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

Filter

Popular Areas

From $3313 per night (USD)
VRBO
Glorious Sunsets and Fun on Private Waterfront in Beautiful, Comfortable Home.
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
3200 sq ft.waterfront, highly energy efficient, 4 bedroom plus flex room (sleeps 8-10 adults plus 3-4 children (max 12)) ...
From $3313 per night (USD)
VRBO
From $1063 per night (USD)
VRBO
Charming 6 Bedroom Cottage in East Chop with Water Views! Walk to Beach & Town!
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
This charming Vineyard home recently completed a large renovation including all new bathrooms, a new, large bunk room an ...
From $1063 per night (USD)
VRBO
From $1042 per night (USD)
VRBO
Quintessential MV home near Oak Bluffs, beach & harbor
Bedrooms:
4
Bathrooms:
4
Sleeps:
9
Pirate’s Cove is a quintessential Martha’s Vineyard vacation home tucked away on a quiet lane in East Chop, just minutes ...
From $1042 per night (USD)
VRBO
From $273 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 $273 per night (USD)
VRBO
From $489 per night (USD)
VRBO
WALK TO BEACHES,HARBOR,EVERYTHING!! IN-TOWN OB! A/C,Large Deck,Gazebo,Yard
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
***IMPORTANT--PLEASE "MESSAGE " HOST FIRST----BEFORE SENDING A BOOKING REQUEST!! ( JUST CLICK ON " CONTACT HOST" (you ...
From $489 per night (USD)
VRBO
From $1314 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 $1314 per night (USD)
Expedia
From $1084 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 $1084 per night (USD)
VRBO
From $757 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 $757 per night (USD)
VRBO
From $447 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 $447 per night (USD)
VRBO
From $1806 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 $1806 per night (USD)
VRBO
Click For Pricing
VRBO
1-Bedroom cottage, 200ft from the beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
1-bedroom cottage. Completely separate from the larger house. Easy access from both front and back yards. Half a block ...
Click For Pricing
VRBO
From $874 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 $874 per night (USD)
VRBO
From $893 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 $893 per night (USD)
VRBO
From $1454 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 $1454 per night (USD)
VRBO
From $664 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 $664 per night (USD)
VRBO
From $820 per night (USD)
Expedia
Sunny 3 bedroom cape with large deck, porch and kayaks. Pet friendly.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
**Ferry reservations available at request for 7/3-7/10 and 7/24-7/31** Seaside serenity awai ...
From $820 per night (USD)
Expedia
From $865 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 $865 per night (USD)
VRBO
From $1319 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 $1319 per night (USD)
Expedia
From $849 per night (USD)
VRBO
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Our amazing property is a perfect place to spend with family and friends! The property is wonderful for everything from ...
From $849 per night (USD)
VRBO
From $2218 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 $2218 per night (USD)
Expedia
From $307 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 $307 per night (USD)
VRBO
From $1271 per night (USD)
Expedia
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 $1271 per night (USD)
Expedia
From $816 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 $816 per night (USD)
VRBO
Click For Pricing
VRBO
Lagoon Waterfront 4 Bedroom Private Sandy Beach Oak Bluffs Martha's Vineyard
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Idyllic Lagoon Front Vacation Home – Oak Bluffs This 4 bedroom, 3.5 bath retreat is the perfect escape for a memorable ...
Click For Pricing
VRBO
From $1965 per night (USD)
VRBO
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 bedroom that sleep ...
From $1965 per night (USD)
VRBO
From $1850 per night (USD)
Expedia
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 $1850 per night (USD)
Expedia
From $1095 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 $1095 per night (USD)
VRBO
From $1074 per night (USD)
Expedia
Charming 3-bedroom w/loft.New Construction home with AC,WiFi. Short walk to town
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
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 $1074 per night (USD)
Expedia
From $801 per night (USD)
VRBO
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 $801 per night (USD)
VRBO
From $809 per night (USD)
Expedia
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 $809 per night (USD)
Expedia
From $715 per night (USD)
VRBO
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 $715 per night (USD)
VRBO
From $627 per night (USD)
Expedia
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 $627 per night (USD)
Expedia
From $1266 per night (USD)
VRBO
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 $1266 per night (USD)
VRBO
From $801 per night (USD)
Expedia
< 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 $801 per night (USD)
Expedia
From $2446 per night (USD)
VRBO
Luxury 4-Bedroom Property with Private Beach on Seaview Ave in Oak Bluffs
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Set back off a bluff with expansive views of Nantucket Sound and beyond to Chappy is this sophisticated waterfront home ...
From $2446 per night (USD)
VRBO
From $650 per night (USD)
VRBO
Walk to Beach Spacious Retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Escape to The Winthrop, a refined Vineyard retreat set on a serene ⅓ acre just moments from the heart of town. Thoughtfu ...
From $650 per night (USD)
VRBO
From $485 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 $485 per night (USD)
VRBO
From $372 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 $372 per night (USD)
VRBO
From $4388 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 $4388 per night (USD)
VRBO
From $1799 per night (USD)
VRBO
Peaceful East Chop Vineyard 6-BR 4-full BA home, AC, large yard, In-law apt.
Bedrooms:
4
Bathrooms:
6
Sleeps:
10
Located in exclusive East Chop area of Oak Bluffs, enjoy what this 6-bedroom house has to offer. Walk to beach, a safe, ...
From $1799 per night (USD)
VRBO
From $844 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 $844 per night (USD)
VRBO
From $383 per night (USD)
Expedia
Make Lasting Memories In This Adorable Vineyard Cottage!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Our quaint Cottage is nestled in a quiet neighborhood of Oak Bluffs - perfect for a romantic getaway, a special place to ...
From $383 per night (USD)
Expedia
From $636 per night (USD)
VRBO
Walk to OB Restaurants, Shopping, Harbor & Beaches! Perfect Location, large yard
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This beautiful, open concept, fully furnished home is just footsteps to Sunset Lake, harbor, beaches, entertainment, res ...
From $636 per night (USD)
VRBO
From $3294 per night (USD)
VRBO
101 Ocean Ave. On the corner of Inkwell beach and Ocean park.
Bedrooms:
5
Bathrooms:
7
Sleeps:
14
Perched on the corner of Ocean Park overlooking Nantucket Sound and across the street from the beach, this elegant home ...
From $3294 per night (USD)
VRBO
From $9022 per night (USD)
VRBO
THE PARK ESTATE! Your Martha's Vineyard Getaway!
Bedrooms:
5
Bathrooms:
6
Sleeps:
16
Our amazing property is a perfect place to spend with family and friends! The property is wonderful for everything from ...
From $9022 per night (USD)
VRBO
From $526 per night (USD)
VRBO
Downtown Oasis, Walk to Beach: Vineyard Vacation Houses Welcomes You!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This lovely, in-town, Garden Level apartment is in a renovated 1800's historic Oak Bluffs cottage. The fenced in back pa ...
From $526 per night (USD)
VRBO
From $514 per night (USD)
VRBO
Fully Renovated & Spacious home within walking distance of Oak Bluffs / Beaches
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Newly renovated three-level home with three bedrooms and two bathrooms within walking distance to the heart of Downtown ...
From $514 per night (USD)
VRBO
From $1742 per night (USD)
VRBO
Martha’s Vineyard 7 Bedroom Vintage Home! 15 min walk to beaches and Oak Bluffs!
Bedrooms:
2
Bathrooms:
7
Sleeps:
16
Fantastic home available from May to October. Seven Bedrooms, one den with pull out couch, two bathrooms and a dreamy o ...
From $1742 per night (USD)
VRBO
From $596 per night (USD)
VRBO
3-BR Oak Bluffs Retreat Near Towns & Beaches
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Escape and exhale in this bright, airy 3-bedroom, 2.5-bathroom retreat that sleeps up to 7. Peaceful and centrally locat ...
From $596 per night (USD)
VRBO
From $2126 per night (USD)
VRBO
9 Bedroom Home in Oak Bluffs with Ocean Views & A/C
Bedrooms:
6
Bathrooms:
9
Sleeps:
18
Completely renovated and updated home in Oak Bluffs across the street from Waban Park and a short walk to Inkwell Beach. ...
From $2126 per night (USD)
VRBO
From $830 per night (USD)
VRBO
Hideaway At Meadow View Farm/Private Tennis Courts with Spacious Bedrooms
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This Martha’s Vineyard Hideaway is nestled in the desirable Meadow View Farms area of Oak Bluffs, and includes access to ...
From $830 per night (USD)
VRBO
From $308 per night (USD)
VRBO
Martha’s Vineyard studio
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Studio apartment on highly sought resort island of Martha’s Vineyard. 500 square feet with private entrance, bathroom, ...
From $308 per night (USD)
VRBO
From $1030 per night (USD)
VRBO
Oak Bluffs Retreat, Walk to Town, Harbor, Ferries
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Escape to our charming 3-bed, 2.5-bath Oak Bluffs home! Perfect for families, this bright retreat features central AC, a ...
From $1030 per night (USD)
VRBO
From $1526 per night (USD)
VRBO
Famous Gingerbread House named Seashrimp across from Oak Bluffs Harbor
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Year-round in-town Historical Famous Seashrimp Gingerbread House across from harbor/Nancy's all on the water restaurants ...
From $1526 per night (USD)
VRBO
From $1003 per night (USD)
VRBO
Heart of Oak Bluffs, No Car Needed! Ocean Views, Walk to Everywhere!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
** NEW HVAC AIR CONDITIONING * Welcome to “Gem of the Ocean”! Martha’s Vineyard vacationers dream! This beautiful condo ...
From $1003 per night (USD)
VRBO
From $1694 per night (USD)
Expedia
Beautiful Custom Home In Oak Bluffs
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Discover 4 spacious bedrooms with well planned living space with a inviting porch that wraps around 3/4 of the house is ...
From $1694 per night (USD)
Expedia
From $1043 per night (USD)
VRBO
The Legacy House: Walk to Inkwell Beach + Historic Charm, Modern Comfort
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Step into the timeless charm of Oak Bluffs while enjoying the comforts of a thoughtfully renovated home. The Legacy Hous ...
From $1043 per night (USD)
VRBO
From $1380 per night (USD)
Expedia
Indulge in the ultimate vacation experience at this exquisite custom log home.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Turnover days are Saturday to Saturday Experience the ultimate in luxury and relaxation in the exclusive Eastville area ...
From $1380 per night (USD)
Expedia
From $510 per night (USD)
VRBO
Fully Renovated & Spacious home walking distance to downtown Oak Bluffs/Beaches
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Newly renovated (2024) three-level home with 3 bedrooms 2 bathrooms within walking distance to the heart of Downtown Oak ...
From $510 per night (USD)
VRBO
From $829 per night (USD)
Expedia
Charming Vacation Home in Oak Bluffs.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Just a stone away from Oak Bluffs and its beaches, this chic 4 bedroom home provides comfort and privacy. The large bedr ...
From $829 per night (USD)
Expedia
From $714 per night (USD)
VRBO
OB Cozy-Cottage-Glam off Circuit with Great Outdoor living
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Location!!! Location!!! This updated cottage is a quick walk to town, beach, Tony’s Deli, tennis and basketball courts, ...
From $714 per night (USD)
VRBO
From $1376 per night (USD)
Expedia
** Vineyard Vacation Retreat ** with HOT TUB
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Gated 2br house with lots of different places to lounge and relax. Drive through the 10’ granite gate onto the shell dri ...
From $1376 per night (USD)
Expedia
From $1636 per night (USD)
VRBO
**Vineyard Vacation Retreat** -3 BR
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Just a stone's throw from Oak Bluffs and it's beaches, this chic 3 bedroom home provides comfort and privacy. The large ...
From $1636 per night (USD)
VRBO
From $457 per night (USD)
VRBO
Tree Top Suite Get-Away
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Our beautiful suite has a private entrance, is a walk down an old fashioned dirt road to a private beach and also right ...
From $457 per night (USD)
VRBO
From $987 per night (USD)
VRBO
Vineyard Social-Spacious 5BR Home in Oak Bluffs
Bedrooms:
4
Bathrooms:
5
Sleeps:
14
Experience comfort and style in this newly completed 5-bedroom home just 1 mile from downtown OB. The home features fant ...
From $987 per night (USD)
VRBO
From $720 per night (USD)
Expedia
New 2 min from Circuit ave
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
* new for 2025: Gameroom with pool table and ping pong table. * Welcome to this beautifully renovated home, located wit ...
From $720 per night (USD)
Expedia
From $1786 per night (USD)
VRBO
Oceanview East Chop Beach House - 4 Bed/2 Bath - 5 min walk to beach
Bedrooms:
1
Bathrooms:
4
Sleeps:
9
The perfect vacation awaits you at Frog Prince Cottage in beautiful East Chop, the finest neighborhood in Oak Bluffs. Ou ...
From $1786 per night (USD)
VRBO
From $785 per night (USD)
Expedia
Spacious 4 BR Home, Steps to Lagoon, Minutes to Downtown Oak Bluffs and Beaches!
Bedrooms:
2
Bathrooms:
5
Sleeps:
8
Spacious two-level four-bedroom house within steps to lagoon located in Oak Bluffs and within minutes (2 Miles) to Downt ...
From $785 per night (USD)
Expedia
From $1270 per night (USD)
VRBO
Walk to town & beach A/C, Strong WiFi, family & pet friendly. Outdoor shower
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summertime! And the living is easy in this comfortable, casual home on Martha's Vineyard. The large front deck is great ...
From $1270 per night (USD)
VRBO
From $951 per night (USD)
Expedia
Charming, Victorian in East Chop
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Relax with the whole family at this peaceful place to stay. Ideally located in East Chop, in walking distance to the B ...
From $951 per night (USD)
Expedia
From $1223 per night (USD)
VRBO
Oak Bluffs Rental - Walk to the Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
This 3 bedroom, one and a two half baths with an outdoor shower, is located on a quiet backroad in East Chop, Oak Bluffs ...
From $1223 per night (USD)
VRBO
From $750 per night (USD)
Expedia
Lovely two bedroom apartment with indoor fireplace
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
It’s very cozy and comfortable, New Construction, if you like to do walk is close to the path and trial, ride bikes, it ...
From $750 per night (USD)
Expedia
Click For Pricing
VRBO
Enchanting bungalow with golf nearby, full kitchen, central AC, & washer/dryer
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Summary: East Chop 90 The Space: Welcome to coastal living on the East Chop, a perfect place to bring loved ones fo ...
Click For Pricing
VRBO
Click For Pricing
Expedia
Historic 11 room Full House Rental in Oak Bluffs walking distance to beach
Bedrooms:
7
Bathrooms:
12
Sleeps:
20
Nestled in the heart of Oak Bluffs, this expansive and beautifully designed home offers the ultimate getaway. Just a sho ...
Click For Pricing
Expedia
Click For Pricing
VRBO
Quintessential Martha's Vineyard cottage with yard/patio - walk to Inkwell Beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: The Pinkletink The Space: Full of classic island charm and beautiful views of the surrounding brush and we ...
Click For Pricing
VRBO
Click For Pricing
VRBO
BLUFF BREEZE - Timeless 6BR East Chop Compound
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
Summary: Nestled in the heart of East Chop, this timeless Oak Bluffs retreat offers an idyllic blend of nostalgic islan ...
Click For Pricing
VRBO
Click For Pricing
VRBO
Updated Coastal Oak Bluffs Retreat - AC, Patio, Walk to Town & Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
For offseason rentals, (fall and winter 2026-2027), please inquire for the dates you are interested in. We will respond ...
Click For Pricing
VRBO
From $874 per night (USD)
VRBO
Inca Gardens Apartment w Large Patio and Deck - Pets OK
Bedrooms:
1
Bathrooms:
4
Sleeps:
6
Inca Gardens is a 2nd-floor apartment of a cute house located in a quiet area of Martha's Vineyard between Oak Bluffs an ...
From $874 per night (USD)
VRBO
From $563 per night (USD)
VRBO
Family cottage in Oak Bluffs. Close to town
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Bright cottage for a small family or friends getaway with a large yard for lounging and outdoor dining. One mile from d ...
From $563 per night (USD)
VRBO
From $1032 per night (USD)
VRBO
Beautiful Oak Bluffs Home, Steps from the Lagoon
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Come enjoy this beautifully designed home. With 3 bedrooms and 3 full bathrooms you will have all the space you need. An ...
From $1032 per night (USD)
VRBO
From $586 per night (USD)
VRBO
Spectacular Martha's Vineyard Island Home!
Bedrooms:
2
Bathrooms:
3
Sleeps:
12
This is our beautiful home on Martha's Vineyard we call Shangri-La! Spectacular setting with a great peaceful view overl ...
From $586 per night (USD)
VRBO
From $902 per night (USD)
Expedia
Luxury Loft Historic Center Oak Bluffs
Bedrooms:
2
Bathrooms:
6
Sleeps:
14
This is a wonderfully designed contemporary loft space that is both chic and comfortable. The couches and chairs are do ...
From $902 per night (USD)
Expedia
From $2735 per night (USD)
VRBO
Fabulous Waterfront 3-Bedroom Martha's Vineyard Cottage
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
This quintessential Vineyard cottage was built in the 1920's, and retains most of its original charm and character. Loca ...
From $2735 per night (USD)
VRBO
From $1836 per night (USD)
VRBO
East Chop beach house, private beach with sunsets views.
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
Quintessential, beach cottage on East Chop near light house. Water views from almost every window. Beach, boating, wate ...
From $1836 per night (USD)
VRBO
From $877 per night (USD)
VRBO
Centrally located Oak Bluffs property next to Bike Path
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Welcome to our vacation rental in Oak Bluffs, Martha's Vineyard! Lovely home in the sought after Meadow View Farms commu ...
From $877 per night (USD)
VRBO
From $390 per night (USD)
VRBO
Perfect location! By Beach, Harbor & Town! Gorgeous Gingerbread Upstairs Aptmt
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
July and August: Turnover day is generally Friday. This lovely, in-town, impeccably renovated 1800's historic Oak Bluff ...
From $390 per night (USD)
VRBO
From $894 per night (USD)
VRBO
6 Beds! Walk to Beach, Ferry, Ocean Park and OB!
Bedrooms:
2
Bathrooms:
6
Sleeps:
12
Our home with 6 Bedrooms and incredible location will comfortably allow your family to vacation in the best part of Oak ...
From $894 per night (USD)
VRBO
From $624 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 $624 per night (USD)
VRBO
$\The Carousel House\ - Ocean Park - Featured in New York Times$
From $2050 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 $2050 per night (USD)
VRBO
From $1479 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 $1479 per night (USD)
VRBO
From $2197 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 $2197 per night (USD)
VRBO
From $4431 per night (USD)
VRBO
Waterfront House On Oak Bluffs Harbor
Bedrooms:
1
Bathrooms:
5
Sleeps:
10
Rarely available, large 5 bedroom home with 2 bathrooms and an outside shower right on Oak Bluffs Harbor. Great for fami ...
From $4431 per night (USD)
VRBO
From $319 per night (USD)
VRBO
Spacious 1 Bedroom Apt - 3 min Walk to the Beach!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
A perfect place for 1-4 people to stay! You will have plenty of room, shared use of a grill, backyard, and outdoor dinin ...
From $319 per night (USD)
VRBO

Search Your Destination Now!

Oak Bluffs Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 293 Rentals