Holiday rentals 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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Guest favourite

Guest house in Barnstable

5.0 out of 5 average rating, 111 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

Guest suite in Oak Bluffs

4.94 out of 5 average rating, 313 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!

Guest favourite

Guest suite in West Tisbury

4.94 out of 5 average rating, 102 reviews

Loft Guest Suite in Modern Barn House

A beautiful guest suite on Martha’s Vineyard with a private entrance on the 2nd floor of the back wing of our newly renovated modern barn house. Surrounded by trees, beside a large meadow, this large 400 square foot suite has vaulted wood ceilings and skylights. Enjoy the outdoor shower and new outdoor sitting area. The location is centrally located, just off historic Music St, a short walk to a small town center which provides amenities. Ask about our other guest suite if you are with others.

Guest favourite

Home in Oak Bluffs

4.94 out of 5 average rating, 172 reviews

Spectacular beach & pool combo; beautiful sunsets!

Close to airport, you’ll love backyard beach, water view, pool/grass yard, ambiance and the outdoors space. Beach & Pool (POOL HEAT STARTS SUMMER, 6/21) is a hard to find combination!! Location is private, yet it's close to the 3 largest towns on Martha's Vineyard. Great for couples, families (with kids), and big groups. Enjoy dinner with the indoor/outdoor Sonos music system during a beautiful sunset! NOTE; Rate increase in high season, pool/spa is a combined unit & ONLY heated in summer!

Guest favourite

Home in Edgartown

5.0 out of 5 average rating, 7 reviews

Chappy Beach House

**OSV STICKERS APPROVED! BOOK Derby dates now** Get away to this lovely 4BR house on Chappy! Conveniently located directly off of the island’s only paved road within minutes of pristine beaches, the Chappy Ferry, and downtown Edgartown. Special features include AC, high-speed wifi, gas grill, and washer/dryer. Whether returning to MVY or first-time visitors, this home gives guests access to the best of all the Vineyard has to offer. We're new to the rental market. Be one of our first guests!

Guest favourite

Cottage in Edgartown

4.96 out of 5 average rating, 52 reviews

Chappy cottage close to ferry & walk to beach

Chappy Cottage. NOTE: THE COTTAGE REQUIRES A 2-MINUTE FERRY TO TOWN. Charming and renovated cottage is a 5-min bike ride to the Chappy ferry & 10-min walk to beach. Located in a quiet wooded setting, the property offers new furniture and beds; reno kitchen with d/w and micro; new bath w/ shower/tub; w/d; hardwood; screen porch; deck; outdoor shower; shed. Cable, wifi (200 megs), AC; ceiling fan, grill, deck furniture, beach chairs & umbrella. The rental season runs mid May through late Oct.

Guest favourite

Home in Edgartown

4.96 out of 5 average rating, 188 reviews

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.

Guest favourite

Flat in Falmouth

4.98 out of 5 average rating, 130 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

Guest favourite

Cottage in Tisbury

4.98 out of 5 average rating, 321 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

4.97 out of 5 average rating, 229 reviews

Sweet little post and beam

A 700 sq ft post& beam guest house that sleeps 2 people. Open kitchen, living, dining area with full bath. Stairs lead to a full second story bedroom- a queen size bed, half bath, separate seating area. Private back patio and outdoor shower. Cozy off season cottage as well- radiant heat and AC. Central location to everything you want to see! Easy bike to town/beach. Very quiet and spacious. Everyone says "so much nicer in person than in the photos". Come see for yourself!

Guest favourite

Cottage in Bourne

5.0 out of 5 average rating, 148 reviews

140 Steps to Beach with Water Views

This small rustic unique cottage is ready for you to enjoy on Buttermilk Bay. It is located within a sought after cape style cottage community. It offers a Private Association Beach. The cottage has water views from both the living room and deck. Grab the provided beach chairs, cooler and walk a 140 steps from the deck to the beach. You can also Walk, Bike, or Fish on Cape Cod Canal 5 min away. Close to restaurants, hiking trails, and Mass Maritime. 20% off wk!

Guest favourite

Holiday home in Edgartown

5.0 out of 5 average rating, 13 reviews

Contemporary Chappaquiddick Retreat

Contemporary four-bedroom retreat with spacious layout, light-filled open living spaces, and direct access to expansive outdoor deck from all bedrooms. Loft in main house has fifth-bed and two-bed bunkhouse offers privacy for guests or kids. 3-acre property affords complete seclusion while still being close to the Chappy ferry, Community Center and Slip Away Farm. Pristine beaches, breathtaking scenery, and total relaxation await — you'll be happy on Chappy!