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Wellfleet Luxury Holiday Rentals

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    Travellers to Wellfleet are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    27 Matching Rentals in WellfleetView all 186 rentals
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    About this property
    This 4 bedroom, 2 bath waterfront Cape-style home, built in 1983, is set on top of sand dune overlooking Wellfleet Harbor, Great Island and Cape Cod Bay beyond. The views are breath taking. There is a stairway (steep) leading to a sandy beach with swimming at mid tides as well as kayaking and...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    6 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    This is a large 6 bedroom, 3 bath 1972 contemporary style, 3 level 'beach house' located at the end of a short sand road in the Chequessett Neck area of Wellfleet. A spiral stairway leads through the 3 levels along with entry doors on the first and second levels. This rental may not be appropriate...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 11
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    Wellfleet Waterfront 5 Bedroom Vacation Home1 / 20
    (6)Very good
    5 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Fun Cape Cod Summer house, Great for Families looking to enjoy all the Cape has to offer. 3 miles from the Beachcomber and 1 mile to Cape Cods white sand beaches. You can Kayak out into Drummer Cove, Lieutenants Island and Wellfleet harbor right from the back yard. This charming 5 bedroom...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 12
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    Private Sandy Beach. Big Beach House. 5 Kayaks.1 / 67
    (3)Very good
    5 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
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    Beautiful, quiet, sandy beach. Enjoy full water views from our south facing 2,000 square foot Cape Cod - Colonial style 2 level home. 1st and 2nd floors, NO basement. Private cottage colony beach with gentle waves. No rip tides to worry about. Great for swimming. Explore the Cape Cod...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 11
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    4 Bedrooms, Sleeps 10 Quick View
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    21 Arthur Cashin Way, LT Island (ID#127763) - Lt. Island 4 Bedroom Cottage With Water Views Enjoy this quintessential beach house beautifully located on Lt. Island. Perched on top of a high dune you will have beautiful water views of Cape Cod Bay from the living room and sun porch. A short way down...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 4 Bedrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Beautiful Wellfleet Geiger-Phillips architect-designed 4 bedroom custom home (2300 sq ft) with all amenities nestled in the woods of Wellfleet - only 1 mile to the center of town and marina. 3 beaches on the bayside (flat, warmer, kid-friendly) are nearby and 3 more on the oceanside (waves, surf,...
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    Wellfleet, Cape Cod 02267
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    New in 2004, this is a centrally air conditioned, spacious 3 bedroom 2.5 bath contemporary Cape-style home located in a private setting about 2 miles from Indian Neck Beach. New for 2015 your pets are allowed as long as they are hypo-allergenic, under 20 lbs. and non-shedding. The house sleeps 7...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    #317 The Captain's House: Private Pool, Tennis Courts, Game Room, Renovated Historic Home with Carriage House. Your family will be over-the-top excited to stay in the Captain's House for a week on Cape Cod! This is an antique home, with all the quirks. Fully updated, refurnished, and stacked...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    This 1980'S 3 bedroom 2 bath contemporary 'beach house', located in the Indian Neck Beach area, has wonderful water views of the bay from the second floor deck and is within walking distance to Burton Baker Beach, a sandy bayside swimming beach.Ductless A/C units were added in 2015, one on each...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    This lovely contemporary home offers plenty of living space, both inside and out. Each bedroom has access to its own bathroom for convenience to its occupants. The lower level bedrooms each have a king size bed, one with a private bath. There is a loft room with a queen size bed and flat screen TV....
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    Wellfleet, Cape Cod 02667
    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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    About this property
    Lt. Island in Wellfleet is Cape Cod's best kept secret. This house is exceptional in every detail. The main house has 3 bedrooms, with a king, a queen and two twin beds, 2.5 baths and a wraparound deck that overlooks the marsh and bay. The master bedroom and the en-suite bathroom are located in...
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    Wellfleet, Cape Cod 02667
    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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    This comfortable and spacious home offers a lovely view of Lieutenant Island in Wellfleet, and beautiful Cape Cod Bay sunsets. Surrounded by Audubon conservation land, this property offers 4 bedrooms and 3 baths, sleeping 8 comfortably. The first level of the property boasts a fully equipped...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    6 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    80 Mill Creek Lane (ID#127321) - 6 Bdrms Close To The Bay and the Village Spacious contemporary home a short distance to Powers Landing (aka. Seashells Beach). This home is nestled at the end of a short dirt road. Three levels with a bathroom on each level. There are many spaces in this house to...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 6 Bedrooms, 2 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    This contemporary style home, located in the Indian Neck area of Wellfleet, overlooks Chipman's Cove and offers water views from almost every room. The first level of the home offers a remodeled kitchen (2012) with views of the Cove, a bedroom with a queen sized bed and a remodeled (2012) bath with...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, 1 Bathroom, Sleeps 10 Quick View
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    80 Briar Lane (ID#128185) - 5 Bedroom Antique Village Home With Barn And Romantic Garden Setting - Wellfleet Village Stately, gracious, expansive & charming, this beautiful, 5 bdrm renovated antique set on almost an acre of gently terraced lawn and gardens is a true jewel in Wellfleet s center....
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 5 Bedrooms, 1 Bathroom, Sleeps 10
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    30 Gulch Rd. 1276211 / 12
    (1)Excellent
    4 Bedrooms, Sleeps 8 Quick View
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    30 Gulch Rd (ID#127621) - Oceanside 4 Bedroom Home-National Seashore SUNDAY RENTAL This Spacious 4 bedroom, 4 bathroom house in Cape Cod National Seashore with distant ocean view, built in the 1950s by renowned modernist architect Serge Chermayeff is available for your enjoyment. This home is set...
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    Wellfleet, Cape Cod 02642
    Holiday Rental House - 4 Bedrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    This is a contemporary, split level home with breathtaking sunset views of Blackfish Creek, Wellfleet Harbor and beyond. It is located down a private dirt road buffered by Audubon Conservation Lands, which offer peaceful beauty for a perfect Cape Cod getaway. On the first level is a Master Suite...
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    Wellfleet, Cape Cod 02667
    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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    This architect designed, multi-level contemporary home,'The Tree House', is located in a residential neighborhood on the ocean side of the highway and offers privacy in a pleasant wooded setting with multiple decks including a roof deck. The living, dining and kitchen areas that comprise the main...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    This contemporary 4 bedroom 3 bath home on Lieutenant Island was built in 1994, is light and airy, nicely furnished, has all the usual amenities and is fairly private. The island's lovely sandy beaches can be reached by paths over the dunes in about 5 minutes. There are two decks, a large deck with...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    A warm and delightful oasis, this light and airy, open concept home is nestled atop a quiet wooded knoll less than two miles from Wellfleet Center. Galleries, beaches, and restaurants are less than five minutes from your doorstep. Cathedral ceilings, well-equipped kitchen, gas grill, WIFI, new flat...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    This newly renovated Antique home offers a brand new modern kitchen, two new bathrooms, and 4 bedrooms, sleeping up to 9. Located on a quiet road right off the center of Wellfleet, shops and restaurants are steps away. Wellfleet Harbor, Mayo Beach and the Town Recreation Center are a short bike...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    Stunning and peaceful, paradise found!1 / 23
    (5)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Waterfront privacy on over 2 acres. Stunning architecturally designed contemporary home with walls of glass high on a knoll overlooking the Fresh Brook Spring and river with safe boating right off your private sandy marsh beach to cape cod bay. Cathedral ceilings, beautiful kitchen with granite...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    About this property
    560 Old Chequessett Neck Road (ID#131177) ~ 4 Bedroom ~ Chequessett Knolls Neighborhood This SPACIOUS HOME WITH AC in the desirable & private Chequessett Knolls Neighborhood is a rental dream. This 4+ bedroom home has wooden deck walkways around the entire back side of the house (can be narrow and...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Balcony
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    • Terrace
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    Newer constructed home located on the Ocean side of Wellfleet, a 1/2 mile from Gull Pond and 1 mile from Newcomb Hollow Beach. Our house has hardwood floors and lots of sunny windows overlooking a secluded hollow in the woods. There is a large south facing deck with bar-b-cue grill and a private...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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