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Holiday Homes in Madison

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    All 32 Rentals in Madison
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    Madison
    Studio, 1 Bathroom, Sleeps 3 Quick View
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    The following rentals are within 25 kilometres of Madison.
    Ennis Cottage with private beach on Branford shore1 / 17
    (16)Excellent
    Branford
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Two bedroom house with private beach and club within walking distance1 / 17
    (5)Excellent
    Branford
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Deep River
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Patio
    • Housekeeping Included
    • Cable/satellite TV
    • Washer
    • Sauna
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Peace Barn is a cozy retreat close to art and culture and parks. You’ll love my place because of the outdoor space and the comfy beds. My place is good for families, couples, and furry friends. The Peace Barn sits on 15 acres of private land which can be used for group retreats, film making,...
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    Deep River, Connecticut 06417
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Clinton
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Ocean Views
    • Waterfront
    • Patio
    • Washer
    • DVD Player
    • Grill
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perched along a luxurious peninsula jutting into the Long Island Sound, the Obstreperous Octopus sinks its tentacles into the sand and represents the finest in CT WATERFRONT real estate. Check us out on line for the latest information--obstreperousoctopus dot com. Undergoing a complete renovation,...
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    Clinton, Connecticut 06413
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Weekly Summer Beach Rental1 / 17
    (4)Excellent
    Old Lyme
    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
    • Washer
    • DVD Player
    • Air Conditioning
    • Patio
    • Waterfront
    • Ocean Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 July 2018
    We had a wonderful week at this home. It is incredibly spacious, clean and equipped with everything imaginable for a fun family beach vacation. The kitchen, in particular, is...
    Reviewed 2 July 2018
    Spacious and clean house just a few houses from the beach. The house is stocked very well and even had some fun games for our kids. This is the second year in a row that we’ve...
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    About this property
    Amazing remodel of this beachside, 4BR, 2Bath colonial. Two private beaches to choose from in this gated community. Dogs are welcome and a fenced area is provided! Plenty of room for 4 to 5 cars off street. The association includes access to basketball court, tennis courts, baseball diamond,...
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    Old Lyme, Connecticut 06371
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 12
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    Branford
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    • Waterfront
    • Hot Tub
    • Air Conditioning
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Special Holiday Offer Waterfront Beautiful Luxury Home, Spa Hot Tub & Private Beach Ideal Beach home Newly furnished 4 bedrooms, 5 bathrooms with panoramic ocean views from every room, including master suite with spa shower & jacuzzi , two wrap around decks and Private Sandy Beach. Large outdoor...
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    Branford, Connecticut 06405
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    Charming 6 Bedroom Oceanfront Cottage By The Sea1 / 38
    (2)Very good
    Clinton
    6 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • DVD Player
    • Waterfront
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Ocean Views
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 July 2018
    We were looking for a Connecticut place on the water, spacious and unpretentious. We found it. Mairzy Doats cottage had just the right charm, overlooking the beach and surf...
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    About this property
    **COTTAGE BY THE SEA** Six bedroom cottage for rent on a PRIME SHORELINE location at Clinton Beach (91 Shore Road, 'Mairzy Doats Cottage'), Clinton, CT. **9 ROOM, WATERFRONT Cottage, situated on a LARGE, PRIVATE BEACH only steps away from the ocean! Charm, Character, & Cleanliness! The cottage is...
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    Clinton, Connecticut 06413
    Holiday Rental House - 6 Bedrooms, 2 Bathrooms, Sleeps 10
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    Westbrook
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Perfect Getaway! Walk to the Beach or Relax on the Patio overlooking the Properties Dock by the River! Close to Area Attractions such as Goodspeed Opera House, Gillette's Castle, Towns of Mystic, Essex and New Haven Near Vineyards, Mohegan Sun & Foxwoods Casinos, Antiquing, Parks, Museums, Art...
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    Westbrook, Connecticut 06498
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Old Lyme
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
    • Grill
    • Wi-Fi
    • Parking
    • Ocean Views
    • Cable/satellite TV
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    I challenge you to find a cottage that provides more than our Pail and Shovel Inn at Old Colony Beach in Old Lyme, Connecticut! Known as - pail and shovel inn - all in one word online, we offer the following: Beds in 3 bedfrooms - King-size Bed (1) - Trundle (two twins) (2) - Twin/Single Bed...
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    Old Lyme, Connecticut 06371
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Cornfield Point Beachfront Small Cottage1 / 8
    (4)Excellent
    Old Saybrook
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Ocean Views
    • Waterfront
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 August 2018
    Cottage was cozy & clean and the beach was right there! Beautiful sunsets and good times. Nick & Andrew we’re very accommodating. Thank you!
    Reviewed 3 July 2018
    Great vacation for my husband and I with my daughter’s family. We were met by a family member when we arrived about 3:15. Everything was shown to us in detail. All our...
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    About this property
    A 2 Room, Small Cottage overlooking the Cornfield Point Private Beach on the Long Island Sound. INCLUDES: A fully stocked kitchen with microwave, coffeemaker, and toaster. A dinette table for four, A full-size custom futon sleeper sofa, a one half bath, with attached outdoor private hot and cold...
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    Location Information
    Old Saybrook, Connecticut 06475
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Guilford
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Patio
    • Grill
    • Wi-Fi
    • Balcony
    • Porch
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The property is located down a dirt road off of the beaten path. Enjoy an extraordinary country wooded vacation, holiday, getaway or reunion retreat for the two of you, the whole family, or up to 6-8 friends and family. Situated on 40 wooded acres of absolute privacy in the middle of 1100 acres of...
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    Guilford, Connecticut 06437
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    East Haven
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Terrace
    • Parking
    • Ocean Views
    • Grill
    • Waterfront
    • Balcony
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly renovated direct beach front house on private beach, beautifully furnished and detailed. All the comforts of home and more! Fully equipped new 'vintage reproduction' kitchen, washing machine and dryer, towels linens, beach chairs, outdoor stove in enclosed screened in porch and cooking area...
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    East Haven, Connecticut 06512
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Branford
    Studio, 1 Bathroom, Sleeps 3 Quick View
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    • Secure Parking
    • Washer
    • Air Conditioning
    • Internet Access
    • Grill
    • Waterfront
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    From generous picture windows enjoy views of Long Is. Sound and quaint Thimble Islands dotted with simple cottages and mansions. Large front room with a small kitchen hidden in a a 1930's armoire. A round dining table is lite from a 60' chandelier fit for a castle. Created by a professional...
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    Branford, Connecticut 06405
    Condo/Apartment - 1 Bathroom, Sleeps 3
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    Westbrook
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Patio
    • Housekeeping Included
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    • Shared Garden
    • Private Garden
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Rates Are Based on A 7 Night Minimum Stay for 2 Guests Located in the Quaint, Historic, Shoreline Town of Westbrook, CT Lies this Unique 2 Bedroom Cottage! Escape from It All ~ Walk to the Beach or Stroll Down to the Dock on the Property's Riverfront. The Cottage is 1/2 mile from Town Center &...
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    Westbrook, Connecticut 06498
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Old Saybrook
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ocean front property the only one in the area that has a huge yard and beach. 4-bedrooms, beautiful sunroom, fireplace, gazebo. Old Saybrook is a quiet beach town that's very family friendly. It's also known for it's many great dining options. In addition to the beach right in front of the house,...
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    Location Information
    Old Saybrook, Connecticut 06475
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    North Haven
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Cable/satellite TV
    • Air Conditioning
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    • Private Garden
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly remodeled home with 4 bedrooms, 1.5 baths, family room, finished basement that can easily accommodate 8 people and is near everything. Just a quick commute to Yale, SCSU, Quinnipiac and University of New Haven, very close to the best restaurants in the greater New Haven area and within...
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    North Haven, Connecticut 06473
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Branford
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Balcony
    • Air Conditioning
    • Grill
    • Patio
    • Cable/satellite TV
    • Waterfront
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Two acres of private New England charm over looking the Thimble Islands. Set atop a hill with a large rolling lawn perfect for all types of family lawn games.The vintage shingle stone home was built in 1932 for a wealthy Connecticut family. They created a sandy beach that rivals the size of the...
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    Branford, Connecticut 06405
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    Save $500 off September CT Lake Front  Victorian Mansion Truly Memorable1 / 21
    (3)Very good
    East Haddam
    7 Bedrooms, 4 Bathrooms, Sleeps 24 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ideal Connecticut location on Beautiful Crystal Clear Bashan Lake. Victorian Mansion with magnificent water views. Perfect setting for family vacations, and family reunions!! Taking reservations thru Dec. 2018. Just 1 3/4 hours from New York or Newport RI or 2 hrs. from Boston! Canoe, kayak,...
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    East Haddam, Connecticut 06423
    Holiday Rental House - 7 Bedrooms, 4 Bathrooms, Sleeps 24
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    East Haven
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Hobbit House has been newly renovated and appointed to be cozy and comfortable with an antique flair. This property is beautiful inside and out. The beach use for this property is private and your rental of this property comes with everything you need to relax at the beach! This house has the...
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    East Haven, Connecticut 06512
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Westbrook
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Housekeeping Included
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape the nearby beaches with a comfortable stay in the tranquil woods. Private room with private bath in an older single-family home on two acres of land. It has its quirks (like strawberry wallpaper) and it's not über-renovated/modern, but we love it! Close to I-95, Route 9, Westbrook, and Old...
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    Location Information
    Westbrook, Connecticut 06498
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Old Saybrook
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Ocean Views
    • Washer
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    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A 3 bedroom, 1 1/2 bath home overlooking the Cornfield Point Private Beach on the Long Island Sound. FIRST FLOOR: A fully stocked kitchen with microwave and coffee maker. A dining area and formal dining room. A one half bath. A bedroom with two twin beds. Laundry Room also available. There is a...
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    Old Saybrook, Connecticut 06475
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Old Lyme
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    The Copper Beech Guest House is conveniently located 2 hours from Boston and NYC. 30 minutes to the Casinos, 25 minutes to Mystic, 10 minutes to Essex and Old Saybrook and 1/2 mile from Historic Lyme Street in Old Lyme. The Beaches are just a 2 minute drive away. The River is less than 1/2 mile...
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    Location Information
    Old Lyme, Connecticut 06371
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    North Haven
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our lovely house in North Haven, CT has been recently remodeled. It is centrally located and just minutes from Yale, Quinnipiac, UNH, SCSU and Albertus as well as shopping, the best restaurants, hiking trails in West Haven, Hamden and Wallingford, state parks and many local attractions including...
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    North Haven, Connecticut 06473
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Old Saybrook
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Central Heating
    • Sauna
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Historic Old Saybrook has been a desired destination for family and friends for over 130 years, and our spacious villas are the perfect place to treat yourself to some quality time with the ones you love. Our villas are equipped with all of the necessities you will need during your stay; two...
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    Old Saybrook, Connecticut 06475
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Old Saybrook
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Skiing: Property Is In A Ski Resort
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to Old Saybrook when you stay at this charming 2-bedroom, 1-bathroom vacation rental cottage. Featuring accommodations for 6 guests, this home is perfect for families or close friends seeking a memorable getaway. This property is nestled in a quiet neighborhood where you can play yard games,...
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    Old Saybrook, Connecticut 06475
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Clinton
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Washer
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    • Waterfront
    • Ocean Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Clinton, Connecticut welcomes you to this lovely 3-bed, 1-bath vacation rental house that sleeps 8. Enjoy colorful sunsets or sunrises with a walk to one of the 2 private beaches, or take the provided bicycles for a spin 2 miles north to Clinton Town Beach near the New Harbor Marina. It will be...
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    Clinton, Connecticut 06413
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    Old Lyme
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    ** Please note this property is connected to the homeowners beach house with a completely separate entrance and unit ** Run away to the Connecticut coast and stay at this breezy 2-bedroom, 1-bathroom vacation rental apartment! Situated in the charming town of Old Lyme, this northeast gem offers...
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    Location Information
    Old Lyme, Connecticut 06371
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Branford
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Connecticut is calling you to stay at this charming 3-bedroom, 1-bath vacation rental apartment! Nestled among the quiet streets of Stony Creek, this pet-friendly getaway boasts sleeping arrangements for 6, modern conveniences, and a prime location, just a 10-minute walk from the beach. Whether you...
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    Location Information
    Branford, Connecticut 06405
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Old Lyme
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    Make the most of your Old Lyme beach vacation when you stay at this newly remodeled 3-bedroom, 1-bathroom vacation rental cottage, just steps from the shores of the Atlantic Ocean. With sleeping accommodations for up to 6 traveling guests, this cottage is perfect for groups of families or friends...
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    Location Information
    Old Lyme, Connecticut 06371
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Old Saybrook
    5 Bedrooms, 2 Bathrooms, Sleeps 14 Quick View
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    • Wi-Fi
    • Terrace
    • DVD Player
    • Balcony
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    • Skiing: Property Is In A Ski Resort
    • Air Conditioning
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your New England getaway awaits you at this one-of-a-kind vacation rental home in Old Saybrook. The 'Nathanial Clarke House' has 5 bedrooms, 2 bathrooms, and provides accommodations for 14 guests. This beautifully decorated home boasts a wraparound porch, gorgeous gardens, and was featured on the...
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    Location Information
    Old Saybrook, Connecticut 06475
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 14
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    North Haven
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Patio
    • Central Heating
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    Pet friendly
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    Smoking allowed
    About this property
    Located within walking distance of the North Haven Fair Grounds, our house is the perfect launch pad for your New England Adventure. We are just minutes from Yale, Quinnipiac, UNH, SCSU & Albertus, shopping, great restaurants, hiking trails, state parks and many local attractions including Stony...
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    North Haven, Connecticut 06473
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
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