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Nantucket Vacation Homes

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    Travellers to Nantucket are booking May dates now. Secure your holiday rental today, and have the perfect trip.
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    Gorgeous home in desirable Cliff location. Home is less than 3 blocks to Steps Beach and only 1/2 mile to Town! Great outdoor space with nice yard, decks and outdoor dining. The ideal location and home to enjoy Nantucket. Central A/c and wireless internet. Tasteful, manicured yard with privacy,...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    3 Bedrooms, Sleeps 8Quick View
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    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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    First Floor Kitchen ,dining room, hallway with full bath and two guest bedrooms.Twin bed and one double bed with trundle. lower level with guest bedroom with twins, laundry room.Den with 32" flat screen tv, dvd player and i pod dock. Second Floor Living room with a sleep sofa and access to deck ....
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, Sleeps 7Quick View
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    A quintessential piece of Nantucket history and charm, this saltbox style home is one of the 50 oldest on the island, as documented by the esteemed island historian, Edouard Stackpole. The ambiance of this home will make you feel part of the true Nantucket experience while you enjoy the modern...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    2 Bedrooms, Sleeps 4Quick View
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    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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, Sleeps 6Quick 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 2554
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, Sleeps 8Quick View
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    Northern Exposure is a New England Upsidedown house located near town center on Lower Orange Street, just beyond West Creek Road at 165 Orange Street. This fully furnished house is conveniently located near bike paths, grocery store, fish market, restaurants, banking/ATM, downtown Nantucket and...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, Sleeps 8Quick View
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    Fresh, attractive, an absolutely perfect rental. Post and Beam,situated in a quiet neighborhood, close to Surfside Beach and the bike path. A welcoming and restful sanctuary awaits. 3 levels of living PLUS a beautiful outdoor deck and yard. Outdoor shower. AC units, many. 1st floor entry, open...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, Sleeps 4Quick View
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    Two bedroom with deck overlooking water views, good two couple or family retreat with one parking space. First Floor- Two bedrooms and one full bath with laundry. Second Floor- Kitchen, living room, dining area, half bath, small deck overlooking the harbor. Additional amenities include: beach...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, Sleeps 4Quick View
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    Second floor one bedroom apartment above a garage just two blocks from Surfside beach. Sunny apartment shares lot with main house rented separately with separate drive. Wonderful sunsets from deck while dining al fresco! Open living room/dining area with sliders to sun deck, kitchen, bath with...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4 Bedrooms, Sleeps 8Quick View
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    Waterfront Property with Magnificent Views on Exclusive Eel Point .... Short walk to the beach. Bright and light summer home at the end of Eel Point Road. Overlooks acres of conservation land and the Nantucket Sound. Views of Madaket harbor as well. Enter into hallway with a bedroom straight ahead...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, Sleeps 10Quick View
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    • Porch
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    Canopache (Wampanoag Indian word for 'place of peace') New 2600 square foot home, completed in October of 2003. You can hear the sound of the surf from this upside down house on 3 acres with cathedral ceilings, tons of sunlight and sweeping ocean views. Warm, light, open, airy and peaceful describe...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, Sleeps 8Quick View
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    Beautiful, three-bedroom/three-bath house with distant ocean views on a private setting. The home has a spacious living area with a vaulted ceiling, pine floors, exposed overhead beams and central AC. There is a separate living area with a desk and a view of the ocean. The fully-equipped,...
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    Siasconset, Nantucket 2554
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, Sleeps 4Quick View
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    "Maison D'Etre" is a little bit of "SoHo" on Nantucket. First floor: Spacious great room, state of the art kitchen, granite counters, stainless steel Miele and KitchenAid appliances, Artemide lighting, sleek and warm wood cabinets opens to yard w/ 2 sets of French doors. Dining/living space is...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    4 Bedrooms, Sleeps 8Quick View
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    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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    4 Bedrooms, Sleeps 10Quick View
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    Designed as a family friendly home, this delightful Surfside house offers an open living room/dining and kitchen area featuring a center fireplace. Master bedroom with bath ensuite. Second bedroom, hall bath and utility room complete the first floor. Covered porch entryway and large covered back...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, Sleeps 8Quick View
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    Lovely spacious four bedroom home with fun upside down floor plan. Great location on Brant Point convenient to Jettys Beach and Town. First floor: Entrance foyer leads to four bedrooms each with private en suite baths and large laundry room. Second floor: Great room with kitchen, breakfast bar...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    3 Bedrooms, Sleeps 6Quick View
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    Sunny house with fun upside-down floor plan abutting 275 acres of conservation land with unobstructed distant views of Nantucket Sound!! Deeded access path to beach, access to Madaket Harbor (ideal for small boats & windsurfers) and tennis courts. Very comfortable home, nicely furnished and well...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    5 Bedrooms, Sleeps 10Quick 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 2554
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, Sleeps 6Quick View
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    Quaint, upside down house with spectacular views of golf course and sunsets. 1st fl: Bedrooms- (ex long twins) and Bedroom ( Queen) , 2 baths, deck overlooking golf course with view. 2nd Fl: Kitchen/dining/living (family) area, deck overlooking golf course. Lower Level: Family room, bedroom...
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    Siasconset, Nantucket 2564
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, Sleeps 8Quick View
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    About this property
    Lovely home with a good floor plan for two couples to share or a family, Porch for outside enjoyment. Convenient to town and Steps Beach. First Floor- Spacious kitchen, dining area, great room with fireplace, bedroom and full bath. Front and side porches to enjoy outside. An open and bright home...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    6 Bedrooms, Sleeps 12Quick View
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    Situated high on the Quidnet moors on nearly 4 acres, High Point is an exceptional family compound with sweeping views of the Atlantic Ocean, Sankaty Lighthouse, and Nantucket’s Eastern Shore. The Main House features 6BR/6.5BA, a 15′ x 36′ heated salt water pool, an outdoor spa, a fire pit,...
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    Siasconset, Nantucket 2554
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    Directly on the Harbor, this home has a private beach and tennis court on the property with central A/C. First Floor- Living room, dining room and a recently upgraded kitchen in 2010. A bathroom and two bedrooms along with with twin beds that convert to a king. Second Floor- Two bedrooms and two...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, Sleeps 10Quick View
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    Paved driveway w/ lots of parking; large, well landscaped front yard. Enter into the spacious open living/dining/kitchen room w/ beautiful view of the pool and backyard. The home has hardwood floor throughout except for carpeted, large family room in the lower level. The gourmet kitchen is on the...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, Sleeps 6Quick View
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    About this property
    Beach house at Smith's Point in Madaket with spectacular sunset water views. A great spot for fishermen who like surf casting. The beach is wonderful. Modestly furnished with simple taste, it is a cozey cottage in the dunes with a large deck overlooking the water. Additional amenities include:...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, Sleeps 5Quick View
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    Description: Tucked in at the end of a very private shell lane, this storybook 2 bedroom, 2 bath home is hidden in the heart of town just off Main Street. Retaining its historic charm and style, this property is totally renovated with all modern conveniences including central air-conditioning,...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    1 Bedroom, Sleeps 4Quick 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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    Ranch style living: Dining area, open kitchen with cathedral ceilings and eating area, livingroom with access to large deck and wrap-around covered porch, bathroom, laundry room. King bedroom, queen bedroom, bunk bedroom, twin bedroom, bath. One bedroom, one bath cottage included. Additional...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 8
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    Large, lovely antique home on a quiet lane just a few blocks from the down town shopping, galleries, restaurants, etc. Completely renovated and in tip top condition. Good living space, very well decorated and nicely appointed. Great little yard and patio extend the living space outdoors. Off street...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    • Grill
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    About this property
    This spacious home has a largeback yard and enjoys the use of a Community pool. House has WIFI First floor: living room, dining room, kitchen, laundry and half bath. Second Floor two masters, each with it own baath, two twin rooms that share a bath. Additional amenities include: beach towels,...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    5 of 5 bubbles
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    4 Bedrooms, Sleeps 9Quick View
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    About this property
    Up to nine travelers can stay in this amenity-filled home. It includes an open kitchen and dining area, a living area, a sun porch, and a deck. Enjoy distant water views and fantastic sunsets from this rental. Three bathrooms are provided for your showering and dressing needs. After doing your...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    3 Bedrooms, Sleeps 6Quick View
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    8 MacLean is a beautiful, recently- updated home nestled in the heart of Nantucket, off the Surfside bike path with access to three beaches. The house has it all from top of the line appliances to custom cabinetry, flat screen TVs, wet bar, marble bathrooms and a great rec room. Sleeps 6 in 3...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Cliff location, not far from the bike paths, beaches and town. Distant water views over the 50 acres of abutting Conservation Land. Multi-level home with 5 bedrooms and 3 baths, plus an outdoor shower. Recently renovated, with AC and new appliances, the house is fresh and ready to go. Perfect...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, Sleeps 6Quick View
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    About this property
    Steps away from the water, double story residence includes en suite bedrooms and a cozy sleeping loft. Enjoy stunning views of the water from both the master balcony and first floor patio, perfect on warm summer nights. A fully equipped kitchen, W/D, off street parking and complimentary Wi-Fi are...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1st Floor: Open kitchen, dining area and sun room. Cozy den. Master bedroom suite. 2nd Floor: Large bedroom suite. 2 bedrooms, each with extra long twin beds. Decks off master bedroom suite, sun room. Front wrap around porch. Additional amenities include: outdoor shower, disposal, bed type 2:...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    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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    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 - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Surrounded by privet hedges and hydrangea this cottage has a very private location near Sconset center. Charming, comfortable, deorated by well known local decorator there is a large living/dining area. Master bedroom has queen bed that opens unoto the sunny deck and well landscaped back yard. The...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, Sleeps 6Quick View
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    About this property
    67 Union was built in 1747 and was completely renovated in 2010. It has all of the modern conveniences, and is a charming and special home. Located just on the edge of town, and a half a mile from the beach, this house is a true gem. Three bedrooms and three full baths, an eat-in kitchen with...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, Sleeps 9Quick View
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    Large home located at the end of a quiet street and abutting Nantucket Conservation Foundation land. Close proximity to the beach. There is a cottage on the property that will be rented separately. Cottage is serviced by it's own drive and landscaped to divide the properties. 1st fl: Open living,...
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    Siasconset, Nantucket 2554
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 9
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    This charming house on a quiet street in the historic district has been remodeled with an upscale kitchen, beautifully restored floors, and is furnished with a mix of antiques and new furniture for elegance and comfort. The upscale kitchen has a Viking range, stainless French door Jenn-Air...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    This charming post and beam house on the moors of Tom Nevers has a fun upside-down floor plan, is furnished tastefully and is in immaculate condition! Deeded access to tennis courts just up the street. This very private and quiet area is great for walking or biking. The Milestone Road bicycle path...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    6 Bedrooms, Sleeps 14Quick View
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    • Wi-Fi
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    • Grill
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    • Private Garden
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    Smoking allowed
    About this property
    Thank you so much considering The Monkey Barrel for your home while visiting Nantucket. We call this house “The Monkey Barrel” because with all of the fun, laughter, and antics that take place while we’re at the beach…this house sometimes happily feels like a barrel of monkeys! This is a newly...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 14
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    3 Bedrooms, Sleeps 8Quick View
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    If you are looking for a unique rental property with old school charm in the heart of Nantucket’s historic district, look no further than Union Jack. Built in 1806 by house carpenter Lot Hinckley, this 3BR/3.5BA home (sleeps 6-8) is the epitome of Nantucket style. Authentic architectural details,...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    At Little Dipper, you enjoy the best of all worlds: walking distance to downtown restaurants/shops (0.5 miles), the Westmoor Club (0.6 Miles), and the beach (0.8 miles) as well as a peaceful, private location situated on over 1.25 acres. Recently renovated in 2010, Little Dipper features 4...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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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    4 Bedrooms, Sleeps 14Quick View
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    Smoking allowed
    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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    Location Information
    Nantucket, Massachusetts 2554
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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