
House holiday rentals in Chappaquiddick
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Top-rated house rentals in Chappaquiddick
Guests agree: These houses are highly rated for location, cleanliness and more.

Walk to EDG Wharf - Beautiful Home with AC & Grill
Just a short walk to Edgartown's shops & restaurants, this cape style home features open concept living, stainless steel appliances, bamboo floors, oversize 2 car garage, washer/dryer & updated features! The master suite includes a sitting area, walk in closet & attached bath with walk-in shower, soaking tub & double vanity. Additional 3 BRs include queen/twin beds & 2 full baths. Home has high ceilings & lots of windows. Kitchen sliders lead to outdoor brick patio with BBQ & dining area.

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.

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.

Waterview, Private, Walk to Beach, Mile to Town
Rustic barn-style home, waterview, spacious natural landscape, serenity, and privacy on 3 acres centrally located 1 mi from Oak Bluffs and Vineyard Haven centers. Walk to beach, bike path nearby, comfortable interiors, memory foam mattresses, cotton linens, 2 HDTVs, high-speed wifi, heat/AC, 2 ocean kayaks, and 2 bikes. Location, amenities and privacy surrounded by natural beauty make staying very easy and relaxing. Ask the host about ferry reservations if they appear to be sold out!

gorgeous waterfront cottage w/4kayaks and 2 SUPs
Small 500 sq ft gem . Quintessential Cape Cod cottage WATERFRONT on big Sandy Pond. Step back in time and enjoy being on Cape Cod in your own Camp. Come enjoy this charming cottage with 2 bedrooms and views of the pond throughout. Kayak, fish and swim from your front door. *1 Paddle Bd *4 kayaks- 4 adult/4 child life vests *Gas Fire-pit *Gas Grill *XL outdoor shower *Quiet lakeside hood *Gorgeous marble counters in the new kitchen *Remote control heating & cooling system *WiFi

**Vineyard Vacation Retreat** -3 BR
Just a stone's throw from Oak Bluffs and it's beaches, this chic 3 bedroom home provides comfort and privacy. The large bedrooms and open concept kitchen/dining/living area accommodate up to 6 people comfortably. A place for you to put your feet up, kick away your worries, and enjoy some rest and relaxation. There is so much to do and explore. The adventure is just starting so make sure to pack up your swimmers, suntan lotion and get out the door. Kick back and relax, you're home.

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!

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.

Private Pond-side Cape Cod Home
Charming 2 bedroom home located on Flax Pond. Enjoy a private sandy beach and dock. Swim, kayak, fish, boat (trolling motors only) and just relax. Enjoy the home’s spacious deck with comfortable seating for the whole family complete with chiminea for late night fires. 2 levels of lodging with central air. 2 full bathrooms, kitchen, dining room and great room. Minutes away from town beaches, bike path, golf, and shopping. Parking for approximately 4 cars.

Juniper Point Cottage With Ocean View
Charming Cape Cod cottage on semi-private road with and ocean view of Vineyard Sound. Renovations completed in mid-July, 2020. Three BR, 2 private attached baths, 1 semi-private bath, fully equipped kitchen, patio with BBQ grill, gas fireplace, cable-TV, WiFi internet, large second-floor deck, a/c.. Close to Vineyard Ferry, bus station and town. Seasonal rent. Please complete a reservation request to determine the rent in effect for your requested dates.

The Luxury Vineyard Yurt
Discover this exceptional Luxury Yurt firsthand! Upon entering, you will be welcomed by a distinctive experience, featuring textured concrete radiant floors and a four-foot circular central skylight. Every aspect has been meticulously designed, allowing you to relax in a generous private yard. Enjoy your evenings under the stars, utilize the complimentary paddling, practice yoga in the spacious loft, and indulge in the beauty of your private island Yurt!

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 3 bedrooms and a loft 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!
Popular amenities for Chappaquiddick house rentals
House rentals with a pool

In-Ground Pool Oasis | 5 Min to Cape Cod Beaches!

18 Menemsha Rd., Popponesset, Pool, 3-Beds, 4 bath

Exclusive New Seabury Home w/ Heated Pool ⛳️🏖🦞☀️🐠

Beautiful Edgartown 3500 sq ft home, heated pool

Home w/ golf view, salted heat pool, mins to beach

Jolly Captain Lighthouse

Renovated ranch with pool access

Private Pool, near beaches, 3 BR/3 BA, Central Air
Weekly house rentals

Vineyard Vacation, 3-Bedroom, Hot-tub, Golf course

Bayview on Seconsett Island

Newer const. Edgartown home A/C, car ferry tkts av

Vineyard Meadow Writer's Cottage with Hot Tub

Sunburst Cottage on Long Pond

Charming and Spacious Home in the Heart of MV

Beautiful Custom Nantucket Home

New Pristine Luxury Home on Martha's Vineyard
Private house rentals

Tucked away Up Island

Classic Edgartown Stunner close to Town and Beach

Walk to the Beach from this Cape Cod Gem!

Wonderful Waquoit Farmhouse

Valentine's Retreat Hot Tub Fire Pit Trails Beach

Simone by the Sea

Ocean View Cape Cod Beach Cottage

Ferry Tickets Available - Cozy Coastal Hideaway
Destinations to explore
- Plainview Holiday rentals
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- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
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- The Hamptons Holiday rentals
- Cape Cod
- Mayflower Beach
- West Dennis Beach
- Craigville Beach
- East Sandwich Beach
- Duxbury Beach
- Easton Beach
- Onset Beach
- Bonnet Shores Beach
- Coast Guard Beach
- Second Beach
- The Breakers
- New Silver Beach
- Pinehills Golf Club
- Sandy Neck Beach
- South Shore Beach
- Cahoon Hollow Beach
- Nickerson State Park
- Lighthouse Beach
- Cape Cod Inflatable Park
- Fort Adams State Park
- Popponesset Peninsula
- Saquish Beach
- Nauset Beach




