Chilmark Rentals
- From $1715 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 $1715 per night (USD)VRBO
- From $285 per night (USD)
VRBO
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 $285 per night (USD)VRBO
- From $499 per night (USD)
VRBO
Classic Cape in ideal, Chilmark location, Pet Friendly \n
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
A recently renovated country home located in the Vineyard's most idyllic town. This 4 bedroom/2 full bath home offers ...
From $499 per night (USD)VRBO
- From $807 per night (USD)
VRBO
Classic, upscale Chilmark Farmhouse and private beach
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
One of Chilmark's most stately and classic farmhouses,which has been thoughtfully and fashionably edited and updated wit ...
From $807 per night (USD)VRBO
- From $1400 per night (USD)
VRBO
Lovely Chilmark home on Abel's Hill with private beach, pond, tennis, and trails
- Bedrooms:
- 4
- Bathrooms:
- 3
- 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 $1400 per night (USD)VRBO
- From $1355 per night (USD)
VRBO
Beautiful Aquinnah Retreat
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
MUDDROOM: Large Closet, Air Conditioner, Stocked with Beach towel's. KITCHEN: Granite counter top's, Dishwasher, Gas Vi ...
From $1355 per night (USD)VRBO
- From $900 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 $900 per night (USD)VRBO
- From $1084 per night (USD)
VRBO
Cool, Mid Century House -- Pool, Lots of Light!!
- 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 $1084 per night (USD)VRBO
- From $800 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 $800 per night (USD)VRBO
- From $430 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 $430 per night (USD)VRBO
- From $1000 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 $1000 per night (USD)VRBO
- From $808 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 $808 per night (USD)VRBO
- From $746 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 $746 per night (USD)VRBO
- From $350 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 $350 per night (USD)Expedia
- From $950 per night (USD)
VRBO
Menemsha Home Fully Renovated w\/ Amazing Waterview's of Vineyard Sound
- Bedrooms:
- 4
- 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 a ...
From $950 per night (USD)VRBO
- From $642 per night (USD)
VRBO
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 $642 per night (USD)VRBO
- From $315 per night (USD)
VRBO
Best deal in Chilmark (Open Memorial Day weekend-Nov. 15)
- Bedrooms:
- 3
- 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 $315 per night (USD)VRBO
- From $1600 per night (USD)
VRBO
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 $1600 per night (USD)VRBO
- From $564 per night (USD)
VRBO
Private guesthouse in Peaceful Chilmark Neigborhood
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This guesthouse is a 2 Bedroom private home in peaceful and secluded Chilmark neighborhood. Spacious outdoor space with ...
From $564 per night (USD)VRBO
- From $385 per night (USD)
VRBO
Authentic Martha's Vineyard Neighborhood
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Welcome to your relaxing vacation rental in West Tisbury on the picturesque island of Martha's Vineyard! Our charming an ...
From $385 per night (USD)VRBO
- From $1100 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 $1100 per night (USD)VRBO
- From $950 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 $950 per night (USD)VRBO
- From $622 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 $622 per night (USD)VRBO
- From $957 per night (USD)
Expedia
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 $957 per night (USD)Expedia
- From $514 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 $514 per night (USD)VRBO
- From $633 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 $633 per night (USD)VRBO
- From $214 per night (USD)
VRBO
Menemsha Village - Davis Cottage - SSA boat reserv. available for some weeks.
- 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 $214 per night (USD)VRBO
- From $314 per night (USD)
VRBO
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 $314 per night (USD)VRBO
- From $929 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 $929 per night (USD)VRBO
- From $1214 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 $1214 per night (USD)VRBO
- From $690 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 $690 per night (USD)VRBO
- From $300 per night (USD)
Expedia
Private cottage nestled in center of island, access to Lambert's Cove beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Vincent Cottage is nestled in the woods of West Tisbury, set in the wheart of Martha's Vineyard on a private drive just ...
From $300 per night (USD)Expedia
- From $457 per night (USD)
VRBO
5BR in heart of West Tisbury with private beach access
- Bedrooms:
- 4
- 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 $457 per night (USD)VRBO
- From $1200 per night (USD)
Expedia
Fully Appointed Water View House Ten Minutes Walk from Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This is a year-round home, built around a converted central barn, which now contains the master bedroom and bath upsta ...
From $1200 per night (USD)Expedia
- From $881 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 $881 per night (USD)VRBO
- From $867 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 $867 per night (USD)VRBO
- From $350 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 porch where you can enjoy some fresh island air. There is a porch ...
From $350 per night (USD)VRBO
- Click For Pricing
VRBO
Beautiful Chilmark Farmhouse W\/ Private South Shore Beach and Outdoor Pool
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 10
This one of a kind farmhouse is located in one of the most desirable areas up-island, and offers all the major amenities ...
Click For PricingVRBO
- From $306 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 $306 per night (USD)VRBO
- From $1358 per night (USD)
VRBO
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 $1358 per night (USD)VRBO
- From $600 per night (USD)
VRBO
Airey Two Bedroom Menemsha cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Built as guest house, this 800 square foot cottage has two bedrooms, gourmet kitchen, bright living dining room, and a q ...
From $600 per night (USD)VRBO
- From $7125 per night (USD)
VRBO
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 $7125 per night (USD)VRBO
- Click For Pricing
VRBO
Beautiful Secluded Property with Vineyard Sound Views and Private Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
This property has two houses, a main house and a guest house, on three acres of wooded, secluded land. Both houses have ...
Click For PricingVRBO
- From $1368 per night (USD)
Expedia
Discounted for Fall '23 -- 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 $1368 per night (USD)Expedia
- From $604 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 $604 per night (USD)VRBO
- Click For Pricing
VRBO
Waterfront Compound - Heated Pool, Hot Tub, Tennis Court, Private Beach, 7 BR
- Bedrooms:
- 5
- Bathrooms:
- 7
- 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 ...
Click For PricingVRBO
- Click For Pricing
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 ...
Click For PricingVRBO
- From $1782 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 $1782 per night (USD)Expedia
- From $575 per night (USD)
VRBO
PRIME FERRY TICKETS AVAILABLE! CHARMING MUSIC ST HOME WITH PRIVATE BEACH ACCESS!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Sunny and bright location on Music Street in the heart of the village of West Tisbury. Renovated in 2016 with new applia ...
From $575 per night (USD)VRBO
- From $1620 per night (USD)
VRBO
Peaceful Chilmark Enclave with Abel's Hill Association Beach and Tennis Courts
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Beautiful up-island family home with Abel's Hill beach, Chilmark Pond access, Association tennis courts, and hiking just ...
From $1620 per night (USD)VRBO
- From $7500 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 $7500 per night (USD)VRBO
- From $3952 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 $3952 per night (USD)VRBO
- From $275 per night (USD)
VRBO
Woodsy island home with large deck, open layout, WiFi, kitchen & ideal location
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Chilmark Charm Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $275 per night (USD)VRBO
- From $1201 per night (USD)
VRBO
Menemsha Pond waterfront cottage
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
still Available 4-11 August 2024 Pond front cottage and attached Silo house, 4-5 bedrooms on large acreage fronting M ...
From $1201 per night (USD)VRBO
- 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 PricingVRBO
- From $375 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 $375 per night (USD)Expedia
- From $400 per night (USD)
VRBO
Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl 2 EV charger.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Remaining '24 summer weeks: July 15-21st, or Aug 7-13th. Petite Guest house is private with its own driveway, yard, and ...
From $400 per night (USD)VRBO
- From $571 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 $571 per night (USD)Expedia
- Click For Pricing
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 ...
Click For PricingVRBO
- Click For Pricing
VRBO
Chilmark pondside cottage with private beach, sweeping views
- 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 ...
Click For PricingVRBO
- From $465 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 $465 per night (USD)VRBO
- From $3018 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 $3018 per night (USD)VRBO
- From $3214 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 $3214 per night (USD)VRBO
- From $2095 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 $2095 per night (USD)VRBO
- Click For Pricing
VRBO
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 PricingVRBO
- From $320 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 $320 per night (USD)VRBO
- From $400 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 $400 per night (USD)VRBO
- From $350 per night (USD)
Expedia
1-13 JUNE BARGAIN! Charming custom home—private ocean beach&pond access+kayaks
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcoming Hillside Cottage is a delightful custom-built, 3 bedroom family home in a quiet, private, country setting. Thi ...
From $350 per night (USD)Expedia
- From $500 per night (USD)
VRBO
Vintage 1920s House W\/Beach Path & Glorious Sunset Water Views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
*** Please make an inquiry before booking. *** This quintessential Up-Island 1920s summer house has panoramic water sun ...
From $500 per night (USD)VRBO
- From $1000 per night (USD)
VRBO
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 $1000 per night (USD)VRBO
- From $395 per night (USD)
VRBO
Beautiful dog-friendly home with water view, balcony & washer\/dryer
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Lady Slipper Hill Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $395 per night (USD)VRBO
- From $10000 per night (USD)
VRBO
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 $10000 per night (USD)VRBO
- From $400 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 $400 per night (USD)VRBO
- From $8000 per night (USD)
VRBO
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 $8000 per night (USD)VRBO
- From $3429 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 $3429 per night (USD)VRBO
- From $1071 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 2024 🏖. Just reach o ...
From $1071 per night (USD)VRBO
- From $681 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 $681 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 ...
Click For PricingExpedia
- From $2393 per night (USD)
VRBO
Stunning Oceanfront Home in Chilmark
- 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 $2393 per night (USD)VRBO
- From $1828 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 $1828 per night (USD)VRBO
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VRBO
Tranquil Setting in Chilmark Off South Road
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This house was built & completed in 2023. It offers bright and easy living in Chilmark. The house is located near Grey ...
Click For PricingVRBO
- From $2322 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 $2322 per night (USD)VRBO
- From $1071 per night (USD)
VRBO
Walk to Beach, Kayak from Backyard Dock, Ocean & Squibnocket Pond Views
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
*We secured ferry reservations for you* -June 1 and 8 -July 13 and 20 -August 24 and 31 -August 31 and September 7 Enjo ...
From $1071 per night (USD)VRBO
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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 ...
Click For PricingExpedia
- From $3575 per night (USD)
VRBO
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 $3575 per night (USD)VRBO
- From $3833 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 $3833 per night (USD)VRBO
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VRBO
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 PricingVRBO
- Click For Pricing
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 ...
Click For PricingExpedia
- From $319 per night (USD)
VRBO
Charming cottage in bucolic Chilmark. Minutes to Menemsha harbor.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Charming, pristine cottage. Adjacent to the historic Cape Higgon, one-room schoolhouse, in bucolic, up-island Chilmark. ...
From $319 per night (USD)VRBO
- From $700 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 $700 per night (USD)VRBO
- 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 PricingVRBO
- Click For Pricing
Expedia
Get Cozy in the Ditty Box cottage of Menemsha Inn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Part of Menemsha Inn, Ditty Box is a cozy cottage with an ocean view, one bedroom with a King bed, full bath, full kitch ...
Click For PricingExpedia
- From $1007 per night (USD)
VRBO
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 $1007 per night (USD)VRBO
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Expedia
Mainstay Suite of Menemsha Inn
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Mainstay is a suite located above reception with an amazing view of the properties' rolling hills and oceanfront. There ...
Click For PricingExpedia
- From $6400 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 $6400 per night (USD)VRBO
- From $250 per night (USD)
Expedia
Nestled in the woods w\/ outdoor shower, firepit, streamside trail, Vincent Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Crossroads Salt Box, built in 2020, combines Up Island charm with modern amenities. Explore the woods on our walking ...
From $250 per night (USD)Expedia
- From $400 per night (USD)
VRBO
Waterfront cottage a short wade to ocean beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Our waterfront cottage on Chilmark Pond is a short wade to a stunning barrier beach on the Atlantic Ocean and has a love ...
From $400 per night (USD)VRBO
- From $500 per night (USD)
Expedia
3BR on 4 acres with yard games, private beach access to Black Point Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Vineyard Vacation Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $500 per night (USD)Expedia
- From $938 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 $938 per night (USD)VRBO
- From $2226 per night (USD)
VRBO
Cozy Family Escape with Private Beach Access and Shared Tennis Courts
- Bedrooms:
- 7
- Bathrooms:
- 8
- Sleeps:
- 11
Exclusive Abel's Hill community. Set on 4.6 acres, this beautifully maintained and updated home has been in the same fam ...
From $2226 per night (USD)VRBO