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Holiday rentals in Oak Bluffs

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Quick stats about holiday rentals in Oak Bluffs

  • Total holiday rentals

    Explore 840 holiday rentals in Oak Bluffs

  • Nightly prices starting at

    Oak Bluffs holiday rentals start at $51 SGD per night before taxes and fees

  • Verified guest reviews

    Over 27,800 verified reviews to help you choose

  • Family-friendly holiday rentals

    570 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 190 rentals that welcome pets

  • Holiday rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    310 properties have a dedicated workspace

  • Wifi availability

    830 of Oak Bluffs holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Self check-in, Gym and BBQ grill across Oak Bluffs rentals

  • 4.8 Average rating

    Oak Bluffs stays are highly rated by guests – averaging 4.8 out of 5!

Top-rated holiday rentals in Oak Bluffs

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A spacious living room is highlighted by a large grey sectional couch adorned with various throw pillows. A wooden coffee table sits in front, featuring storage compartments. Two abstract paintings in calming blues are displayed above the couch, while soft lighting illuminates the area.
Guest suite in Oak Bluffs
4.95 out of 5 average rating, 432 reviews

Lovely 2 BR Oak Bluffs Apartment

This 100% private apartment is on the first floor of a shared house where owners and their son live upstairs. There are no shared spaces. You have a private entrance and parking. The living room, bedrooms, bathroom, and kitchenette are bright and clean. It is exactly 1 mile from Oak Bluffs Center, a half mile from The Cottages and Farm Neck Golf Course, and a block from Tradewinds walking trails. Across the street is the bike path, & the bus stop is on the corner for easy island transportation!

ValueLocationSleep quality

Guest favourite
Cottage in Oak Bluffs
4.92 out of 5 average rating, 26 reviews

#Islandbeachrose. Walk To Beach and Town!

Charming, 1870's Victorian beach cottage located in the highly desirable, historic Copeland District in Oak Bluffs on the island of Martha's Vineyard. Home not located in the Campground Trinity Park, it's 150 ft from downtown Oak Bluffs and short walk from the beach! No need for a car! Just grab a towel and walk to the beach! Lifeguards monitor the beach in the summer. Walk to the quaint boutiques and restaurants. Buses/Ferry services a stroll away! #Islandofmarthasvineyard MA ID #C0169742210

LocationValueOutdoor spaces

Top guest favourite
An open studio space features a cozy sleeping area with a spacious bed covered in light bedding. A soft armchair and a wooden bench provide additional seating. Natural light streams in from a window, enhancing the room's bright atmosphere. Shelving displays books and decorative items.
Flat in Oak Bluffs
4.98 out of 5 average rating, 239 reviews

Sunny Studio Apartment on Martha's Vineyard

Our Sunny Studio is centrally located on Martha's Vineyard. A down-island location with an up-island feel. Open and airy studio with kitchenette and bath. The apartment has all the essentials. The apartment is located within walking distance of hiking and biking trails. A 10 to 15 minute car ride to any down-island town / beach. ***Please Note: Although conveniently located we are not within walking distance to Bars or Restaurants. We do recommend first time visitors rent or bring a car.

LocationFamilyBeach

Top guest favourite
Home in Oak Bluffs
4.94 out of 5 average rating, 18 reviews

Casa Luca| Serene 3BR| SunRm, Outdr Shwr, A/C, BBQ

1 last summer week available! Tucked away on a quiet, private dead-end road in Oak Bluffs, this sun-filled three-bedroom retreat strikes the perfect balance: you’re close to everything the Vineyard has to offer (only 1 mile from Circuit Ave and OB Town Beach), yet the moment you turn onto that shaded dirt road, the outside world melts away. It’s the kind of neighborhood where kids can run freely in the yard, where the pace slows down, and where a vacation actually feels like a vacation.

ValueFamilyComfort

Top guest favourite
A charming two-story house is featured, showcasing shingle-style architecture and a welcoming front porch. White pillars support a broad balcony, while large windows allow for natural light. The well-maintained exterior is accented by a well-paved path and surrounding greenery.
Home in Oak Bluffs
4.98 out of 5 average rating, 58 reviews

Pinkletink Plantation

Your family will be close to everything when you stay at this centrally-located place. Less than a mile from the heart of Oak Bluffs and Circuit Ave., where you'll find all the famous restaurants, harbor & night life. A half mile from Eastville Beach (fabulous sunsets). Take a morning stroll around "the chop"-East Chop & walk or run a 5K. Less than 2.5 miles from Farm Neck Golf Club- & 2.5 miles to State Beach. It has a well equipped kitchen, laundry, outside shower, & back yard!

LocationFamilyGetting around

Guest favourite
A dining area features a dark wooden table surrounded by six chairs, with a combination of woven and painted finishes. Above, a chandelier with multiple lights hangs elegantly. A decorative mirror with a sunburst design is mounted on the wall, reflecting the soft, natural light.
Home in Oak Bluffs
4.78 out of 5 average rating, 137 reviews

Beach home just 0.8 miles to Farm Neck Golf Club!

Our home is located in the heart of Oak Bluffs!! This 3-unit property is in a quiet neighborhood, within walking distance of public transportation (0.4 miles), a mile from the pond, and only 0.8 miles to Farm Neck Golf Course. It is a short bike or car ride to Circuit Ave and the Flying Horses (1.7 miles) - where you'll find all the famous restaurants, nightlife & bars - and 2.5 miles to State Beach. It has a well-equipped kitchen, laundry, outside shower, and an amazing backyard!

FamilyValueCheck-in

Guest favourite
An open living area is highlighted by high ceilings and large windows allowing natural light. A comfortable sectional sofa with a blue and white throw sits atop a textured rug. The kitchen area features a white island with seating, connecting to a lofted space above.
Home in Oak Bluffs
4.98 out of 5 average rating, 87 reviews

New Pristine Luxury Home on Martha's Vineyard

This brand new, stylish luxury home is located in a quiet neighborhood in Oak Bluffs and is centrally located; close to town, beaches, steamship, bike path and more. Our entirely private home has 2 bedrooms with King size beds and loft sleeping area with 2 sets of bunk beds, making it a perfect stay for 2 families with children. This home is equipped with everything you need. Parties are not permitted at this home as it is in a quiet residential neighborhood.

FamilyValueCheck-in

Top guest favourite
A modern kitchen features a spacious island with two black bar stools. Stainless steel appliances, including a microwave and toaster, complement quartz countertops. Natural light fills the space through large windows, revealing a glimpse of greenery outside.
Cottage in Oak Bluffs
4.97 out of 5 average rating, 186 reviews

111I Beautiful and walk to everything Oak Bluffs!

This is a beautiful cottage in the heart of Oak Bluffs! Walk to town, the inkwell beach and the harbor! This modern and comfortable space will be the perfect home base for you and your family. Enjoy all the amenities including central air. Coffee maker, full laundry, outdoor shower and a beautiful patio too. We are on property eager to make your stay as magical as possible. Please check the reviews of our other listings to see how guests enjoy our properties.

LocationValueHiking

Top guest favourite
The exterior of the yurt showcases a circular wooden structure with large, rounded windows, complemented by a metal roof. A private yard features lush greenery, colorful flora, and outdoor seating arrangements, creating an inviting space for relaxation and outdoor activities.
Home in Oak Bluffs
4.93 out of 5 average rating, 316 reviews

The Luxury Vineyard Yurt

Discover this exceptional Luxury Yurt firsthand! Upon entering, you will be welcomed by a distinctive experience, featuring textured concrete radiant floors and a four-foot circular central skylight. Every aspect has been meticulously designed, allowing you to relax in a generous private yard. Enjoy your evenings under the stars, utilize the complimentary paddling, practice yoga in the spacious loft, and indulge in the beauty of your private island Yurt!

LocationValueGetting around

Superhost
The charming Cape Cod-style home is framed by lush greenery and a well-kept yard. A welcoming red staircase leads to the front door, while gravel paths and decorative stones outline the landscape, inviting guests to explore the outdoor space.
Home in Oak Bluffs
4.88 out of 5 average rating, 68 reviews

Oak Bluffs 4BR • 5 Min Drive to Downtown

Just 5 minutes from Downtown Oak Bluffs and nearby beaches, this spacious 4-bedroom home sleeps up to 8 guests and offers comfort, privacy, and a peaceful cul-de-sac setting. Enjoy an open-concept living area, fully equipped kitchen, private deck with BBQ, and large backyard with hot/cold outdoor shower. Both full bathrooms are newly renovated with floor-to-ceiling tiled showers and luxury top-shelf bath amenities for a spa-like experience.

ValueLocationParking

Guest favourite
An open-concept living area features a spacious, light-filled layout with modern furnishings. A comfortable sofa is positioned opposite a wall-mounted television. Bar stools are arranged along an island with sleek finishes, enhancing the inviting kitchen space. Natural wood flooring complements the neutral decor.
Home in Oak Bluffs
4.94 out of 5 average rating, 18 reviews

Charming 3-Bedroom Home in the Heart of Oak Bluffs

Welcome to your perfect Martha’s Vineyard getaway! Nestled in the heart of Oak Bluffs, this charming 3-bedroom home offers the ultimate convenience and comfort. Located just above Sunset Park, you'll be steps away from Oak Bluffs Marina, Circuit Avenue, Inkwell Beach, East Chop Beach, the Campground, and Ocean Park. With easy access to State Beach and the surrounding towns, this is the ideal home base for your island adventure.

ValueFamilyWalkability

Top guest favourite
A spacious, newly constructed home is showcased with a dark blue exterior and white accents. The façade features a prominent front porch with chairs and a large garage. A gravel driveway leads to the entrance, framed by a lush green lawn and trees.
Home in Oak Bluffs
4.98 out of 5 average rating, 54 reviews

The Blue Lagoon, Oak Bluffs

Come enjoy this beautifully designed, brand new home. With 3 bedrooms and 3 full bathrooms you will have all the space you need. An outdoor patio with gas grill is the perfect spot to relax after a day at the beach. Just a few steps away is the lagoon where you can paddle board, kayak, dig clams, or just take in the amazing sunsets! Summer rentals are Saturday to Saturday. Please send a message if you have any questions.

LocationFamilyBiking

Popular amenities for Oak Bluffs holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Oak Bluffs's top sights

Inkwell Beach

54 locals recommend

Martha's Vineyard Museum

71 locals recommend

Martha's Vineyard Camp Meeting Assn

43 locals recommend

Oak Bluffs Town Beach

20 locals recommend

Farm Neck Golf Club

28 locals recommend

Owen Park Beach

25 locals recommend

Other great holiday rentals in Oak Bluffs

Guest favourite
A charming blue house features a welcoming front entrance with white double doors and steps leading up to it. A bicycle is parked on the gravel path, surrounded by lush greenery and colorful flowers, enhancing the home's exterior appeal.
Home in Oak Bluffs
5.0 out of 5 average rating, 6 reviews

Martha’s Vineyard Boutique Beach Cottage!

LocationFamilyHospitality

Top guest favourite
A cozy living area features a lightweight sofa adorned with colorful cushions, complemented by a pink upholstered chair. Large windows reveal ocean views, allowing natural light to fill the space. A small table holds fruit and a book, creating a welcoming setting.
Cottage in Chappaquiddick
5.0 out of 5 average rating, 35 reviews

Beachfront Cottage + Studio w. Town Access

LocationFamilyGetting around

Top guest favourite
Home in Oak Bluffs
5.0 out of 5 average rating, 40 reviews

Relaxing oasis in center of Oak Bluffs

FamilyValueNearby

Top guest favourite
A cozy living area features a light-colored sofa along with two blue armchairs, creating a comfortable seating arrangement. Natural light fills the space through large windows, while an entertainment unit is present with a flat-screen TV. Decorative pillows and a round coffee table enhance the inviting atmosphere.
Home in Oak Bluffs
5.0 out of 5 average rating, 19 reviews

Chic Oak Bluffs Home with Hot Tub, Walk to Town

FamilyLocationCondition

Top guest favourite
A sunlit living area features a cozy white sofa next to a warm wooden table set for two. Neutral walls are complemented by a red accent wall and large windows with light curtains, allowing natural light to fill the space. A rustic cabinet and vibrant floral arrangement add character.
Flat in Oak Bluffs
4.89 out of 5 average rating, 309 reviews

Town/Beach: Vineyard Vacation Houses welcomes you!

FamilyValueAmenities

Top guest favourite
The cottage exterior is framed by lush greenery and stone landscaping, featuring a welcoming porch with rocking chairs. Colorful flower pots and pumpkins are placed around, while a serene view of the water is visible in the background.
Cottage in Oak Bluffs
5.0 out of 5 average rating, 12 reviews

The WestLake

LocationFamilyQuiet

Top guest favourite
Cabin in Oak Bluffs
4.92 out of 5 average rating, 12 reviews

Newly built rustic cabin in Oak Bluffs

LocationCheck-inCheckout

Top guest favourite
An aerial view captures the neighborhood surrounding #CozyBluffs, highlighting its proximity to the waterfront. The coastline features numerous boats and a scenic marina, while lush greenery and residential homes dot the landscape, all framed by the expansive blue sea.
Home in Oak Bluffs
5.0 out of 5 average rating, 28 reviews

#CozyBluffs #OakBluffs Walk to Beach/Town/Ferries

LocationValueWalkability

When is the best time to visit Oak Bluffs?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$486 SGD$498 SGD$485 SGD$387 SGD$552 SGD$646 SGD$737 SGD$873 SGD$539 SGD$394 SGD$468 SGD$485 SGD
Avg. temp0°C0°C3°C7°C12°C17°C21°C21°C18°C13°C8°C3°C

Frequently Asked Questions

  • What are the best places to stay in Oak Bluffs?

    Look for vacation rentals near the harbor, in historic cottage areas, or close to beaches for easy access to local attractions and community events. Many accommodations blend Victorian architecture with modern comforts.

  • What are the best things to do in Oak Bluffs with kids?

    Kids often enjoy riding the Flying Horses Carousel, playing at local beaches, and eating homemade ice cream on the harbor. Mini-golf courses and kid-friendly parks bring playful energy to family outings.

  • What are some of the best things to do in Oak Bluffs?

    Stroll the Gingerbread Cottages, enjoy local seafood near the harbor, or relax in Ocean Park. Riding the Flying Horses Carousel and browsing art galleries are also frequently suggested activities.

  • How is the weather in Oak Bluffs?

    Oak Bluffs has chilly winters around 25–44°F (-4–7°C) with some rain, while summers bring milder weather near 63–76°F (17–24°C) and less frequent showers. Packing layers and a light raincoat can be helpful year-round.

  • When is the best time to visit Oak Bluffs?

    Late spring through early fall is often recommended for outdoor activities, pleasant temperatures, and lively community festivals. Cooler months have a quieter pace but are still welcoming for strolls and cozy cafes.

  • What are the best places to visit in Oak Bluffs?

    Explore the unique Gingerbread Cottages, stroll through Ocean Park, and ride the historic Flying Horses Carousel. The harbor area and local art galleries are frequently suggested stops as well.

  • What are some hiking trails in Oak Bluffs?

    Oak Bluffs has walking paths through nature preserves, shaded forest trails, and coastal routes for ocean views. Some trails pass by ponds or wind through conservation land with interpretive signs.

  • What are some family activities we can do in Oak Bluffs?

    Families often explore the Flying Horses Carousel, play at local beaches, or stroll around Ocean Park. Picnics, miniature golf, and community festivals create a lively atmosphere for all ages.

  • What are some of the best day trip ideas from Oak Bluffs?

    Explore scenic island towns, visit local art galleries, or relax at sandy beaches nearby. Nature preserves, lighthouse tours, and locally rooted culinary experiences are often recommended for a fulfilling day away from Oak Bluffs.

  • Are there any pet friendly accommodations available in Oak Bluffs?

    Oak Bluffs has a range of pet-friendly accommodations, including vacation rentals and cottages that welcome dogs. Look for listings with outdoor spaces or proximity to parks for convenient walks.

  • What are some local tips for visiting Oak Bluffs?

    Enjoy an early morning walk around the harbor, try local bakeries for fresh treats, and check community boards for seasonal pop-up events. Exploring side streets often reveals colorful cottages and mural art.

  • What is Oak Bluffs known for?

    Oak Bluffs is known for its storybook Gingerbread Cottages, historic Flying Horses Carousel, and vibrant harbor scene. Its blend of Victorian architecture, community festivals, and public parks sets a welcoming tone.

  • What are the best hidden gems to explore in Oak Bluffs?

    Seek out small local art galleries, tucked-away coffee shops, or quiet corners of public parks. Some visitors enjoy discovering mural art or sunrise views from less traveled beaches.

  • What are the best foods to try in Oak Bluffs?

    Sample New England clam chowder, fresh lobster rolls, and homemade ice cream. Locally roasted coffee and bakery treats are favorites among visitors and residents alike.

  • What should I bring for a trip to Oak Bluffs?

    Pack layers for variable coastal weather, comfortable walking shoes, and a reusable water bottle. Sunscreen, a swimsuit, and a light rain jacket are often useful, especially for outdoor activities.

  • What is the nightlife in Oak Bluffs like?

    Oak Bluffs has lively waterfront bars, music venues, and social spots with island-inspired drinks and local bands. Some venues host open mic nights or community gatherings for a relaxed evening vibe.

  • What are the most popular events or festivals in Oak Bluffs?

    The Grand Illumination Night, Oak Bluffs Harbor Festival, and the summer fireworks display are frequently suggested community events. Seasonal festivals and art fairs often bring live music and local flavor.

  • Are there family friendly vacation rentals in Oak Bluffs?

    Oak Bluffs has many family-friendly vacation rentals featuring multiple bedrooms, kitchens, and outdoor spaces. Look for homes near parks or beaches to make group outings easy.

Destinations to explore