Chappaquiddick Island vacation rentals

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Top-rated vacation rentals in Chappaquiddick Island

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Guest favorite

Guest suite in Oak Bluffs

4.94 out of 5 average rating, 308 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!

Jan 4 – 11

G$21,496 GYD per night

Guest favorite

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.

Sep 16 – 23

G$42,275 GYD per night

Guest favorite

Home in Oak Bluffs

4.94 out of 5 average rating, 170 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!

Apr 18 – 25

G$138,827 GYD per night

Guest favorite

Apartment in Oak Bluffs

4.97 out of 5 average rating, 163 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.

Dec 15 – 22

G$43,338 GYD per night

Guest favorite

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.

Feb 26 – Mar 5

G$64,881 GYD per night

Guest favorite

Apartment in Falmouth

4.98 out of 5 average rating, 120 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

Nov 22 – 29

G$18,790 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!

Apr 2 – 9

G$122,770 GYD per night

Superhost

Guest suite in Falmouth

4.8 out of 5 average rating, 372 reviews

Summer into Fall is when Falmouth is at its best!

Falmouth beaches are great year round. Falmouth is fully open with lots of great live music on weekends and trivia in many different locations mid week. The weather is generally warm enough now for hiking, biking, golf and scenic beach walks. I do not charge a cleaning fee & ask you to respectfully treat the space with care and clean up after yourself. I make sure the space is more diligently cleaned and disinfected between guests. Sorry but this is a no pet space.

Jul 29 – Aug 3

G$31,053 GYD per night

Guest favorite

Apartment in Barnstable

4.99 out of 5 average rating, 231 reviews

Your dog will love it here and you will too.

If you love to travel with your dog (dogs), like I do, then this is the perfect place for you and your dog. We have a large fenced in yard for your dog to play in and for you to relax in with your dog. We have a one bedroom apartment with a full kitchen, bath, living room and dining area When you book would you PLEASE let me know whether or not you will be traveling with a dog and if you are what breed of dog will you be bringing. Thanks!

Jan 1 – 8

G$27,338 GYD per night

Guest favorite

Guest suite in Oak Bluffs

4.98 out of 5 average rating, 133 reviews

Quiet Hide Away

Lovely efficiency suite with private entrance in a quiet neighborhood. Private space located over attached garage. Plenty of space for two guests. Comfortably appointed with queen bed, dining set, living area with tv and full bath. Enjoy a coffee or cocktail on the private deck. Toaster oven, refrigerator and coffee maker will start your day right before heading to nearby beaches, golf courses or shopping.

Oct 3 – 10

G$56,974 GYD per night

Guest favorite

Home in Edgartown

4.97 out of 5 average rating, 149 reviews

20-minute walk to Edgartown Village!

This 1550 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 It has 3 bedrooms and sleeps 8. 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!

Dec 31 – Jan 7

G$117,583 GYD per night

Guest favorite

Apartment in Edgartown

4.94 out of 5 average rating, 174 reviews

The Osprey - Short walk to Edgartown & beach

Two-room suite in a private setting. Sun-filled bed and living rooms with stone fireplace and two separate entrances. Private patio in large garden. 20 minute walk to downtown Edgartown and to State Beach. Direct access to bike and walking paths. VTA public bus stop on Beach Road and a two minute walk from the property's private lane.

Feb 26 – Mar 5

G$47,986 GYD per night