Welcome Home

Bildad’s Roost is a home away from home, and the quality of your experience is the most important thing. With a 25-year rental history with many returning families and couples, you’re invited to make your own memories with family and friends this summer at Bildad’s Roost.

Explore the Home

Request a

Please fill out the request form and click on the week(s) you are interested in on the calendar below. Please note one-week minimum, Saturday to Saturday preferred. Thank you.

Please note all bookings are subject to:

  • Commonwealth of Massachusetts & Town of West Tisbury Short-Term Rental Tax: 11.7%
  • Cleaning Fee: $350 per week
  • Refundable Security Deposit: $1,500 or 10% of total rental rate on multiple weeks.
  • Check-In at 3:00 PM, Check-Out at 10:00 AM.





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- Available
- Reserved
- Arrival / Departure

Seasonal Rates

Jun 1 – 5: $4000 per week
Jun 6 – 12: $4500 per week
Jun 13 – 26: $5000 per week
Jun 27 – Jul 3: $7500 per week

Jul 4 – Aug 28: $8850 per week
Aug 29 – Sep 4: $6000 per week
Sep 5 – 18: $5000 per week
Sep 19 – Nov 30: $4000 per week

All the Amenities of Home

Bildad’s Roost has four-zone air conditioning, includes sheets, bath and beach towels, workout and yoga gear, croquet and bocce sets, games and puzzles, and more – nearly everything for a perfect vacation.

Peace & Privacy

Lower Deck

A favorite spot at Bildad’s Roost, the lower deck is the perfect spot to sunbathe, read a book, eat al fresco, and create vacation memories. All while enjoying ocean views and warm Vineyard breezes.

Explore The Lower Deck

Upper Deck

Live like a king or queen atop the upper deck. With a teak table and chairs, this is a prime place for morning coffee and evening drinks.

Explore The Upper Deck


Surrounded by the natural beauty of Upper Makonikey on Martha’s Vineyard’s north shore, the 5-acre grounds of Bildad’s Roost promise peace and privacy. Open fields, mature trees, ancient stone walls, and views of the Vineyard Sound ensure exclusivity.

Explore The Grounds

Your Private Beaches Await

One of the best things about Upper Makonikey’s beaches is privacy. Two secluded beach shores offer all the recreation or relaxation you desire.

Upper Beach is a sight to see. With a gorgeous ocean vista greeting you upon arrival, the view only gets better. Meander the steps through the beach plums and flowers, and the shoreline reveals itself in grand splendor. And come back after dinner for one of the best sunset spots on Martha’s Vineyard.

View this beach

Lower Beach provides a simpler and more casual excursion. Walk straight onto the beach, pitch your towels, cooler, and umbrella, and swim or stroll along the shoreline. This is the perfect spot for a relaxing beach day with the family, young and old. And in the garage for your convenience, you’ll find beach chairs, boogie boards, pool noodles, an umbrella, and all the gear you’ll need to make amazing sandcastles.

View this beach