Chilmark Rentals
From $420 per night (USD)VRBO
Bright and cozy menemsha cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
The Little House was built in 1960 as a one room studio/cabin. Since then a gourmet kitchen wing has been added, as well ...
From $420 per night (USD)VRBO
From $1170 per night (USD)Expedia
Waterfront, Privacy and Tranquility on Tisbury Great Pond
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This gorgeous new home sits on farmland at the edge of Tisbury Great Pond. Enjoy a peaceful, rural feel with the comfort ...
From $1170 per night (USD)Expedia
From $1054 per night (USD)VRBO
Post and Beam home with westward views of the ocean and sunsets
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to the barn! This beloved home started as a post and beam barn built in 1983. 10 years later it was expanded; on ...
From $1054 per night (USD)VRBO
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Peaceful Scenic Up-Island Retreat With Private Martha's Vineyard Beach
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Simpler, secluded living, just 5 minutes walk through woods to a gorgeous private beach, where stairs lead down from a s ...
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From $597 per night (USD)VRBO
Beautiful Chilmark beach house. Great screen porch. Fun house. Pet friendly.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Wonderful screen porch overlooking gorgeous setting. Right off South Road, a few minutes to fishing village of Menemsha ...
From $597 per night (USD)VRBO
From $398 per night (USD)Expedia
Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Chilmark Guest House The Space: Tucked away in a private glen on three secluded acres, this light-filled h ...
From $398 per night (USD)Expedia
From $1268 per night (USD)VRBO
Private Hillside Home, Fully Equipped Kitchen, Dog-Friendly, A/C, W/D
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Hillside Oak The Space: Nestled in the serene scrub oak forest of Chilmark, this stunning 4-bedroom home o ...
From $1268 per night (USD)VRBO
From $1727 per night (USD)Expedia
Amazing sunsets, a welcoming home, and island adventures. Lifetime memories!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Gracefully situated atop the hills of Spring Point in Chilmark, our 4 BR (sleeps 8-10) home features panoramic water vi ...
From $1727 per night (USD)Expedia
From $15547 per night (USD)VRBO
Oceanfront Home w Private Beach!
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 10
This spacious main house and guest house sit on the south shore of Chilmark, with an expansive yard and private stairs d ...
From $15547 per night (USD)VRBO
From $1225 per night (USD)VRBO
5-bedroom, 3-bath house on 5 Acres in Chilmark
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Located just a 5 minute walk from Chilmark's famous North Tabor Farm, this charming house is a dream for families or gro ...
From $1225 per night (USD)VRBO
From $5656 per night (USD)VRBO
Private beach compound. Please do not book without contacting the host
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 6
Amazing Chilmark summer compound. On the Cliffs! 2 separate houses that can be rented together or separately. Privacy. G ...
From $5656 per night (USD)VRBO
From $1523 per night (USD)VRBO
Chilmark Home, AC, WiFi, Pet friendly, 2 Tennis ct
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to this spacious and inviting Chilmark retreat set on three private acres in the desirable Prospect Hill communi ...
From $1523 per night (USD)VRBO
From $2803 per night (USD)VRBO
Private Chilmark Estate on 3 Acres, Beach Access
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to 15 Old Farm Road, a private and beautifully designed Chilmark retreat set on over three acres of landscaped g ...
From $2803 per night (USD)VRBO
From $3766 per night (USD)VRBO
Chilmark Estate with Pool & Beach Access
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Discover a truly unique retreat just off the main road, yet worlds away. Nestled on a tranquil 22-acre estate in Chilmar ...
From $3766 per night (USD)VRBO
From $1001 per night (USD)VRBO
Beautiful house on Chilmark Pond with water view, pool & access to private beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful, open modern house set in four acres overlooking Chilmark Pond with access to private beach by boat across the ...
From $1001 per night (USD)VRBO
From $1285 per night (USD)VRBO
3 Bedroom House with Guest Cottage on 3 Acres off Middle Road
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Well located off beloved Middle Road, property embodies all of the natural beauty of Chilmark: old stone walls, perenni ...
From $1285 per night (USD)VRBO
From $470 per night (USD)VRBO
Charming Rustic Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Charming rustic cottage located a short distance off South Rd just past Abels Hill in Chilmark. Chilmark is very rual w ...
From $470 per night (USD)VRBO
From $572 per night (USD)VRBO
Vintage 1920s House W/Beach Path & Glorious Sunset Water Views
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
*** Please make an inquiry before booking. *** This quintessential Up-Island 1920s summer house has panoramic water sun ...
From $572 per night (USD)VRBO
From $362 per night (USD)VRBO
Light and airy modern holiday cottage with access to private beach
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful, open holiday cottage that offers a secluded and affordable base for a wonderful Martha's Vineyard holiday. De ...
From $362 per night (USD)VRBO
From $552 per night (USD)Expedia
Menemsha Pond views & access! Mid-century renovated beach house. Dogs welcome.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Japanese inspired, Mid-Century Modern beach house with sweeping views of Menemsha pond, Vineyard sound, Aquinnah. Pond a ...
From $552 per night (USD)Expedia
From $470 per night (USD)VRBO
Unwind in Guest House overlooking Menemsha Pond. Dogs ok+ Lv-2 EV charger.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Petite Mid-century, renovated guest house is private with own driveway, yard, and easy walk to Menemsha Pond, harbor, pu ...
From $470 per night (USD)VRBO
From $1315 per night (USD)VRBO
Luminous rural retreat with spectacular ocean views.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Tucked into the woods, this elegant house offers a panoramic view of the full sweep of the Vineyard Sound from Woods Ho ...
From $1315 per night (USD)VRBO
From $548 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 $548 per night (USD)VRBO
From $808 per night (USD)VRBO
Charming Chilmark beach house with private Abel's Hill beach access
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Lovely house at the top of Abel's Hill with access to private Abels' Hill Beach a half mile away. The house is wonderful ...
From $808 per night (USD)VRBO
From $995 per night (USD)VRBO
Spectacular Newly Renovated Home in Menemsha
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
This spectacular newly renovated home in Menemsha on Martha's Vineyard, was originally designed by a Frank Lloyd Wright ...
From $995 per night (USD)VRBO
From $652 per night (USD)Expedia
Menemsha Home Fully Renovated w/ Amazing Waterview's of Vineyard Sound
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
The "Grapevine" is located on a private road in Menemsha, It was completely rebuilt not to long ago. originally it was ...
From $652 per night (USD)Expedia
From $693 per night (USD)VRBO
Tucked Away on Tea Lane, Chilmark
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
A hidden gem tucked in the woods of the desirable Tea Lane neighborhood. A freshly painted interior, brand new second fl ...
From $693 per night (USD)VRBO
From $638 per night (USD)VRBO
Best Deal in Chilmark Spring Fling: Book May or June for 10% off. 4-day minimum.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
"Chilmark is quiet, laid back and much less congested than down-island counterparts. If you want to spread out and relax ...
From $638 per night (USD)VRBO
From $2023 per night (USD)VRBO
Light Open Vacation Home, Sweeping Waterviews, Hill Top, Private
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Spectacular light large home with beautiful water views towards the Vineyard Sound and Naushon Island. The light open ki ...
From $2023 per night (USD)VRBO
From $2898 per night (USD)VRBO
10 minutes walk to Lucy Vincent Beach
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Location! Location! Location! Charming, and nestled away, this must see post and beam home is situated on the edge of t ...
From $2898 per night (USD)VRBO
From $856 per night (USD)VRBO
Gracious Prestige Landmark ~ 2 Private Beaches ~ Fabulous View
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
A storied property in Chilmark for almost 150 years, the hilltop Tower House combines current taste, comfort and eleganc ...
From $856 per night (USD)VRBO
From $551 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 $551 per night (USD)VRBO
From $829 per night (USD)VRBO
Open July 20-27th w/RT Ferry! 4 BR Cape in Chilmark - Pet Friendly
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
A recently renovated country home located in the Vineyard's most idyllic town of Chilmark, close to the West Tisbury lin ...
From $829 per night (USD)VRBO
From $383 per night (USD)VRBO
Secluded house in the woods with deck, streamside firepit, Vincent Beach nearby
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Relax at this retreat in the woods when you are not spending time on Lucy Vincent Beach or enjoying the sunset down the ...
From $383 per night (USD)VRBO
From $470 per night (USD)VRBO
Peaceful Wooded Retreat, Short Car Ride to Everything. Week is Friday to Friday
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Comfortable home, providing wonderfully peaceful and refreshing quiet, set on a white oak wooded lot, with 2 fireplaces ...
From $470 per night (USD)VRBO
From $1016 per night (USD)VRBO
Mid-Century Modern - All Glass House - Designed By Frank Lloyd Wright Apprentice
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Mid-Century modern glass house, in Menemsha, on Marthas Vineyard. Designed by a Frank Lloyd Wright apprentice, this all ...
From $1016 per night (USD)VRBO
From $427 per night (USD)VRBO
Menemsha - Davis House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in Menemsha Village. This quaint cottage is located a stones throw from the Menemsha Harbor. It is the smallest ...
From $427 per night (USD)VRBO
From $936 per night (USD)VRBO
Striking 5BR/4BA Chilmark Contemporary with Views of the Sound
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
Come enjoy the secluded beauty of this award-winning, architect-designed home in Chimark on almost four acres of land. R ...
From $936 per night (USD)VRBO
From $1949 per night (USD)VRBO
House in Chilmark/Menemsha, Martha's Vineyard w/ Private Beach, Sunset View.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Best view of sunset on island. Fully equipped modern house; air conditioning, large deck, barbecue, outdoor shower, line ...
From $1949 per night (USD)VRBO
From $942 per night (USD)VRBO
Spectacular Chilmark Sunset Water Views, Walk to Private Beach, Trails, Tennis!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
*** We have transferrable car ferry reservations ⛴ for guests who would like to book for summer 2026 🏖. Just reach out ...
From $942 per night (USD)VRBO
From $1050 per night (USD)VRBO
Walk to Beach, Kayak from Backyard Dock, Ocean & Squibnocket Pond Views
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Round-trip Transferable Ferry Tickets Available for July 4-11 and July 11-18! Perfect for a family or group of friends ...
From $1050 per night (USD)VRBO
From $867 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 $867 per night (USD)VRBO
From $1135 per night (USD)VRBO
Walk to private beach from beautiful Abels Hill house
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 13
The house is a large family house in the Abels Hill community of Chilmark. The community shares use of a private south s ...
From $1135 per night (USD)VRBO
From $4004 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 $4004 per night (USD)VRBO
From $3073 per night (USD)VRBO
Stunning private family home - spectacular sunsets
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Our family home is a 4-acre waterfront paradise with wonderful sunsets. The private location sits between a large wooded ...
From $3073 per night (USD)VRBO
From $774 per night (USD)VRBO
Waterfront cottage a short boat ride to the ocean beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Our waterfront cottage on Chilmark Pond is a short boat ride to a stunning barrier beach on the Atlantic Ocean. There i ...
From $774 per night (USD)VRBO
From $1163 per night (USD)VRBO
Chilmark two bedroom, one bath cottage with waterfront and private beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
A wonderful two bedroom cottage nicknamed The Palace ,and it truly is one! on a private estate with private access to th ...
From $1163 per night (USD)VRBO
From $886 per night (USD)VRBO
Chilmark pond side cottage with beach access, sweeping views
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Everyday is a beach day! A magical beach retreat cottage at the water's edge, nicknamed Gadget. at Wades Cove at lower ...
From $886 per night (USD)VRBO
From $685 per night (USD)VRBO
Classic Vineyard Summer Cottage; Private Waterfront Access; Menemsha Pond Views.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Classic Vineyard summer cottage with private waterfront access to cove on Menemsha Pond on 1.5+/- acres within a few min ...
From $685 per night (USD)VRBO
From $1398 per night (USD)VRBO
Lovely Chilmark home on Abel's Hill with private beach, pond, tennis, and trails
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
A unique opportunity to spend your vacation in peaceful Abel’s Hill in Chilmark. This lovely cottage is located in the h ...
From $1398 per night (USD)VRBO
From $1279 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 $1279 per night (USD)VRBO