Oak Bluffs is one of the most charming towns in Massachusetts. Known for its idyllic beaches and laid-back islands, it’s the perfect destination to get away from the stress of daily life. Swimming, sightseeing, and relaxing are what this coastal town has to offer. The best part? Whether you’re bringing a car or not, it won’t make much of a difference since everything is close to one another. You can enjoy scenic walks or explore the town by bike. For stay, check out our list of the top Airbnb vacation rentals in Oak Bluffs, Massachusetts.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on April 09, 2024.
1. Brick-walled home with an expansive backyard (from USD 300)
Another excellent accommodation for two is this brick-walled home. Featuring an expansive backyard containing a mini garden with blooming flowers and lush trees, this home is an ideal dwelling place for travelers who are after a breath of fresh air. The backyard also contains a table with two seats, a perfect place to enjoy your morning coffee. Its bedroom is spacious and has the comfiest bed that guarantees a good night’s rest. With its location, you’ll have easy access to Oak Bluff’s main attractions, including public beaches and restaurants.
Top guest reviews
Amenities & Room:
plenty of room for two people and great amenities in the housefully standalone cottage open timber construction with fully equipped kitchen and very clean modern amenitiesthe living room provided more than plenty of space for relaxingthe outdoor shower and patio area were fabulous and the house was spacious while still feeling cozysuper cute and clean place for 2 loved having the amenities of an apartment for the week vsCleanliness:
very clean and comfortableexceptionally clean very private and modernthe place is very clean and spaciousthe place is beautiful - very clean and comfortableit was beautifully decorated and spotlessly cleanHost:
thank you for being a wonderful accommodating hostsusan is a delightful host toosusan was a wonderful host and was readily available to answer any questions we hadsusan was a great hostsusan is an outstanding hostRead more reviewsLocation:
great central location short walk to townthe location is greatgreat location walking distance to downtown oak bluffsthe place and location was perfectan excellent mix of location and privacy
Superhost
2. Charming condo with modern amenities (from USD 229)
Surprise your loved ones with a holiday treat to one of the city’s most stunning accommodations. An entire condo unit to your disposal, promising you an unforgettable trip. With wood ceilings that complements its all-white walls and furnishings, everything about this condo will make you want to stay indoors. This studio includes a functional kitchen, a full bathroom, a cozy couch, and a queen-size bed that can sleep up to four people. Those looking for a more active holiday, there’s an outdoor pool and tennis courts available on the premises. Plus, Martha’s Vineyard and Joseph Sylvia State Beach are located nearby.
Top guest reviews
Cleanliness:
this place was spotless the beds were very comfortable and so cleancute spot clean and comfyvery clean place close enough to shops and beachesRead more reviewsHost:
nice place and the people was very helpfulgreat facility small efficiency apartment friendly staff
3. One-bedroom home with shared patio (from USD 646)
If you’re looking for a place to stay that is close to everything the town has to offer, we’d recommend booking this charming home. Located within walking distance to town and the beach, this one-bedroom home is ideal for both solo and couple travelers. Its kitchen and dining area are well-equipped. The bathroom contains all the necessities you’ll need for a great shower. The best part? It has a patio and a deck containing lounge seats, perfect for basking under the sun.
Top guest reviews
Amenities & Room:
loved the full kitchen and washer and dryerbrian's place is in a great location-next to tony's market- very convenient- excellent coffee and breakfast sandwichesi loved the big tv in the bedroom with an exceptional selection of free moviesthe cottage made for a great and cozy off-season first time visit to martha’s vineyardvery comfortable bed and everything we needed was thereCleanliness:
very clean easy check inthe condo is very clean and cozyextremely clean and great for two peoplethe appartment was really clean and well equipedthe place was very clean and well equippedHost:
very fast and friendly responses to questionshighly recommend and thank you to brian for being a great hostbrian was a great hostbrian was a great host we would highly recommend this place to anybodyhost provided hand sanitizer and other ppe that was super helpfulRead more reviewsLocation:
location is great toothe house and location were idealgreat location easy walk to shopping and beachesnice place and great locationgreat cute spot within walking distance of all the action in oak bluffs
4. Beachfront cottage with amazing views (from USD 350)
Feel right at home in this beautiful beachfront cottage right on the famous Martha’s Vineyard. One of the places you shouldn’t miss when in Oak Bluffs is the stunning Martha’s Vineyard- and what’s better than choosing an accommodation that seats right on it? By choosing to stay here, you’ll have all the time you need to explore its beauty. Its surrounding nature is also a plus. With its expansive bedroom, it’s the perfect retreat for couples. It also has a fire pit and other amenities that will guarantee a great stay.
Top guest reviews
Cleanliness:
wonderful clean and stocked cottagethe place is clean and privatethe house was very clean and invitingit was very clean and right on the waterthe bed is very comfortable and everything is very cleanHost:
anne was a wonderful host and very responsiveanne is a great host toomany thanks to our exellent hostsanne was an excellent host 10/10 would recommendanne and greg are fantastic hostsRead more reviewsLocation:
an incredible location and beautiful cabinthe location was close to town but still quiet and peacefulwe received detailed location instructions and great local tipslocation makes it easy to get to vineyard haven oak bluffs or edgartown for shopping or food/drinksexcellent location direct access to the beach
5. Simple and cozy home with a private entrance (from USD 214)
Experience a simple country retreat in this cozy studio home in a barn, which can accommodate three guests. It’s a private apartment on the second floor of the owner’s workshop, which has its private entrance. Its kitchen is functional, and the bathroom is in pristine condition. It’s an ideal home to stay in if you’re one of those people who love to explore rather than spending their time lounging at home. One of the things to love about this home is its serenity, especially after a long day of being out on the busy streets of the town.
Top guest reviews
Amenities & Room:
cute space with everything you need for an overnight stay including coffee tea and air conditioningthe bed was super comfy and the coffee provided was wonderful toothe king size bed had a new mattress so i slept like a rockher barn is nicely decorated and has all amenities needed to have a comfortable stayfrank is a big fan of barns and he loved studying the incredible constructionCleanliness:
clean and peacefulclean and loving flatthe place was clean and comfortablevery nice clean and spacious roomthe space is gorgeous clean and modernHost:
the host was super quick to respond to our questionsthe hosts are responsive and kindgreat hosts too highly recommendcorrina was very accommodating and went out of her way to make us feel welcomecorinna was a perfect host and did everything she could to make us feel at homeRead more reviewsLocation:
wonderful place in a great locationgreat central spot for visiting the islandperfect location away from the hustle of oak bluffs but easy to walk or ride intogreat location we walked to and from townlocation is super close to downtown the beaches and ferry terminal
6. Two-bedroom home with a lovely interior (from USD 88)
One thing you’ll notice about this home is how everything inside is either grey or white, aside from the other wood furnishings. Its interior is aesthetically pleasing to the eyes. The two massive bedrooms have queen-size beds that can sleep up to four guests. The living room is elegant. With a long cozy couch, a bean bag, and wide flat-screen TV, recharging will be easy. And if you’re someone who prefers making your meals, the kitchen is ready for you to use. Also, you might enjoy riding a bike around the neighborhood to witness some lovely views.
Top guest reviews
Amenities & Room:
wifi was great as well as the streaming services on the living room tvupdated tv's in all rooms and fans made the stay enjoyablejasmine did an incredible job making this 2 bed room apartment feel like a home away fromjasmine’s apartment was the perfect stay for our family of fourjasmine's place is perfect i stayed with 2 friends for 3 nights and we were more than comfortableCleanliness:
clean clean cleanclean cozy comfortable and convenientthe apartment was clean and cozythe place was spotlessly clean and spaciousit’s super clean and comfyHost:
host was gracious and quick with responses no issues at alljasmine was a great hostthe host is very responsive and nicejasmine is a wonderful host and goes above and beyond in servicejasmine was a great hostRead more reviewsLocation:
the location was idealgreat spot close to everythinggreat location close to oak bluffsgreat location away from the hustle and bustlegreat place in a convenient location
7. Stylish home with a tropical ambiance (from USD 275)
Experience the best of Oak Bluffs with style. This brand new luxurious home near the beach is the perfect escape. It has a tropical vibe that complements its setting, with the beach being just a few steps away. The bedroom is spacious and contains an artsy wall decor, a vanity, and a queen-size bed. Apart from its great exterior, the interior of the house is picture-worthy. Upon entry, the cozy living room containing two comfy couches with throw pillows will welcome you. Adjacent to it is an L-shaped kitchen and a well-organized dining area.
Top guest reviews
Amenities & Room:
the living room furniture was super comfortable the dining chairs tooit has heating air conditioning and overhead fans which means it’s lovely in any weathereasy check-in new and nicely decorated…comfortable bed and nice bath/hot tub linensCleanliness:
the place is lovely very clean and cozyeverything was stylish clean and well laid outeverything was perfect super clean new and modern and so comfortable you will not be disappointedthis place is beautiful very light super stylish clean quiet - very homeyit was very clean and cute and we would definitely rent it againHost:
very responsive ownersshe is helpful and responsivedawn and richard are great hosts always available to answer any questionsdawn was a wonderful host responsive and easily reacheddawn was very responsive and helpful hostRead more reviewsLocation:
beautifully designed and decorated guest house with easy access to bus lines and lagoon pond beachalso a nice central location and easy to get anywhere on the islanddawn’s place is an ideal spot for a couple to enjoy a vacation on martha’s vineyardmy husband and i felt cozy and comfortable from the minute we walked inbeautiful space great hosts close to oak bluffs would thoroughly recommend
8. Three-bedroom home with a pristine bathroom (from USD 800)
This recently renovated home is close to downtown and features top-notch amenities. Surrounded by tall trees, this home offers a whole lot of privacy. It has three bedrooms, which feature dim-colored walls and furnishings. It can accommodate six guests, making it ideal for small groups. One of the places in the house that you’ll love is the bathroom. It’s pristine, has a vanity, and the walls are white, which makes it perfect for taking bathroom mirror selfies. Apart from that, its large deck is also a plus. The lagoon is also nearby.
Top guest reviews
Amenities & Room:
one of my favorite amenities was the outdoor showerthe space is well lit open and very comfortableRead more reviewsLocation:
close to oak bluffs' main streets it's tucked far enough away to be restful and quietwonderful home great location close to everythingcaitlin's house is an absolutely wonderful location with great touches for your time on mvyou’re also really close to tony’s market and some other good restaurantsgreat location comfortable clean and accommodating fully equipped kitchen
9. Spacious home with an outdoor patio (from USD 199)
Its proximity to all the attraction in Oak Bluffs makes it an ideal place to stay for travelers who love to explore. It’s also convenient if you don’t have a car at your disposal. The house is spacious and has everything you’ll need for a comfortable stay, including a fully functional kitchen, a full bathroom, and a cozy living room. The bedroom is big enough to sleep up to four people. Apart from that, all furnishings and appliances are modern and in excellent condition, you won’t have to worry about tools not working. Make sure to enjoy a picnic on the outdoor patio.
Top guest reviews
Amenities & Room:
patio is nice with large grill and comfortable seating for 4the linens and mattress in the bedroom were comfortablemy favorite part of the cottage was the outside showerthe lawn furniture is comfortable and the gas barbecue / grill appears to be professional standardthe back yard is so private and comfortableCleanliness:
very clean and modernvery clean and comfortablethe space was clean and modernextremely clean and fantastic sitting area outsidevery clean up to date propertyHost:
beautiful property and great hostbrian is a great host who is knowledgeable about martha's vineyardbrian is a great host and the property is very nicelastly brian is a great host and was responsive to all of our questionshe was very nice and extremely responsiveRead more reviewsLocation:
amazing place in an awesome locationamazing location walk through the mv cottages to get to downtowngreat place downtown and beach was walking distanceeverything you need in a great location withthe location was wonderful in oak bluffs right near the downtown and adjacent to a grocery/convenance store
10. Homey cottage with a porch (from USD 300)
Immaculate is the word that best describes this homey cottage in the serene neighborhood of Oak Bluffs. From its walls to its furnishings, everything in the house is white with a hint of grey and pink, making the place look elegant. It’s a two-story house that can accommodate two guests. The first level contains a cozy living room, a half bathroom, and a functional kitchenette. The outdoor porch has a table that can seat up to six people and an umbrella for when it’s a sunny day. On the second floor, there’s a bedroom and a mini lounge. It’s the perfect getaway!
Top guest reviews
Amenities & Room:
the cottage was cozy warm and filled with carethe ac unit upstairs made our sleep very comfortablethe bedroom upstairs was cozy and the ac was perfectit is super cozy and stylish with so many amenitiesthe cute touches of flowers towels and shampoo in the outside shower were greatCleanliness:
the cottage was lovely spotlessly clean and tastefully decoratedthe place was very clean and a great cottage to stay in for a couple daysa little slice of heaven clean comfortable & cuteit was cute clean and comfortableHost:
jayme was a wonderful hostjayme was a fantastic host - we especially appreciated her quick responses and helpful tipsgreat place and fantastic hostjayme was an incredible host - whenever we reached out with questions her responses were fast & helpfuljayme was very helpful and accommodatingRead more reviewsLocation:
the location was perfectlocation was great to downtown oak bluffslocation is convenient and beautiful toogreat location for walking or biking distance to local establishments but yet quiet and relaxinggreat location near beaches ferry and restaurants
Scenic walks and lovely times in Oak Bluffs
Whether you’re after a relaxing time or an adventure, Oak Bluffs is always a great choice. With its stunning coasts and charming streets, you’ll have a lot of things you can do to keep yourself entertained. Be sure to check out our above list of the top Airbnb vacation rentals in Oak Bluffs, Massachusetts, for an unforgettable stay.
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