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

Oak Bluffs Rentals

From $523 per night (USD)
VRBO
Beautiful Contemporary Farmhouse close to Oak Bluffs
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Beautifully maintained contemporary farmhouse features an open floor plan. The first floor has an open kitchen, dining, ...
From $523 per night (USD)
VRBO
From $1098 per night (USD)
VRBO
Big Beach House - Ocean Views!
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
Original 1900 Victorian home, updated in 2006, located in the historic Copeland District just one block from the beach. ...
From $1098 per night (USD)
VRBO
From $261 per night (USD)
VRBO
Contemporary Pet-friendly Retreat. Just one 2025 summer week left: Aug 30-Sep 6
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Contemporary with open living/dining area, cathedral ceilings, and air conditioning throughout. Sliding and French door ...
From $261 per night (USD)
VRBO
From $424 per night (USD)
VRBO
Martha's Vineyard Beachfront Condo in Oak Bluffs
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy all that Martha's Vineyard has to offer in this spacious two bedroom, two full bath beautifully furnished condo ov ...
From $424 per night (USD)
VRBO
From $566 per night (USD)
VRBO
Classic Downtown Property
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
The home has been tailored for modern tastes and conveniences. Ideally located on a private lane, just a short distance ...
From $566 per night (USD)
VRBO
From $1077 per night (USD)
Expedia
Secluded Escape- Central AC & Wireless Internet Access.
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
This gorgeous, contemporary air-conditioned private home is perfect for your luxurious vacation on the island. It is 270 ...
From $1077 per night (USD)
Expedia
From $222 per night (USD)
VRBO
Sea Captain's Victorian studio bedroom apartment. Pets OK
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Stay in an original sea captain Victorian for less than the cost of a hotel. This is a fully furnished studio apartment ...
From $222 per night (USD)
VRBO
From $535 per night (USD)
VRBO
Peaceful Escape Beautiful Contemporary Perfect For Families Walk To Town
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Need a change of scenery? This charming three bedroom, two bath contemporary sleeps 8 and is conveniently located near ...
From $535 per night (USD)
VRBO
From $910 per night (USD)
VRBO
Lovely waterfront home with private, sandy beach and mooring on Lagoon Pond
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Relax on the gorgeous wraparound deck, let the sea breeze caress your face, listen to the chirping birds, and drink in t ...
From $910 per night (USD)
VRBO
From $649 per night (USD)
Expedia
Spacious Waterview Condo - Steps To The Beach, Right Across The Street!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Prime location close to the center of town in the fabulous SeaView Condo building in the heart of Oak Bluffs. Highly des ...
From $649 per night (USD)
Expedia
From $305 per night (USD)
VRBO
Quiet 2-Bed, 2-Bath Condo with Spacious Sundeck & Tennis Courts
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy a peaceful retreat in this cozy 2-bedroom, 2-bath condo with air conditioning, offering the perfect space to relax ...
From $305 per night (USD)
VRBO
From $1741 per night (USD)
VRBO
Glorious Sunsets and Fun on Private Waterfront in Beautiful, Comfortable Home.
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Ask about Discounts if 8 or fewer guests. ...
From $1741 per night (USD)
VRBO
From $1253 per night (USD)
VRBO
Martha's Vineyard waterfront with Dock
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
A delightful oasis on the water's edge. A serene retreat that will ensure relaxation! Nestled overlooking the lagoon wit ...
From $1253 per night (USD)
VRBO
From $1819 per night (USD)
VRBO
7/6-7/13 AVAILABLE DUE TO LAST MINUTE CANCELLATION! Walk to Beach!
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
LAST MINUTE CANCELLATION FOR JULY 6TH - 13TH, 2025!! This charming Vineyard home just completed a large renovation incl ...
From $1819 per night (USD)
VRBO
From $1499 per night (USD)
VRBO
Family Friendly Quiet Neighborhood Heated In-ground Pool SUNDAY CHECKIN
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Cape style home with heated in ground pool located only a 4 minute walk to Sengekontacket Pond where you can kayak or pa ...
From $1499 per night (USD)
VRBO
From $614 per night (USD)
Expedia
A Charming Vineyard Cottage Just Off the Pond
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Remember when summer vacations meant spending long perfect days near the water? This simple wooden Vineyard cottage wit ...
From $614 per night (USD)
Expedia
From $804 per night (USD)
VRBO
The quintessential MV home. Now booking for 2025!
Bedrooms:
4
Bathrooms:
4
Sleeps:
9
Pirate's Cove is a young, Victorian-style home, designer-decorated and nestled on a quiet lane in East Chop, located jus ...
From $804 per night (USD)
VRBO
From $598 per night (USD)
VRBO
Beautiful Landscaped Grounds and Pond & Kayaks
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Welcome to paradise!!! This beautiful property is located in prestigious fresh pond estates. It sits tucked away in the ...
From $598 per night (USD)
VRBO
From $336 per night (USD)
VRBO
Central location for your vacation
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Centrally located from nearby Vineyard Haven, Oak Bluffs, Edgartown and West Tisbury. Beaches and trails in close proxi ...
From $336 per night (USD)
VRBO
From $466 per night (USD)
VRBO
WALK TO BEACHES,HARBOR,EVERYTHING!! IN-TOWN OB! A/C,Large Deck,Gazebo,Yard
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
***IMPORTANT--PLEASE "MESSAGE " HOST FIRST----BEFORE SENDING A BOOKING REQUEST!! ( JUST CLICK ON " CONTACT HOST" (you ...
From $466 per night (USD)
VRBO
From $584 per night (USD)
VRBO
Hamletts' Haven - Spectacular Summer Getaway! Tues. 8/27 - Sat. 9/7 AVAILABLE!!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Hamletts' Haven - The Vacation Get Away! Book for two days or two weeks - the choice is yours. Enjoy!!!! ...
From $584 per night (USD)
VRBO
From $904 per night (USD)
Expedia
Great Martha's Vineyard House: Everything You Need - Nothing You Don't!
Bedrooms:
1
Bathrooms:
3
Sleeps:
9
Property rents Monday to Monday. 3 bedroom/ 2 and 1/2 bathroom Contemporary Vineyard house with wraparound deck, outdoor ...
From $904 per night (USD)
Expedia
From $410 per night (USD)
VRBO
Carriage House, Swimming, Boating, Kayaking, just steps from your door...
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
WELCOME TO PARADISE!!! we sanitize!!!!! We have implemented a system so you are able to check in and out without and per ...
From $410 per night (USD)
VRBO
From $942 per night (USD)
VRBO
Large, Charming Vintage Cape Cod Cottage, 2 Blocks to Town and Beaches!
Bedrooms:
1
Bathrooms:
5
Sleeps:
10
Victorian Cape Cod Cottage located in the highly desired Oak Bluffs Copeland District in Martha's Vineyard. Large family ...
From $942 per night (USD)
VRBO
From $481 per night (USD)
VRBO
West Tisbury Country Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Custom home with many amenities. Nicely furnished. Beautiful interiors with natural woodwork, oak floors, deck, big secl ...
From $481 per night (USD)
VRBO
From $1628 per night (USD)
VRBO
Luxe 4 Bed/4 Ensuite Bath, A/C In-Town Vineyard Haven, Gunite Pool and Spa
Bedrooms:
4
Bathrooms:
4
Sleeps:
9
Luxury Home in private cul-de-sac in Vineyard Haven. Just a short two block walk to downtown restaurants, shops, harbor, ...
From $1628 per night (USD)
VRBO
From $1746 per night (USD)
VRBO
Modern & Spacious Edgartown Home with Pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Enjoy your vacation in this wonderfully charming three bedroom home with an in-ground heated pool. Head to the beach or ...
From $1746 per night (USD)
VRBO
From $1750 per night (USD)
Expedia
Dog-friendly home with beautiful deck & AC - close to 3 towns & great beaches
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Martha's Hideaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $1750 per night (USD)
Expedia
From $396 per night (USD)
VRBO
Charming Oak Bluffs Cottage: Prime Location, Stylish Comfort & Serene Privacy
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to your Vineyard getaway! Nestled in a peaceful neighborhood in Oak Bluffs, this cozy two-bedroom, one-bath cott ...
From $396 per night (USD)
VRBO
From $586 per night (USD)
VRBO
Historic Home in East Chop
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Renovated home in East Chop, Oak Bluffs, Martha’s Vineyard. Built in 1872 by my great, great grandfather, the house has ...
From $586 per night (USD)
VRBO
From $428 per night (USD)
VRBO
Updated Beautiful Cottage in Edgartown w/ Central AC
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
A true island charmer. Light, airy and central-air-conditioned, well-designed home offers all the comforts of modern liv ...
From $428 per night (USD)
VRBO
From $581 per night (USD)
VRBO
Oak Bluffs Retreat - The perfect getaway!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Six minute drive to beach! This two floor beauty with central AC boasts ample yard space and all the amenities you look ...
From $581 per night (USD)
VRBO
From $1245 per night (USD)
VRBO
Modern, luxury 5-bed, 4.5-bath w/full basement! Now booking for 2025!
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Pirate's Reef is a NEW and beautifully decorated residence that offers 5 spacious bedrooms (2 master suites!) with 4.5 b ...
From $1245 per night (USD)
VRBO
From $1875 per night (USD)
VRBO
Welcome to The “SUMMER WIND” House! 5-Minutes to the Beach!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
THE “SUMMER WIND” HOUSE - WALK TO EVERYTHING! We have completely renovated our 5-bedroom, 3-full bathroom home with cent ...
From $1875 per night (USD)
VRBO
From $357 per night (USD)
VRBO
In-Town-WALK TO EVERYTHING! PETS WELCOME! Screened Porch, A/C, Outdoor Shower
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
***IMPORTANT--PLEASE "MESSAGE " HOST FIRST----BEFORE SENDING A BOOKING REQUEST!! ( JUST CLICK ON " CONTACT HOST" (you w ...
From $357 per night (USD)
VRBO
From $606 per night (USD)
VRBO
Lovely vacation home within walking distance to Oak Bluffs and the beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your summer vacation home! This is a 3 bedroom 2 1/2 bath home located less than a mile from downtown Oak Bl ...
From $606 per night (USD)
VRBO
From $1223 per night (USD)
VRBO
Relax & Renew at this Luxury Villa with Heated Pool & Hot Tub, Tennis, Firepit!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
This newly renovated, luxury home with pool is centrally located! 1.5 miles to downtown Oak Bluffs and less than 2 miles ...
From $1223 per night (USD)
VRBO
From $577 per night (USD)
Expedia
Lagoon Pond House with Beach Access - Kayaker Paradise
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy the water view from the deck and house. This house has a private path to the head of Lagoon Pond, and a large yar ...
From $577 per night (USD)
Expedia
From $577 per night (USD)
VRBO
Oak Bluffs - Quiet neighborhood
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
Less than a mile from downtown, harbor and beach. Located in a quiet neighborhood, guests are sure to enjoy a memorable ...
From $577 per night (USD)
VRBO
From $989 per night (USD)
VRBO
Newly Renovated Cape In Edgartown
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
POINT B EXCLUSIVE - This newly renovated Cape sits back in a quiet neighborhood near the Vineyard Golf Club. It has been ...
From $989 per night (USD)
VRBO
From $768 per night (USD)
VRBO
Elegant Dream Home w/ Luxurious Living Spaces, Full Kitchen, & Wraparound Porch
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Oak Manor Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $768 per night (USD)
VRBO
From $2938 per night (USD)
VRBO
ILLUMINATION WEEK 8/16-8/23/25 ON MARTHA'S VINEYARD IS OPEN FOR BOOKING
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This luxury enclave, complete with 4 bedrooms and 3.5 bathrooms, is located in a private community that is centrally loc ...
From $2938 per night (USD)
VRBO
$A BRILLANT WAY\nCentral Location To Beach/Shops/Restaurants/Arcade/Family Bowling$
From $586 per night (USD)
VRBO
A BRILLANT WAY\nCentral Location To Beach/Shops/Restaurants/Arcade/Family Bowling
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
A Brillant Way is a Brilliant Condo located in the heart of Oak Bluffs. Second level has 2 bedrooms - Queen size bed in ...
From $586 per night (USD)
VRBO
From $439 per night (USD)
VRBO
Oak Bluffs Cutie Near Beach + Town Center! Ferry tix available for some dates!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Enjoy both worlds - a peaceful atmosphere with many comfortable places to escape to read, nap or chat, near the heart of ...
From $439 per night (USD)
VRBO
From $643 per night (USD)
VRBO
Oak Bluffs Gingerbread Cottage near Downtown, Beach, Ferry and Ocean Park!
Bedrooms:
1
Bathrooms:
5
Sleeps:
8
- Magnificent front porch for rocking and peaceful island observations! - All furniture is whimsical and light to match ...
From $643 per night (USD)
VRBO
From $775 per night (USD)
Expedia
LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This newly renovated 2 bedroom house is a stone's throw from the ferry terminal, main street, restaurants & beaches in V ...
From $775 per night (USD)
Expedia
From $410 per night (USD)
VRBO
Martha’s Vineyard Condo w/ Pool minutes from Ferry
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Cozy 1 bedroom, 1 full bath, Condo located minutes from Vineyard Haven Harbor on Martha’s Vineyard. Nice landscaped surr ...
From $410 per night (USD)
VRBO
From $389 per night (USD)
Expedia
Waterfront condo with scenic views of Vineyard Haven harbor and beyond
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Completely updated/renovated 1 bedroom (sleeps 4), 1bath condo with eat in kitchen. Fantastic views with private beach ...
From $389 per night (USD)
Expedia
From $507 per night (USD)
VRBO
Perfect Home For A Family Vacation With All The Amenities
Bedrooms:
4
Bathrooms:
4
Sleeps:
13
This professionally designed & decorated vacation home is great for a quiet get away for one or two couples/families or ...
From $507 per night (USD)
VRBO
From $416 per night (USD)
VRBO
Spacious family house, short walk to the Lagoon & close to Oak Bluffs center
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
The 'Anchor Inn' on Carole Avenue is the perfect spot for your family to relax and enjoy the Vineyard! The home is a 4 ...
From $416 per night (USD)
VRBO
From $303 per night (USD)
VRBO
Held July weeks open & discounted! Updated Oak Bluffs home! Close to everything!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This home was updated in 2023! Beautiful detached 2 bedroom within walking distance to the center of Oak Bluffs. The ext ...
From $303 per night (USD)
VRBO
From $1080 per night (USD)
VRBO
OB Watrfront 4+ BR. Quiet/Walk to Town. Beachy, classic, great ocean/pond views.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Best of everything: We are located on the back side of Farm Pond, which overlooks Harthaven, Nantucket Sound, and Chappa ...
From $1080 per night (USD)
VRBO
$\The Carousel House\ - Ocean Park - Featured in New York Times$
From $1882 per night (USD)
VRBO
\"The Carousel House\" - Ocean Park - Featured in New York Times
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
This house, built in 1865, was featured in the New York Times article on Oak Bluffs, 'The President Was Here (Grant, Tha ...
From $1882 per night (USD)
VRBO
From $1189 per night (USD)
VRBO
CENTRAL AIR! Quiet East Chop Retreat Walk 2 Town and Beach.
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
GAME ROOM!!! We have converted the room in the garage as a place where our guests can go should you have a rainy day or ...
From $1189 per night (USD)
VRBO
From $693 per night (USD)
VRBO
Ocean Views from East Chop
Bedrooms:
3
Bathrooms:
5
Sleeps:
9
Easy access to Oak Bluffs or Vineyard Haven, quiet street overlooking Crystal Lake and the Vineyard Sound. House has fi ...
From $693 per night (USD)
VRBO
Click For Pricing
Expedia
Swim And Sunsets At The Lagoon! Conveniently Located 2 Miles From Town!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Cape-style 3 bedroom home with 3 bedrooms and 2 full baths, plus an outdoor shower. Open style floor plan downstairs wi ...
Click For Pricing
Expedia
From $442 per night (USD)
VRBO
Well-Appointed 3 bedrm 4 bathrm with AC and 50+ 5-star reviews!
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
*** IF INTERESTED IN BOOKING, PLEASE SEND AN INQUIRY (click on ’contact host’) PRIOR TO SENDING A BOOKING REQUEST. BOOK ...
From $442 per night (USD)
VRBO
From $726 per night (USD)
Expedia
Waterfront Getaway With Beautiful Views Of Senge Pond.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This fully air-conditioned 3 bedroom cottage sits directly on Sengekontacket Pond in the town of Edgartown. You will be ...
From $726 per night (USD)
Expedia
From $997 per night (USD)
VRBO
AMENITIES GALORE IN OAK BLUFFS PRIVATE COMMUNITY, DOCK, TENNIS, CENTRAL AC
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
Our wonderful vacation home has been renovated adding central AC, new carpeting, new quartz countertops in both kitchens ...
From $997 per night (USD)
VRBO
From $950 per night (USD)
VRBO
Multiple Ensuites, Central Air, Perfect Location
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Our home is approximate 2200sf and has 4 bedrooms including 3 bedrooms with en-suite bathrooms (all on second floor) an ...
From $950 per night (USD)
VRBO
From $1053 per night (USD)
VRBO
Gingerbread cottage with stunning Oak Bluffs Harbor View
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Amazing vacation spot Enjoy beautiful views of Oak Bluffs Harbor and beyond Historic gingerbread cottage Large front por ...
From $1053 per night (USD)
VRBO
From $748 per night (USD)
VRBO
Beautiful cape located 2 blocks from Lagoon!
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
It's all about Location!!! This cape style home is located on a quiet road very close to the Lagoon in Oak Bluffs and is ...
From $748 per night (USD)
VRBO
From $773 per night (USD)
VRBO
Location, Location, Location- Updated East Chop Year Round Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Oak Bluffs: Located in East Chop! Beautiful year round home steps to Oak Bluffs Harbor, East Chop Beach Club, Jetty Beac ...
From $773 per night (USD)
VRBO
From $439 per night (USD)
VRBO
Martha's Vineyard Beachfront Cottage in Oak Bluffs but closer to Vineyard Haven
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Small beachfront cottage; back deck is right on the water and the front door is on Beach Rd. where you can flag down a b ...
From $439 per night (USD)
VRBO
From $610 per night (USD)
VRBO
Charming Island House-Close to Ginger Bread Cottages, Beaches, Shops...
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Come experience the magic of the Vineyard in our island home. This charming residence is clean, cozy and boasts modern f ...
From $610 per night (USD)
VRBO
From $400 per night (USD)
Expedia
Family-Friendly Tisbury Escape - Walk to Town
Bedrooms:
2
Bathrooms:
5
Sleeps:
8
Experience the magic of Martha’s Vineyard firsthand at this completely renovated ranch-style retreat! Boasting a large s ...
From $400 per night (USD)
Expedia
From $542 per night (USD)
VRBO
GREAT PRICE!PETS WELCOME! 2 Decks, Porch,Linens Included,Outdoor Shower, A/C
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
***IMPORTANT--PLEASE "MESSAGE "HOST FIRST----BEFORE SENDING A BOOKING REQUEST!! ( JUST CLICK ON " CONTACT HOST" (you wi ...
From $542 per night (USD)
VRBO
From $2146 per night (USD)
VRBO
Relaxing Beach Front Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
The Perfect Vineyard Vacation: This beautiful beachfront home is on the east side of Lagoon Pond, in the town of Oak Blu ...
From $2146 per night (USD)
VRBO
From $550 per night (USD)
VRBO
Your Summer Home - Close to Beach, Shops, Cafes, & Ferry! 50+ ⭐️⭐️⭐️⭐️⭐️ Reviews
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
With more than Fifty, 5-STAR REVIEWS, you can book with confidence. This beautifully appointed home features luxe furni ...
From $550 per night (USD)
VRBO
From $578 per night (USD)
VRBO
Pristine with central air and outdoor shower
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
A 15 minute walk from Main Street and Vineyard Haven Ferry Terminal (as well as playground near by), makes this new cons ...
From $578 per night (USD)
VRBO
From $446 per night (USD)
VRBO
Lovely Home Prvt Apt- 2 bedrms1.5 baths full kitch living /dining rm 2 car prkng
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Lovely private first floor of raised ranch house. Sleeps Four in 2 bedrooms (queen and two singles). One and a half bat ...
From $446 per night (USD)
VRBO
From $949 per night (USD)
VRBO
Vineyard Haven Beach House
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Wake up surrounded by amazing water views in our sunny, airy beach house! The open floor plan gives you great views from ...
From $949 per night (USD)
VRBO
From $1022 per night (USD)
VRBO
CHARMING HISTORIC ISLAND HOME--WEEKLY RENTAL-- OAK BLUFFS
Bedrooms:
2
Bathrooms:
5
Sleeps:
9
Welcome to "Eventide." Your historic vacation home is nestled at 63 Temahigan Ave. in Oak Bluffs- Martha's Vineyard. Con ...
From $1022 per night (USD)
VRBO
From $467 per night (USD)
VRBO
Quiet, Pet Friendly, Close to Edgartown and Oak Bluffs Beaches - FIVE STARS
Bedrooms:
1
Bathrooms:
2
Sleeps:
7
This home was built in 2019 specifically for the vacation rental business. 2025 improvements including a finished baseme ...
From $467 per night (USD)
VRBO
From $1075 per night (USD)
VRBO
Historic Waterfront Home in Downtown Vineyard Haven
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
Incredibly convenient, gracious home, perfect for large families. Spend days relaxing on the wraparound porch watching t ...
From $1075 per night (USD)
VRBO
From $643 per night (USD)
VRBO
Convenient In-Town (Oak Bluffs) Location
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Great Vineyard location on Vineyard Avenue in Oak Bluffs. Built in 1920 and thoughtfully restored in 1999, this house is ...
From $643 per night (USD)
VRBO
From $1277 per night (USD)
VRBO
Oak Bluffs Family Retreat - Private Roundabout, Walk to the Beach & Downtown OB.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Renovated in 2022, The Panola House is tucked away on a private lot with its own roundabout driveway. Walk to the cente ...
From $1277 per night (USD)
VRBO
From $730 per night (USD)
Expedia
Airy, Quiet Vacation Rental Home, pool, tennis, FERRY TIX on MV
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Families and children feel right at home in this clean, comfortable, contemporary house with large living/dining area, f ...
From $730 per night (USD)
Expedia
From $306 per night (USD)
VRBO
Historic Oak Bluffs home, short walk to town, beach, and harbor.
Bedrooms:
0
Bathrooms:
3
Sleeps:
6
Family owned and kept charming 19th century home in Oak Bluffs highlands near Baptist Temple park. This house is about ...
From $306 per night (USD)
VRBO
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Expedia
Cute 4-BR House within walking distance of Circuit Avenue
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
It is all about location! Leave the car at the house, and walk right into town. This 4 bedroom, 2 bath home features a l ...
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Expedia
From $499 per night (USD)
VRBO
Steps to the beach - Vineyard Summer home
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This charming summer cottage offers the quintessential vacation experience close to Vineyard Haven center. Walk to the b ...
From $499 per night (USD)
VRBO
From $718 per night (USD)
VRBO
Completely renovated, air conditioned cottage close to the beach. Dog friendly.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This property has something for the whole family to enjoy. A large wrap-around porch, screened in dining area on side po ...
From $718 per night (USD)
VRBO
From $587 per night (USD)
VRBO
Location, Charm, & Steps to Town/Beach -- Central AC, 100% Renewable Energy
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
(Note: for 2025, we are renovating the upstairs bath and creating a more spa-like shower. New Photos by late March, rou ...
From $587 per night (USD)
VRBO
From $462 per night (USD)
VRBO
Charming, Clean And Well Maintained Home Walking Distance To Town And Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Charming Vineyard Haven Retreat, Walk to Downtown & Beaches: Experience a relaxing getaway in this charming two-bedroom ...
From $462 per night (USD)
VRBO
From $4032 per night (USD)
VRBO
Oceanfront, Private Dock and Harthaven Private Beach - Walk to Noman's, Inkwell
Bedrooms:
2
Bathrooms:
6
Sleeps:
12
6 Bedrooms, Sleeping Porch, 3 Full Baths, 2 Half Baths, Sleeps 12+ A timeless Martha’s Vineyard escape awaits you at th ...
From $4032 per night (USD)
VRBO
From $1229 per night (USD)
VRBO
Modern 4 bed/3.5 bath Farmhouse, private HEATED POOL and AC on bike path
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Enjoy everything the island has to offer in a spacious, custom-built, fully-stocked modern farmhouse and backyard oasis ...
From $1229 per night (USD)
VRBO
From $639 per night (USD)
VRBO
A Vineyard Home Perfect For Family Gatherings
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
"A beautiful and private spot for your family vacation, reunion of friends, or just a space to be alone and create. This ...
From $639 per night (USD)
VRBO
From $489 per night (USD)
VRBO
Close to town, beautifully updated
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
*** For stays between 9/1/2024 and 6/14/2025, Please inquire about a discounted cleaning rate***. Renovated Oak Blu ...
From $489 per night (USD)
VRBO
From $454 per night (USD)
VRBO
Comfortable Island Home, Easy Access to Beaches and Town
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
Salt Box style Log Home with open floor plan built by my family with a country feel, located on a wooded lot in the down ...
From $454 per night (USD)
VRBO
From $438 per night (USD)
Expedia
Cottage w/ water views from front yard, central ac & fireplace
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Island Home Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $438 per night (USD)
Expedia
Click For Pricing
VRBO
Vineyard Gem < 2 Mi to Beach & Oak Bluffs!
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Boasting one of the most optimal locations on the island, this 3-bedroom, 2.5-bath vacation rental home sits within a qu ...
Click For Pricing
VRBO
From $525 per night (USD)
Expedia
Family & dog friendly; walk to beach, cliff, town, ferries, all bedrooms w/AC
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Best of both worlds! Quietly situated among beautiful trees with few neighbors plus it is walking distance to swim and O ...
From $525 per night (USD)
Expedia
From $492 per night (USD)
VRBO
Delilah & Joseph Pierce House
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Travel and Enjoy! Built by international artist, curator, educator, advocate, and diplomat Delilah W. Pierce, and her fa ...
From $492 per night (USD)
VRBO
From $767 per night (USD)
Expedia
Dog-friendly home with fenced yard- walking distance to beach, ferry & town
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Wayland Victorian Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $767 per night (USD)
Expedia
Click For Pricing
VRBO
Historic Home with Gorgeous Antiques & Mondern Conveniences
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
The Samoset Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
Click For Pricing
VRBO
From $1117 per night (USD)
VRBO
Waterfront Home in Oak Bluffs - Walk to Town and Beach
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This lovely four-bedroom shingled Cape overlooks Farm Pond, Harthaven, and Nantucket Sound. It is a vintage cottage com ...
From $1117 per night (USD)
VRBO
From $458 per night (USD)
VRBO
Breezy Oak Bluffs Condo - Steps to Inkwell Beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Planning a family or couple's getaway to Martha's Vineyard? Then you'll love calling this delightful Oak Bluffs vacation ...
From $458 per night (USD)
VRBO
From $307 per night (USD)
Expedia
Cozy cottage 3/4 mile from Oak Bluffs harbor
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Family owned/charming home in Oak Bluffs, 1/2 mile walk to East Chop Lighthouse and slightly more to the town harbor, wh ...
From $307 per night (USD)
Expedia
From $538 per night (USD)
VRBO
Cozy, exceptional view, quiet, high speed WIFI, close to all island attractions
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This comfortable house provides up and downstairs amenities. The master bedroom with bath is on the ground floor; the o ...
From $538 per night (USD)
VRBO
From $901 per night (USD)
VRBO
Mill Hill - Walking Distance From Town And Ferry With Ocean View
Bedrooms:
3
Bathrooms:
6
Sleeps:
11
“Mill Hill” is a wonderful in-town historic home which comfortably sleeps 11 people. The property sits a close five-min ...
From $901 per night (USD)
VRBO

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