Holiday rentals in Chappaquiddick Island

Guest house in Barnstable

5 out of 5 average rating, 138 reviews

Modern Fireplaced Carriage House with Beach Permit

Feel at home & relax in our new one bedroom carriage house. Modern yet classic Cape Cod style and elegance. Rest easy on a new Stearns & Foster king size mattress with designer linens and furnishings. Cozy up to the fireplace and flat screen TV. Custom bathroom, Bosch laundry units and small deck. Kitchenette with dishwasher drawer, under cabinet refrigeration, microwave, toaster, Keurig coffee maker, Starbucks coffee and various teas. We offer beach chairs, bags & towels for your convenience.

4.83 out of 5 average rating, 69 reviews

Spacious, Old Vineyard charm with Private Beach

This is a classic, rare vintage Vineyard property: a beautifully simple, comfortable, and charming family house located directly on its own private beach on Katama Bay. Peaceful and secluded, yet a short walk or bike ride to the popular, public surf beach, and 3 miles from bustling, historic Edgartown. The house is both intimate and expansive: equally perfect for small families or larger groups, for quiet retreats or festive reunions. Spacious and soulful indoors and out. A magical refuge. .

Superhost

Guest suite in Edgartown

4.91 out of 5 average rating, 99 reviews

Step Away; A Martha's Vineyard Retreat

Studio apartment addition attached to our family home. Our home is located three miles to downtown Edgartown with bus service & bike path close by. Private entrance, mini fridge, coffee press & accessories, private bath with shower, washer/dryer, bed in a loft area (ladder access only) with queen size sofa bed available below for additional sleeping. This is our family home with two baby boys. We try our best to keep quiet, but it is important to note their presence; rental has a sound machine.

4.97 out of 5 average rating, 66 reviews

Cottage in Edgartown

Chappy cottage close to ferry & walk to beach

Charming and renovated cottage is a 5-minute bike ride to the Chappy ferry point & beach and a 10-15 minute walk to the Mary 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.

Guest suite in West Tisbury

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

Guest suite in Oak Bluffs

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!

4.98 out of 5 average rating, 206 reviews

Flat in Oak Bluffs

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

Flat 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

4.91 out of 5 average rating, 254 reviews

Home in Oak Bluffs

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!

Superhost

Tiny home in Edgartown

4.85 out of 5 average rating, 149 reviews

Unique Vineyard Tiny House “The Banana Stand”

A Martha’s Vineyard tiny house perfect for a relaxing trip to the island. Included with a parking spot and private entrance, this tiny house has the privacy and amenities you need for an island getaway. Located just 2-miles from all the shops and dining that downtown Edgartown has to offer, staying in "The Banana Stand" provides full use of the kitchenette, bathroom, outdoor shower, sofa bed, wifi, outdoor fireplace, and grill. Vineyard uniqueness meets tiny house comfort.

4.94 out of 5 average rating, 18 reviews

Chappy Whispering Pines

Peace and quiet, and access to fabulous East Beach, Mytoy, Wasque and the many wonderful walking trails of Chappaquiddick, this lovely home among "whispering Pines" will be your warm welcoming retreat after a day at the beach, exploring Chappy by bike or fishing to your hearts delight. We provide a comfy, well furnished and beautifully decorated home outfitted with all cotton bedding, linens and fresh pillows, and lovely quilts, wool and cotton rugs, and so much more.

5 out of 5 average rating, 108 reviews

Flat in Edgartown

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

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Other great holiday rentals in Chappaquiddick Island

4.91 out of 5 average rating, 33 reviews

Chappaquiddick, Edgartown, MA

ToddRating, 5 stars8 months ago

Our third time visiting for the Derby. Perfect for our group in an ideal location. Susan always makes it easy. Not only is it a great deal and as advertised, Susan saved the day when one of our cars died out on the beach. Game changer!

Holiday home in Edgartown

5 out of 5 average rating, 16 reviews

Peaceful Chappaquiddick Retreat

AnneRating, 5 stars8 months ago

Perfect place to spend a long weekend as an extended family! Something for everyone, beaches, walking, and hunting. Hosts could not be more accommodating. Can’t wait to come back.

Superhost

4.88 out of 5 average rating, 42 reviews

Edgartown Cottage By The Pond

ThomasRating, 5 stars6 months ago

House was impeccably clean, with bathrooms and kitchen welcoming. The kitchen had everything one could need to cook and comfortably prepare meals. Overall, an excellent house - strongly recommended!

4.82 out of 5 average rating, 11 reviews

Private house with beautiful beach on Chappy!

AlanRating, 5 stars4 weeks ago

Thank you for an extraordinary vacation. We had a great time on the island and your home was a great place to stay while experiencing the island Thank you for sharing your home Alan,Lori , Erik and Vivi

4.86 out of 5 average rating, 7 reviews

Waterfront Oasis

LisaRating, 5 stars9 months ago

Absolutely beautiful cottage and location! We had an amazing weekend and the house was immaculate. Vito and Kerry were super responsive and helpful throughout the trip. I would highly recommend this place for a wonderful stay on Chappy!

4.96 out of 5 average rating, 28 reviews

Luxury Chappaquiddick Home with Oceanviews

MargaretRating, 5 stars2 months ago

Another great weekend on Chappy. The house was perfect for our family and the location can’t be beat. Lisa was responsive throughout the weekend and quickly addressed a few questions we had along the way. Looking forward to coming back in a few months!