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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 home today, and have the perfect trip.
    428 Matching Rentals in NantucketView all 1,092 rentals
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    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    5 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Charming house on quiet in-town side street off Pleasant Street. First floor: Open plan kitchen with modern appliances that opens to dining area with a large table that seats 10. Spacious living area with Master Bedroom and bath off to the side. Second floor: 3 bedrooms and 1 bathroom. Great yard...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 9
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Upside-down floor plan takes advantage of the beautiful sunsets and distant water views. Approximately 1500+ square feet of living space, simple comfortable furnishings and a peaceful setting. Four decks. Convenient to Dionis Beach. This beach house shares the property with a main residence in the...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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 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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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Monomoy Village Cottage: Adorable fully renovated and nicely decorated. Open floor plan - fully equipped kitchen. The cottage is a short walk to a secluded harbor beach. Warm, charming, and a short distance to downtown Nanttucket. Additional amenities include: beach towels, cd players: 4, bed type...
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    Nantucket, Massachusetts 2554
    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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    Smoking allowed
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    Lovely home in the historic district of Nantucket. Spacious deck and gardens.Top end appliances. First floor: Open kitchen with family room and tv, Dining room, living room, and powder room. Deck with hot tub. Second floor: Master bedroom with King Bed and bath and TV,Two bedrooms with shared full...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    About this property
    This lovely up-side down house features 3 bedrooms as well as a nice yard and outdoor shower and is ideally located close to Madaket beach and the bike path. 1st Floor: Enter front to an open living area with a large, flat screen TV, fireplace and plenty of furniture make this area very cozy. Off...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Great Brant Point location; walking distance to Jetties Beach, Children's beach, Town. Generous covered porch, fabulous yard. First floor; living room with fireplace, sunporch, covered porch. Dining room,, large kitchen with breakfast table. Bath with tub. One twin bedded bedroom .Second floor:...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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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 2554
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    Smoking allowed
    About this property
    Newly renovated for the 2013 season this house has a stylish modern interior and a traditional Nantucket shingled facade. Enter the house through the front door or through the updated kitchen which features a gas range and large breakfast bar. The first floor includes a dining room, sitting room,...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Smoking allowed
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    Totally charming, beautifully appointed upside-down house in the historic district of town. Located a stones throw from Nantucket Harbor and just a couple blocks from the heart of town. Tastefully decorated in English country and French cottage style with pretty painted floors and fun details....
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    This newly renovated has one bedroom cottage with a queen bed and a twin daybed that will sleep three. Bathroom has a shower and tub. There are a kitchen and private side patio for your enjoyment. Conveniently located in short distance to Downtown Nantucket. Off street parking available upon...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Quarter mile from Main Street, this home has a first floor twin bedroom and three bedrooms on the second floor. Additional amenities include: dist. to beach: 1.5 miles, disposal, bed type 2: queen, outdoor shower: none, baths: 4, area: town, ironboard, dist.totown: 0.25 miles, heat, internet...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
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    CISCO BEACH HOUSE - Fabulous Cisco house with excellent views of Hummock Pond and the Atlantic Ocean plus a swimming pool, spa, pool house, lovely gardens & a koi pond. Spacious, attractive oak post and beam, upscale 4 bedroom, 3.5 bathroom upside down house in great location. Convenient to...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
    About this property
    Five bedroom home on a culdesac in Naushop. Central AC and Wifi. Three floors of living. Community swimming pool and tennis courts. Off street parking. First floor:Dining room, powder room, great room with kitchen/living room , Private back and side yards with outdoor furniture and grill. Master...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    2 Bedrooms, 2 Bathrooms, Sleeps 2 Quick View
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    Pet friendly
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    Smoking allowed
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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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    5 Bedrooms, 7 Bathrooms, Sleeps 10 Quick View
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    Smoking allowed
    About this property
    This historic house was built between 1720 and 1726 for Lydia Starbuck and Benjamin Barney, and renovated in 1969 by the Nantucket Historic Trust. Unusually charming house with lots of panelling & a fireplace in each room. Steps away from Main Street, shops, restaurants. Well furnished in Nantucket...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Smoking allowed
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    Charming rose covered cottage on historic upper Main St.a short distance to town center. Vaulted ceiling in living area, french doors open to secluded and quiet deck, hardwood floors, completely updated kitchen and bathroom, beautiful garden. Additional amenities include: beach towels, outdoor...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
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    Smoking allowed
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    This Antique home on Orange Street has been carefully and tastefully updated and expanded to blend old world charm and modern conveniences in perfect harmony. Marvel at the Antique details throughout including original doors, antique pine flooring, tin ceiling and countless other details. Custom...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Smoking allowed
    About this property
    This renovated house is just 1/2 mile from Main Street; it features a custom kitchen, wood floors throughout the house. The main floor has an open plan living and dining area, the kitchen has island seating. There is a queen master bedroom with full hall bath on the first floor as well. The second...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    An excellent in-town location, ”Mill View” is an adorable cottage just a short walk to Main Street and close to beaches. A private bluestone deck with chaise lounges, outdoor dining table, gas grill and enclosed outdoor shower can be accessed from the king master bedroom via sliding patio doors. A...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 1 Bedroom, 2 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, 3 Bathrooms, Sleeps 7 Quick View
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    About this property
    This classic historical sea captain's house is located just up the street from the Jared Coffin House in Nantucket Town on a quiet tree lined street just blocks from Main Street. This is the perfect 'avoid having to drive into town' option for families on the go who want town access but also a...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 7
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Built on the site of the former carriage house at 8 West Chester, this cottage is near the center of the Historic District, one block from the Oldest House, four blocks from Children's Beach and the center of town. It is located on a secluded site which borders the Lily Pond, and has its own...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    5 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    About this property
    Beautiful town house with living room, dining room, library to porch, family room and kitchen. Second floor: Master ensuite, queen ensuite, twin bedroom ensuite. Third floor: Two bedrooms each one with twin, and shared bath. Additional amenities include: cd players: 1, bed type 2: queen, beach...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Smoking allowed
    About this property
    Out from the town on Cliff Road, after passing Crooked Lane, turn left on Wannacomet Road, go to #5, turn left onto 200' crushed shell driveway; enter house across front porch and brick patio (receives afternoon sun and view of sunsets) into spacious cathedral living room with expansive view of the...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    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 2554
    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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    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 2554
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Located on wonderful Jefferson Lane in the heart of the historic district. This Newly built house has a gracious floor plan with three levels of beautiful living space. The first floor has a dining room, kitchen with high-end appliances and granite counters, a living room with french doors that...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Lovely 2 bedroom, 2 bath 'Sconset cottage in the heart of the village on a quiet lane just blocks from the beach. Nicely furnished with a mix of comfortable contemporary, original art and fabulous antiques. Very attractive and fully equipped. Great patio overlooking a pretty fish pond in the yard....
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    Siasconset, Nantucket 02554
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Adorable cottage on a quiet side street in the heart of town. This sweet little house is attractively decorated, well maintained and fully equipped. A little patio for outdoor grilling adds to the fun. Just a short distance to Main Street shops, galleries, restaurants and all that town has to...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    First Floor includes a high ceiling living room and a large back porch, dining area, kitchen and a small private study, one half bath and two bedrooms. The backyard opens onto wide conservation land with wide open views. Second floor has a master bedroom, large private study, a loft and master...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    About this property
    Light, bright comfortable home.Large living room with fireplace and french doors to side deck. Open kitchen, dining area and two bedrooms with shared jack and jill bath. Powder room Second floor: Master bedroom with deck, second bedroom with two twins and single. Full Bath. Additional amenities...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 9
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Delightful 'Sconset house on prestigious Baxter Road. Beautifully decorated with Persian rugs, white upholstered furniture and a gorgeous Stephen Swift dining set. Lovely, landscaped lawn and a private sun deck. Second floor ocean views. Living room has cathedral ceilings and master bedroom 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 8 Quick View
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    Pet friendly
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    About this property
    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 2554
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    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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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Patio
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    Pet friendly
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    Smoking allowed
    About this property
    •5 Bedrooms / 4 1/2 baths - Sleeps 10 •Historic Renovated Home / Luxurious Accommodations •Convenient Location: Walk to Main Street / Walk to Beach •Beautiful Landscaped Property / Private Enclosed Lawn & Garden •Designer Kitchen / Sub Zero & Wolf Appliances •Marble Bathrooms with Heated Floors...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Comfortable 2 Bedroom Apartment in separate building from owners residence. Private patio with table and chairs. There is off-street parking for one vehicle but you may consider leaving it home as an 8 minute stroll will find you amidst the Main Street Shops and there is a shuttle stop nearby for...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    LONG-TERM SUMMER 2018: 1BR/1BA cheerful, secluded, air-conditioned, in-Town home faces The Old Mill. Near Main Street, restaurants, beaches, bike paths. Washer/dryer, dishwasher Wi-Fi, patio, outdoor shower, private off-street parking spaces for two cars but no car is necessary; the house is a...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Smoking allowed
    About this property
    Combined living room and dining room on the first floor along with a kitchen and half bath. Second floor consists of the master bedroom with a queen and a second bedroom with twins and a loft. Additional amenities include: cd players: 1, outdoor shower: none, TVs: 1, year built: 1988, 1/2 bath:...
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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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    Pet friendly
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    Smoking allowed
    About this property
    Newly completed and furnished home on a quiet cul-de-sac has all the comforts of home. High ceilings and many windows, the house is flooded with light. The rear of the house faces a small pond and acres of Conservation land. An ideal location with easy access to Town, Cisco Beach, Bartlett Farm and...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    About this property
    Nice home in Miacomet. Great back yard. First floor: Open plan with laundry room , living, dining kitchen with access to a nice deck.Half bath. Two bedrooms with shared bath,deck. Second Floor: Sitting room, two masters with King beds and full baths. Additional amenities include: cd players: 2,...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming, comfortable, quaint. Close to Sconset beach (4 minute walk), easy access to Sconset town center. Cathedral ceiling living room/dining area. Sunny deck, queen bed master bedroom, lofty with twin beds. Fullyequipped kitchen. Additional amenities include: beach towels, quarterboard: etc.,...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4.5 Gay Street1 / 11
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Completely renovated ********* 4+ bedroom home in the heart of the historic district. Convenient to ferry, beaches, shopping. Gourmet kitchen with antique charm but all of the modern amenities: Viking range and refrigerator, granite countertop, 3' hard rock maple butcher block island. Formal dining...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    About this property
    Relax in this bright and comfortable home ideally located in town on a quiet one-way street. New improvements have been completed over winter 2016, including all new updated bathrooms, a complete repaint of the interior, refinished hardwood floors, new furniture and décor, and new tile flooring in...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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    1 Howard Street1 / 8
    (1)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Smoking allowed
    Reviewed 18 August 2014
    Loved the home and location, although the furniture was dated and not at all "Nantuckety". House was not clean when we arrived at 3:00 check-in. In fact, maids had...
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    About this property
    Complete renovation in 2001. Very nicely appointed and decorated. Excellent location on a quiet street. First floor: Living room , kitchen/dining area and breakfast counter. Bedroom with queen bed. Bathroom with shower. Second floor: Master with bath with tub shower, bedroom with twins, bedroom...
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    Location Information
    Nantucket, Massachusetts 2554
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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