Vacation rentals in East Chop

Guest suite in West Tisbury

The exterior of a modern barn house is visible, featuring a black shingle facade and multiple skylights along the sloped roof. A private entrance is framed by a small, leafy tree, with a stone pathway leading through a lush green lawn.

4.91 out of 5 average rating, 127 reviews

Studio Guest Suite in Modern Barn House

A beautiful guest suite on Martha’s Vineyard with a private entrance on the back wing of our newly renovated modern barn house. Surrounded by trees, beside a large meadow, this airy suite has vaulted wood ceilings with skylights. Enjoy the outdoor shower and new outdoor sitting area. The location is prime and centrally located, just off historic Music St, a short walk to our small town center which provides many amenities. Ask about our other private guest suite if you are traveling with others

An aerial view highlights a shoreline featuring sandy beaches and a long wooden pier extending into calm blue waters. Surrounding the area are residential homes and green landscapes, with boats visible on the water. The clear sky and vibrant hues create a scenic coastal environment.

4.99 out of 5 average rating, 114 reviews

Sea View Waterfront Beachfront Apartment

Prime location- right across the street from a sandy beach, a few minutes walk to the harbor, downtown, and transportation (boat, bus, etc). This beautiful street-level one-bedroom apartment sits across the street from the ocean, where you can take a dip and enjoy the beach. The apartment was recently redone and has a small bedroom with a queen size bed, small bathroom, full kitchen, and living room area with pull-out couch. Convenient to take the ferry into Oak Bluffs and walk to the apartment

A sliding barn door crafted from light-colored planks is viewed against a textured wood wall. The door features a black handle and a metal track, providing a modern touch. Nearby, a diamond-shaped mirror is mounted, adding visual interest to the room.

4.95 out of 5 average rating, 365 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!

4.93 out of 5 average rating, 125 reviews

A spacious backyard is visible, featuring a vegetable garden with grapevines climbing along the wooden porch. Nearby, a pile of firewood is stacked, and a garden bed is outlined, with lush greenery surrounding the area. The setting is quiet and peaceful, ideal for relaxation.

Apartment in Tisbury

Harbor view apartment, a quick walk from the ferry

This is a great one bedroom apartment on the second floor of a house. My place is close to the beach, public transport, the Steamship Authority ferry, Black Dog Tavern, Main Street Vineyard Haven, Stop & Shop grocery, and lots of great shopping. You’ll love the convenience! Walk to the apartment right off the ferry boat. Lots to do in walking distance, and onsite parking. The Martha's Vineyard Museum is a 5 minute walk, down the same street. My place is great for couples and solo adventurers.

A wooden deck is visible, showcasing a simple bench and a couple of potted plants. Lush green grass and a variety of trees and flowering bushes create a serene garden setting, inviting quiet moments outdoors. Light filters through the greenery, enhancing the peaceful atmosphere.

4.98 out of 5 average rating, 206 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.

4.97 out of 5 average rating, 225 reviews

A spacious bedroom featuring a wooden bed frame and a large bed with neutral bedding. A colorful wall art piece adds visual interest above the bed. Natural light enters through two windows, and a full-length mirror is positioned nearby on one side.

Apartment in Falmouth

Modern Luxury Apt. | 7 min from Commons

This luxury 1Br + 1bth apartment is the perfect getaway. - 650 square feet, newly renovated - 15 Minutes from Old Silver Beach, South Cape Beach, and Falmouth Heights beaches - Steps from 1,700 acres of walking trails (Crane Wildlife) - 7 minutes to Mashpee Commons (shops and restaurants) - 15 minutes to Main Street Falmouth - 13 minutes to Ferry for Marthas Vineyard - 85” smart TV - 5 minutes to Shining Sea Bike Trail - Coffee/Espresso Machine - 2 minutes from Paul Harney Golf Course

4.98 out of 5 average rating, 342 reviews

A wooden deck is shown with outdoor seating, including a table and chairs. Surrounding the deck are blooming rose bushes and lavender plants, adding vibrant colours to the natural landscape. The space is bordered by natural stone and pebbles, leading into a wooded area.

Cottage in Tisbury

Martha's Vineyard Getaway Cottage

Contemporary cottage on quiet, private, wooded lot. Pristine, bright & comfortably furnished. Open living area, hardwood floors, vaulted ceilings, indoor/outdoor fireplaces, well appointed kitchen, washer/dryer, cable/internet/phone with unlimited national calling, SmartTV with Netflix and additional internet streaming services. Walk or bike to beaches and trails, 5 minute drive from downtown shops and restaurants. Property abuts West Chop Woods with lovely, quiet walking trails.

4.91 out of 5 average rating, 254 reviews

Unique Luxury Yurt w/ Free kayaking

Step into this unique yurt house! As soon as you walk in, you'll be greeted with a one-of-a-kind experience, from the textured concrete floors to the large circular skylight. Every detail is carefully planned, and you'll have the opportunity to unwind in a spacious private yard. Spend your evenings stargazing, take advantage of complimentary paddling, participate in our scheduled chicken feedings, do yoga in the roomy loft, and revel in the splendor of your exclusive island yurt!

4.97 out of 5 average rating, 135 reviews

A charming outdoor pathway lined with vibrant flowers and greenery is shown, leading towards a white door nestled between two cottages. The clear blue sky enhances the inviting atmosphere of the landscaped area, creating a welcoming approach to the properties.

Cottage in Oak Bluffs

Beautiful and walk to everything Oak Bluffs!

This is a beautiful and brand new 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.

Superhost

A spacious outdoor deck area is surrounded by greenery, featuring wooden seating and a table complemented by a sun umbrella. The deck leads to a gravel pathway, accompanied by landscaped plants and a wooden fence, creating a serene outdoor atmosphere suited for relaxation.

4.78 out of 5 average rating, 318 reviews

Cottage suite between the harbors: no minimum stay

Nestled between Oak Bluffs and Vineyard Haven harbors, our relaxing suite is a perfect way to extend your weekly rental, or to enjoy a day or two on this special island we call The Rock. Our cozy guest suite, newly renovated has two bedrooms, living space, kitchenette, full bath, deck with grill, outdoor shower, and footwash (hot H20), W/D (in unit) and a private entrance. An easy walk to town and beaches. Parking is available in our driveway. Enjoy our historic home!

A well-lit staircase is visible, featuring beige carpeting with a subtle striped pattern. A wooden handrail runs along one side, leading upwards. At the top of the stairs, a framed picture is mounted on the wall, adding a touch of decoration to the space.

4.99 out of 5 average rating, 168 reviews

Quiet Hide Away

Lovely efficiency suite with private entrance in a quiet neighborhood. Private space located over attached garage. Plenty of space for two guests. Comfortably appointed with queen bed, dining set, living area with tv and full bath. Enjoy a coffee or cocktail on the private deck. Toaster oven, refrigerator and coffee maker will start your day right before heading to nearby beaches, golf courses or shopping.

An airy lounge area features a large sectional sofa adorned with decorative pillows, arranged around a rustic coffee table. Skylights above provide natural light, illuminating the wooden beams and walls of glass that create a bright, inviting space.

4.92 out of 5 average rating, 118 reviews

** Vineyard Vacation Retreat ** with HOT TUB

Gated 2br house with lots of different places to lounge and relax. Drive through the 10’ granite gate onto the shell driveway. The house is filled with art from local artist Alan Whiting, Colin Rule, Kara Taylor and Scott McDowell. There is so much to do and explore. The adventure is just starting so make sure to pack up your swimmers, suntan lotion and get out the door. Kick back and relax, you're home.

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Other great vacation rentals in East Chop

5 out of 5 average rating, 17 reviews

A bright living area features a gray sectional sofa facing large windows, allowing natural light to fill the space. The vaulted wood ceiling adds warmth, while the kitchen is equipped with stainless steel appliances and a wooden dining table, enhancing the open-concept design.

Home in Tisbury

Family Friendly 5 BR, Walk to Town, Beach & Ferry!

LindsayRating, 5 stars5 days ago

What a wonderful stay we had! The house was stocked with anything you could think of and the host Caroline was readily available for any questions. Will absolutely come back and recommend to all!

A covered porch area features two wicker chairs, each adorned with patterned cushions, positioned beside a white railing. Lush greenery is visible in the background, with a glimpse of a bicycle on a path. The inviting space is perfect for relaxation.

4.92 out of 5 average rating, 39 reviews

Martha's Vineyard Waterfront | Large Home + Yard

MarkRating, 5 stars1 week ago

This spot is exceptionally beautiful, even for a place as picturesque as Martha’s Vineyard. The space and the yard exceeded our expectations in every way. It’s spacious and warm with old world charm and practicality. It felt like we were staying in a family friend’s home, where it was cozy, peaceful, and private. The views out of the upstairs bedrooms are surreal but nothing steals the show like the sun setting over the water every evening. We grew so fond of it we opted for takeout most nights because dinner on the back porch followed by a walk down to the private beach for sunset beat the ambience of any restaurant on the island. The owners are amazing too- quick to reply, helpful, and so generous. This house is a treasure and we look forward to staying there again.

4.68 out of 5 average rating, 142 reviews

Fantastic beach Ap 0.8 miles from Farm Neck Golf!

AntoniaRating, 5 stars8 months ago

What a lovely little flat this is. Very peaceful and beautifully decorated. Fabulous outside space as well. The linen, towels and utensils were of a good quality. lovely to have beach towels. Didn't find the sloping ceiling a problem at all. we are 6 foot and 5'9. Town is a 30 min walk we hired bikes which I highly recommend. it's an easy 10mins on a bike. Host was happy to offer us an early and late check-in and out but realise this is probably as we are now at the end ofvthe season so could be accommodated. Very kind of her thank you

A dining area features a patterned tablecloth on a large table surrounded by white chairs. Soft lighting illuminates the space, complemented by granite countertops and modern appliances in the adjoining kitchen. A window allows natural light to brighten the room.

4.92 out of 5 average rating, 60 reviews

Martha's Vineyard Apt ~ 1 Mile to Inkwell Beach!

JaneRating, 5 stars9 months ago

Hosts were great and the apartment was in a perfect location for us...quiet but within walking distance of Oak Bluffs

A coastal house is positioned by the shoreline, surrounded by small stones and pebbles. The structure features multiple levels, with a balcony overlooking the water. A quiet road runs alongside, leading into the landscape, with hints of distant houses visible in the background.

5 out of 5 average rating, 5 reviews

Private setting nestled in the heart of East Chop

RyanRating, 5 stars9 months ago

My group and our dogs had a wonderful stay at Tree Tops. The property was exactly as advertised, with plenty of indoor space and a big upper deck. John was super responsive and accommodating of our special requests as well. Would definitely stay here again.

The charming exterior of a studio is framed by two tall evergreen trees, contributing to a sense of privacy. A small gravel patio features a round table with decorative chairs, adding outdoor seating. The front door is flanked by potted plants, enhancing the inviting entrance.

4.69 out of 5 average rating, 13 reviews

Studio near the beach & town with AC

JasonRating, 5 stars2 months ago

Cozy cottage. Well appointed. Perfect for a couple. Conveniently located near everything Oak Bluffs. Will book again

A winding wooden path leads through a pebbled area, ending at a blue adirondack chair positioned to face the ocean. Lush greenery and a wooden fence frame the scene, with water visible in the background under a clear sky.

4.71 out of 5 average rating, 14 reviews

The Boat House

LiliRating, 5 stars9 months ago

Joe's Boat House exceeded our expectations. To be that close to the water is a transcendent experience. From the bedroom windows the views of the water completely fills the frames. The tides are high. We swam in the water in mid September and the water was warm and gentle by my standards (66 degrees F). The beach and surface under the water has round pebbles as others had noted so we brought water shoes which worked out well. It is rustic as described. The first night we were there the winds howled due to a weather event which my husband and I found invigorating, and the subsequent nights were gentle. The neighborhood is open and residential without feeling touristy at all, yet is a short drive or bike ride to the Oak Bluffs town center. The kitchen is ample. We cooked seafood literally every meal. It was absolutely an extremely rare experience, that we will treasure always and hope to return soon.