Holiday houses in Martha's Vineyard

Lovely 2 BR Oak Bluffs Apartment

*To returning guests: Airbnb has restructured their fees; so while our nightly price may look higher at first glance, it is our same pricing overall This private apartment is on the 1st floor of a family home with a personal entrance & parking; owners and their son live upstairs. There are no shared spaces. It is a mile from Oak Bluffs Center, a half mile from the Cottages and Farm Neck Golf Course, and across the street is a bike path. The bus stop is on the corner for easy island wide travel!

One Bedroom Cottage in Vineyard Haven

Small private cottage on a large quiet property nestled among trees with a wrap around deck. Perfect for a couple’s getaway weekend. Walk to Vineyard Haven shops, restaurants and Owen Park beach. It's one mile to town and the ferry (5 min drive/20 min walk with sidewalks). Cottage features vaulted ceilings, sitting room with kitchenette that includes coffee + tea station, mini fridge and microwave. Includes beach towels, toiletries, hairdryer & steam iron. Queen bed, AC, bath with tub & shower.

Chappy cottage close to ferry & walk to beach

Booking for '26 Season. Charming cottage is a 5-minute bike ride to the Chappy ferry & beach and a 10-15 minute walk to the Frances Preserve beach. Located in a quiet wooded setting, the property offers new furniture and beds; renovated kitchen with dishwasher and microwave; new bath w/ shower/tub; washer/dryer; hardwood; screen porch; deck & outdoor shower. Cable, wifi (200 megs), AC, ceiling fan, grill, deck furniture, beach chairs & umbrella. The rental season runs mid May through late Oct.

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.

impeccable cottage STEPS to downtown OB & beach!

Unique opportunity to stay in an impeccable cottage in Downtown Oak Bluffs. With a front porch with rocking chairs, a back deck & grill, & an outdoor shower, and A/C! - this is the ideal oasis for your Vineyard Vacation. Turn right and find yourself steps from restaurants & shops on Circuit ave. Turn left and walk 5 mins to beautiful beaches. Everything you want out of vacation at your fingertips. Relax, and truly experience the Vineyard the way it was meant to be, at the @WeePackemInn

Custom crafted Makonikey home

Newly built, well crafted home in quiet neighborhood of gorgeous natural beauty. Large yard with lovely trees, gardens, and sitting areas. Great flow indoors and out. Walk down dirt road to private association beach (and further on down the beach to Lamberts Cove). Near great walking trails, ponds, and farm stands. A peaceful haven, and only a 7 minute drive from Vineyard Haven. If ferry car reservations are tricky, we have a vehicle option available. Please see in details section.

Martha's Vineyard Cottage: Walk to Town and Beach

Updated 1920s Cottage in Edgartown Village – Walk to Beach, Harbor and Main Street Step into classic Vineyard charm at this fully updated 4-bed, 3-bath craftsman cottage in the heart of Edgartown. Two blocks from Main Street’s restaurants, galleries, and harbor and a quick walk to Fuller St Beach & Lighthouse Beach. Fully winterized + AC, high-speed Wi-Fi, three workstations. Ideal for families, bachelorette parties or anyone craving a New England coastal escape.

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.

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!

Beachfront Cottage w. Yard + Town Access

Welcome to The Mizzen Cottage! Updated 1930's cottage on an ocean front compound on beautiful Chappaquiddick. Complete with a picturesque porch overlooking the outer harbor, side deck, outdoor shower, washer/dryer, dishwasher. Stunning views of the Edgartown lighthouse and Cape Poge. Access to a private beach. Access town with just a 10 minute walk (or 1 minute drive) to the Chappaquiddick Ferry, and be in downtown Edgartown in 15 minutes or less!

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.

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.