Chappaquiddick Island vacation rentals

5 out of 5 average rating, 137 reviews

Guesthouse in Barnstable

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. .

Superhost

Guest suite in Edgartown

4.91 out of 5 average rating, 99 reviews

Step Away; A Martha's Vineyard Retreat

Studio apartment addition attached to our family home. Our home is located three miles to downtown Edgartown with bus service & bike path close by. Private entrance, mini fridge, coffee press & accessories, private bath with shower, washer/dryer, bed in a loft area (ladder access only) with queen size sofa bed available below for additional sleeping. This is our family home with two baby boys. We try our best to keep quiet, but it is important to note their presence; rental has a sound machine.

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 Oak Bluffs

4.95 out of 5 average rating, 365 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!

4.94 out of 5 average rating, 33 reviews

Apartment in Edgartown

Katama Loft

Newly remolded apt 2 miles to either downtown or beach with bike path across the street! Restaurants and general store within a half mile. One bedroom ,living room area, kitchen with stove, microwave, and convection oven and cookware. Grill, outdoor dining, smart tv, wifi, beach gear, laundry, and more! Bikes and kayaks available on request. Apartment is just newly renovated August 2022 (was rented year round for past 7 years). Thoughtful touches throughout and your comfort always in mind.

4.98 out of 5 average rating, 206 reviews

Apartment 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.

4.91 out of 5 average rating, 86 reviews

Guesthouse in Edgartown

Martha’s Vineyard Cottage - A Glamping Experience!

This is your vineyard home, where you can walk or ride a bike less than a mile to the beach or two into town. Get the glamping experience with kitchenette, A/C, an outdoor shower, a composting toilet, a queen bed in the loft and futon couch that can sleep two more in the living room. Enjoy outdoor games, outdoor seating, a Weber grill for bbq, tv, WiFi, cozy indoor space and more, right on the bike path with a bus stop for easy accessibility or free car parking. Whatever you want!

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!

Superhost

Loft in Edgartown

4.89 out of 5 average rating, 72 reviews

Sweet Triangle loft, close to beach, free parking

Great for couples or families with young kids (not ideal for 4 adults), centrally located. Enjoy the Vineyard with a car (free parking) or without, from here. * On the bike path * 1 mile from State Beach * 1 mile from Main Street, Edgartown & Chappy ferry * Close to trail walking paths * walking distance to restaurants * walking distance to groceries * On VTA bus line ( easy access to all towns/ferries) We send guide book with recs on food, activities, etc upon booking

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

Apartment 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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Popular amenities for Chappaquiddick Island vacation rentals

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BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Chappaquiddick Island

4.98 out of 5 average rating, 58 reviews

Bungalow in Barnstable

Cozy Cape Cod Beach House Bungalow

AlliRating, 5 stars1 month ago

My husband and I had an incredible stay at the beach house. It was so relaxing, comforting and cozy. We took day trips to Nantucket and Martha’s Vineyard, and both agreed that we would have almost rather stayed at the beach house to take in the beautiful scenery! We are already planning a trip back next fall. By far the most memorable Airbnb stay we have had!

4.91 out of 5 average rating, 54 reviews

Updated Beautiful Cottage in Edgartown AC

RayRating, 5 stars7 months ago

Kenneth Is a great host communicates very well and has a genuine concern for his guests Ray

4.99 out of 5 average rating, 69 reviews

Piece of Katama Heaven near South Beach,Edgartown

RebeccaRating, 5 stars1 month ago

Beautiful, large home! It was perfect for a family get-together. Very nice location and well-stocked with everything we needed. We really enjoyed having use of the bicycles in the shed and rode the bike trail near the house. The kids loved playing ping pong and foosball in the wonderful basement. The basement/game room, in particular, was a great place for my brother's toddler, who made good use of the huge variety of toys down there. We had a great time in this lovely house, thank you!

Superhost

4.88 out of 5 average rating, 42 reviews

Edgartown Cottage By The Pond

ThomasRating, 5 stars6 months ago

House was impeccably clean, with bathrooms and kitchen welcoming. The kitchen had everything one could need to cook and comfortably prepare meals. Overall, an excellent house - strongly recommended!

5 out of 5 average rating, 7 reviews

Townhouse in Edgartown

Bright townhome with private ponds, pickleball

JamieRating, 5 stars10 months ago

Whitney & Emma were extremely responsive and kind hosts. They accommodated requests and ensured we had a smooth stay. The townhome is very cute, decorated perfectly to give you a MV feel, with cooling on the second floor and beautiful cross breeze from the outdoor patio. They provide all the little necessities for cooking and cleaning during your stay. Thanks so much for the hospitality and we look forward to staying again.

5 out of 5 average rating, 6 reviews

Home in Yarmouth

Sauna I Walk2Beach I Pet Friendly I Fire Pit

MollyRating, 5 stars5 days ago

We loved our stay here! Spent the weekend with our two young children and the house had everything we could need and more. It was walking distance to the beach and near great restaurants. Victoria also provided a list of local recommendations which we took a few of and loved them all! Would recommend staying here.