Aquinnah Rentals
From $586 per night (USD)VRBO
Magical House in the Trees with Water View - Secluded Area
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Our home is a simple, quaint beach house on a quiet dirt road. We are the first house on the right so no long, bumpy dir ...
From $586 per night (USD)VRBO
From $1220 per night (USD)Expedia
Luxury Home in Exclusive Aquinnah
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Tucked away down a private dirt road, this spacious retreat features 5 bedrooms and 3.5 baths on more than 2 acres. The ...
From $1220 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 $819 per night (USD)Expedia
Modern beach house - Walking distance to Philbin Beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This beach house is a ten minute walk from Philbin Beach, the town beach on the surf side of Aquinnah. It is an “upsi ...
From $819 per night (USD)Expedia
From $1380 per night (USD)VRBO
Ocean Views: Every Room - Walk to Ocean Beach, Dog Friendly \n
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 7
The last week of August is now open after a recent cancellation. Excellent ferry reservations are available. Magnifice ...
From $1380 per night (USD)VRBO
From $551 per night (USD)Expedia
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)Expedia
From $1400 per night (USD)VRBO
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)VRBO
From $706 per night (USD)Expedia
Beautiful home, walk to beach, has AC. Long-term winter rental considered.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This spacious home is located in a private woodland, just a short walk to Lobsterville beach. The house is welcoming, we ...
From $706 per night (USD)Expedia
From $1432 per night (USD)VRBO
Beautiful, Modern Beach Home in Aquinnah With A Spectacular Roof Top Deck.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Three Winds is a modern beach home on Martha's Vineyard available for rent year-round by the week. It is located in Aqui ...
From $1432 per night (USD)VRBO
From $872 per night (USD)Expedia
Beachfront Aquinnah home. Beautiful views!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Location Location: Beachfront home on Lobsterville Beach in Aquinnah, This wonderful beach house is waiting for you! Enj ...
From $872 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 $586 per night (USD)Expedia
Aquinnah condo at cliffs, walk to beach! July prices just reduced!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Walk to the beach! Featuring a wraparound porch, ocean views from every room, outdoor (and indoor) shower, grill, and ...
From $586 per night (USD)Expedia
From $707 per night (USD)VRBO
Water-view Vacation Home in the Heart of Aquinnah
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
A lovely 2,400 square foot, 4 bedroom, 2.5 bath (plus an outdoor shower), located on over 13 private acres of land. The ...
From $707 per night (USD)VRBO
From $533 per night (USD)Expedia
Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Spacious and comfortable beach cottage on 2 secluded acres in prime Aquinnah location, dripping with quintessential MV c ...
From $533 per night (USD)Expedia
From $1380 per night (USD)VRBO
Glorious Water View, private beach
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
This spectacular beach house with stunning water views is located 20 feet from the edge of a grassy cliff overlooking Vi ...
From $1380 per night (USD)VRBO
From $951 per night (USD)Expedia
Aquinnah Beachfront, Perfect Sunsets, Private Beach
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 8
*NOTE* We Just opened the calendar for the month of August! These weeks will go quickly. This is a very rare opportunity ...
From $951 per night (USD)Expedia
From $775 per night (USD)VRBO
As featured in Vineyard Style
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
As featured in the Summer 2023 issue of Vineyard Style Magazine, this house is ideally located in the highlands area of ...
From $775 per night (USD)VRBO
From $702 per night (USD)Expedia
Secluded Waterfront - North Shore - Private Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 5
Charming waterfront cottage on the North Shore of Aquinnah overlooking the Elizabeth Islands with panoramic water views. ...
From $702 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 $989 per night (USD)Expedia
Secluded Waterfront Rental with Private Beach
- Bedrooms:
- 4
- Bathrooms:
- 2
- Sleeps:
- 6
This well-furnished and architecturally unique two-to-three bedroom house is located on 2.5 secluded acres in Aquinnah. ...
From $989 per night (USD)Expedia
From $768 per night (USD)VRBO
New Rates! Ocean Views! Lovely Secluded Home, Short Walk To Spectacular Beach!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Escape to this delightful summer haven just a short walk from Philbin Beach, Martha’s Vineyard's most beautiful. The spe ...
From $768 per night (USD)VRBO
From $688 per night (USD)Expedia
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)Expedia
From $1162 per night (USD)VRBO
Nine Acres Quiet Escape
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Happily isolated from the bustle of Oak Bluffs and Vineyard Haven, this tranquil residence a 15 minute walk from the cli ...
From $1162 per night (USD)VRBO
From $1355 per night (USD)Expedia
Spectacular Ocean View Home w\/ Private Beach & tennis, Dog friendly
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Bring the kids and dogs for a fun relaxing stay in the secluded Aquinnah end of Martha's Vineyard. Our home is rustic an ...
From $1355 per night (USD)Expedia
From $5665 per night (USD)VRBO
Spectacular Site Overlooking Vineyard Sound
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Our Martha’s Vineyard property is a great vacation home to experience the beautiful island setting in the town of Aquinn ...
From $5665 per night (USD)VRBO
From $934 per night (USD)Expedia
Classic Charming and Whimsical Martha’s Vineyard Home, with Private Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Nestled in Aquinnah, not far from the Gay Head lighthouse, this enchanting home in a beautiful pastoral setting with a p ...
From $934 per night (USD)Expedia
From $868 per night (USD)VRBO
Spacious private Aquinnah home, walk to lighthouse and cliff overlook
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Tanager House - This spacious 4-bedroom home is nestled on 3 acres in scenic Aquinnah, offering privacy and tranquility. ...
From $868 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 $933 per night (USD)VRBO
August Ferry Tickets Available for Spacious, Air-Conditioned Home Close to Beach
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
This beautiful three-story house is recently available for rentals again. With room to spread out for up to 10 guests, t ...
From $933 per night (USD)VRBO
From $1426 per night (USD)Expedia
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)Expedia
From $319 per night (USD)VRBO
Up-Island Treehouse with Roofdeck and Waterviews
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 3
Welcome to our getaway. The Up-Island Treehouse offers an open, light-filled and breezy spot on the western tip of Marth ...
From $319 per night (USD)VRBO
From $423 per night (USD)Expedia
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)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
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 $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 $1285 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 $1285 per night (USD)VRBO
From $3112 per night (USD)Expedia
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)Expedia
From $1141 per night (USD)VRBO
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)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 $298 per night (USD)VRBO
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)VRBO
From $734 per night (USD)Expedia
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)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 $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 $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 $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 $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 $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 $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 $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 $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 $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
From $8417 per night (USD)Expedia
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)Expedia
From $391 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 $391 per night (USD)VRBO
From $1103 per night (USD)Expedia
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)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