Menemsha Pond Rentals
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 $614 per night (USD)Expedia
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)Expedia
From $416 per night (USD)VRBO
Classic Cape home with full kitchen, W\/D, firepit & gas grill - walk to beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Whistling Hill House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $416 per night (USD)VRBO
From $576 per night (USD)Expedia
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)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 $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
From $536 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 $536 per night (USD)VRBO
From $1481 per night (USD)Expedia
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)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 $614 per night (USD)Expedia
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)Expedia
From $746 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 $746 per night (USD)VRBO
From $394 per night (USD)Expedia
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)Expedia
From $862 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 $862 per night (USD)VRBO
From $301 per night (USD)Expedia
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)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
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 $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 $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 $968 per night (USD)Expedia
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)Expedia
From $688 per night (USD)VRBO
Gorgeous Home in Aquinnah, Walk to the Beach, AIR CONDITIONING
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Unwind at this beautiful custom built home. Located in one of Martha's Vineyard's most peaceful and scenic areas, its j ...
From $688 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
From $1400 per night (USD)Expedia
Aquinnah Skye Ln:Private Custom Post & Beam,Walk to Beach,Water View,Central A\/C
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
***Please note: we prefer and give preference to multi-week rentals. However, sometimes single weeks become available, s ...
From $1400 per night (USD)Expedia
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 $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 $830 per night (USD)Expedia
Water-view home with large deck, balcony, enclosed sunroom & peaceful location
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Lobsterville Landing Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $830 per night (USD)Expedia
From $602 per night (USD)VRBO
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)VRBO
From $270 per night (USD)Expedia
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)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
From $1518 per night (USD)Expedia
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)Expedia
From $4074 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 $4074 per night (USD)VRBO
Click For PricingExpedia
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 PricingExpedia
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 $401 per night (USD)Expedia
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)Expedia
From $862 per night (USD)VRBO
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)VRBO
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 $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 $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