Holiday rentals in Chappaquiddick Island

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

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!

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.

Brand new gorgeous 2 bedroom guest house.

This is a gorgeous brand new 2 bedroom guest house on the bike path that leads to downtown Edgartown and both State Beach and South Beach, as well as 1/4 of a mile from the famous Morning Glory Farm Stand. There are cathedral ceilings in the living room, which provide a open, spacious feel. There is a large deck on the front of the house with a grill, table and chairs. Part of it is covered in shade. Separate parking for guests with privacy, as it sits 200+ feet from the main house.

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

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.

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.

Not Your Great Aunt's Island Cottage

F͟R͟E͟E͟ ͟C͟A͟R͟ ͟F͟E͟R͟R͟Y͟ ͟R͟E͟S͟E͟R͟V͟A͟T͟I͟O͟N͟ ͟F͟O͟R͟ ͟A͟U͟G͟U͟S͟T͟ ͟2͟2͟-͟2͟9͟!͟ In town, 1930's cottage, lovingly updated by architect-owner. • Stylish decor, open floor plan, granite terrace • 2 blocks to Main St/harbor/ferry/town beach/playhouse • Central Air • Close to bike rentals, restaurants, shops, spa, library, mini-golf, etc. • Large yard with wood/gas grills, bocce, corn hole, beach chairs, fire pit • Outdoor shower • 3BR + sleeping loft

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!

Stylish retreat | walk to town | fire pit

* Private garden patio: table & chairs, propane grill, propane fire pit & enclosed outdoor shower * 10 min walk to Edgartown's dining & boutiques * Cable TV, Streaming services, Sonos * High-speed WiFi, comfortable workspace in the bedroom * USB charging ports in the BR & LR * Small but mighty fully stocked kitchen for home-cooked meals * Organic, local bath products * Board games & a small library * HW floors, SS Bosch appliances, DW, W/D, HVAC

The Sea-Cret Garden, Guest Apartment

Kick back and relax in this calm, stylish space! This comfortable and peaceful guest apartment is situated in an ideal location in a quiet, beautiful neighborhood that is close to beaches and a short drive to downtown. Take a quick stroll to the West Falmouth Market or the Shining Sea Bike Path. With easy access to Chapoquoit & Old Silver Beach, this perfectly situated apartment is in an ideal spot for your next Falmouth getaway!

Sleep 6 @ New Seabury w/ Pool Access, All Seasons!

Welcome to Your Coastal Getaway at The Mews, New Seabury – Mashpee, MA Tucked inside the beautiful New Seabury Country Club, our cozy Cape-style condo offers the perfect balance of relaxation and adventure on Cape Cod. Enjoy access to a private condo association pool just a 3-minute walk away, and a beach that is 5 min drive or 10 min bike ride or 30 min walk (walk cuts through golf course-ask host for directions).