dead-end lane next to tranquil pond and small town park. Two-minute walk to beach and town's attractive Main street with shops, art galleries and restaurants.The new...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Rockport
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • DVD Player
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    • Waterfront
    • Wi-Fi
    • Patio
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This unique beachfront vacation home has been completely remodeled but retains hints of its historical importance; it was the original U.S. base for the first Trans-Atlantic Cable in 1884. Originating in Ireland, the cable went from Nova Scotia to Cape Ann and back to France. Here is an excerpt...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Ipswich
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One of the few seaside old family cottages of Gloucester that is ready to welcome you for a unique experience. Fully equipped with a gorgeous view of colorful sunsets and a home that delivers a great living space near Halibut Point on the water. A very large home with 4 bedrooms and bunk room;...
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    Ipswich, Massachusetts 01930
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Marblehead
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Home originally built in 1923. Purchased and completely renovated in 2004. 1600 sq. ft. As you step onto a mahogany front porch, you open a walnut wood front door into a spacious open floor plan. Diningroom, livingroom and kitchen are bright and cheerful. First floor private guest bedroom with...
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    Marblehead, Massachusetts 01945
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Rockport
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Rockport in town private cottage within walking distance to town and all Rockport has to offer: beaches, restaurants, art galleries, shops, Shalin Liu performing arts center, Bearskin neck and the train. *The cottage is 2 floors. On the first floor is a fully equipped kitchen, with a cooler for...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Rockport
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This delightful summer vacation rental cottage, overlooking broad stretches of the Atlantic Ocean and Rockport's Hoop Pole Cove, is a perfect retreat for anyone looking to experience the best of New England. The wraparound porch and expansive yard allow you to fully enjoy Cape Ann's natural beauty....
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    Rockport, Cape Ann 01966
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Rockport
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Cable/satellite TV
    • Ocean Views
    • Wi-Fi
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    • Waterfront
    • Washer
    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Last week of Aug. and all of Sept still AVAILABLE. Unobstructed OCEAN VIEW from every window! 3 BR HOUSE WEEKLY VACATION RENTALS - The Glenellen Cottage Delightful, late 1800's, newly renovated kitchen with 1st & 2nd floor full bathrooms, non obstructed Ocean View House on a rise overlooking...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Gloucester
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
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    • Terrace
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the views, breezes and scent of the sea from this lofty perch overlooking Gloucester's famed waterfront. Stacy Boulevard is home to the iconic 'Gloucester Fisherman at the Wheel' sculpture -- a symbol of the fishing port's rich history as a working waterfront and as the subject of poets,...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Gloucester
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    About this property
    This large and comfortable vacation home is just steps from the white sands of Long Beach--a perfect summer location! Built in the early 1900's, much of its early charm still remains but is augmented with an updated kitchen and many amenities. On the ground floor there is living room with plenty...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    Ipswich
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Wi-Fi
    • Shared Garden
    • Air Conditioning
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Swedish Room is themed with open wood plank floors and hand-crafted bed cover. It is particularly cozy with sun-streamed angled dormers and built in closet and drawers. It can accommodate up to 4 people with its queen and twin beds. Private bath. One of New England's most charming B&Bs with...
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    Ipswich, Massachusetts 01938
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Ipswich
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Terrace
    • Grill
    • Central Heating
    • DVD Player
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 weeks left. August 5-12 and August 12-19. $2,000 in idyllic Island of Little Neck. . Surrounded by water views. . Private beach for Little Neck. A stones throw to Cranes beach and castle. This is a gated community with lovely cottages and friendly neighbors. Private dock to launch your boat....
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    Ipswich, Massachusetts 01938
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Rockport
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    From it's private deck, enjoy the views of Sandy Bay dotted with sailboats. Or walk down the quiet lane to Granite Pier and experience the unsurpassed views of the sun rising over the Atlantic Ocean, and of fishing boats moored nearby. The full moon over Granite Pier is spectacular, and even...
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Rockport
    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This sweet and comfortable vacation rental cottage is just across the street from Folly Cove, one of the most striking coves on Cape Ann. The living room has views of the water (just across the street) and off of the living room is a nice screened porch with views and a granite floor. The large...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 7
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    Gloucester
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Internet Access
    • Waterfront
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perched overlooking the Wonson Cove’s prismatic waters, this 4 bedroom, 2.5 bath vacation rental home situated in Gloucester’s cultural district known as Rocky Neck will take your breath away. From Eastern Point to the Dog Bar Breakwater, from lighthouses to glorious sunrises, the views from Wonson...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Gloucester
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lovely beach house has it all: prime Good Harbor Beach location, views, historic charm and modern comfort and style. The original cottage was built as a stone carriage house to a neighboring estate. A wonderful octagonal addition has created a three bedroom/two full bath home that boasts a...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Rockport
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Wi-Fi
    • DVD Player
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you are looking for a beach house, this is it. Walk to Long or Cape Hedge beaches in 5 minutes or just relax at this fun vacation rental home and enjoy the water views from one of two decks. Sea Vagabond House is actually two houses in one; the original cottage downstairs (which was built in...
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    Rockport
    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Midway between two picturesque places, the seaside village of Rockport and the historic fishing port of Gloucester, Sage Hill is the perfect vacation destination. Walk to Long Beach (it’s about a 5 minute walk), or take a short drive to Good Harbor Beach. Sage Hill is well appointed, with a...
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 7
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    Rockport
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
    • Waterfront
    • Patio
    • DVD Player
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This waterfront vacation rental is a wonderful inviting family vacation home with bountiful space, located in the highly desirable area of 'The Avenues' at the northern end of Rockport. Boasting 5 bedrooms/3.5 baths and the ability to comfortably sleep 12 people, this is a house to bring the...
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    Rockport
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Waterfront
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    From its waterfront perch, this 4BR vacation rental home overlooks Rockport's picturesque Pigeon Cove harbor and has spectacular, unobstructed views of Sandy Bay. The location of the home is ideal, away from all the hustle of town, but within a 10-15 minute walk to everything you might want,...
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Cove View: Sweet cottage across from beautiful Folly Cove1 / 29
    (1)Very good
    Rockport
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • DVD Player
    • Waterfront
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 August 2017
    Cove view cottage is a little gem in our view. We had an amazing 10 day stay here in August and didn't want to leave. The cottage was built in 1805 and has amazing character...
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    About this property
    This utterly sweet vacation rental cottage overlooking Rockport's beautiful Folly Cove has all modern amenities but maintains the ambiance of the year 1805, when it was built. A thoughtful eye has preserved the property's historical integrity while adding modern comforts. Bright and sunny, the...
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    Gloucester
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    located in quiet, wooded neighborhood. Older summer cottage close to the beach. Very comfortable for families. Good size living room for visiting. Separate dining room. Deck with small BBQ. Warm outside shower for after the beach or anytime. Close to Gloucester with easy access to highway....
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Gloucester
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Patio
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy views of Gloucester's outer harbor, and the private sandy beach, across the quiet private road from almost every room in this fantastic vacation rental home. There are two glorious slate patios that flank the front door from which you may also enjoy the views of the sunrise. On a clear day,...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    Ipswich
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Secure Parking
    • Wi-Fi
    • Ocean Views
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This well appointed home sits on a Hill overlooking plum Island sound with water access across the street. 10 minute walk to a Sandy private beach. A gated Wrap around deck is easily locked. Open airy light filled floor plan throughout makes this the perfect vacation spot to enjoy the water views....
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    Location Information
    Ipswich, Massachusetts 01938
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Ipswich
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Private Garden
    • Grill
    • Mountain Views
    • Cable/satellite TV
    • Washer
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This large house on Little Neck hill will be a great vacation experience for your family this season. Five beds, numerous hangout spaces, great kitchen, 2 bathrooms. Access to the private beach is just a few hundred yards away. Same with Pavilion Beach. Visit the area beaches and seaside towns, go...
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    Location Information
    Ipswich, Massachusetts 01938
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Gloucester
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Balcony
    • Patio
    • Ocean Views
    • Terrace
    • Waterfront
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Waterfront tri-level, with 4 bedrooms, 2 full baths, fire pit and a dock will accommodate up to 10 people. Located on Little River, a tidal inlet, just off the Annisquam River, we have water access mostly all day. The yard, screened porch and patio face west for the most spectacular sunsets. The...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Gloucester
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    My place is close to walk to or short drive to restaurants and dining, family-friendly activities, the beach, nightlife, whale watching . You’ll love my place because of the coziness , the comfy bed, the relaxed and easy atmosphere, and close proximity to all Gloucester, Rockport and Cape Ann have...
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    Location Information
    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Ipswich
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The quaint town of Ipswich, Massachusetts is one of the oldest settlements in the United States, originally inhabited by Native Americans and later colonized in 1633. Thanks to Ipswich's close proximity to the Atlantic Ocean and Ipswich River, Ipswich continues to be one of the state's top...
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    Location Information
    Ipswich, Massachusetts 01938
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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