Chilmark, Massachusetts Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Chilmark, Massachusetts on RentalSaver.com!

Chilmark Rentals

From $1388 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 $1388 per night (USD)
VRBO
From $1285 per night (USD)
Expedia
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 $1285 per night (USD)
Expedia
$Cozy efficiency apartment\/heated pool$
From $423 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 $423 per night (USD)
VRBO
From $1294 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 $1294 per night (USD)
Expedia
From $614 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 $614 per night (USD)
VRBO
$Secluded mid-century home with wraparound deck, yard, grill, partial AC, & W\/D$
From $447 per night (USD)
Expedia
Secluded mid-century home with wraparound deck, yard, grill, partial AC, & W\/D
Bedrooms:
2
Bathrooms:
5
Sleeps:
8
Chilmark Beauty Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $447 per night (USD)
Expedia
From $576 per night (USD)
VRBO
Peaceful Chilmark Farmhouse by Menemsha Beach
Bedrooms:
3
Bathrooms:
6
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 $576 per night (USD)
VRBO
From $5697 per night (USD)
Expedia
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)
Expedia
From $3112 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 $3112 per night (USD)
VRBO
From $536 per night (USD)
Expedia
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 $536 per night (USD)
Expedia
From $695 per night (USD)
VRBO
Peaceful Scenic Up-Island Retreat With Private Martha's Vineyard Beach
Bedrooms:
2
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 $695 per night (USD)
VRBO
From $803 per night (USD)
Expedia
Newly Renovated Charming Guest House in Chilmark with WiFi, AC, Covered Porch
Bedrooms:
2
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 ...
From $803 per night (USD)
Expedia
$Glamorous Chilmark Home w\/ Ocean Views & Pool, Brand new deck, Refurbished bthrm$
From $1481 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 $1481 per night (USD)
VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
From $447 per night (USD)
VRBO
Charming Rustic Cottage
Bedrooms:
2
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
$Vintage 1920s House W\/Beach Path & Glorious Sunset Water Views$
From $1141 per night (USD)
Expedia
Vintage 1920s House W\/Beach Path & Glorious Sunset Water Views
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
*** Please make an inquiry before booking. *** This quintessential Up-Island 1920s summer house has panoramic water sun ...
From $1141 per night (USD)
Expedia
From $3197 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 $3197 per night (USD)
VRBO
From $5645 per night (USD)
Expedia
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 $5645 per night (USD)
Expedia
From $394 per night (USD)
VRBO
Secluded house in the woods with deck, streamside firepit, Vincent Beach nearby
Bedrooms:
2
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 $394 per night (USD)
VRBO
From $298 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 $298 per night (USD)
Expedia
From $734 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 $734 per night (USD)
VRBO
$Spectacular Oceanfront, 4 BR\/4 bath, Hottub, Private Beach, Tennis, AC, WiFi$
From $7372 per night (USD)
Expedia
Spectacular Oceanfront, 4 BR\/4 bath, Hottub, Private Beach, Tennis, AC, WiFi
Bedrooms:
6
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)
Expedia
$Private Oceanfront Compound, 1\/3 mi Private Beach, AC, Chilmark, WiFi$
From $8414 per night (USD)
VRBO
Private Oceanfront Compound, 1\/3 mi Private Beach, AC, Chilmark, WiFi
Bedrooms:
5
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 $8414 per night (USD)
VRBO
$Two Separate 3 Bed \/ 3 Bath Offerings - Private Beach in Chilmark, WiFi, AC$
From $3928 per night (USD)
Expedia
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)
Expedia
From $624 per night (USD)
VRBO
Chilmark Vista and Lucy Vincent Beach
Bedrooms:
3
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 $1285 per night (USD)
Expedia
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)
Expedia
From $1034 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 $1034 per night (USD)
VRBO
From $1416 per night (USD)
Expedia
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 $1416 per night (USD)
Expedia
From $643 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 $643 per night (USD)
VRBO
From $862 per night (USD)
Expedia
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 $862 per night (USD)
Expedia
From $301 per night (USD)
VRBO
Menemsha Village - Davis Cottage - last minute July Opening
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 $301 per night (USD)
VRBO
$Striking 5BR\/4BA Chilmark Contemporary with Views of the Sound$
From $946 per night (USD)
Expedia
Striking 5BR\/4BA Chilmark Contemporary with Views of the Sound
Bedrooms:
4
Bathrooms:
6
Sleeps:
14
Come enjoy the secluded beauty of this award-winning, architect-designed home in Chimark on almost four acres of land. R ...
From $946 per night (USD)
Expedia
$House in Chilmark\/Menemsha, Martha's Vineyard w\/ Private Beach, Sunset View.$
From $614 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 $614 per night (USD)
VRBO
From $746 per night (USD)
Expedia
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 $746 per night (USD)
Expedia
From $1508 per night (USD)
VRBO
Gracious Landmark Home ~ Fabulous Water Views ~ 2 Private Beaches
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Sunrises, sunsets and all-day sunlight grace this welcoming, elegant and beautifully-kept hilltop home. Its glorious wr ...
From $1508 per night (USD)
VRBO
From $458 per night (USD)
Expedia
Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches!
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Superb fields-to-ocean-to-islands views from this charming guesthouse, on a historic Chilmark property. You'll enjoy a ...
From $458 per night (USD)
Expedia
$Quintessential 4 BR Cape in wooded Chilmark location - Pet Friendly \n$
From $614 per night (USD)
VRBO
Quintessential 4 BR Cape in wooded Chilmark location - Pet Friendly \n
Bedrooms:
3
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 $614 per night (USD)
VRBO
From $480 per night (USD)
Expedia
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)
Expedia
From $1266 per night (USD)
VRBO
Charming Chilmark beach house with private Abel's Hill beach access
Bedrooms:
4
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 $1266 per night (USD)
VRBO
$\Over South\, Family farm house in Chilmark$
From $519 per night (USD)
Expedia
\"Over South\", Family farm house in Chilmark
Bedrooms:
3
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 $519 per night (USD)
Expedia
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
$Cool, Mid-Century House -- Lucy Vincent Beach and Pool!!!\n$
From $1131 per night (USD)
Expedia
Cool, Mid-Century House -- Lucy Vincent Beach and Pool!!!\n
Bedrooms:
4
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 $1131 per night (USD)
Expedia
From $968 per night (USD)
VRBO
Spectacular Newly Renovated Home in Menemsha
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
This spectacular newly renovated home in Menemsha on Martha's Vineyard, was originally designed by a Frank Lloyd Wright ...
From $968 per night (USD)
VRBO
From $820 per night (USD)
Expedia
Tucked Away on Tea Lane, Chilmark
Bedrooms:
3
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 $820 per night (USD)
Expedia
$Best deal in Chilmark\/May 15-Nov. 15$
From $596 per night (USD)
VRBO
Best deal in Chilmark\/May 15-Nov. 15
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
"Chilmark is quiet, laid back and much less congested than down-island counterparts. If you want to spread out and relax ...
From $596 per night (USD)
VRBO
From $1903 per night (USD)
Expedia
Light Open Vacation Home, Sweeping Waterviews, Hill Top, Private
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Spectacular light large home with beautiful water views towards the Vineyard Sound and Naushon Island. The light open ki ...
From $1903 per night (USD)
Expedia
From $1113 per night (USD)
VRBO
Private Hillside Home with Open Property and a Fully Equipped Kitchen
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 $1113 per night (USD)
VRBO
From $602 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 $602 per night (USD)
Expedia
From $408 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 $408 per night (USD)
VRBO
From $3431 per night (USD)
VRBO
Cozy Sanctuary with Water Views
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Welcome to your Martha's Vineyard getaway, where every room boasts breathtaking views of lush meadows gently rolling int ...
From $3431 per night (USD)
VRBO
From $270 per night (USD)
VRBO
Charming 3-bedroom water view home, Path to Menemsha Beach Passes to Lucy
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to this charming Waterview farmhouse in Chilmark Marthas Vineyard. This phenomenal property boasts 3 bedrooms - ...
From $270 per night (USD)
VRBO
From $750 per night (USD)
Expedia
Walk to private beach from beautiful Abels Hill house
Bedrooms:
4
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 $750 per night (USD)
Expedia
From $954 per night (USD)
VRBO
Spectacular Chilmark Sunset Water Views, Walk to Private Beach, Trails, Tennis!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
*** We have transferrable car ferry reservations ⛴ for guests who would like to book for summer 2025 🏖. Just reach out ...
From $954 per night (USD)
VRBO
From $2777 per night (USD)
Expedia
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 $2777 per night (USD)
Expedia
From $1518 per night (USD)
VRBO
Walk to Beach, Kayak from Backyard Dock, Ocean & Squibnocket Pond Views
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Enjoy spectacular panoramic views of the ocean, dunes, beach and Squibnocket Pond. Perfect for a family that is lookin ...
From $1518 per night (USD)
VRBO
From $782 per night (USD)
Expedia
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)
Expedia
Click For Pricing
VRBO
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 Pricing
VRBO
From $4074 per night (USD)
Expedia
CHILMARK WATERFRONT WITH PRIVATE DOCK
Bedrooms:
4
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)
Expedia
From $1040 per night (USD)
VRBO
Chilmark Farmhouse and Barn
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Enjoy lazy summer days at this restored 19th century farmhouse and barn. Steps to Gray Barn and the Yoga Barn, and a s ...
From $1040 per night (USD)
VRBO
From $737 per night (USD)
Expedia
Chilmark spacious garden farmhouse 4 bedroom
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Lush relaxing garden setting in a private Chilmark neighborhood association with access to Chilmark's private beaches. ...
From $737 per night (USD)
Expedia
$Beautiful dog-friendly home with water view, balcony & washer\/dryer$
From $653 per night (USD)
VRBO
Beautiful dog-friendly home with water view, balcony & washer\/dryer
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
Lady Slipper Hill Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $653 per night (USD)
VRBO
Click For Pricing
Expedia
Peaceful House on Menemsha Hill - 2 min from beach!
Bedrooms:
3
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 ...
Click For Pricing
Expedia
Click For Pricing
VRBO
Private Hilltop Chilmark Estate with private tennis court, gym and hot tub
Bedrooms:
4
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 Pricing
VRBO
From $915 per night (USD)
Expedia
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 $915 per night (USD)
Expedia
$Chilmark pond side cottage with beach access, sweeping views\n$
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 $862 per night (USD)
Expedia
Menemsha Pond waterfront Available July 21 till 10 August, June,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 $862 per night (USD)
Expedia
From $401 per night (USD)
VRBO
In Menemsha Village - Sunset House
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 $401 per night (USD)
VRBO
$Oceanfront Home & Guest House w\/ Private Beach!$
From $13484 per night (USD)
Expedia
Oceanfront Home & Guest House w\/ Private Beach!
Bedrooms:
5
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 $13484 per night (USD)
Expedia
From $499 per night (USD)
VRBO
Charming Chilmark Cottage With Big Atlantic View; Private Pond And Beach
Bedrooms:
2
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 $499 per night (USD)
VRBO
From $22400 per night (USD)
Expedia
60 Acres of Oceanfront Property with Private Beach!
Bedrooms:
4
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 $22400 per night (USD)
Expedia
From $8417 per night (USD)
VRBO
Private Home in Gated Community with Private Beach!
Bedrooms:
4
Bathrooms:
4
Sleeps:
3
*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 $8417 per night (USD)
VRBO
From $1257 per night (USD)
Expedia
Classic, upscale Chilmark farmhouse and PRIVATE BEACH KEY
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
One of Chilmark's most stately and classic Captains House, THE BLUE BARQUE has been thoughtfully and fashionably edited ...
From $1257 per night (USD)
Expedia
From $1223 per night (USD)
VRBO
Lovely Chilmark home on Abel's Hill with private beach, pond, tennis, and trails
Bedrooms:
4
Bathrooms:
5
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 $1223 per night (USD)
VRBO
From $391 per night (USD)
Expedia
Menemsha Harborside Cottage.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Cancellation: A FULL refund will be given if we are able to re-rent the week cancelled. Menemsha cottage adjacent to Me ...
From $391 per night (USD)
Expedia
From $1103 per night (USD)
VRBO
Classic Modern House on its Own Point of Land with Astounding Views
Bedrooms:
3
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 $1103 per night (USD)
VRBO
From $20106 per night (USD)
VRBO
Paradise in Chilmark, Very Private Modern Home with Heated Pool & Ocean Views
Bedrooms:
6
Bathrooms:
4
Sleeps:
8
Welcome to your summer sanctuary in Chilmark! Nestled on the serene shores of Martha's Vineyard, this newly constructed, ...
From $20106 per night (USD)
VRBO
From $4851 per night (USD)
VRBO
Stunning private family home - spectacular sunsets
Bedrooms:
7
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 $4851 per night (USD)
VRBO
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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 ...
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Expedia
From $1221 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 $1221 per night (USD)
VRBO
From $1053 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 $1053 per night (USD)
Expedia
From $391 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 $391 per night (USD)
VRBO
From $2106 per night (USD)
Expedia
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 $2106 per night (USD)
Expedia
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Expedia
PRIME FERRY TICKETS AVAILABLE! CHARMING MUSIC ST HOME WITH PRIVATE BEACH ACCESS!
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Sunny and bright location on Music Street in the heart of the village of West Tisbury. Renovated in 2016 with new applia ...
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Expedia
From $1117 per night (USD)
Expedia
2 House Compound Surrounding in-Ground Pool
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Delightful rustic intergenerational or multi-family compound with large pool. Main house has upstairs master BR with ki ...
From $1117 per night (USD)
Expedia
$Cozy & serene custom home. Private ocean beach\/pond access, 3 kayaks. FERRY RES.$
From $551 per night (USD)
VRBO
Cozy & serene custom home. Private ocean beach\/pond access, 3 kayaks. FERRY RES.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcoming Hillside Cottage is a delightfully comfortable, custom-built, 3 bedroom family home in a quiet, private, count ...
From $551 per night (USD)
VRBO
From $1636 per night (USD)
Expedia
New Waterfront Modern Farmhouse on Tisbury Great Pond
Bedrooms:
5
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 $1636 per night (USD)
Expedia
From $479 per night (USD)
VRBO
Martha's Vineyard Cozy Getaway Near Picturesque Philbin Beach
Bedrooms:
2
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 $479 per night (USD)
VRBO
From $958 per night (USD)
Expedia
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)
Expedia
From $460 per night (USD)
VRBO
Vineyard Hearth - Where Coastal Calm Meets Countryside Comfort.
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Welcome to Vineyard Hearth—a charming 3-bedroom, 2 bathroom retreat nestled in the pastoral heart of Martha’s Vineyard. ...
From $460 per night (USD)
VRBO
From $447 per night (USD)
Expedia
Tranquility and Beauty inside and out.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Gorgeous!! Great Location!! Recently renovated with beautiful maple floors, cherry cabinetry and granite counter tops ...
From $447 per night (USD)
Expedia
From $981 per night (USD)
VRBO
Historic Captains House - Newly Renovated Primary Bathroom and Upgraded Kitchen
Bedrooms:
4
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 $981 per night (USD)
VRBO
$KEY TO BEST PRIVATE BEACH! \nBeautiful 6-br home, sleeps 10 on Tisbury Great Pond$
From $1029 per night (USD)
Expedia
KEY TO BEST PRIVATE BEACH! \nBeautiful 6-br home, sleeps 10 on Tisbury Great Pond
Bedrooms:
5
Bathrooms:
6
Sleeps:
8
This home is old Vineyard at its best. Step back in time to this 6-acre 6 bedroom antique home, in a conservation-like ...
From $1029 per night (USD)
Expedia
From $490 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 $490 per night (USD)
VRBO
Click For Pricing
Expedia
Family home in West Tisbury
Bedrooms:
3
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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Expedia
From $2186 per night (USD)
VRBO
Oceanfront Estate with Panoramic Views, Private Beach, House + Guest House
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Secluded beachfront estate perched on a bluff with unsurpassed panoramic views of Vineyard Sound and the Elizabeth Islan ...
From $2186 per night (USD)
VRBO
From $1225 per night (USD)
Expedia
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 $1225 per night (USD)
Expedia
From $633 per night (USD)
VRBO
Charming Whaling Captain's Farmhouse with modern updates in West Tisbury
Bedrooms:
3
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 $633 per night (USD)
VRBO
From $559 per night (USD)
Expedia
Cozy 3BR Cottage with Lambert's Cove Beach access
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Nestled in the woods right in front of Grey Barn, this charming 3-bedroom cottage is the perfect retreat. With plenty of ...
From $559 per night (USD)
Expedia
From $1426 per night (USD)
VRBO
Beautiful Aquinnah Home: Ocean View, Walk to Beach
Bedrooms:
3
Bathrooms:
6
Sleeps:
9
Martha's Vineyard: where days are best spent exploring nature, showering outdoors, and admiring ocean vistas. Here, you' ...
From $1426 per night (USD)
VRBO
From $1159 per night (USD)
Expedia
Cozy Family Home Centrally Located in West Tisbury
Bedrooms:
3
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 $1159 per night (USD)
Expedia

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Results: 101 Rentals