Nashaquitsa Pond Rentals
From $1956 per night (USD)VRBO
Gracious Landmark Home ~ Fabulous Water Views ~ 2 Private Beaches
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Sunrises, sunsets and all-day sunlight grace this welcoming, elegant and beautifully-kept hilltop home. Its glorious wr ...
From $1956 per night (USD)VRBO
From $629 per night (USD)VRBO
Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Superb fields-to-ocean-to-islands views from this charming guesthouse, on a historic Chilmark property. You'll enjoy a ...
From $629 per night (USD)VRBO
From $480 per night (USD)VRBO
Pet-Friendly Historic Chilmark Cottage
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Renovated historic barn (1870). Lofts converted to open bedrooms, private main bedroom, roomy living room/dining/kitchen ...
From $480 per night (USD)VRBO
From $497 per night (USD)VRBO
\"Over South\", Family farm house in Chilmark
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Situated on the quiet end of the Island, yet only a 20 minute drive from Vineyard Haven, this rustic, authentic Chilmark ...
From $497 per night (USD)VRBO
From $1089 per night (USD)VRBO
Classic Modern House on its Own Point of Land with Astounding Views
- Bedrooms:
- 1
- Bathrooms:
- 5
- Sleeps:
- 11
Designed by a student of the famous architect Walter Gropius, our house was built in 1949. The house is open and light, ...
From $1089 per night (USD)VRBO
From $909 per night (USD)VRBO
Quintessential Chilmark Retreat - Marthas Vineyard
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Everything you think of when you dream of Chilmark... pastural rolling 2+ acres with water views and stone walls. Ideal ...
From $909 per night (USD)VRBO
From $474 per night (USD)VRBO
Cozy efficiency apartment/heated pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Small, but cozy bedroom with smart TV, kitchenette with microwave, refrigerator, toaster oven and Keurig coffee maker. ...
From $474 per night (USD)VRBO
From $1142 per night (USD)VRBO
Menemsha Pond waterfront Available July 21 till 1 August, Sept ,Oct 2025
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
DEEP FALL DISCOUNT SEPT/OCT Pond front cottage and attached Silo house, 4-5 bedrooms on large acreage fronting Menems ...
From $1142 per night (USD)VRBO
From $5697 per night (USD)VRBO
Amazing Water Views in Chilmark, 4-BR, Waterfront, Key to Zak’s Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
*PLEASE NOTE: THE PRICES YOU CURRENTLY SEE ON THE WEBSITE ARE THE PRICES FOR 7 NIGHTS OR MORE THAN 7 NIGHT STAYS. FOR AN ...
From $5697 per night (USD)VRBO
From $523 per night (USD)Expedia
Serene September! Cozy custom home. Private beach&pond access + use of 3 kayaks.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcoming Hillside Cottage is a delightfully comfortable, custom-built, 3 bedroom family home in a quiet, private, count ...
From $523 per night (USD)Expedia
From $9610 per night (USD)VRBO
Oceanfront Home & Guest House w/ Private Beach!
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 11
*PLEASE NOTE: THE PRICES YOU CURRENTLY SEE ON THE WEBSITE ARE THE PRICES FOR 7 NIGHTS OR MORE THAN 7 NIGHT STAYS. FOR AN ...
From $9610 per night (USD)VRBO
From $2695 per night (USD)VRBO
Stunning Oceanfront Home in Chilmark. 2 minutes to the beach.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
*PLEASE NOTE: THE PRICES YOU CURRENTLY SEE ON THE WEBSITE ARE THE PRICES FOR 7 NIGHTS OR MORE THAN 7 NIGHT STAYS. FOR AN ...
From $2695 per night (USD)VRBO
From $1072 per night (USD)VRBO
Walk to Beach, Kayak from Backyard Dock, Ocean & Squibnocket Pond Views
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
*Transferrable Ferry Tickets - Depart Woods Hole on July 19 and return on July 26* Enjoy spectacular panoramic views of ...
From $1072 per night (USD)VRBO
From $4074 per night (USD)VRBO
CHILMARK WATERFRONT WITH PRIVATE DOCK
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Chilmark waterfront rental home with a dock located on Quitsa Pond with views across Quitsa and Menemsha ponds out to th ...
From $4074 per night (USD)VRBO
From $782 per night (USD)VRBO
Pet-Friendly Historic Chilmark House
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Renovated historic house (1870). Large living room/dining area. 4 bedrooms sleep 8 plus sofa sleepers. 3 full bathrooms. ...
From $782 per night (USD)VRBO
From $482 per night (USD)VRBO
Quaint & Quiet Quitsa: 3-bedroom house with WiFi, AC in peaceful Chilmark
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Make yourself at home in this brilliant 3-bedroom retreat. Nestled on Quitsa Pond, in walking distance of Squibnocket Be ...
From $482 per night (USD)VRBO
From $2030 per night (USD)VRBO
Waterfront, 4-bed/4-bath Contemporary on Menemsha Pond with Private Beach & A/C
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Headline: Waterfront, 4-bedroom/4-bath Contemporary on Menemsha Pond with Private Beach & A/C This New to the M ...
From $2030 per night (USD)VRBO