Oak Bluffs Rentals
From $4289 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 $4289 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 $504 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 $504 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 $726 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 $726 per night (USD)VRBO
From $592 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 $592 per night (USD)VRBO
From $498 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 $498 per night (USD)VRBO
From $959 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 $959 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 $750 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 $750 per night (USD)VRBO
From $394 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 $394 per night (USD)VRBO
From $683 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 $683 per night (USD)VRBO
From $3455 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 $3455 per night (USD)VRBO
From $598 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 $598 per night (USD)VRBO
From $391 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 $391 per night (USD)VRBO
From $666 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 $666 per night (USD)VRBO
From $1179 per night (USD)Expedia
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 $1179 per night (USD)Expedia
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 $529 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 $529 per night (USD)VRBO
From $467 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 $467 per night (USD)VRBO
From $319 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 $319 per night (USD)VRBO
From $1069 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 $1069 per night (USD)VRBO
From $577 per night (USD)Expedia
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)Expedia
From $1196 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 $1196 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
From $397 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 $397 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 $503 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 $503 per night (USD)VRBO
From $834 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 $834 per night (USD)Expedia
From $980 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 $980 per night (USD)VRBO
From $1551 per night (USD)VRBO
Glorious Sunsets and Fun on Private Waterfront in Beautiful, Comfortable Home.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
FREE!!! A Transferable Round-trip SSA auto reservation is included for the July 19-26, 2025 week. ...
From $1551 per night (USD)VRBO
From $1851 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 $1851 per night (USD)VRBO
From $879 per night (USD)Expedia
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 $879 per night (USD)Expedia
From $320 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. You are not able to get your car ...
From $320 per night (USD)VRBO
From $581 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 $581 per night (USD)VRBO
From $415 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 $415 per night (USD)VRBO
From $1093 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 $1093 per night (USD)Expedia
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 $772 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 $772 per night (USD)Expedia
From $293 per night (USD)VRBO
Discover the magic of Martha’s Vineyard! NEW ! Build in 2020 !
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Build in 2020 ! New lovely studio apartment. Clean, bright and comfortable. 700 sq feet ! Great for couples, work trip ...
From $293 per night (USD)VRBO
From $2949 per night (USD)Expedia
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Our amazing property is a perfect place to spend with family and friends! The property is wonderful for everything from ...
From $2949 per night (USD)Expedia
From $527 per night (USD)VRBO
Sunny 3 bedroom cape with large deck, porch and kayaks. Pet friendly.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Seaside serenity awaits you at this Oak Bluffs retreat! Immerse yourself in the charms of island life while staying at t ...
From $527 per night (USD)VRBO
From $902 per night (USD)VRBO
New to the rental market! Air conditioned family home, 1 mile from Circuit Ave
- Bedrooms:
- 0
- Bathrooms:
- 4
- Sleeps:
- 10
New rental! Get away from it all in this Oak Bluffs secluded family friendly home offering 4 bedrooms, 2 full bathrooms, ...
From $902 per night (USD)VRBO
From $809 per night (USD)VRBO
Family friendly, walking distance to town, harbor, shops, restaurants, beaches
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 6
Canary Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $809 per night (USD)VRBO
From $642 per night (USD)Expedia
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Nestled in the charming town of East Chop, this 3-bedroom vacation home offers the perfect escape for your next getaway. ...
From $642 per night (USD)Expedia
From $707 per night (USD)VRBO
Modern Apt Near Martha's Vineyard Beaches!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Whether you’re embarking on a couple’s weekend retreat or an upscale beach adventure with friends, this Oak Bluff vacati ...
From $707 per night (USD)VRBO
From $335 per night (USD)Expedia
Dog-Friendly Downtown Home w/Free WiFi, Deck, Water Views, & Partial A/C
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Marsh Walk Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $335 per night (USD)Expedia
Click For PricingVRBO
Charming salt box in quiet woodsy neighborhood - centrally located!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful Fireplace! Hardwood floors throughout. A spacious kitchen with updated appliances - plus, a propane grill for ...
Click For PricingVRBO
Click For PricingExpedia
Vineyard charm island memories
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
Great location,wonderful front porch,incredible kitchen,outdoor gas grill,walking distance to downtown,beaches,A/C,Marth ...
Click For PricingExpedia
From $810 per night (USD)VRBO
Peaceful Summer Oasis
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
4 bedroom 2 bathroom home on a quiet street. The outdoor swing provides a lovely outdoor spaces reading snd relaxing. ...
From $810 per night (USD)VRBO
From $617 per night (USD)Expedia
Quintessential Martha's Vineyard cottage with yard/patio - walk to Inkwell Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Pinkletink Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $617 per night (USD)Expedia
From $791 per night (USD)VRBO
COZY 3 BR/2 BA CAPE COD IN QUIET NEIGHBORHOOD. CLOSE TO OB CENTER AND LAGOON.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Located in the beautiful Lagoon Heights neighborhood, you'll enjoy this lovely 3 Bedroom, 2 Bath cozy Cape Cod home with ...
From $791 per night (USD)VRBO
From $1033 per night (USD)VRBO
Fresh Quiet Hidden Gem, Pet & Kid Friendly, close to V.T.A., VH and farmstand-5*
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Sea Glenn Flowers is a beautiful home located in the heart of Martha's Vineyard, a short drive from all the amenities of ...
From $1033 per night (USD)VRBO
From $508 per night (USD)VRBO
In the heart of East Chop. Walks on East Chop Dr. Then relax on the private deck
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Great East Chop (Oak Bluffs) location! Take morning walks on world famous East Chop Drive, or watch the sunset from ther ...
From $508 per night (USD)VRBO
From $1771 per night (USD)VRBO
An Oasis on Martha's Vineyard-A 4 Bedroom 4.5 Bath Home In Historical Oak Bluffs
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This newly renovated, beautifully landscaped, air conditioned, spacious 3 level Cape Cod style home is situated on a qui ...
From $1771 per night (USD)VRBO
From $612 per night (USD)VRBO
Bright Modern House AC 3full baths, 3+ bedrooms, 2 balconies, deck & parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Bright air conditioned house has common space living TV room, dining and kitchen together. 1st floor has 1 bedroom with ...
From $612 per night (USD)VRBO
From $744 per night (USD)VRBO
Centrally located home in private neighborhood of Oak Bluffs.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Relax and unwind in this comfortable spacious 3 bedroom 2 bath open concept home in a quiet neighborhood. Enjoy your di ...
From $744 per night (USD)VRBO
From $1122 per night (USD)VRBO
Spacious 5-bedroom house with AC and WiFi in brilliant Oak Bluffs
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Perched on a grassy hill, this majestic home has sweeping views of Oak Bluffs Harbor and is just minutes from East Chop ...
From $1122 per night (USD)VRBO
From $1201 per night (USD)Expedia
Oak Bluff's Victorian Walk to Town & Beaches
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
About this space First floor has AC and hosts windowed living, dining, work space, kitchen and garden apartment that sle ...
From $1201 per night (USD)Expedia
From $706 per night (USD)VRBO
Location , Location , Location ! Walking distance to the beach.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Bellavista at the Seaview. This oceanfront condo is a coveted two bedroom , two bathroom home that was comple ...
From $706 per night (USD)VRBO
From $887 per night (USD)Expedia
Charming home near downtown & beach with patio, outdoor shower, grill, & W/D
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Blissful Island Haven Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $887 per night (USD)Expedia
From $726 per night (USD)VRBO
Cozy vineyard cottage close to downtown with outdoor living space and amentiies.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
2 Decks, hot tub and close to everything. Has all new stainless appliances, wi-fi, cable, grill, about one mile walk t ...
From $726 per night (USD)VRBO
From $1097 per night (USD)VRBO
Heart of Oak Bluffs - A Newly Renovated Gem, 5 Minute Walk to Town!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover the perfect blend of location and luxury in this beautifully renovated charmer, centrally situated in Oak Bluff ...
From $1097 per night (USD)VRBO
From $584 per night (USD)VRBO
Walking to the beach. Bars and Restaurants.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Walking distance to the beach. 5 minutes away from downtown, steamship, ice cream, and restaurants. Lovely backyard with ...
From $584 per night (USD)VRBO
From $688 per night (USD)Expedia
Private island house with close beach access and water view from deck
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 10
Soundmeadow House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $688 per night (USD)Expedia
From $1636 per night (USD)VRBO
Lagoon Waterfront 3 Bedroom Private Sandy Beach Oak Bluffs Martha's Vineyard \n
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
This three-bedroom idyllic vacation home offers the perfect escape for a truly memorable summer vacation on Martha's Vin ...
From $1636 per night (USD)VRBO
Click For PricingExpedia
Cozy Family Cottage Circuit Ave OB Walk to Everything
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Stay comfortably in Oak Bluffs at this 4-bedroom cottage. With 2 full beds a twin beds, this quaint property is perfect ...
Click For PricingExpedia
From $468 per night (USD)VRBO
Charming studio with amazing location near town & beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Sankofa Studio Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $468 per night (USD)VRBO
From $1229 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 $1229 per night (USD)Expedia
From $391 per night (USD)VRBO
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 $391 per night (USD)VRBO
From $779 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 $779 per night (USD)Expedia
From $1354 per night (USD)VRBO
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 $1354 per night (USD)VRBO
From $847 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 $847 per night (USD)Expedia
From $642 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 $642 per night (USD)VRBO
From $815 per night (USD)VRBO
Delightful and Roomy 4-bedroom house in OB, 4 bed, 4 bath, Central A/C
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Make yourself at home in this fabulous 4-bedroom Oak Bluffs retreat. With 3 queen beds, 2 twins, and 2 sofa beds, this a ...
From $815 per night (USD)VRBO
From $793 per night (USD)VRBO
Charming 3-bedroom w/loft.New Construction home with AC,WiFi. Short walk to town
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This Oak Bluffs home boasts 3 inviting bedrooms and a cozy loft, including 2 king beds, 2 full beds and a queen sofa bed ...
From $793 per night (USD)VRBO
From $846 per night (USD)Expedia
House with guest studio close to town and beach with grill, games, AC & patio
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Sankofa Martha's Vineyard Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $846 per night (USD)Expedia
From $1201 per night (USD)VRBO
Modern Cottage Walk To Town & Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy one of Oak Bluffs’ newest accommodations perched at the peak of the Highlands boasting just a 10 minute walk to to ...
From $1201 per night (USD)VRBO
From $866 per night (USD)VRBO
Charming 3-bedroom house in Oak Bluffs with AC, WiFi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to Noble House, your ideal getaway on Martha’s Vineyard. Nestled in the heart of Oak Bluffs at 21 Pheasant Lane, ...
From $866 per night (USD)VRBO
From $1029 per night (USD)VRBO
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)VRBO
From $429 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 $429 per night (USD)Expedia
From $465 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 $465 per night (USD)VRBO
From $1192 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 $1192 per night (USD)Expedia
From $417 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 $417 per night (USD)VRBO
From $361 per night (USD)Expedia
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 $361 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 $584 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 $584 per night (USD)VRBO
From $977 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 $977 per night (USD)VRBO
From $503 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 $503 per night (USD)VRBO
From $882 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 $882 per night (USD)VRBO
From $729 per night (USD)VRBO
Oak Bluffs Retreat! Spacious Vineyard Home Near Beaches & Downtown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to your home away from home! Experience the charm of Oak Bluffs in this spacious 3-bedroom, 2.5-bathroom beautif ...
From $729 per night (USD)VRBO
From $661 per night (USD)VRBO
Charming 3-bedroom house in OakBluffs, walking distance to Circuit Ave!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Nestled in Oak Bluffs, this delightful house offers 4 bedrooms including 1 king bed, 2 queen beds, and 1 bunk bed. With ...
From $661 per night (USD)VRBO
From $2872 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 $2872 per night (USD)VRBO
From $3468 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 $3468 per night (USD)VRBO
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 $2406 per night (USD)VRBO
Gorgeous 7BR/6BA Ocean views Walk to Beach & Town - 10% off two week stay!
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 10
Large Private Home formerly known as the SeaSpray Inn and featured on the reality television show "The Vineyard", this l ...
From $2406 per night (USD)VRBO
From $802 per night (USD)VRBO
Perfect location! Beach, Harbor & Town. Beautiful 1st Floor Apartment Oasis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This lovely, in-town, first-floor apartment is in a renovated 1800's historic Oak Bluffs cottage with a fenced in landsc ...
From $802 per night (USD)VRBO
From $724 per night (USD)VRBO
Private Waterfront, Beachfront, and 90' Dock. Views. Newly Renovated 3Bd 2.5Bath
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Spectacular water views from classic Martha's Vineyard waterfront home! Perched atop a bluff overlooking the Nantucket ...
From $724 per night (USD)VRBO
From $642 per night (USD)VRBO
Walk to OB Restaurants, Shopping, Harbor & Beaches! Winter monthly rental avail.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This beautiful, open concept, fully furnished home is just footsteps to Sunset Lake, harbor, beaches, entertainment, res ...
From $642 per night (USD)VRBO