House vacation rentals in Chappaquiddick Island

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Top-rated house rentals in Chappaquiddick Island

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

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Guest favorite

Home in Edgartown

4.88 out of 5 average rating, 110 reviews

Edgartown Village: Walk to Everything

This delightful Edgartown Village home is part of a three-house compound surrounding a large lawn and extensive perennial gardens. Located on Cooke St. south of Cannonball Park, this home is within close walking distance of everything Edgartown has to offer: restaurants, movie theater, Main St. shops, and the harbor. You’ll love it because of the location and the ambiance. It's great for couples and families (with kids). There is also a 2-bedroom 1 1/2 bath house across the lawn that sleeps 4.

Jan 10 – 17

G$173,679 GYD per night

Guest favorite

Home in West Tisbury

4.98 out of 5 average rating, 122 reviews

Secluded Up Island Cottage

Charming Martha's Vineyard post and beam house on two secluded acres with two bedrooms in West Tisbury. The master bedroom has a queen bed, the second bedroom has a full bed, the loft has a full size futon. It is peacefully tucked away at the end of a road with only three other houses on it. It has easy access to beaches, bike paths and walking trails. Enjoy some family time in the wooded backyard grilling or relaxing with an outdoor shower or napping in the hammock after a day at the beach.

Apr 18 – 25

G$56,553 GYD per night

Guest favorite

Home in Oak Bluffs

4.93 out of 5 average rating, 169 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!

Mar 17 – 24

G$121,199 GYD per night

Guest favorite

Home in Falmouth

4.97 out of 5 average rating, 238 reviews

The Driftwood Home, 5 min from Mashpee Commons, AC

-1600 square feet, Newly built -Old Silver Beach, South Cape Beach, and Falmouth Heights Beachs all within 15 min drive -Outdoor deck with sectional seating, fire pit, and BBQ grill -5 minutes from Mashpee Commons -Central Air Conditioning -55" smart TV w/ Netflix, Hulu, etc. -Shining Sea Bike Trail 10 min away -Spacious Kitchen w/ all utensils, flatware, and appliances -Falmouth Country Club, Cape Cod Country Club, Quashnet Valley Country Club within 10 minutes -15 min from Falmouth main st.

Oct 22 – 29

G$41,778 GYD per night

Guest favorite

Home in Edgartown

4.96 out of 5 average rating, 187 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.

Feb 25 – Mar 4

G$64,999 GYD per night

Superhost

Home in Oak Bluffs

4.91 out of 5 average rating, 126 reviews

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

Feb 26 – Mar 5

G$167,948 GYD per night

Guest favorite

Home in Oak Bluffs

4.92 out of 5 average rating, 207 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!

Dec 19 – 26

G$56,480 GYD per night

Guest favorite

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!

Feb 23 – Mar 2

G$83,860 GYD per night

Superhost

Home in Edgartown

4.87 out of 5 average rating, 141 reviews

Martha's Vineyard Vacation Home

My place is close to the Bike Path, Edgartown, South Beach, Katama General Store, Katama Farm, Edgartown Lighthouse, great views. Take the bike path either direction for all of the island's attractions. You’ll love my place because of the Renovated Kitchen, Renovated Bathrooms, Comfortable Furniture, Convenience to Everything, Outdoor Shower, Deck. My place is good for couples, solo adventurers, and families (with kids).

Oct 22 – 29

G$85,959 GYD per night

Guest favorite

Home in Edgartown

5.0 out of 5 average rating, 116 reviews

Close to Edgartown Village Center!

This 1800 square foot Ranch-style Condo with loft was built in 2018 and is set on a large nicely landscaped lot with plenty of room inside and out. It has 4 bedrooms and sleeps 9. It’s a 20-minute walk to the Edgartown village center, a 10-minute walk to Morning Glory Farm, and just a 10-minute drive to South Beach! All updated furnishings, beds, linens, appliances. Read our reviews! Immaculate!

Nov 3 – 10

G$111,309 GYD per night

Guest favorite

Home in Barnstable

5.0 out of 5 average rating, 108 reviews

Cape Cod Cotuit Cottage, 3 Bed Near Beaches

5 star rental Cottage in the beautiful village of Cotuit! This quaint 3-bedroom cottage is perfect for a getaway for friends and family. It is just a short distance to nearby beaches, local fresh market, walking trails, Cape Cod league baseball stadium, shopping and restaurants. Relax on the private patio area and enjoy the peaceful, natural setting. Bring along your dog too!

Mar 20 – 27

G$43,606 GYD per night

Guest favorite

Home in Mashpee

4.96 out of 5 average rating, 166 reviews

Gorgeous sunsets! Private family beach - Cape Cod!

Saturday to Saturday weekly rental during summer months. Wrap around deck, beach and waterfront. Open layout. Perfect for families & Couples with a family beach . Stunning sunsets, very private and close to Mashpee commons, Falmouth and New Seabury all 10 minutes away. We are happy to have you for stays longer than 7 days! Just send us a note!

Jan 6 – 13

G$71,165 GYD per night