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Wellfleet Luxury Holiday Homes

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    Travellers to Wellfleet are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    20 Matching Rentals in WellfleetView all 136 rentals
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    Carpe Diem 4-bedrooms, ocean views1 / 23
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
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    • Grill
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    150 Compass Hill Road (ID #137929) ~ Beautiful Tidal And Island Views You will want to hurry home each evening to catch the sunset over Cape Cod Bay, Wellfleet Bay, Loagy Bay and Lieutenant Island from this newly renovated home just steps from the shoreline. Enjoy drinks and dinner from the...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Grill
    • Ocean Views
    • DVD Player
    • Wi-Fi
    • Waterfront
    • Cable/satellite TV
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Recently renovated kitchen, with all new appliances, and amenities. Located right on the Harbor in Wellfleet, this property has superb waterviews, and large decks for entertaining. It's a short walk to town across Uncle Tim's Bridge. There is a private Beach on the property. Pets are welcome....
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Patio
    • DVD Player
    • Washer
    • Grill
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    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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 8
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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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    30 Gulch Rd. 1276211 / 12
    (2)Excellent
    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Washer
    • Patio
    • Grill
    • DVD Player
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    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 August 2018
    An easy walk to Gull Pond as well as Newcomb Hollow Beach. This house is great for a group -- two bedrooms have private bathrooms, the modern open design flows easily to an...
    Reviewed 4 July 2017
    3 households (my sons + wives) and my husband + myself just returned from a family location at this venue. Perfect in every way. Modernized kitchen and bathrooms, patios or...
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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, 1 Bathroom, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Central Heating
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 2 bedroom, 1 bath home has an open floor plan with rustic cathedral ceilings. Cable TV and unlimited Wi-Fi Internet access along with central air-conditioning will keep you and your family comfortable. There is a patio outdoors with a table and chairs and a gas grill as well as an outdoor...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Washer
    • Air Conditioning
    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    4 BR | 3.5 BA | Sleeps 8 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...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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, 3 Bathrooms, Sleeps 12
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    Waterfront on private bayside beach1 / 30
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Central Heating
    • Outdoor Dining Area
    • Parking
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 June 2014
    Early September in Wellfleet at this cottage was spectacular. Quiet yet social at the B&B on same premises if we felt like it. Clean, bright, small kitchen but stocked with...
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    About this property
    Our cottage was new in 2013 and shares the gardens and beach with our B&B,Aunt Sukies B&B. We live at the B&B,have 2 guest rooms,adults only, and have been in operation for 24 summers. The Cottage is surrounded by flower gardens, water views and the wonderful private beach,fun at low tide for...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Lieutenant Island Panoramic Water Views1 / 23
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Balcony
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    • Terrace
    • Air Conditioning
    • Ocean Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 August 2018
    Great views, loved the out door shower. Beds comfortable , new washer and dryer . Quiet area, it was fun being on the island . You need to plan ahead for food and drinks...
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    About this property
    Sweeping panoramic views on Lieutenant Island, a very special spot in Wellfleet. Lieutenant Island is accessed by following a wooden bridge over to the island and then dirt roads lead you through the wooded landscape to the very tip ending at 'Lands End', this beautiful waterfront home that sleeps...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • DVD Player
    • Parking
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    360 Eastwind Circle (119173) ~ Bayside ~ Wellfleet Four Bedroom Home SUNDAY to SUNDAY RENTAL Bayside Four bedroom central a/c home. Two full bathrooms. Nicely decorated and well maintained home in South Wellfleet. Bright Open floor concept, living room kitchen, dining area. Great wrap around...
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    Wellfleet, Cape Cod 02420
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Sauna
    • Wi-Fi
    • Washer
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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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    Sea Breeze Cottage at Surf Side  Walk to ocean beach in National Seashore1 / 18
    (5)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • DVD Player
    • Grill
    • Internet Access
    • Porch
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 May 2015
    Everything you could need in a rental, this little cottage has.The screened in porch with cheery white wicker is idyllic.The kitchen and bathroom shiny and so clean. The...
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    Sea Breeze is a 3 bedroom, 1 bath cottage that is 360 steps from the top of the sand dune that leads down to the Cape Cod National Seashore beach at LeCount Hollow in South Wellfleet. It has one queen size bed in each of two bedrooms and two twin beds in the third bedroom. There is one bathroom...
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    Wellfleet, Cape Cod 02663
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Wellfleet Waterfront 5 Bedroom Vacation Home1 / 17
    (6)Very good
    5 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Grill
    • Washer
    • Parking
    • Waterfront
    • DVD Player
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 October 2017
    Great view , great for families. everything you need in the kitchen- steve was great to respond to any issues we had.
    Reviewed 25 July 2014
    I rented here to have a place where several score members of my family could have meals and participate in our croquet game (trophy to the winners), as well as house my children...
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    About this property
    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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    Stunning and peaceful, paradise found!1 / 23
    (5)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Internet Access
    • Grill
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Washer
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 8 Quick View
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    • DVD Player
    • Balcony
    • Washer
    • Parking
    • Cable/satellite TV
    • Patio
    • Internet Access
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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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    Location Information
    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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    • Cable/satellite TV
    • Parking
    • Private Garden
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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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    Location Information
    Wellfleet, Cape Cod 02667
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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