Karen M. Overtoom Logo
Your connection to all Martha's Vineyard Real Estate and Vacation Rentals
508-693-7832
Karen M. Overtoom Logo
508-693-7832

West Tisbury Vacation Oasis

"Idyllic Island Setting!"

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Welcome to Fleetwood Farm — a modern barn set into ancient farmland, down a quiet lane and surrounded by a permanently protected landscape of rolling fields and old stone walls. You’re a short drive from the beaches and harbors, with fresh seafood in Menemsha and produce from several farms nearby. Designed for gathering, the house brings together beautiful light, open spaces, and sweeping views of field, pond, and sky. THE SPACE The house balances historic Island charm with modern comfort, with a strong sense of place through thoughtful materials and local art. The layout has an easy flow between indoor and outdoor living. Adjacent to generous living and dining areas, the chef's kitchen is set up for effortless cooking and entertaining. Outside on the back deck is an outdoor kitchen, complete with a gas grill and sink, dining table with bench seating, as well as a firepit for enjoying nights under the stars. Two ground-floor bedrooms with queen beds share a spacious bathroom with double sinks, heated floors, and zellige-tile shower. A powder room is just off the front entrance. The master suite has the top floor to itself — nestled high into the trees with cathedral ceilings, open beams, and an en-suite bathroom with rain shower and heated porcelain floors. Exposed on three sides, the airy lower level has a more casual flair than the rest of the house. The walkout basement is its own space: a private "in-law suite" with a separate entrance. It's great for kids and teens, movie nights, or mixing drinks at the bar, providing flexibility and privacy for groups who appreciate some separation. The light-filled bedroom with two twin beds is adjacent to a TV lounge with a kitchenette/wet bar, as well as a spacious bathroom with large vanity, heated floors, and tub/shower combo. This is a space for quality time — cooking together, playing games, relaxing in the hammock, stargazing by the fire, or stepping out for activities in town. Guests are minutes from several walking trails, art galleries, 7a Cafe, Alley's Store, the Yoga Barn, as well as the island’s farmers market and artisan fair via Music Street. 10 minute drive to Lamberts Cove Beach 15 minute drive to Mememsha Beach GUEST ACCESS Guests have exclusive access to the entire main house. The large front/back yard is also yours to enjoy during your stay. Please note, while the field is accessible to guests, it is shared in a trust between neighbors. The pond is not accessible to guests -- no swimming, boating, or fishing are permitted. No parties or large gatherings Each approved guest over the maximum number of guests (8 max) will incur a $100 per night (per person) fee. For an additional fee the housekeepers can come more frequently. Cost depends on your needs. Designed for families and friends seeking a quiet, natural setting, this home is fully equipped to ensure your island getaway is both memorable and deeply restful.


Rental Overview:

  • Price Range:$8,000 - $12,000
  • Minimum Days Renting: 7
  • Security Deposit: $1,000.
  • Cleaning Fees: $450.
  • Check In: 4:00PM
  • Check Out: 10:00 AM
  • Property ID: WT141

Notice: Rates and availability are subject to change without notice until confirmed. State and local taxes apply.

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JUNE 2026
S M T W T F S Cost
 
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Call
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        Call
               
JULY 2026
S M T W T F S Cost
     
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$7,200.
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$7,200.
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$7,200.
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$7,200.
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  $7,200.
               
AUGUST 2026
S M T W T F S Cost
           
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$7,200.
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$8,500.
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$8,500.
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$8,500.
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$7,000.
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          $6,500.
SEPTEMBER 2026
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$6,500.
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$6,500.
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$5,600.
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$5,600.
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      $5,600.
               



Make a Reservation Request:








Rental Overview:


  • Location West Tisbury
  • Number of bedrooms 4
  • Number of bathrooms 3 plus half bath
  • Accommodates 8
  • Turnover Day TBD
  • Distance To Beach 5 miles
  • House Style Contemporary
  • Parking Yes
  • Square Footage
  • Property Size 3 acres
  • Pets No
  • Ferry Tickets No
  • Water View Peak of Pond
  • Waterfront No
  • General Amenities:


  • Air Conditioning Mini splits throughout
  • Ceiling Fans No
  • Fans
  • Iron & Board Yes
  • Phone Landline
  • Sofa Bed
  • Vacuum Yes
  • Washer Yes
  • Dryer Yes
  • Heating Yes
  • Outdoor Amenities:


  • Grill Gas grill yes
  • Deck Yes
  • Patio
  • Screened Porch
  • Outdoor Furniture Yes
  • Pool
  • Tennis
  • Dock
  • Beach Access Public
  • Beach Chairs Yes
  • Grassy Yard Yes
  • Outdoor Shower Yes
  • Bedrooms - Floor Level:


  • Bedroom 1 Queen, second floor
  • Bedroom 2 Queen, first floor
  • Bedroom 3 Queen, first floor
  • Bedroom 4 Twins, basement
  • Bath Configurations:


  • Full Bath Shower, first floor
  • Full Bath Shower, second floor
  • Full Bath Bath and shower, basement
  • Half Bath Yes, first floor
  • Bedroom Linens:


  • Sheets TBD
  • Bath Towels TBD
  • Beach Towels TBD
  • Kitchen Amenities:


  • Dinner Seating 8+
  • Dishwasher Yes
  • Stove Gas
  • Microwave Yes
  • Coffee Maker Yes
  • Toaster Yes
  • Blender Yes
  • Food Processor
  • Lobster Pot Yes
  • Pots & Pans Yes
  • Bakeware Yes
  • Dishes Yes
  • Entertainment/Technology:


  • Internet/WiFi Yes
  • Cable/Satellite
  • Television Yes
  • DVD Player
  • Stereo
  • Board Games
  • Yard Games