Chilmark 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 $691 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 $691 per night (USD)VRBO
From $1172 per night (USD)VRBO
Classic, upscale Chilmark farmhouse and PRIVATE BEACH KEY
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
One of Chilmark's most stately and classic Captains House, THE BLUE BARQUE has been thoughtfully and fashionably edited ...
From $1172 per night (USD)VRBO
From $1163 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 $1163 per night (USD)VRBO
From $1057 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 $1057 per night (USD)VRBO
From $852 per night (USD)VRBO
Cool, Mid-Century House -- Lucy Vincent Beach and Pool!!!\n
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Think resort-type elegance in a relaxed beach house vibe. 4BR, 3 bath, outdoor shower, 4-ft deep spa pool. Lots of light ...
From $852 per night (USD)VRBO
From $644 per night (USD)Expedia
Historic Captains House - Newly Renovated Primary Bathroom and Upgraded Kitchen
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Beautiful restored 130 year old Sea Captain's House on historic Music Street in the heart of West Tisbury. The home was ...
From $644 per night (USD)Expedia
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 $760 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 $760 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 $958 per night (USD)VRBO
Walk to Beach Beautiful Ocean Views
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 14
Private setting on 5 acres, wonderful for family retreats, weddings. Natural fabrics and wood floors, can have cook and ...
From $958 per night (USD)VRBO
From $869 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 $869 per night (USD)VRBO
From $439 per night (USD)VRBO
Tranquility and Beauty inside and out.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Gorgeous!! Great Location!! Recently renovated with beautiful maple floors, cherry cabinetry and granite counter tops ...
From $439 per night (USD)VRBO
From $754 per night (USD)VRBO
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 $754 per night (USD)VRBO
From $621 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 $621 per night (USD)VRBO
From $590 per night (USD)VRBO
July Special. $2,800/week, Flexible Dates. Extra night for free. (July 12-26 )
- 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 $590 per night (USD)VRBO
From $1914 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 $1914 per night (USD)VRBO
From $598 per night (USD)VRBO
Vineyard Hearth - Where Coastal Calm Meets Countryside Comfort.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Vineyard Hearth—a charming 3-bedroom, 2 bathroom retreat nestled in the pastoral heart of Martha’s Vineyard. ...
From $598 per night (USD)VRBO
From $1285 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 $1285 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 $391 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 $391 per night (USD)VRBO
From $636 per night (USD)VRBO
Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
The Eliot Noyes Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $636 per night (USD)VRBO
From $568 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 $568 per night (USD)VRBO
From $945 per night (USD)VRBO
Mid-Century Modern - All Glass House - Designed By Frank Lloyd Wright Apprentice
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Mid-Century modern glass house, in Menemsha, on Marthas Vineyard. Designed by a Frank Lloyd Wright apprentice, this all ...
From $945 per night (USD)VRBO
From $327 per night (USD)VRBO
Menemsha Harbor - 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 $327 per night (USD)VRBO
From $408 per night (USD)VRBO
Tilton House - Menemsha Harborside
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Menemsha cottage adjacent to Menemsha Harbor in the Town of Chilmark. Historic village cottage for four people. 100 f ...
From $408 per night (USD)VRBO
From $793 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 $793 per night (USD)VRBO
From $626 per night (USD)VRBO
House in Chilmark/Menemsha, Martha's Vineyard w/ Private Beach, Sunset View.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Best view of sunset on island. Fully equipped modern house; air conditioning, large deck, barbecue, outdoor shower, line ...
From $626 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 $383 per night (USD)VRBO
Private cottage nestled in center of the Vineyard
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Vincent Cottage is nestled in the woods of West Tisbury, set in the heart of Martha's Vineyard on a private drive just o ...
From $383 per night (USD)VRBO
From $829 per night (USD)VRBO
5BR in West Tisbury village with private beach access
- Bedrooms:
- 1
- Bathrooms:
- 5
- Sleeps:
- 9
Spacious house in heart of historic West Tisbury, under 5 minutes walk from: Library, playground, Alley's, 7a, Grange Ha ...
From $829 per night (USD)VRBO
From $1085 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 $1085 per night (USD)VRBO
From $1362 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 $1362 per night (USD)VRBO
From $1082 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 $1082 per night (USD)VRBO
From $463 per night (USD)Expedia
Martha's Vineyard Cozy Getaway Near Picturesque Philbin Beach
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
This rental is a 3 bedroom, 2 full bath house with a deck, where you can enjoy the fresh island air. A porch swing on t ...
From $463 per night (USD)Expedia
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 $1600 per night (USD)VRBO
New Waterfront Modern Farmhouse on Tisbury Great Pond
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
We have been visiting Martha's Vineyard for over 20 years and instantly fell in love with its rural unspoiled beauty and ...
From $1600 per night (USD)VRBO
From $403 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 $403 per night (USD)VRBO
From $7372 per night (USD)VRBO
Spectacular Oceanfront, 4 BR/4 bath, Hottub, Private Beach, Tennis, AC, WiFi
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
One of the most spectacular oceanfront rentals available on the exclusive Island of Marthas Vineyard. This unique reside ...
From $7372 per night (USD)VRBO
From $956 per night (USD)VRBO
Secluded retreat in Seven Gates Farm on 7 Acres, Private Beach, Tennis, Pond
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 16
Hickory Hollow located in Seven Gates Farm is a charming and tranquil setting within a 1600 acre association on West Tis ...
From $956 per night (USD)VRBO
From $1005 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 $1005 per night (USD)Expedia
From $624 per night (USD)VRBO
Chilmark Vista and Lucy Vincent Beach
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 9
Enter our vacation world up a 0.2 mile paved driveway through the woods to the private hilltop with only two other house ...
From $624 per night (USD)VRBO
From $431 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 $431 per night (USD)VRBO
From $2043 per night (USD)VRBO
Spacious Country Home centrally located on the island of Martha's Vineyard.
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 20
Don't miss out on the very best downtown West Tisbury has to offer! A Vineyard location that can't be beat. A charming u ...
From $2043 per night (USD)VRBO
From $7576 per night (USD)VRBO
Private Oceanfront Compound, 1/3 mi Private Beach, AC, Chilmark, WiFi
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
This private Chilmark compound has breathtaking views out to the Atlantic Ocean and 1/3 mile of private beach in your ba ...
From $7576 per night (USD)VRBO
From $3928 per night (USD)VRBO
Two Separate 3 Bed / 3 Bath Offerings - Private Beach in Chilmark, WiFi, AC
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Two rental opportunities are being offered within this one listing: The Upper House & Studio Apartment The Lower House & ...
From $3928 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
Click For PricingVRBO
Private Hilltop Chilmark Estate with private tennis court, gym and hot tub
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Private 8 acre estate with new hot tub and tennis court. Enjoy your walks through 56 acres of preservation land and the ...
Click For PricingVRBO
From $292 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 $292 per night (USD)Expedia
From $330 per night (USD)VRBO
Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl2 EV charger.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Petite Guest house is private with its own driveway, yard, and easy walk to Menemsha Pond. Amazing location; walk to Men ...
From $330 per night (USD)VRBO
From $625 per night (USD)Expedia
Secluded mid-century home with wraparound deck, yard, grill, partial AC, & W/D
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Chilmark Beauty Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $625 per night (USD)Expedia
From $622 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 $622 per night (USD)VRBO
From $622 per night (USD)VRBO
Chilmark pond side cottage with beach access, sweeping views\n
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Everyday is a beach day! A magical beach retreat cottage at the water's edge, nicknamed Gadget. Wades Cove at Chilmark ...
From $622 per night (USD)VRBO
From $573 per night (USD)VRBO
Peaceful Chilmark Farmhouse by Menemsha Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Experience Martha's Vineyard 'up-island' at this tucked-away 4-bedroom, 3-bath gem in Chilmark. Situated just a short wa ...
From $573 per night (USD)VRBO
From $5922 per night (USD)VRBO
Modern Luxury Waterview Home, Private Beach Access, 4 BR, 3 bath
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
*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 $5922 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 $2346 per night (USD)VRBO
PRIVATE CHILMARK HOME, 5BR,5 bath, 2 outdoor showers, AC
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
*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 $2346 per night (USD)VRBO
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Peaceful House on Menemsha Hill - 2 min from beach!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
A brand new listing! You are very welcome to this peaceful, quiet and private house in Menemsha village, just minutes fr ...
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From $409 per night (USD)VRBO
Menemsha Village - Recent opening 7/24-7/31. Discounted to: 2500 + fees + taxes
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
You can enjoy the Menemsha Sunsets from your own private deck. This summer cottage was converted from an early fishing ...
From $409 per night (USD)VRBO
From $447 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 $447 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 $503 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 $503 per night (USD)VRBO
From $1041 per night (USD)VRBO
Great two house compound, inground pool, and free ferry tickets
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Delightful rustic intergenerational or multi-family compound with large pool. Main house has upstairs master BR with ki ...
From $1041 per night (USD)VRBO
Click For PricingVRBO
Beautiful dog-friendly home with water view, balcony & washer/dryer
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Lady Slipper Hill Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
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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 $535 per night (USD)VRBO
Charming Chilmark Cottage With Big Atlantic View; Private Pond And Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This secluded Chilmark cottage, beautifully landscaped, sits on a high point off of Meeting House Road with a sweeping v ...
From $535 per night (USD)VRBO
From $1642 per night (USD)VRBO
60 Acres Oceanfront 5-BR, Private Beach! AC, WiFi, TV
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
This one of a kind property boasts 60 acres directly on the South Shore of Martha's Vineyard with direct access to over ...
From $1642 per night (USD)VRBO
From $859 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 $859 per night (USD)VRBO
From $552 per night (USD)Expedia
Private Hillside Home, Fully Equipped Kitchen, Dog-Friendly, A/C, W/D
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Hillside Oak Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $552 per night (USD)Expedia
Click For PricingVRBO
Family home in West Tisbury
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Main floor living space is wide open. Perfect for families. Hickory hardwood floors throughout. Tons of windows to let i ...
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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 $1191 per night (USD)VRBO
Oceanfront Estate with Panoramic Views, Private Beach, House + Guest House
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Secluded beachfront estate perched on a bluff with unsurpassed panoramic views of Vineyard Sound and the Elizabeth Islan ...
From $1191 per night (USD)VRBO
From $3267 per night (USD)VRBO
Private Sanctuary in Chilmark
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 7
This beautiful and special Chilmark home offers lovely and open interior spaces as well as several outside living spaces ...
From $3267 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 $388 per night (USD)Expedia
Water-view home in great location with spacious backyard, grill, kayaks, dogs OK
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Wayside Camp Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $388 per night (USD)Expedia
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 $4771 per night (USD)VRBO
Stunning private family home - spectacular sunsets
- Bedrooms:
- 6
- Bathrooms:
- 8
- Sleeps:
- 16
Our family home is a 4-acre waterfront paradise with wonderful sunsets. The private location sits between a large wooded ...
From $4771 per night (USD)VRBO
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Beautiful Chilmark - Blueberry Ridge - August!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This property is available August 5-19, 2023. Located just off North Road in Chilmark, this Blueberry Ridge guest house ...
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From $1136 per night (USD)Expedia
Spacious and gracious architect designed home on 3 acres off Middle Road.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Our home is off Middle Road in Chilmark. It features a chef's kitchen with convectionoven, screen porch, roof deck, out ...
From $1136 per night (USD)Expedia
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
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House in the woods in Chiomark
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
3 bedroom, 3 bath house on 11 acres in Chilmark outdoor grill, dining. large open space large living room, dining room.s ...
Click For PricingExpedia
From $931 per night (USD)VRBO
Cozy Family Home Centrally Located in West Tisbury
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Escape to your perfect Martha's Vineyard getaway at this beautifully renovated family home in West Tisbury. With four be ...
From $931 per night (USD)VRBO
From $824 per night (USD)VRBO
Beautiful Aquinnah Home: Ocean View, Walk to Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Martha's Vineyard: where days are best spent exploring nature, showering outdoors, and admiring ocean vistas. Here, you' ...
From $824 per night (USD)VRBO
From $331 per night (USD)VRBO
Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Chilmark Guest House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $331 per night (USD)VRBO
From $1181 per night (USD)VRBO
Newly Renovated Charming West Tisbury Retreat
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
Beautiful new renovation! Centrally located near Alley's General Store and the West Tisbury Library, enjoy easy access ...
From $1181 per night (USD)VRBO
From $510 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 $510 per night (USD)VRBO
From $726 per night (USD)Expedia
The Field House - Peaceful Martha’s Vineyard Escape with Serene Field Views
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
Welcome to The Field House — a beautifully designed modern home overlooking a serene island pasture, where open-concept ...
From $726 per night (USD)Expedia
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 $748 per night (USD)VRBO
Walk to private beach from beautiful Abels Hill house
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
The house is a large family house in the Abels Hill community of Chilmark. The community shares use of a private south s ...
From $748 per night (USD)VRBO
From $1153 per night (USD)VRBO
Historic 4-bedroom Farmhouse on Martha's Vineyard
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Centrally located in West Tisbury, this 1743 family farmhouse offers all you will need for the quintessential Vineyard V ...
From $1153 per night (USD)VRBO
From $442 per night (USD)VRBO
Bright Summer Cottage in lovely West Tisbury with Beach Pass, AC, WiFi
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This lovely Summer Cottage in West Tisbury is the perfect retreat for guests looking to relax and unwind. Close to beach ...
From $442 per night (USD)VRBO
From $802 per night (USD)VRBO
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 ...
From $802 per night (USD)VRBO
From $773 per night (USD)VRBO
Charming Whaling Captain's Farmhouse with modern updates in West Tisbury
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
**As you can see, we currently have no reviews since this is our first year renting our farm that has been in the family ...
From $773 per night (USD)VRBO
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Charming 3-bedroom water view home, Path to Menemsha Beach Passes to Lucy
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to this charming Waterview farmhouse in Chilmark Marthas Vineyard. This phenomenal property boasts 3 bedrooms - ...
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From $1294 per night (USD)VRBO
Glamorous Chilmark Home w/ Ocean Views & Pool, Brand new deck, Refurbished bthrm
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 11
About this space Make great summer memories in this charming and spacious farmhouse. Watch the sunset over the Vineyard ...
From $1294 per night (USD)VRBO
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Newly Renovated Charming Guest House in Chilmark with WiFi, AC, Covered Porch
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This newly renovated one bedroom guest house with open-style living is the perfect Chilmark get away for a couple with o ...
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From $543 per night (USD)VRBO
Orginal 1710 Farmhouse Seeks Artist, Writer, Composer or Musician
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
1710 Farmhouse In Chilmark Convenient North Road location - close to Menemsha Beach, Chilmark Store and picturesque hiki ...
From $543 per night (USD)VRBO
From $493 per night (USD)VRBO
Aquinnah cottage private,serene, easy beach access ,sleeps 4
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Aquinnah cottage on a private road with a short drive to the amazing beaches Aquinnah is famous for. Updated, bright ,cl ...
From $493 per night (USD)VRBO
From $2364 per night (USD)VRBO
Chilmark Luxury | Quansoo Beach Access-4BR
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Discover privacy and coastal charm at this exceptional 7.25-acre rental in Chilmark. Enjoy exclusive access to Quansoo B ...
From $2364 per night (USD)VRBO