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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.
    24 Matching Rentals in NantucketView all 1,026 rentals
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    6 Bedrooms, 8 Bathrooms, Sleeps 12 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    6 Bedrooms, 6 Bathrooms, Sleeps 13 Quick View
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    Smoking allowed
    About this property
    Waterfront! Spacious Timberpeg house and cottage on 3 acres with stunning views. 1st floor: Living/family room with fireplace and cathedral ceiling. Dining room: half bath; master suite; kitchen and den, laundry with door to an outdoor shower. French door to deck, grill, fenced yard. 2nd floor:...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 13
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    About this property
    Rent your own B & B! This historic home captures the elegance and charm of old Nantucket with all the modern conveniences. Built in 1846, this renovated Greek revival style home is on a cobblestone street only two blocks from town. This house has high ceilings, large bedrooms and lots of light-the...
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    Siasconset, Nantucket 02554
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
    5 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    • Internet Access
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    Pet friendly
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    Smoking allowed
    About this property
    This gorgeous custom-built house is located on a secluded setting which is adjacent to conservation land in Quidnet, and has views of Polpis Harbor and the Sankaty Lighthouse. There are four bedrooms on the first floor, which connect to a wraparound deck, which also leads into a comfortable...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 13
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    About this property
    The first floor features the kitchen, living room, two bedrooms (1 queen bed each) and one full bath. Take the ships ladder to the super cozy loft floor where there are two rooms: one with two twins and one with one twin. Both rooms with TV's. In the basement there is a living area with game...
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    Siasconset, Nantucket 02554
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Private Garden
    • Wi-Fi
    • Cable/satellite TV
    • Secure Parking
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This custom built home with traditional Nantucket exterior architecture boasts a newly renovated modern day living interior. conveniently located in Nantucket's Historic District, Watercolors is part of the Nantucket Art House rental family, which is known for capturing the spirit of Nantucket...
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    Siasconset, Nantucket 02554
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    Pet friendly
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    Smoking allowed
    About this property
    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 02554
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Out from the town on Cliff Road, pass Crooked Lane, turn left on Wannacomet Road, go to #5, turn left onto 200' crushed shell driveway; enter cottage parking (on left). Enter cottage across front porch (receives afternoon sun and view of sunsets) into first floor with cathedral living area, with...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    About this property
    This cottage is expansive and multi-level, with a large screened-in porch. High, vaulted ceilings give the place an airy feel, and with easy access to the screened-in porch as well as a deck, outdoor entertainment is easy to transition into the indoor living area. The luxurious gourmet kitchen has...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    4 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This newly renovated home has an open gourmet kitchen, dining area with fireplace, livingroom and den with Sofabed. Private Patio. Second floor:Ensuite master bedroom , ensuite queen bedroom ensuite full bedroom. Third floor: Ensuite bedroom. Additional amenities include: bed type 3: full, bed...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 10
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    Smoking allowed
    About this property
    This spacious Surfside upside down beach house is perfect for family gatherings with two large living areas on separate levels and great wrap around decks with oceanviews! Approximately 300+ feet to public access stairs to Surfside Beach. 1st fl: BR w/ twin beds, BR w/ 2 sets of bunks; BR w/ Queen;...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming vintage style house with total privacy, surrounded by woodland. There are porch, patio and outside shower. First floor consists of kitchen, bright living and dining room with a lots of day light, double bedroom, shower bathroom and queen sofa bed.There are glass doors from the living room...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This house has loads of Nantucket charm. Hardwood floors throughout with Claire Murray rugs in every room. Widows walk with views of town. Gourmet kitchen. Cozy living room with fireplace. Each bedroom has private full bath and walk-in closet. Great wrap around deck with wicker deck furniture....
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely four bedroom home 'in town' on a private shell lane, a short distance to Main Street. Bright, cheerful and attractively landscaped with wisteria coverd pergola over back deck. 1st Flooor: Dining room, well equipped galley kitchen, living room with gas fireplace, master bedroom with ensuite...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Internet Access
    • Cable/satellite TV
    • DVD Player
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Rent your own B & B! This historic home captures the elegance and charm of old Nantucket with all the modern conveniences. Built in 1846, this renovated Greek revival style home is on a cobblestone street only two blocks from town. This house has high ceilings, large bedrooms and lots of light-the...
    View all property information
    Location Information
    Nantucket, Massachusetts 2554
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
    6 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Internet Access
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This one-of-a-kind family compound sits on almost six private acres overlooking Weeweeder Marsh. Surrounded by conservation the property boasts a six bedroom main house with central air conditioning, an infinity edge pool, cabana, par-three golf course (three holes, nine tee boxes) and an outdoor...
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    Siasconset, Nantucket 02554
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 10
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
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    Pet friendly
    Kid friendly
    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...
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    Siasconset, Nantucket 02554
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • Central Heating
    • Private Garden
    • Internet Access
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    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....
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    Siasconset, Nantucket 02554
    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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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    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
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Conveniently located in the historic District and exclusive Cliff Road area, the house is just 1/4 mile from Steps Beach, Jetties beach, The Oldest House, and the Center of Town. The house is located close to Something Natural, a local bakery and sandwich shop. The lovely front porch allows for...
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    Siasconset, Nantucket 02554
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Internet Access
    • Washer
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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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