Vacation rentals in Chappaquiddick

5 out of 5 average rating, 137 reviews

A charming carriage house with shingle siding is set against a blue sky adorned with fluffy clouds. A black Jeep is parked in front, showcasing the gravel driveway. Lush greenery surrounds the property, enhancing its inviting appearance.

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.

4.97 out of 5 average rating, 66 reviews

An aerial view captures the serene landscape of Chappaquiddick Island, showcasing sandy beaches, wooded areas, and the winding shoreline. Calm waters reflect the surrounding land, while a ferry is seen approaching the island, highlighting the connection to the mainland. Docked boats line the marina, indicating a vibrant coastal activity.

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 West Tisbury

The exterior of a modern barn house is visible, featuring a black shingle facade and multiple skylights along the sloped roof. A private entrance is framed by a small, leafy tree, with a stone pathway leading through a lush green lawn.

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

Guest suite in Oak Bluffs

A sliding barn door crafted from light-colored planks is viewed against a textured wood wall. The door features a black handle and a metal track, providing a modern touch. Nearby, a diamond-shaped mirror is mounted, adding visual interest to the room.

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!

4.98 out of 5 average rating, 206 reviews

A wooden deck is visible, showcasing a simple bench and a couple of potted plants. Lush green grass and a variety of trees and flowering bushes create a serene garden setting, inviting quiet moments outdoors. Light filters through the greenery, enhancing the peaceful atmosphere.

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.

4.97 out of 5 average rating, 225 reviews

A spacious bedroom featuring a wooden bed frame and a large bed with neutral bedding. A colorful wall art piece adds visual interest above the bed. Natural light enters through two windows, and a full-length mirror is positioned nearby on one side.

Apartment in Falmouth

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

4.98 out of 5 average rating, 342 reviews

A wooden deck is shown with outdoor seating, including a table and chairs. Surrounding the deck are blooming rose bushes and lavender plants, adding vibrant colours to the natural landscape. The space is bordered by natural stone and pebbles, leading into a wooded area.

Cottage in Tisbury

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.

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!

A newly renovated kitchen is highlighted with modern appliances and sleek quartz countertops. Natural light floods the space, enhancing the adjacent dining area with a round table for six. Stylish cabinetry provides ample storage, while decorative artwork adds a touch of elegance.

4.95 out of 5 average rating, 113 reviews

Walk To Town - Beautiful Edgartown Cottage

Walk to downtown Edgartown in minutes while staying in this newly renovated 2-story home in the heart of Upper Main St. The 3-bedroom, 2-bathroom house has been completely renovated, with brand new bathrooms, kitchen appliances, etc. You cannot beat the location of this home! You're a short 10 min walk from Edgartown's amazing restaurants & shops, in addition to a short bike ride to Katama's famous South Beach or Oak Bluff's State Beach. Both easily accessible via bike paths.

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

Superhost

A classic white lighthouse is situated on the sandy beach, with a brick path leading to its base. The horizon features hues of orange and purple as the sun sets, casting a warm glow across the water. Gentle waves lap at the shore nearby.

4.86 out of 5 average rating, 166 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).

Guest suite in Oak Bluffs

A well-lit staircase is visible, featuring beige carpeting with a subtle striped pattern. A wooden handrail runs along one side, leading upwards. At the top of the stairs, a framed picture is mounted on the wall, adding a touch of decoration to the space.

4.99 out of 5 average rating, 168 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.

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Other great vacation rentals in Chappaquiddick

5 out of 5 average rating, 40 reviews

A wooden staircase leads down from a sandy path to a calm beach, framed by low shrubs and trees. Soft sand is visible alongside the clear water, with smooth rocks in the distance. The scene is tranquil, reflecting a serene coastal environment.

Guest suite in Edgartown

Cheerful, Romantic Retreat for Two

HaileyRating, 5 stars9 months ago

Julie’s place was amazing! It was very clean, had anything you could possibly need, was in a quiet neighbourhood and had a very comfy bed. It was also more spacious than we expected it to be. Truly the best air bnb we have stayed in! We would definitely go back

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!

4.98 out of 5 average rating, 46 reviews

A cozy cottage is framed by lush greenery, showcasing a charming front porch with potted plants. The entrance features a black door and large windows, inviting natural light. A small dining area is visible on the side, complemented by an umbrella for shade.

Cottage in Tisbury

One Bedroom Cottage in Vineyard Haven

AdamRating, 5 stars2 weeks ago

We loved staying at Jessica and Mike’s perfect cottage. The home is absolutely delightful, beautifully decorated, and the surroundings quiet and serene. We rented bikes, got an Uber from the rental place to drop our bags and them straight back to get the bikes. It’s an easy ten minute bike ride from the cottage to all the action in Vineyard Haven (and only five to the Museum and Cat Boat Coffee on the water.) Just totally awesome.

A wooden staircase leads up to a welcoming entrance, flanked by decorative planters filled with vibrant flowers. The railing displays a simple lattice design, enhancing the exterior's rustic charm while providing a cozy approach to the home's entryway.

5 out of 5 average rating, 13 reviews

Katama Hideaway

KatieRating, 5 stars6 months ago

Staying at Rebecca’s Hideaway was a wonderful experience! I stayed with the family during the Thanksgiving holiday during the offseason and the location was absolutely beautiful. The hosts went above and beyond to make us feel comfortable and even left us treats at the house! The location of the house was private, but a close enough drive into downtown Edgartown to get drinks and dinner or do some shopping. There are many options to relax outdoors and it’s a close walk to get to South Beach to enjoy nature. I would definitely recommend staying here and would rebook in a heart beat!

5 out of 5 average rating, 64 reviews

Home in Dennis

Beachfront· Sauna· Screened Patio· 2Kings· DogsYes

MichaelRating, 5 starstoday

Amazing home. Fantastic location. Peaceful and relaxing. One of our favorite vacation stays ever. Never turned the tv on… unusual for me. Hosts really thought of everything and more. Highly recommend if you are visiting Cape COD. 5+ stars.

The vintage beach house exterior is framed by lush greenery and blooming flowers, showcasing classic Cape cedar shingles. A glimpse of Katama Bay and sailboats is visible in the background, contributing to the property's serene coastal setting.

4.82 out of 5 average rating, 68 reviews

Spacious, Old Vineyard charm with Private Beach

NathalieRating, 5 stars2 weeks ago

Liza’s place is magical. The house is so much more than a beach house. It has a soul! Thank you Liza for being such an exquisite host.

5 out of 5 average rating, 7 reviews

A series of white shelves is mounted on a wall, displaying an assortment of colorful books and decorative items. Notable elements include a model sailboat, a lighthouse figurine, and a potted plant. A woven light fixture hangs above, casting a warm glow on the arrangement.

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.