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Smoking Allowed Holiday Rentals in Nantucket

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    Travellers to Nantucket are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    126 Matching Rentals in NantucketView all 1,215 rentals
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    8 Bedrooms, 5 Bathrooms, Sleeps 22 Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Newly renovated Saltbox new 'Five Corners'. Handicap accessible. Large, fully fenced in yard, pine floors, open, airy and light. A/C and gas heat. Two story with open living room and fully equipped kitchen.Open circular staircase to second floor with open loft sitting area overlooking living room...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Smoking allowed
    About this property
    Long white stone driveway leads to this recently renovated 5+ acre oceanfront compound. Enjoy the outdoor pool and spa or take a short stroll down the steps to the ocean! First Floor: Open entry hall leads to Master bedroom with en-suite bath and spectacular ocean side views. Guest bedroom with...
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    Siasconset, Nantucket 02554
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Cute cottage a hundred yards from downtown.Tucked away off the street on a quiet lane, one minute walk to town. Completely renovated kitchen and all new stainless steel appliances. First Floor: Large open livingroom,dining area and kitchen, door off the dining room leads to the rear deck. Off the...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
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    Please be advised that 1 Week Minimum Stay applies to this property during the peak season: Mid- June through Mid-September.
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    The beach is 200 yards away and town is 3 miles north. This 2 bedroom home is a hop skip and a jump from Surfside Beach. Surfside Beach is the only Nantucket beach with a concession stand and has a lifeguard. It is also a short drive or bike ride into town. Additional amenities include: outdoor...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Light, bright, updated Cape Cod house. Peaceful, private, well maintained near Dionis Beach. First floor: living room open to dining room, sun room, kitchen, laundry room. Two bedrooms, full bathroom. Second floor: two bedrooms, full bathroom. Large back deck, enclosed outside shower. Additional...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    First floor:Kitchen- living- dining open area, master bedroom with full bath. Screened in porch. Second floor: three bedrooms and full bath. Additional amenities include: outdoor shower, cd players: 1, bed type 2: queen, TVs: 1, barbeque grill: charcoal, internet connection: wireless, baths: 2,...
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    Siasconset, Nantucket 02554
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Great location for this adorable 'in town' cottage. Just renovated 2013. First Floor: Living room w/ pull out sofa, kitchen, dining, full bath. Porch and small patio. Second floor: two queen bedrooms, landing with futon, full bath. Laundry on first floor. Two parking spaces. Short walk to center of...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Charming two bedroom, 2 bath home across from Wauwinet Hotel. Beach rights to beach in front of hotel and beach access to ocean beach. Additional amenities include: beach towels, winter, cd players: 1, quarterboard: mushroom, outdoor shower: none, TVs: 1, baths: 2, year built: 1980, dist.totown:...
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    Siasconset, Nantucket 02554
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    ** Wonderful four bedroom home set back off road. One acre very private and perfect!** Home features a covered porch, open living room with a gas fireplace surrounded by built-in's, a dining area with a farm table, a Chef's kitchen with a granite island, pantry, laundry, mud room, 2 master bedroom...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Central Heating
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    Well maintained cottage in a beautiful private location. 1st floor: Living room with woodstove, kitchen and dining area with half bath. 2nd floor: Master bedroom and bathroom. 8 Week Minimum Rental Applies
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Shared Outdoor Pool (Unheated)
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    About this property
    This lovely Nantucket summer home is ideally located near 'Sconset center. The property boasts a 5 bedroom main house, a guest apartment and a heated pool. New furnishings were added in 2008. There is a lovely garden with a patio by tall privet and a sprawling private lawn. Many other bonus...
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    Siasconset, Nantucket 2564
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    About this property
    Featured in the April 2010 design issue of Nantucket Today, this adorable Nantucket country cottage is an ideal spot to enjoy an island vacation; a short distance from downtown and conveniently located to shopping, markets and beaches. 1st fl: Living room, dining area, galley kitchen includes...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    CUSTOM BUILT CONTEMPORARY / COLONIAL HOME on a quiet historic lane just one block off Main Street! A handsome spacious first class rental property with every creature comfort. Great sun deck & covered porch extend summer living out doors. Terrific house for family gatherings. FIRST FLOOR: Living...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Recently built this 3 bedroom Main House with a 1 bedroom guest suite in the Carriage House will delight you. Tucked away in Madequecham, it's just a short drive down a sandy road to one the islands best beaches & everything is brand new! The first floor of the main house welcomes you into the...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 2 Quick View
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    Two bedroom, 1.5 bath cottage on Miacomet Pond. central A/C, parking. Additional amenities include: beach towels, outdoor dining table, outdoor shower, beach umbrella, bed type 2: twins, 1/2 bath: 1, dist. to beach: 1 mile, area: miacomet, ironboard, lobster pot, heat, internet connection:...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 2
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Enjoy the charm of an historic home built in 1850s with large modern addition and complete renovation. Located in town and easy 1/2-mile walk to Children's Beach, Steps and Jetties. Comfortable in-door and out-door living space. KITCHEN: Large kitchen with family dining area (seats 10) has...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Wonderful, waterfront house abutting hundreds of acres of conservation land at Eel Point! Last house on the point with magnificent views looking west through the dunes towards Tuckernuck Island, Muskeget Island, Nantucket Sound and Madaket Harbor. Great sunsets! A very bright, light, lovely home,...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Please be advised that 1 Week Minimum Stay applies to this property during the peak season: Mid- June through Mid-September.
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    This unusually private in-town property is beautifully landscaped complete with a Koi pond, mature weeping willows, chaise lounges...a perfect spot for a restful vacation, peaceful and rejuvenating. House has been totally renovated 2008! First Floor: Living room with a beautiful fireplace with...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Located on Hulbert Ave, just minutes from town and several public beaches, this comfortable and well maintained home sleeps six and has two full bathrooms. The first floor offers a master bedroom with private bath and walk in closet, cathedral ceiling combination living room/dining room and a fully...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Conveniently located in a private setting between town and Cisco beach, this custom built 3 bedroom 2 and a half bath home is the perfect getaway. 1st floor: Enter into a foyer which includes stairs to the second floor. To your left is a set of French doors leading to a large living room with a...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Nestled back 200 feet from the activity of Washington Street, 'Tucked Inn', is quiet and private. Wooden decks surround much of the house. Large living area containing living room, dining room and kitchen. Gas fireplace in living room. Laundry room with washer/dryer and storage. Three bedrooms with...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Wonderful bright 1840 Antique house with loads of charm. Fabulous outdoor patio. Nicely furnished and equipped. Three floors of living. First floor. Livingroom, large dining room with table to accomadate 12. Great for entertaining, sunroom, kitchen and full bath. Second floor: Bedroom with king,...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Very attractive one bedroom cottage near Surfside Beach has a great Nantucket look. Patio with furniture and BBQ grill extends living outdoors. Ample parking and easy access to bike path which takes you to beach or town. Open living / dining / kitchen, queen bedroom with full bath, laundry chute to...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Watch terrific Nantucket sunsets from this amazing Dionis location. Contemporary upside down house and cottage with contemporary furnishings, great light, super outdoor licing, plenty of privacy. Get the best of all worlds...easy access to harbor side beach and a short ride into town. Additional...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Modern house that is really fun! Separate wing for bedrooms. Kitchen renovated 2006. The dining room overlooks Hither Creek. From the roof there is a great view of Madaket Harbor as well as the Creek for watching sunsets. Additional amenities include: beach towels, wood stove, outdoor shower, cd...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Centrally located in the historic district, this quaint duplex cottage offers a genuine Nantucket experience at an attractive price. Walk to Main Street in the center of town in 15 minutes (.5 miles). Bike to Jetties Beach or Children's Beach in 10 minutes, or be picked up by the nearby shuttle to...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Private Garden
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    This charming 2 bedroom home offers the best of both modern day living and antique charm. This home has a fully equipt kitchen, washer, and dryer, a private deck off of the master bedroom overlooking the beautiful private backyard patio amongst a tranquil lush garden. With the center of Nantucket’s...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Gambrel roof historic house in the heart of town. Formal living room and a second informal living room along with a dining room and bright kitchen make for comfortable family living. The outdoor deck is convenient for outdoor dining. The entire house is sun filled. First floor: Living, dining, full...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Enjoy Nantucket the way it used to be in charming Wauwinet. This bright and cheery beach house is just steps from the Atlantic ocean and the best Bass fishing beach on the East Coast. It's also a short bike ride to the famed Nantucket Moors and a hundred miles of secluded mountain bike trails. It...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Walking distance to Monomoy Beach. Three bedroom house with comfortable living room with dining area and kitchen. Living room has cathedral ceilings and wood paneling. Good yard for children. Old Nantucket at its best. Additional amenities include: beach towels, cd players: 1, off street parking:...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    The Francis Barker House Antique rental house recently restored with new kitchen and bathrooms. Waterviews from all three floors - decks on two floors. Third floor bedroom suite with spectacular views of harbor. Six fireplaces, original King George wide-plank pine floors, handmade doors from...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Lovely newer home located in a quiet area convenient to Town and beaches. First floor has gracious center entry. High ceilings, granite counter tops, Subzero fridge and cook island. Dining area with wall of windows overlooking landscaped back yard. Fireplace in living room w/ crown molding and wall...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    6 Bedrooms, 4 Bathrooms, Sleeps 15 Quick View
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    Spacious and charming, this Madaket home has a large wooden deck for viewing the great sunsets, ocean and conservation land. First Floor-Five bedrooms and a dan with a pull out couch. 3.5 bathrooms and a laundry room. Second Floor-Master bedroom with a cedar walk in closet and a bathroom with a...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 15
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    Upside down, three decks, fantastic ocean views, beach stairs 60 seconds away. Additional amenities include: outdoor shower, bed type 2: queen, off street parking: 2, internet connection: cable, year built: 1986, fireplace: usable, 1/2 bath: 1, lobster pot, dist. to beach: across street, deck or...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Easy living in this Cisco home. Wide open spaces....comfortable living space leads to decks for outdoor living in this 4 bedroom home 1/4 mile walk to Cisco beach. Convenient to Miacomet Golf Course, Bartlett Farm and Cisco Brewery as well as 4 miles form town. Additional amenities include: beach...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Overlooking the Cisco dunes with ocean views, this 4 bedroom house has a spacious open plan living room with fireplace, dining room and kitchen. Doors lead from the living room onto the large deck for easy outdoor living. Main floor has one master bedroom with ensuite bathroom and two guest rooms....
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Last house on Warrens Landing Rd, great views of great sunsets. First Floor- Three bedrooms with twin beds, two bathrooms and a sitting room with a large back deck. Second Floor- Living/dining room, kitchen, master bedroom with a queen bed and full bathroom. Great deck with wonderful views of...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    4 Bedrooms, 5 Bathrooms, Sleeps 6 Quick View
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    Kid friendly
    Smoking allowed
    About this property
    A Modern Gem in the heart of the historic district on beautiful Orange Street, one of the most desirable streets on Nantucket with seasonal water views.The special qualities of this home, that was renovated by the owner, a master craftsman and complemented with interior touches by the co-owner, a...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    First Floor Description -- Open floor plan with water views. Fully equipped kitchen with dining room area out to deck, living area and large wrap around deck. First floor master with a king bed with full bathroom. Second Floor Description- Beautiful spiral staircase leads to the loft area with...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming 2 Bedroom Cottage with modern kitchen, surrounded by gardens and patios. 1 1/2 Bath plus outside shower. Washer and Dryer. Master bedroom has queen size bed. Two twin beds in second bedroom. Large family room area for relaxing and entertaining. Outside grill and patio furniture. Kitchen...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Nice cozy cottage close to beach in Madaket. Additional amenities include: beach towels, outdoor shower, barbeque grill: charcoal, baths: 2, bed type 2: twins, fireplace: usable, ironboard, lobster pot, heat, internet connection: wireless, bed type 3: twins, heat type: elec., deck or patio furn.,...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
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    About this property
    Charming cottage for one or two in Sconset Center. Spacious living -dining room, queen bed and country antiques for your enjoyment of a true summer village spirit. Short distance to 'Sconset marketplace with cute shops, cafes and tennis court. A bus stop is very close, and 'the Wave' will take you...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    First floor: Master suite with private full bath, laundry room, two bedrooms and another full bath. Second floor: Open living/dining/kitchen area and decks to view the ocean and beach, half bath. Quiet street! Added blue tooth sound system, new flat screen tv, and updated some linens and dishes....
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Waterfront
    • Hot Tub
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    Pet friendly
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    Smoking allowed
    About this property
    Spacious, attractive craftsman built home right on Hither Creek with spectacular views of Madaket Harbor, Smith's Point, Esther's Island, Tuckernuck and Eel Point. Quiet spot in old Madaket. Two great decks and a covered porch. A private dock in front for boaters!! 1st Floor: Large open room great...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    1St floor condo. Open floor plan- large deck, 2 large queen bedrooms, 1 bath, fireplace. Additional amenities include: beach towels, disposal, bed type 2: queen, beach umbrella, outdoor shower: none, TVs: 1, baths: 1, quarterboard: creek view, ironboard, lobster pot, dist.totown: 1/4 mi, radios:...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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