Holiday rentals in Edgartown South Beach

Chappy cottage close to ferry & walk to beach

Booking for '26 Season. Charming cottage is a 5-minute bike ride to the Chappy ferry & beach and a 10-15 minute walk to the 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.

The Lobster Pot: Lake Tashmoo, beachfront

Welcome to The Lobster Pot, your cozy beach cottage on the tranquil shores of Martha's Vineyard. Nestled on the waterfront, this charming retreat is ideal for a paradise getaway. Wake up to the soothing sound of waves, enjoy panoramic ocean views from your private deck, and relax in the gentle sea breeze. With its inviting décor and relaxed ambiance, The Lobster Pot offers a perfect blend of relaxation and adventure. Savor fresh seafood, stroll along the sandy beach, or enjoy stunning sunsets.

Luxury Guest Suite w/ Private Patio • Near Town

This apartment was newly built just a few years ago & still feels brand new. Located above the garage of our main residence, it has a private side entrance completely separate from the main house for total privacy. Set at the end of a beautiful subdivision just 2 miles from downtown Vineyard Haven, guests enjoy a private patio w/ gardens & a gas fire pit. Inside features stylish Vineyard décor, crisp A/C, fully equipped kitchen, large bedroom w/ queen memory foam bed & a large walk-in shower.

Chappy Beach House

Welcome to this charming 4-bedroom retreat tucked just off Chappaquiddick’s only paved road. Perfectly situated minutes from the Chappy Ferry, downtown Edgartown, and some of the island’s most pristine, uncrowded beaches. Features include AC, high-speed WiFi, a washer/dryer, and a gas grill for laid-back summer dinners. Whether you’re a longtime Vineyard lover or discovering Chappy for the first time, this home offers the ideal base to experience the island’s quiet beauty and classic charm.

Vineyard Meadow Writer's Cottage with Hot Tub

This lovely retreat is just steps from miles of trails. Walk to the beach or meander through woods of Long Point Wildlife Refuge, experiencing the serenity of this untouched corner of Martha's Vineyard. After a day of enjoying the outdoors, come home to the light and airy writer's retreat. The HOT TUB IS OPEN! It also has an outdoor shower and a wonderful kitchen. This is the perfect location for a get-away with family and friends or for a creative retreat with your fellow artists.

Juniper Point Cottage With Ocean View

Charming Cape Cod cottage on a quiet semi-private road with beautiful views of Vineyard Sound. This inviting coastal retreat features 3 bedrooms, 2 private en-suite baths, 1 semi-private en-suite bath, a fully equipped kitchen, gas fireplace, cable TV, WiFi, and air conditioning. Relax on the second-floor deck with water views or enjoy outdoor dining on the patio with the BBQ grill. Conveniently located near the Martha’s Vineyard ferry, bus station, beaches, shops, and town.

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.

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!

Beachfront Cottage w. Yard + Town Access

Welcome to The Mizzen Cottage! Updated 1930's cottage on an ocean front compound on beautiful Chappaquiddick. Complete with a picturesque porch overlooking the outer harbor, side deck, outdoor shower, washer/dryer, dishwasher. Stunning views of the Edgartown lighthouse and Cape Poge. Access to a private beach. Access town with just a 10 minute walk (or 1 minute drive) to the Chappaquiddick Ferry, and be in downtown Edgartown in 15 minutes or less!

Stylish Getaway|Outdoor Shower|Patio|No car needed

* 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

The Ideal Spot

The perfect getaway in Falmouth for all seasons! Our home is beautifully located overlooking Bourne’s Farm and we are steps away to the picturesque Shining Sea Bike Path. Enjoy a beautiful scenic 8.5 mile ride winding your way thru the Sippewisset marsh and along the coastline to the seaside village of Woods Hole. Where you can enjoy the local restaurants ,shops and science learning or jump on the ferry to Marta’s Vineyard.

Arrowsmith Cottage-Oak Bluffs near Eastville Beach

Welcome to Arrowsmith Cottage! If you are considering bringing your pet, please note - one small dog will be considered, but please first contact me directly (scroll down on the cottage's listing page and click on the "Contact Host" button), and tell me a little bit about him/her, as pets require homeowner's written approval and guest’s agreement to the pet fee (generally $100 per stay) and homeowners’ pet rules.