Holiday rentals in Chappaquiddick Island

Guest house in Barnstable

5 out of 5 average rating, 137 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.

4.82 out of 5 average rating, 68 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. .

4.95 out of 5 average rating, 229 reviews

Cottage in Sandwich

WOW VIEW! Waterfront w/ Private Beach, King Bed!

Wake up to magnificent panoramic views of a beautiful lake with waves lapping below your window! Search on YouTube for tour: "WOW View! Cape Cod Lakefront Cottage. Private Beach, King bed" Guests love this stylish and open cottage on the shore of a large recreation lake with its own private beach. Wall-to-wall floor-to-ceiling windows with a new modern kitchen, luxurious King gel/coil bed, office space, bathroom with curved shower, and much more! It's like being on your own luxury houseboat!

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

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

4.98 out of 5 average rating, 342 reviews

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

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!

5 out of 5 average rating, 23 reviews

Valentine's Retreat Hot Tub Fire Pit Trails Beach

LOCATION LOCATION ✅ Rated Top 5% of Homes ✅Cleanliness, Fully stocked kitchen ✅Pet-Friendly, Minutes from ferry & beaches ✅ Peaceful & private neighborhood ✅ HotTub, Fire Pit, Trails at your door step, perfect for peaceful strolls or energetic hikes through lush landscapes. AND Flexibility, with Every detail curated for comfort and style, you'll feel at home the moment you step inside. Located with the island's natural beauty around you, unwind and reconnect with nature.

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

5 out of 5 average rating, 40 reviews

Guest suite in Edgartown

Cheerful, Romantic Retreat for Two

HaileyRating, 5 stars9 months ago

Julie’s place was amazing! It was very clean, had anything you could possibly need, was in a quiet neighbourhood and had a very comfy bed. It was also more spacious than we expected it to be. Truly the best air bnb we have stayed in! We would definitely go back

5 out of 5 average rating, 6 reviews

Flat in Edgartown

Martha's Vineyard Retreat Close to Town and Beach

CherryRating, 5 stars10 months ago

Clean rental in a great location. Short drive to everything that is “happening” in town. Full kitchen with coffee pot, great water pressure in the shower — I would definitely recommend renting this apartment. Perfect for couples!

Superhost

Guest suite in Oak Bluffs

4.76 out of 5 average rating, 42 reviews

Tree Top Suite Get-Away

CoraRating, 5 stars3 weeks ago

Thanks for a great weekend in Oak Bluffs, we were only there for a short trip this occasion but we were so comfortable and relaxed there. The bed and pillows were fantastic, easy to get wrong, and it can ruin a trip, so we loved it and were well rested. The property was well stocked with shampoos, body wash, towels, iron and board, hairdryer couldn’t ask for me. I would recommend and I would return. Thanks

4.98 out of 5 average rating, 46 reviews

Cottage in Tisbury

One Bedroom Cottage in Vineyard Haven

AdamRating, 5 stars2 weeks ago

We loved staying at Jessica and Mike’s perfect cottage. The home is absolutely delightful, beautifully decorated, and the surroundings quiet and serene. We rented bikes, got an Uber from the rental place to drop our bags and them straight back to get the bikes. It’s an easy ten minute bike ride from the cottage to all the action in Vineyard Haven (and only five to the Museum and Cat Boat Coffee on the water.) Just totally awesome.

4.96 out of 5 average rating, 23 reviews

Home in Oak Bluffs

Coastal Chic Cape Centrally Located Oak Bluffs, MA

Michelle And GregRating, 5 stars8 months ago

We loved the location at the end of a little road so no through traffic (fresh eggs next door too). The pond is fun with lots of wildlife, sometimes we could hear the roosters next door. The sunsets are lovely from the home as well. Seating in the living room great and found it to be quiet when sleeping at night. The two bedrooms on the lower level both have heat pumps (for heat/cooling) we have always had great luck with (for temperature control in the bedrooms). Loved sitting on the back deck and having the resident geese wandering around. Lovely property!

4.76 out of 5 average rating, 49 reviews

Guest house in Edgartown

Marthas Vineyard 1BR Cottage 10 min to beach/town

ThomasRating, 5 stars3 weeks ago

We really enjoyed our stay at this cottage. It was clean, comfortable, and close to town and the beach. Michael was an excellent host!

4.81 out of 5 average rating, 62 reviews

Guest suite in Edgartown

Private studio overlooking Morning Glory field.

HowardRating, 5 stars5 days ago

We had a wonderful, relaxing, comfortable and memorable week in Maria Clara’s studio. It’s located in a beautiful, quiet and picturesque area conveniently close to town. The studio is very well stocked with all necessary amenities, including a washer and dryer. Maria Clara is a wonderful hostess who took care of all our needs and communicated promptly. Blessings come in different forms and at different times in our lives when we least expect them. This find was an unforgettable blessing. Gracias, Maria Clara!🙏