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

Dukes Area Rentals

From $359 per night (USD)
VRBO
Island Inn - Studio Suite- 25F - Dog-friendly - Oak Bluffs, MA
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Your stay in this charming ground-floor, one-bedroom, one-bath unit is made comfortable with all the essential ...
From $359 per night (USD)
VRBO
From $496 per night (USD)
Expedia
Island Inn - Studio Suite - 4B - Dog-friendly - Oak Bluffs, MA
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: This ground floor unit at the Island Inn combines cozy charm with modern convenience, making it a perfect retr ...
From $496 per night (USD)
Expedia
From $676 per night (USD)
VRBO
Island Inn - 2 Bedroom & 2 Bath Townhouse - 48G - Oak Bluffs, MA
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Your stay in this charming second-floor corner two-bedroom, two-bath unit is made comfortable with all the ess ...
From $676 per night (USD)
VRBO
From $400 per night (USD)
Expedia
Island Inn - Residential Suite - 30G - Oak Bluffs, MA
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Summary: Your stay in this charming first-floor corner one-bedroom, half-wall bedroom, one and half-bath unit is made c ...
From $400 per night (USD)
Expedia
From $352 per night (USD)
VRBO
Island Inn - Residential Suite - 37G - Oak Bluffs, MA
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Your stay in this charming first-floor one-bedroom, half-wall bedroom, one and half-bath unit is made comforta ...
From $352 per night (USD)
VRBO
From $685 per night (USD)
Expedia
Island Inn - 2 Bedroom & 2 Bath Townhouse - 50G - Oak Bluffs, MA
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Your stay in this charming second-floor corner two-bedroom, two-bath unit is made comfortable with all the ess ...
From $685 per night (USD)
Expedia
From $355 per night (USD)
VRBO
Island Inn - Queen Studio - 24F - Oak Bluffs, MA
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Your stay in this charming ground-floor, one-bedroom, one-bath unit is made comfortable with all the essential ...
From $355 per night (USD)
VRBO
From $338 per night (USD)
Expedia
Island Inn - King Studio - 27F - Oak Bluffs, MA
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Your stay in this charming ground-floor, one-bedroom, one-bath unit is made comfortable with all the essential ...
From $338 per night (USD)
Expedia
From $407 per night (USD)
VRBO
Island Inn - Studio Suite - 18D - Dog-friendly - Oak Bluffs, MA
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Your stay in this charming first-floor corner two-bedroom, one-bath unit is made comfortable with all the esse ...
From $407 per night (USD)
VRBO
From $347 per night (USD)
Expedia
Island Inn - Studio Suite - 3B - Dog-friendly - Oak Bluffs, MA
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: This cozy and convenient ground-floor rental offers everything you need for a restful and comfortable stay. Th ...
From $347 per night (USD)
Expedia
From $371 per night (USD)
VRBO
Island Inn - Studio Suite - 13D - Dog-friendly - Oak Bluffs, MA
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Step into this inviting suite that offers a perfect blend of comfort and functionality. This unit features two ...
From $371 per night (USD)
VRBO
From $414 per night (USD)
Expedia
Island Inn - Residential Suite - 38G - Oak Bluffs, MA
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Summary: Your stay in this charming first-floor one-bedroom, half-wall bedroom, one and half-bath unit is made comforta ...
From $414 per night (USD)
Expedia
From $559 per night (USD)
VRBO
Island Inn - 2 Bedroom & 1.5 Bath Townhouse - 43G - Dog-friendly - Oak Bluffs, MA
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: Your stay in this charming second-floor corner two-bedroom, one and half-bath unit is made comfortable with al ...
From $559 per night (USD)
VRBO
From $949 per night (USD)
Expedia
Island Inn - Cottage - 21E - Oak Bluffs, MA
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Your stay in this charming first-floor corner two-bedroom, each with a Queen Bed, an additional full Sofa-bed ...
From $949 per night (USD)
Expedia
From $679 per night (USD)
VRBO
Island Inn - 2 Bedroom & 2 Bath Townhouse - 47G - Oak Bluffs, MA
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Your stay in this charming second-floor, two-bedroom, two-bath unit is made comfortable with all the essential ...
From $679 per night (USD)
VRBO
From $349 per night (USD)
Expedia
Island Inn - Studio Suite - 17D - Oak Bluffs, MA
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: This unit offers a bright, airy retreat with spacious interiors featuring two comfortable beds adorned with cr ...
From $349 per night (USD)
Expedia
From $677 per night (USD)
VRBO
Quiet Getaway Within Walking Distance Of All Oak Bluffs Has To Offer.
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
An enchanting Cape Cod cottage nestled on a quiet road with Farm Pond and ocean views. Share family dinners and conversa ...
From $677 per night (USD)
VRBO
From $569 per night (USD)
Expedia
Island Inn - Residential Suite - 31G - Dog-friendly - Oak Bluffs, MA
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Summary: Your stay in this charming first-floor one-bedroom, half-wall bedroom, one and half-bath unit is made comforta ...
From $569 per night (USD)
Expedia
From $1171 per night (USD)
VRBO
Beloved 5-bedroom house with Beach Passes, AC, fenced in yard, and hot tub
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
This 5-bedroom house in West Tisbury by is perfect for your escape to relaxation. Enjoy the convenience of a pet and chi ...
From $1171 per night (USD)
VRBO
From $503 per night (USD)
Expedia
Oak Bluffs 3-Bedroom Victorian Cottage, Steps from Sunset Lake/Park
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Step Into Vineyard history—with a modern twist. Originally part of the historic Methodist Campground in Oak Bluffs, this ...
From $503 per night (USD)
Expedia
From $1468 per night (USD)
VRBO
Waterfront home in Vineyard Haven. Walking distance to shops and dining.
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This waterfront house is the perfect home base for your trip to Martha's Vineyard. A stay at this great location will pu ...
From $1468 per night (USD)
VRBO
From $793 per night (USD)
Expedia
Breathtaking Waterviews with Private Beach - Harbour House with AC and Heat
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Breathtaking views, with a short (2 minute) walk to the private beach and the most prestigious golf course on the island ...
From $793 per night (USD)
Expedia
From $239 per night (USD)
VRBO
Charming studio with AC and WiFi in enjoyable Edgartown
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Consider this studio your home away from home while you visit Edgartown. This lovely rental offers a serene atmosphere p ...
From $239 per night (USD)
VRBO
From $1320 per night (USD)
Expedia
Exquisite privacy and luxury just minutes from upscale Edgartown
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
A stylish, very private property, on Chappaquiddick Island ten minutes from the sophisticated bustle, shops and fine res ...
From $1320 per night (USD)
Expedia
From $476 per night (USD)
VRBO
Updated Vineyard Farmhouse - Walk to Town & Ferry
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
This well maintained, bright and cheery Vineyard farmhouse includes 4 bedrooms and 2.5 renovated bathrooms with outdoor ...
From $476 per night (USD)
VRBO
From $276 per night (USD)
Expedia
Cozy and private 1-bedroom apartment in Katama / Edgartown with AC, WiFi
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Stay comfortably in the Katama region of Edgartown at this 1-bedroom apartment. Near the beach and nestled in the woods, ...
From $276 per night (USD)
Expedia
From $376 per night (USD)
VRBO
Modern 1-bedroom apartment in private Edgartown neighborhood w/ tennis court
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This brand new, modern apartment is located in a tranquil Edgartown neighborhood and includes all the amenities needed f ...
From $376 per night (USD)
VRBO
Click For Pricing
Expedia
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 - ...
Click For Pricing
Expedia
From $628 per night (USD)
VRBO
Charming Vineyard Classic Home, Walk to Town & Boat
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Enjoy a charming and comfortable stay in our Martha's Vineyard home, built in 1920 and recently updated with modern amen ...
From $628 per night (USD)
VRBO
From $290 per night (USD)
Expedia
Beautifully handcrafted arts and craft style carriage house chalet
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Beautifully handcrafted chalet carriage house with details of fine woodworking and old beams creating a uplifting feelin ...
From $290 per night (USD)
Expedia
From $798 per night (USD)
VRBO
West Tisbury Gem with Association Pool + Hiking Trails, Close to All
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Spacious, secluded yet close to everything, this light-filled gem began renting in summer '23. Each bedroom has its own ...
From $798 per night (USD)
VRBO
From $3483 per night (USD)
VRBO
Spacious 9-bedroom house with Waterview, WiFi, AC in delightful Oak Bluffs
Bedrooms:
4
Bathrooms:
9
Sleeps:
18
Get ready to relax in this 9-bedroom house in Oak Bluffs. This superb property boasts 3 king beds, 5 full beds, and 2 tw ...
From $3483 per night (USD)
VRBO
From $882 per night (USD)
VRBO
Your perfect summer retreat
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Enjoy a summer getaway in gorgeous Martha's Vineyard. Open and airy family home walking distance to downtown Vineyard Ha ...
From $882 per night (USD)
VRBO
From $1145 per night (USD)
Expedia
Beautiful home with screened porch, deck, W/D, family room, & central AC
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Blissful Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $1145 per night (USD)
Expedia
From $831 per night (USD)
VRBO
Martha’s Vineyard magic awaits ✨
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
2100+ sq ft home with 3 bedrooms and a loft, 2 full bathrooms, plus an enclosed outdoor shower. The best part? A stunnin ...
From $831 per night (USD)
VRBO
$Edgartown Village - Spacious, Light-filled Classic Vineyard Home W/Guest House\n$
From $1489 per night (USD)
VRBO
Edgartown Village - Spacious, Light-filled Classic Vineyard Home W/Guest House\n
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
It doesn't get any better than sitting on a porch swing in the heart of Edgartown? Welcome to our classic Vin ...
From $1489 per night (USD)
VRBO
From $577 per night (USD)
VRBO
South Beach | Katama | Outdoor Shower ☀️ 🏖
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Minutes from South Beach, escape to this spacious and beautifully appointed home in Edgartown, MA, where comfort meets c ...
From $577 per night (USD)
VRBO
From $764 per night (USD)
Expedia
Waterfront Home w/ Guest Cottage
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Experience the magic of Martha's Vineyard from our beachfront retreat. Nestled in a quiet neighborhood, yet conveniently ...
From $764 per night (USD)
Expedia
From $598 per night (USD)
VRBO
Charming 3-Bedroom Home in the Heart of Oak Bluffs
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your perfect Martha’s Vineyard getaway! Nestled in the heart of Oak Bluffs, this charming 3-bedroom home offe ...
From $598 per night (USD)
VRBO
From $948 per night (USD)
VRBO
Lovely peaceful MV 3-bedroom island home, sleeps 12, with air and comm. pool.
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Make yourself at home in our lovely 3-bedroom West Tisbury retreat. Perfect for families and friends looking for a peace ...
From $948 per night (USD)
VRBO
From $846 per night (USD)
VRBO
July 13-21 available! for Marvelous Edgartown 5-bedroom walk to town
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Edgartown is waiting for you at this 5-bedroom house. This adorable and large property features 1 king bed, 4 queen beds ...
From $846 per night (USD)
VRBO
From $189 per night (USD)
VRBO
2-bedroom house, Short walk to beach, with AC and WiFi in Oak Bluffs
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Private Home and yard a block from the Lagoon in Oak Bluffs. Easy walk to quiet neighborhood beach. Brand new kitchen/ba ...
From $189 per night (USD)
VRBO
From $852 per night (USD)
VRBO
Victorian cottage overlooking downtown Oak Bluffs and the Harbor.
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Come stay at our quaint Victorian cottage overlooking downtown Oak Bluffs and the Harbor, which are just a few blocks aw ...
From $852 per night (USD)
VRBO
From $1006 per night (USD)
VRBO
EXQUISITE MARTHA'S VINEYARD HOME, HEATED POOL, 10 MIN WALK TO OAK BLUFFS FERRY
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
This luxurious home offers the perfect blend of comfort, style, and convenience. Featuring a heated 16 x 32' pool with v ...
From $1006 per night (USD)
VRBO
From $2856 per night (USD)
VRBO
WE’RE BACK! Oak Bluffs Retreat. NEW PRIVATE POOL -- FERRY TIX!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Large beautifully appointed three bedroom, 2 1/2 bath house, with a den perfect for space for everyone to enjoy themselv ...
From $2856 per night (USD)
VRBO
From $566 per night (USD)
VRBO
Spacious private Aquinnah home, walk to lighthouse and cliff overlook
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Tanager House - This spacious 4-bedroom home is nestled on 3 acres in scenic Aquinnah, offering privacy and tranquility. ...
From $566 per night (USD)
VRBO
From $1315 per night (USD)
VRBO
DISCOUNTED RATES! 4 BDR house with CUSTOM POOL, SPA and FIRE PIT in Edgartown.
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Exceptional home ideally situated between downtown Edgartown (.75 mile) and South Beach (1.8 mile) and only a few hundre ...
From $1315 per night (USD)
VRBO
From $752 per night (USD)
VRBO
Charming 3-bedroom cottage in Oak Bluffs with AC, WiFi
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Escape to this renovated 3-bedroom home in Oak Bluffs, across from Farm Neck Golf Club. The Beach is just a 4-minute dri ...
From $752 per night (USD)
VRBO
From $1033 per night (USD)
VRBO
Peaceful East Chop Vineyard 5-BR 3-BA home, AC, large yard, Guest apt add-on.
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Located in exclusive East Chop area of Oak Bluffs, enjoy what this 5-bedroom house has to offer. Walk to beach, a safe, ...
From $1033 per night (USD)
VRBO
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
From $4141 per night (USD)
VRBO
Brand New Spacious Luxury Home on Edgartown Great Pond with Pool and Spa
Bedrooms:
8
Bathrooms:
7
Sleeps:
14
STUNNING NEW 7 BEDROOM LUXURY HOME, 7 BATHS, HEATED SALTWATER POOL, MULTIPLE DECKS, SCREENED PORCH, WATERVIEW, ON THE ED ...
From $4141 per night (USD)
VRBO
From $596 per night (USD)
VRBO
4 Mi to Inkwell Beach: Home in Oak Bluffs!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
'Clark's Cove' | Idyllic Tree-Lined Surroundings | Outdoor Shower | 3 Mi to Ferry Terminal Your own slice of paradise a ...
From $596 per night (USD)
VRBO
From $696 per night (USD)
VRBO
3-bedroom house in charming Oak Bluffs with WiFi, AC. Start your vacation
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Make yourself at home in this 3-bedroom Oak Bluffs retreat. This beautiful house features 2 king beds, 1 queen bed, a fu ...
From $696 per night (USD)
VRBO
From $1468 per night (USD)
Expedia
Downtown brand new construction 3 bed & 3 bath
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Brand-new, high-end 3BR/3BA home in the heart of Vineyard Haven—just one block from the ferry terminal. Walk to restaura ...
From $1468 per night (USD)
Expedia
Click For Pricing
VRBO
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 ...
Click For Pricing
VRBO
From $1461 per night (USD)
VRBO
Walk to Edgartown! Sun at South Beach! Privacy & relaxation at special home.
Bedrooms:
4
Bathrooms:
1
Sleeps:
10
IMMACULATE, CONVENIENT, CHARMING! Big Families & Groups of Friends LOVE this house! First floor has comfortable open f ...
From $1461 per night (USD)
VRBO
From $561 per night (USD)
VRBO
Short Walk to Town - Nice Comfortable -Reasonable
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This property is new to VRBO, however it has been hosting guests for several years on another site with 5 star reviews. ...
From $561 per night (USD)
VRBO
From $996 per night (USD)
Expedia
Charming 3-bedroom family home with WiFi and AC in Vineyard Haven.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Enjoy this family home with 3 bedrooms, a spacious loft with half bath, and comfortable amenities. This property has a l ...
From $996 per night (USD)
Expedia
From $2090 per night (USD)
VRBO
Welcome to your perfect island retreat nestled in a private Oak bluffs Enclave
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
This light filled modern, five ensuite bedrooms plus half bath home has everything you need for a perfect getaway. On t ...
From $2090 per night (USD)
VRBO
From $834 per night (USD)
VRBO
Completely Renovated Oak Bluffs Retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Fully renovated for 2025, this stylish 3-bed, 2.5-bath townhome invites you to unwind with a community pool, tennis cour ...
From $834 per night (USD)
VRBO
From $1760 per night (USD)
VRBO
European Style Compound Private In-Town Edgartown
Bedrooms:
3
Bathrooms:
4
Sleeps:
11
Discover the beauty of Edgartown from this European Style Home located in a very desirable part of Edgartown. It is on a ...
From $1760 per night (USD)
VRBO
From $2246 per night (USD)
Expedia
6bedroom, 4bath, chefs kitchen, central air, ping pong, walking distance to town
Bedrooms:
4
Bathrooms:
6
Sleeps:
13
This NEWLY RENOVATED 6-bedroom house in Vineyard Haven is just a 10 minute walk to public beach, downtown restaurants, b ...
From $2246 per night (USD)
Expedia
From $1452 per night (USD)
VRBO
Modern 4BR Escape w Jeep Wrangler. Near Town. Patio, Fire Pit & Hot Tub
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
UPDATED PHOTOS COMING SOON! More furniture, decor & landscaping almost done. Tastefully renovated single-family home, ...
From $1452 per night (USD)
VRBO
From $1029 per night (USD)
Expedia
Comfortable 4BR Oak Bluffs Farmhouse
Bedrooms:
1
Bathrooms:
1
Sleeps:
8
Unwind in Oak Bluffs at this lovely house. With amenities like WiFi, AC, and a washing machine, guests can relax and enj ...
From $1029 per night (USD)
Expedia
From $1118 per night (USD)
VRBO
Spacious 4-bedroom house in charming West Tisbury
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Escape to a wonderful 4-bedroom house in West Tisbury. This serene retreat features a king bed, full bed, queen bed, and ...
From $1118 per night (USD)
VRBO
From $1452 per night (USD)
Expedia
Stunning Tisbury Retreat with Pool
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Escape to this brand-new luxury home in Vineyard Haven, minutes from downtown and the ferry. Designed for comfort and st ...
From $1452 per night (USD)
Expedia
From $855 per night (USD)
VRBO
Charming 2-bedroom house in Katama with WiFi, AC
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Welcome to your Katama retreat! This sun-filled 2BR/2.5BA home is perfectly located between Edgartown and South Beach. E ...
From $855 per night (USD)
VRBO
From $774 per night (USD)
VRBO
Downtown Edgartown, Prime Location, Sleeps 8
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
Welcome to your Martha's Vineyard escape in the heart of downtown. This charming home is just two blocks from the histor ...
From $774 per night (USD)
VRBO
From $323 per night (USD)
VRBO
Quaint, ranch style home in Oak Bluffs with central air
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
The Rootskeller Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $323 per night (USD)
VRBO
From $852 per night (USD)
VRBO
Charming 3BR Vineyard Retreat, Lg Deck w/ Kitchen, Near Beach, Town Ctr & Ferry
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to RoBree Farm – Your Martha’s Vineyard Retreat in the Heart of Oak Bluffs Escape to the serenity and magic of ...
From $852 per night (USD)
VRBO
From $823 per night (USD)
VRBO
Charming home with walkable beach, large yard, deck, fire pit, and A/C
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
Beach House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $823 per night (USD)
VRBO
From $557 per night (USD)
VRBO
Charming 2-bedroom townhouse in Oak Bluffs with WiFi, AC
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Sengekontacket pond in Oak Bluffs is waiting for you at this quiet 2-bedroom townhouse with a private deck overlooking a ...
From $557 per night (USD)
VRBO
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)
Expedia
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)
Expedia
From $487 per night (USD)
VRBO
Edgartown convenience to beach, restaurants, shopping and public transportation.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Located in Edgartown, this apartment is a dream. With a daybed with two twin beds and a Queen sleigh bed. Fits 4 very co ...
From $487 per night (USD)
VRBO
From $1861 per night (USD)
Expedia
Spacious, Family-Friendly Edgartown Home – 3BR, Sleeps 14, Renovated in 2025
Bedrooms:
2
Bathrooms:
3
Sleeps:
14
Spacious & Family-Friendly Edgartown Retreat – Fully Renovated in 2025 Welcome to your perfect Martha’s Vineyard getawa ...
From $1861 per night (USD)
Expedia
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
From $626 per night (USD)
Expedia
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Dogs Welcome w/ Fee | Beach Across Street | Postcard-Worthy Sunsets Easy island living awaits at this 3-bedroom, 1-bath ...
From $626 per night (USD)
Expedia
From $369 per night (USD)
VRBO
Walk to Beach & Lighthouse: Oak Bluffs Studio!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Pets Welcome w/ Fee | Solo Getaway or Couple's Retreat Island charm meets laid-back comfort at this 1-bathroom studio i ...
From $369 per night (USD)
VRBO
From $1083 per night (USD)
Expedia
Private house with jetted tub, deck, grill, central AC and large yard
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Family Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $1083 per night (USD)
Expedia
From $436 per night (USD)
VRBO
Private suite with roof deck, near golf, bus stop, shops, and trails
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Garage Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $436 per night (USD)
VRBO
From $494 per night (USD)
Expedia
MV Modern Queen 1BR and Qu. sofa bed private bedroom apartment sleeps 4 to 6
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Make yourself at home in this marvelous 1-bedroom with spacious private living room that converts to a Queen bedroom, Ti ...
From $494 per night (USD)
Expedia
From $701 per night (USD)
VRBO
Walk to Beach Spacious Retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Escape to our vineyard home, a charming haven nestled on 1/3 acre of land within steps to the center of town. This retre ...
From $701 per night (USD)
VRBO
From $4494 per night (USD)
VRBO
Private island retreat in Katama: pool, gourmet kitchen + stunning ocean views.
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Nestled in Katama just minutes from pristine beaches and Edgartown, this private newly constructed four-bedroom retreat ...
From $4494 per night (USD)
VRBO
From $666 per night (USD)
VRBO
Spacious house with private yard, firepit - option to rent car
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
3 Sisters Vineyard Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply en ...
From $666 per night (USD)
VRBO
Click For Pricing
Expedia
3-bedroom townhome in charming Edgartown with WiFi, AC. Start your vacation now
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Make yourself at home in this 3-bedroom Edgartown retreat. This fabulous townhome boasts 2 queen beds and 1 full bed, pe ...
Click For Pricing
Expedia
From $1374 per night (USD)
VRBO
Chilmark 1-bedroom Bunk house, WiFi, AC. Private Beach, Pets. No kitchen
Bedrooms:
0
Bathrooms:
1
Sleeps:
3
Your cozy retreat in Chilmark with 1 bedroom featuring 3 comfortable twin beds upstairs in the loft. This charming house ...
From $1374 per night (USD)
VRBO
From $1132 per night (USD)
Expedia
Wishing Well Oak Bluffs: 4-bedroom house with WiFi, AC - Close to Beach and Town
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Consider this house your home away from home while you visit Oak Bluffs. With 4 charming bedrooms including a queen bed, ...
From $1132 per night (USD)
Expedia
From $691 per night (USD)
VRBO
Serene private home w/ large deck & yard on conservation land
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
The Big Easy Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $691 per night (USD)
VRBO
$Oasis in downtown Oak Bluffs: 2 x King BR Condo, AC & Prime Location, sleeps 6\n$
From $700 per night (USD)
Expedia
Oasis in downtown Oak Bluffs: 2 x King BR Condo, AC & Prime Location, sleeps 6\n
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to 'Whale Tail', one of the most iconic and talked-about properties in Oak Bluffs! Located directly above Vineya ...
From $700 per night (USD)
Expedia
From $1393 per night (USD)
VRBO
Classic Cape & Bunk House Nearby Downtown
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This house is the perfect home away from home for your Vineyard holiday. The sitting & dining areas with the fully equi ...
From $1393 per night (USD)
VRBO
From $268 per night (USD)
VRBO
< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Pet Friendly w/ Fee | BBQ Ready | Outdoor Shower Seeking a relaxing Martha’s Vineyard escape? Look no further than this ...
From $268 per night (USD)
VRBO
From $2281 per night (USD)
VRBO
Fantastic Waterfront Private Beach & Dock on West Chop
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Enjoy everything you love about the Vineyard staying in this updated 4 bedroom house on the outer Vineyard Haven harbor. ...
From $2281 per night (USD)
VRBO
From $1159 per night (USD)
Expedia
Modern Saltbox in Edgartown Village
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This exceptional house is the perfect location for all your Vineyard adventures. Just a stone's throw from Main Street i ...
From $1159 per night (USD)
Expedia
From $614 per night (USD)
VRBO
Peaceful Island Getaway with Pool and Exclusive Beach Pass
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to your Island Retreat on Martha's Vineyard! Nestled on a quiet dirt road in West Tisbury among nearly 2 acres, ...
From $614 per night (USD)
VRBO
From $586 per night (USD)
VRBO
2-bedroom home with Pool and Tennis/Pickleball Court
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
The guest house is part of a larger property (ID# 748468) and is available for exclusive rental (i.e., the main house re ...
From $586 per night (USD)
VRBO
From $609 per night (USD)
VRBO
IN TOWN! Charming 1-bedroom condo in downtown Edgartown
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Ground level 1 bedroom condo right in the heart of Edgartown! The space offers 1 bedroom, a fully equipped kitchen, cozy ...
From $609 per night (USD)
VRBO
From $1994 per night (USD)
Expedia
Soothing 4-bedroom house with a built full yard andAC in charming Tisbury
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
This 4-bedroom house in Tisbury is perfect for your escape. With 1 king bed, 2 queen beds, 2 twin bed, and 2 futon, ther ...
From $1994 per night (USD)
Expedia
From $838 per night (USD)
VRBO
Charming Harborside hotel suite in enchanting Edgartown with AC
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover the beauty of Edgartown from this 1-bedroom hotel suite. The room features a welcoming queen bed, perfect for a ...
From $838 per night (USD)
VRBO
From $810 per night (USD)
VRBO
Updated cozy home, tranquil neighborhood yet close to everything in Edgartown!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Warm and cozy, tastefully decorated, post and beam three bedroom Edgartown home close to Morning Glory Farm, with a shor ...
From $810 per night (USD)
VRBO

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