Vacation rentals in Oak Bluffs

4.92 out of 5 average rating, 109 reviews

The historic property is displayed from the street level, showcasing its architectural charm with a multi-story design. A covered porch is visible, featuring ornate woodwork. Shops line the street, contributing to a lively town atmosphere. Clear skies and bright sunlight enhance the inviting appearance.

Apartment in Oak Bluffs

Absolute Best Location on the Island

Ideal location for visitors in the middle of the most lively, diverse, fun town on Martha's Vineyard. This property is certified by the United States Department of Interior as a National Historic Property. The ferry terminal, restaurants, shops, markets, harbor, historic sites, entertainment, public transportation, and a clean sandy beach are all within minutes. A vehicle is not necessary. IF UNAVAILABLE: SIMILAR WALKABLE SISTER PROPERTY in Vineyard Haven: https://www.airbnb.com/rooms/49016488?

4.94 out of 5 average rating, 110 reviews

Home in Mashpee

Newly Renovated! Seconds to sand, fire pit, A/C

Recently Renovated! This Cape Cod Cottage is completely refreshed top to bottom. Less than 60 seconds to the sand. Cape cod vacations do not get any better than this! Located on idyllic Monomoscoy Island known for its gorgeous wildlife and stunning waterways, our home is the perfect choice to rent on Cape Cod. We are less than 10 Mins to Mashpee Commons and famous Mashpee Town Beach, Less than 5 mins to New Seabury and the Popponesset Inn, and only 15 mins to downtown Falmouth. Linens included!

4.93 out of 5 average rating, 106 reviews

Home in Fairhaven

Cozy Beach House with 270° Spectacular Views

Enjoy your getaway at our elevated beach house, the Fairhaven Seaside Retreat! Named one of Fodor's Top Ten Airbnbs for Socially Distanced Getaways in 2020 for its seclusion, stunning views, and easy access to many of New England's vacation spots, our home is perfect for adventurous vacations, quiet retreats, or remote working. Featuring 270 degree views that include the Atlantic ocean and a protected state marsh, our cozy home is also close to local restaurants, grocery stores, and shops.

4.95 out of 5 average rating, 168 reviews

The kitchen features a spacious granite countertop with seating at three bar stools. Large windows and overhead lighting enhance the bright and airy atmosphere. Appliances including a stove and refrigerator are integrated into the cabinetry, providing a modern look in the renovated space.

Apartment in Oak Bluffs

Beautiful private apartment walk to everything!

This is an incredible property! Renovated and spotless with all the amenities to make your stay feel like home, only better. Downtown Oak Bluffs and her beautiful beaches are within a five-minute walk. There is a local market and deli right next door where you can find anything you need in a pinch, and a great BBQ restaurant across the street. This second floor apartment has one bedroom with a queen-sized bed and a queen pullout couch. Smart TVs, full kitchen and laundry plus much more!

5 out of 5 average rating, 28 reviews

A serene outdoor area features four black Adirondack chairs arranged around a small fire pit on lush green grass. The cottage's charming exterior, highlighted by a wooden deck and American flag, is visible in the background, surrounded by trees.

Home in Sandwich

The Cape Cottage Fireplace * Kid Friendly * PetsOK

The Cape Cottage is a private, tranquil Cape Cod-style cottage nestled near historic downtown Sandwich and just 6 minutes from the ocean. Newly renovated, this home is tastefully designed with a blend of coastal, farmhouse and antique design elements. We thoughtfully curated the home's details to evoke the comforts of home and give it unique charm that pays homage to quintessential New England and Cape Cod's scenic beauty. Check out our IG @thecapecodcottage for more pictures and vibes.

4.83 out of 5 average rating, 218 reviews

A tranquil shoreline is depicted, featuring gently sloping grass leading to a calm body of water. Soft ripples reflect the blue sky and fluffy clouds. In the distance, a house is visible, framed by the natural landscape.

Cottage in Fairhaven

Cottage by the Bay

Cottage in Fairhaven, perfect for a vacation for a small family, a romantic getaway or a home away from home if you are in the area for business. Enjoy all a vacation has to offer. During warmer weather, walk to the public beach and boat ramp - swim, sun, boat. Spend evenings by the outdoor fireplace. When it is cold out side, enjoy parks, museums, arts and cultural events, with evenings spent enjoying hot chocolate in front of the gas stove as the fire blazes providing a cozy warmth.

4.93 out of 5 average rating, 44 reviews

Home in Mashpee

Tranquil Cape getaway#2 with AC Kid & Pet friendly

Welcome to this peaceful Cape retreat! With its charming Cape style home and serene surroundings, this two-level residence offers a perfect getaway for relaxation and quality time with loved ones. Property Features: Four Cozy Bedrooms Outdoor Deck and Grill Complete Fenced-In Yard Swing Set Whether you're looking to relax indoors, enjoy outdoor activities, or spend quality time with family and friends, this idyllic haven offers all the necessary amenities for a memorable vacation.

A newly renovated kitchen is highlighted with modern appliances and sleek quartz countertops. Natural light floods the space, enhancing the adjacent dining area with a round table for six. Stylish cabinetry provides ample storage, while decorative artwork adds a touch of elegance.

4.95 out of 5 average rating, 111 reviews

Walk To Town - Beautiful Edgartown Cottage

Walk to downtown Edgartown in minutes while staying in this newly renovated 2-story home in the heart of Upper Main St. The 3-bedroom, 2-bathroom house has been completely renovated, with brand new bathrooms, kitchen appliances, etc. You cannot beat the location of this home! You're a short 10 min walk from Edgartown's amazing restaurants & shops, in addition to a short bike ride to Katama's famous South Beach or Oak Bluff's State Beach. Both easily accessible via bike paths.

4.91 out of 5 average rating, 54 reviews

Updated Beautiful Cottage in Edgartown AC

A true island charmer. Light, airy and central-air-conditioned home offers all the comforts of modern living centrally located in Edgartown. Recently completed extensive upgrades completed enhance all of the space, including a new kitchen, both bathrooms, basement, and more. A spacious outdoor furnished deck with enclosed outdoor shower and an expansive grassy lawn make for a great space to relax. Great location makes Island travel a breeze.

A welcoming entrance is framed by a neat sidewalk leading to a white front door, flanked by two windows. The exterior showcases classic shingle siding, with vibrant flowering shrubs and a well-maintained lawn adding charm to the inviting facade.

4.98 out of 5 average rating, 174 reviews

20-minute walk to Edgartown Village!

This 1550 square foot Ranch-style Condo with loft was built in 2018 and is set on a large nicely landscaped lot with plenty of room inside and out. It has It has 3 bedrooms and sleeps 8. It’s a 20-minute walk to the Edgartown village center, a 10-minute walk to Morning Glory Farm, and just a 10-minute drive to South Beach! All updated furnishings, beds, linens, appliances. Read our reviews! Immaculate!

4.92 out of 5 average rating, 259 reviews

A private deck is showcased, featuring a white wicker chair positioned on a wooden surface. Lush green lawns and trees, including blooming cherry blossoms, are visible in the distance, creating a serene outdoor environment.

Loft in Centerville

Cottage by the Sea ... Entire Loft

Cute cottage by the Sea.... Is located in the quaint mid-cape village of Centerville...Total separate out building... One mile to beautiful sandy beach.....Walk to Four seas ice cream...Walk to Centervillle candy store...Nantucket and Vineyard ferries 2 miles away.... Close to whale watching tours plus fun in the sun

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Oak Bluffs vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Oak Bluffs's top sights

Flying Horses Carousel82 locals recommend

ArtCliff Diner58 locals recommend

Lookout Tavern52 locals recommend

The Black Dog Tavern52 locals recommend

Linda Jean's Restaurant48 locals recommend

Martha's Vineyard Museum46 locals recommend

House rentals in Oak Bluffs

The exterior of a newly constructed home is presented, featuring a sloped roof and two skylights. A welcoming porch extends across the front, lined with decorative lighting. Green shrubs and a gravel driveway lead up to the entrance, surrounded by trees that enhance the private setting.

4.96 out of 5 average rating, 68 reviews

Newly constructed home with AC , new furniture.

4.88 out of 5 average rating, 133 reviews

The exterior of the home is presented at dusk, featuring soft outdoor lighting and classic blue siding. A pathway of stone leads to the entrance, flanked by neatly manicured shrubs and a lawn. A small porch area and steps provide access to the front door.

Home in Marstons Mills

The Mills Retreat- 3BR/2Bath - Beach pass included

5 out of 5 average rating, 36 reviews

A well-maintained exterior of a two-story home is surrounded by landscaped greenery. A stone pathway meanders through the neatly trimmed lawn, with flowering bushes and trees providing natural shade. The house features a combination of wood and shingle siding, with a small balcony visible on the upper level.

Home in East Falmouth

Spacious and immaculate custom home.

5 out of 5 average rating, 59 reviews

A spacious home is set against a backdrop of lush trees, showcasing a unique architectural design with a multi-level roof. A wrap-around deck is visible, enhancing the outdoor space surrounded by greenery and landscaped gardens.

Home in Vineyard Haven

Well-Appointed 3 Bedrm 4 Bathrm w/ 50+ 5* Reviews

4.77 out of 5 average rating, 26 reviews

The exterior of the home is shown, featuring a spacious deck with seating overlooking a large, grassy backyard. The landscape is bordered by trees, with a fenced area visible in the background. A storage shed is located to the left in the distance.

Home in Sandwich

Holiday in the sun!

4.75 out of 5 average rating, 4 reviews

A serene view of two houses surrounded by trees on a gravel pathway. The larger house features a stone exterior and a sloped roof, while the guest house, attached to a two-car garage, showcases a light-colored facade, creating a peaceful atmosphere in the natural setting.

Home in Falmouth

NEW! 2 Houses, Main House plus Guest House

4.8 out of 5 average rating, 81 reviews

An open kitchen and dining area features modern appliances and a central island with seating. Sunlight streams through large windows, illuminating the space. Light-colored cabinetry complements the warm wooden flooring, while pendant lighting adds a contemporary touch.

Home in Oak Bluffs

Martha's Vineyard house near Lagoon Pond Beach

4.85 out of 5 average rating, 67 reviews

A single-story house is surrounded by a lush green yard, with various flowering bushes along the front. Large windows allow natural light to fill the space, and a shaded area is created by overhead trees, adding to the tranquil atmosphere.

Home in Centerville

Family Friendly, Close to everything, Beach Pass,

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Cottage rentals in Oak Bluffs

4.94 out of 5 average rating, 131 reviews

A serene waterfront scene is displayed with calm waters reflecting a clear blue sky. Green grasses and scattered stones line the shore, while small boats can be seen floating in the distance. The tranquility of nature is captured in this peaceful setting.

Cottage in Fairhaven

Seaside cottage

4.9 out of 5 average rating, 203 reviews

A serene beach scene features gentle waves lapping at the sandy shore under a clear blue sky. Lush green grasses frame the beach, leading to the calm water, creating a peaceful atmosphere for relaxation and exploration.

Cottage in Sandwich

Gold Anchor Cottage - private hot tub getaway!

4.79 out of 5 average rating, 103 reviews

The exterior view of the cottage is framed by lush greenery and vibrant purple flowers. A small outdoor seating area is visible, featuring a table and chairs next to a barbecue grill. The textured siding and shingled roof highlight the charm of the beach cottage.

Cottage in Bourne

Adorable Gray Gables Beach Cottage

4.92 out of 5 average rating, 261 reviews

Cottage in Sandwich

Hideout at Water's Edge, 131 North Shore Blvd, #4

4.89 out of 5 average rating, 123 reviews

A quaint beach cottage is positioned close to the shore, featuring light wood siding and multiple windows that invite natural light. A picnic table sits on the deck, accompanied by a blue umbrella and a potted plant, creating a charming outdoor space.

Cottage in Sandwich

Steps to Cape Cod Private Beach!

4.89 out of 5 average rating, 204 reviews

The cottage features a welcoming facade with light wood siding and a shingled roof. A front porch is visible, adorned with potted plants. Lush green grass surrounds the property, and a parking area is seen to the right, with a car parked nearby.

Cottage in Wareham

Cape Cod cottage with Water Views

4.93 out of 5 average rating, 169 reviews

A wooden picnic table is set in a grassy area by the water, surrounded by colorful Adirondack chairs. Trees frame the scene, providing a natural backdrop with a glimpse of the calm water in the distance.

Cottage in East Falmouth

“Cozy Cottage” on Great Bay

4.88 out of 5 average rating, 134 reviews

A sandy beach extends towards the horizon, bordered by gentle grasses on the left. The sky above is clear with scattered clouds, allowing sunlight to reflect off the beach surface, creating a serene and open atmosphere.

Cottage in Barnstable

Osterville Charming Cottage in the Heart of Wianno

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Condo rentals in Oak Bluffs

4.55 out of 5 average rating, 66 reviews

A well-equipped kitchen features oak cabinets and modern stainless steel appliances, including a gas stove and refrigerator. A wooden dining table with four chairs is positioned beside the kitchen area, with light from a nearby window illuminating the space.

Condo in Barnstable

Oceanside Cottage Apt next to Craigville beach

A modern kitchen features sleek white cabinetry and a spacious countertop. Natural light fills the area through a window, highlighting a gas stove and stainless steel appliances. A small door leads outside, while a patterned rug adds warmth to the floor.

4.98 out of 5 average rating, 50 reviews

Short Walk into Town - Nice Comfortable Reasonable

5 out of 5 average rating, 21 reviews

A clear, inviting pool is seen with a smooth surface reflecting the sky above. Lounge chairs are arranged neatly around the pool area, with several placed alongside a white picket fence. The tranquil setting is enhanced by distant views of the horizon.

Condo in Vineyard Haven

Relax....You're on Island Time......

A screened-in porch features a glass table surrounded by comfortable seating. Natural light filters through the windows, illuminating the space. The backdrop includes lush greenery, enhancing the tranquil outdoor setting.

4.91 out of 5 average rating, 47 reviews

Private 3bdrm Condo Tashmoo Woods

A communal unheated pool is surrounded by a white fence, featuring a spacious deck with lounge chairs. The water appears clear and inviting under a partly cloudy sky with greenery visible in the background.

4.9 out of 5 average rating, 72 reviews

Sunny 2bedroom condo w pool, walk to town

4.96 out of 5 average rating, 27 reviews

A balcony view features two white rocking chairs beside a glass-top table, overlooking a sandy beach and clear ocean waters. A wooden pier extends into the sea, while the shoreline enjoys a serene, unobstructed vista.

Condo in Oak Bluffs

LOCATION LOCATION!! Ocean- View TOP Floor Condo

4.73 out of 5 average rating, 15 reviews

A serene lake is shown, surrounded by lush greenery with trees reflecting gently on the calm water surface. The clear sky above features fluffy white clouds, and the sandy shore is visible in the foreground, providing a peaceful natural setting.

Condo in Falmouth

Condo in Falmouth MA

The exterior of a cozy blue condo is shown, surrounded by green grass and trees. A wooden fence and picnic table are visible in the foreground, as well as a large tree with budding leaves. The building features multiple windows with white shutters.