Holiday houses in Chappaquiddick Island

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Top-rated holiday rentals in Chappaquiddick Island

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite

Guesthouse 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.

Guest favourite

Home in Edgartown

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. .

Guest favourite

Cottage in Sandwich

4.95 out of 5 average rating, 229 reviews

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!

Top Guest favourite

Cottage in Edgartown

4.97 out of 5 average rating, 66 reviews

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 favourite

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

Top Guest favourite

Apartment in Oak Bluffs

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.

Top Guest favourite

Apartment in Falmouth

4.97 out of 5 average rating, 225 reviews

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

Top Guest favourite

Cottage in Tisbury

4.98 out of 5 average rating, 342 reviews

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.

Guest favourite

Home in Oak Bluffs

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!

Top Guest favourite

Home in Edgartown

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.

Guest favourite

Home in Edgartown

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.

Top Guest favourite

Apartment in Edgartown

5 out of 5 average rating, 108 reviews

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