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Wellfleet Luxury Holiday Rentals

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    Travellers to Wellfleet are booking September dates now. Secure your holiday rental today, and have the perfect trip.
    21 Matching Rentals in WellfleetView all 144 rentals
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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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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    Carpe Diem 4-bedrooms, ocean views1 / 23
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    This 4 bedroom cottage sleeps 8 with two bedrooms upstairs and two on the main floor. It is located on a quiet street that dead-ends into the dunes of the beach in the Cape Cod National Seashore. There is a second floor deck over the entrance way with is a great place to do morning yoga or to enjoy...
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    Wellfleet, Cape Cod 02663
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 1 Bathroom, Sleeps 10 Quick View
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    21 Arthur Cashin Way, LT Island (ID#127763) - Lt. Island 4 Bedroom Cottage With Water Views 2018- Available July 28 - Aug. 1st. Four nights at $500 per night. Enjoy this quintessential beach house beautifully located on Lt. Island. Perched on top of a high dune you will have beautiful water views...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, 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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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    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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    30 Gulch Rd. 1276211 / 12
    (1)Excellent
    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    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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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    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, 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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    5 Bedrooms, 5 Bathrooms, 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, 5 Bathrooms, Sleeps 10
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    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    55 Pole Dike Road (ID #137632) ~ Well Appointed & Cozy With Central A/C ~ Wellfleet Village Area Two master bedroom suites within walking distance to Wellfleet Village and with CENTRAL A/C! The house concept features a first floor open-living plan with high ceilings and spaciousness, grounded by...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    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
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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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    Wellfleet Waterfront 5 Bedroom Vacation Home1 / 17
    (6)Very good
    5 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
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    • Waterfront
    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 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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    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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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
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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 8 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
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    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, 4 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    Pet friendly
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    Smoking allowed
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    Set within the trees and surrounded by the neighborhood wildlife, this charming 4 bedroom, 3.5 bath home has everything one would need for the perfect Cape Cod vacation, including stunning sunset views across the Wellfleet Bay and a gorgeous stretch of private beach that is just a minute walk from...
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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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    • DVD Player
    • Balcony
    • Washer
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    • 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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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Waterfront on private bayside beach1 / 60
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Central Heating
    • Outdoor Dining Area
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    • Grill
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    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 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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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    30 Captain Bellamy Road (ID#134336) - Central AC - Marconi Beach Area - Bike Trail Airy, bright, 3-bedroom family house with CENTRAL A/C and EVERYTHING YOU NEED in coveted Wellfleet location near Cape Cod Rail Trail. Walk or bike 1.5 miles to Cape Cod National Seashore. Luxuriously furnished with...
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    Wellfleet, Cape Cod 02667
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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