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Wellfleet Holiday Homes

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    Travellers to Wellfleet are booking June dates now. Secure your holiday rental today, and have the perfect trip.
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    THIS PROPERTY HAS BEEN SOLD1 / 8
    (3)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 1 Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    PET-FRIENDLY CLOSE TO NEWCOMB'S HOLLOW BEACH!1 / 18
    (3)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    WATERFRONT – This updated 2 bedroom, 1 bath cottage is part of the Wellfleeter Condominium complex located at the end of Mayo Beach on Wellfleet Bay with access to the Private Association Beach. The cottage has a kitchen-dining area, living room and 2 bedrooms with one with a double bed and the...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Patio
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    140 B Long Ave (ID#136851) ~ Drummer Cove 3 Bedroom Home Ready for 2018 bookings. A perfect and relaxing rental in South Wellfleet near Drummer Cove on the bay and Lecount Hollow Beach on the ocean side. While sitting on the deck you can see Drummer Cove sparkling through the pine trees. Take...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    15 Way 625 (ID#127548)-Pond Front Cottage in the woods, set quietly on its own 4+ acre parcel perched above Long Pond. This rustic retreat surrounded by park lands offer extreme privacy. Tap into lifes simple pleasures, screened in porch area with rough hewn furnishings, many outdoor living areas...
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    Wellfleet, Cape Cod 02642
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    This newly built, newly listed 4 bedroom contemporary home has everything your family may need on vacation! Central air, open floor plan, enclosed outdoor shower comfortably sleeps 8. Located on the ocean side of Wellfleet, it is a short drive to Oceanview Drive along with Wellfleet’s freshwater...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    180 Holbrook Ave (ID #127332) Wellfleet Village Area Come explore Wellfleet from this cherished Cape Cod home, quietly set back off of Holbrook Ave. just down the lane from Main Street and near the Bay. This home has 2 bedrooms on the main level. Go through the front door into a homey living area...
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    Wellfleet, Cape Cod 02646
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    This comfy cottage sits high on a hill offering amazing views of Chipmans Cove. Come and relax on the back deck and enjoy the view and the famous Cape Cod sunsets. Enter the lower level and you will find a nice TV room, full bath and on the other side a washer/dryer. Up the stairs on the main...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Grill
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    Mayo Beach. 3 Bedrooms, 2 Baths. Outdoor Shower. Kayaks Included. Great location across from Mayo Beach! Great sandy South-facing for swimming, boating, exploring. This renovated cottage still retains it's 'Olde Cape Cod' charm with original wood floors, an open layout, and exposed beam ceilings....
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    285 Blue Heron Road 191011 / 8
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    285 Blue Heron Road (19101) ~ South Wellfleet ~ Three Bedroom with A/C and Wireless Internet Marconi Beach is nearby...Contemporary style house with a bright open floor plan, lots of glass, quiet wooded lot. Living/dining/kitchen area with eat-at counter, picturesque fireplace (for looking at, not...
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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 8 Quick View
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    This nice three bedroom Wellfleet home sits in a quiet area near Lt. Island. The home is unique with its use of multi-level decks, screened in porch, and spaces for privacy and lots of room to entertain. This comfortable ranch home has a well equipped kitchen and an open floor plan that includes...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    This 4 bedroom, 2.5 bath upside down house sits at the end of a sand road and overlooks Drummer’s Cove, a tidal estuary, offering picturesque views.  Upon entrance, you will find 4 bedrooms and 2 full baths on the first floor.  The master bedroom, with en suite bath and views of the Cove, has a...
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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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    This lovely 3 bedroom, 2 bath home is located on the Oceanside of Wellfleet, with quick access to Wellfleet’s freshwater Ponds and Beaches. On the first floor you will find a fully stocked kitchen open to the dining area – which will comfortably seat 8 people - a full bath and the Master bedroom...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    20 White Tail Lane 991471 / 20
    (1)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    20 Whitetail Lane (99147) ~ Bayside ~ Wellfleet Beaches Nearby Privately located contemporary style home in Wellfleet. Centrally located to explore the outer Cape from Provincetown to Orleans and all the magnificent beaches, dining and shopping in between. A quick ride to Mayo Beach on the...
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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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    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    85 Old Truro Road (ID #127840) - 3 Bedroom Antique With Soaring lofted Guest Barn Enjoy this beautifully renovated 1850 s Farmhouse with original barn that has been converted into a charming, bright and airy, lofted guesthouse. Each beautifully situated within their shared 1.91 acres of great...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    This well maintained 2 bedroom, 2 bath, contemporary home is situated in a private, wooded area near the ocean side beaches off Route 6. The first floor has a fully equipped kitchen adjacent to the dining area, as well as two sets of sliders leading to the expansive deck. The living area has a...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    This cottage is located in the Indian Neck area of Wellfleet and is bright with an open floor plan which includes the living room, dining area and kitchen. There are 3 bedrooms, one with a king sized bed, one with a double bed and one with 2 twin sized beds. There are two baths, one with a stall...
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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 is a 1970's contemporary style house with a newer studio cottage offering a total of 4 bedrooms and 2.5 baths. The main house has one bedroom with 2 twins on the ground floor along with a full bath, the living, dining, and kitchen areas as well as a screened porch. The 2nd floor has a half...
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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 7 Quick View
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    This rustic waterfront house is located at the tip of Pleasant Point with views from every room of the house. It offers an open living room, dining room and kitchen space with Central Air Conditioning & WIFI. In the house, you have beautiful views from wherever you sit or stand. Down the hallway...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    This secluded and rustic National Seashore home with 3 Bedrooms and 1.5 baths is a great spot for a peaceful getaway to the Cape. There is a cathedral ceiling, rough hewn barnboard walls and an open living and dining room with sliders in the kitchen and Master Bedroom that lead out to the multiple...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 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...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    60 B Long Ave 1274671 / 12
    (1)Excellent
    2 Bedrooms, Sleeps 4 Quick View
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    60 B Long Ave (ID#127467) - 2 Bedroom Cottage - Drummer Cove Area This cute 2 bedroom cottage is one of 18 units that comprise the 'Drummer Boy Condo Complex' on the edge of Black Fish Creek in S. Wellfleet. Two bedrooms plus a double size pull out sofa in the living room offer plenty of sleeping...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 2 Bedrooms, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Gaze out at the charms of downtown Wellfleet from your second-floor balcony in this 4BR/3BA home. Restaurants, shops, and the coastal town’s famous galleries are just steps away. Head down Main Street towards the Town Pier, Mayo Beach, and Wellfleet Harbor. Refreshing Atlantic beaches are a quick...
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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 6 Quick View
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    Pet friendly
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    Smoking allowed
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    Unique net zero/solar power home tucked away in the hills of Wellfleet. Close to town, bay and ocean beaches. Sleeps 6. This lovely contemporary Cape is tucked into the hills of Wellfleet just a 15 minute walk into town and a 10 minute drive to Newcomb Hollow Beach and all of the beaches on Ocean...
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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 8 Quick View
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    This 3 bedroom, 1.5 bath contemporary is located in the ponds area of Wellfleet's National Seashore. It features sprawling decks overlooking the woods of Wellfleet! There is plenty of deck furniture and a gas grill - perfect for summer barbeques with family & friends. The first level of the home...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    This traditional 3 bedroom 1.5 bath beach cottage, built in the early 1900's, is located across the street from Wellfleet Harbor and Mayo Beach. The first floor has a small kitchen with a dining area, living room with another dining area, 2 bedrooms - 1 bedroom has a double bed and a twin bed and...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, Sleeps 4 Quick View
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    75 Cassick Valley Road, Unit #4 (ID# 131364) ~ 2 Bedroom Cottage Oceanside ~ Lecount Hollow Beach Area Enjoy this modern and updated 2 bedroom cottage that is nestled in the woods of Cassick Valley in S. Wellfleet. This cottage offers easy access to Lecount Hollow Beach, a beautiful oceanside...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 2 Bedrooms, Sleeps 4
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    175 Old County Road (ID #134332) ~ Oceanside Pet Friendly With A/C This Cape Cod home is a charming classic Cape home that is perfect for six or cozy enough for two. It is decorated with classic New England antiques. The first floor has a bedroom with a queen and the two bedrooms upstairs have 2...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    This 2 bedroom, 1 bath cottage is part of the Wellfleeter Condominium complex located at the end of Mayo Beach on Wellfleet Bay. The cottage has a kitchen-dining area, a living room, two bedrooms one with a double bed and the other with 2 twin beds and a bath with a shower only. There is a path...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Porch
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    Walk to town from this quiet, newly renovated home just one street away from Main St. The first floor has a large living room, den with cable TV & DVD player. Yes, the house has WIFI . The newly renovated bathroom has a shower with shelves of towels for the home & for the beach. Right outside the...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    The quintessential Cape experience - cedar cottage nestled in the woods on a quiet road in 'Deck 2' with wood fireplace, vaulted ceilings, and 2 decks. 5 minutes to the beach or town; easy to get to but hard to leave! he cottage is thoughtfully-architected with vaulted ceilings, efficient layout,...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    This three bedroom, two bath light and bright contemporary Cape features a cathedral ceiling and great location close to Wellfleet Village Center. There are two bedrooms on the first floor, each with two twin sized beds, and a third bedroom on the second floor featuring a queen sized bed. The...
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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 7 Quick View
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    This 3 bedroom 2 bath contemporary Cape-style home was built in 2004 and is located on a knoll in a small residential neighborhood on the ocean side of Route 6, between Gross Hill Road and Gull Pond Road. The interior is bright and open and there is a front porch as well as a deck off the dining...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Sauna
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    Immerse yourself in the natural beauty of Massachusetts when you stay at this 4-bedroom, 3-bath vacation rental house which sleeps 8 to 10 in Wellfleet. Nestled at the dead end of a road on 2 secluded acres, this charming bungalow offers plenty of features - including several windows, wraparound...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    This salt box style home is in a quiet neighborhood within walking distance to Dyer Pond and a short drive to the ocean, Wellfleet Center and bay beaches. The large deck provides space to lounge outside and the home offers two newly renovated bathrooms (2012) and new windows throughout (2012). The...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 minute walk from Wellfleet Harbor & Blackfish Creek Centrally located, restored Captain's house / farmhouse on secluded Wellfleet 4 acre lot! 5 bedrooms, 2 1/2 baths, screened-in porch, and outdoor shower. Large terraced garden and patio, very private. Within minutes to ocean beaches, ponds and...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 5
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    This 1950's one level ranch with a separate cottage is located in the Pleasant Point/ Paine Hollow area of Wellfleet in a private wooded setting adjacent to 'Fox Island Conservation' area. Surrounded by 40+ acres of conservation land, it's perfect for a writer, or someone who wants to relax and...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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, 3 Bathrooms, Sleeps 7
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    This 3 bedroom, 2 bath house is located in a quiet, residential neighborhood on the bayside of Wellfleet about 1.2 miles to Burton Baker Beach and about 1.4 miles to Indian Neck Beach. This property offers great natural light and has an open concept with a great back deck. Walk into the living...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    This 3 bedroom, 1 bath cottage is part of a group of cottages,The Wellfleeter Condominiums,located at the end of Mayo Beach on Wellfleet Bay. It has a kitchen with a dishwasher,a dining area, a living room, 3 bedrooms, one with a queen and the other two with 2 twin beds in each. The bathroom has...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Smoking allowed
    About this property
    This contemporary cape style home is a lovely vacation rental. With lots of room inside and out, this is a great home for any group of friends or a family vacation. The main floor is spacious and comfortably furnished with ample sitting room for all. The open floor plan is great for preparing and...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    This is a charmingly rustic two bedroom cottage, a favorite due to its quiet location nestled amongst pines and oaks in the back of this spacious compound. It is also one of the larger cottages, second in space only to the main cabin roadside. It has a fully equipped (new in 2015) eat-in kitchen,...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    This lovely and bright 3 bedroom home has a spacious family room and study. It’s equipped with a Steinway grand piano, a ping-pong table, an enclosed outdoor shower and an excellent kitchen. The property features three bedrooms, two with a queen sized bed and one with two twin sized beds, as well...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Smoking allowed
    About this property
    This is a 3 bedroom, 2 bath contemporary house with cathedral ceilings built in 1970 and renovated in 1990. It is filled with light from the cathedral ceilings, many windows and sliding glass doors that lead to decks that encircled the house. There are two bedrooms on the main floor, one with a...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    This is a 1970's 2 bedroom,1 bath ranch-style cottage overlooking Long Pond. There is a small deck and nice yard with a sandy beach directly in front of the cottage. There are two bedrooms, one with a queen bed and the other with 2 twin beds and 1 cot as well as a bath with tub and shower. The...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Retreat to this 1300 square foot, 4 bedroom, 1.5 bath traditional Cape Cod summer cottage offering you an escape and a chance to truly unplug this summer. Sit by a private kettle pond in a blissfully serene setting surrounded by the Cape Cod National Seashore Park. Take a walk through the woods to...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    Located in a peaceful neighborhood, this comfy home offers peace and quiet with easy convenience to the best of Wellfleet. Just a mile and a half from town center, restaurants and shops are easy to get to and popular Mayo Beach is a short trip away. The house has 3 bedrooms and 2 and a half...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Smoking allowed
    About this property
    241 Main Street (ID #134371) ~ Wellfleet Village Three Bedroom Greek Revival Enjoy the in-town location of this beautifully, and meticulously renovated 1826, Greek Revival, antique home. Easy access to the restaurants, galleries, library, Preservation Hall, farmers Market, pier, Mayo Beach and...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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