Holiday rentals with a fire pit in Dukes County

2 BR-Private guest house with Hot Tub and Fire Pit

Welcome to our charming 2-bedroom private guest house, nestled in a peaceful Chilmark neighborhood. Enjoy the spacious outdoor area, perfect for gatherings, featuring an 8-person dining set, a wood-burning fire pit, a BBQ grill, a 6-person hot tub, and a seasonal outdoor shower. Our location offers easy access to local attractions: just a 4-minute drive to Alleys General Store, West Tisbury Center, and the library, and only 5 minutes to the stunning Lucy Vincent Beach and Chilmark town center.

Stunning 4/2.5 Water View, Hot Tub, Dogs ok

Custom home with beautiful water views of Lagoon Pond. Surrounded by Land Bank and Sheriff's Meadow, this very private home offers easy access to miles of hiking trails and pristine waters. Enter the home from the covered porch; the main level features an open floor plan, high ceilings in the living areas - open to the dining room and kitchen, where large windows frame the Lagoon. Sleeps up to 8. Outdoor shower! Wifi speed 430 MBPS download speed Dogs ok with owner approval ; fee applies

Vineyard Haven Walk to Ferry

I love this neighborhood! It is quiet, peaceful, and only a short walk to either Tashmoo Beach or downtown Vineyard Haven and the ferry. The house has plenty of outdoor space with it's own wood fired pizza oven, fire pit, and decks. There are nice seating areas near the fire pit, on the lower deck and on the upper deck. Walk through the backyard, down a dirt road and be at the water in five minutes. Beach towels included! Plenty of sliding glass doors and LOTS of light. Vitamix included!

Quaint Roomy Ranch

Enter this light filled and airy home with soaring cedar lined ceilings and an entire southern facing wall of windows. This surprisingly spacious home has enough room for the whole family and more. Kids will love having the bunk room to themselves while parents can enjoy the rest of the living area in peace. Located in a quiet neighborhood, this is a perfect family retreat. Enjoy the expansive deck while you grill lunch or dinner and finish up the evening with s'mores by the fire pit.

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!

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.

Ferry (Car) Reservations Available for Summer 2026

F͟R͟E͟E͟ ͟C͟A͟R͟ ͟F͟E͟R͟R͟Y͟ ͟R͟E͟S͟E͟R͟V͟A͟T͟I͟O͟N͟ ͟F͟O͟R͟ ͟A͟U͟G͟U͟S͟T͟ ͟2͟2͟-͟2͟9͟!͟ In town, 1930's cottage, lovingly updated by architect-owner. • Stylish decor, open floor plan, granite terrace • 2 blocks to Main St/harbor/ferry/town beach/playhouse • Central Air • Close to bike rentals, restaurants, shops, spa, library, mini-golf, etc. • Large yard with wood/gas grills, bocce, corn hole, beach chairs, fire pit • Outdoor shower • 3BR + sleeping loft

Saltwind Cottage | Beach Walk • Cozy Fireplace

Escape to this cozy Cape Cod cottage—just 6 mins to Menauhant, 8 to Surf Drive, and 14 to Old Silver Beach. Adorably decorated in coastal style, it features 2 TVs, a gas fireplace, outdoor shower, BBQ grill, and an outdoor fireplace with a TV for magical movie nights under the stars. Relax by scenic Green Pond, stroll to Main Street shops and restaurants, and savor fresh seafood, homemade ice cream, salty air, and sunset skies in this charming seaside town.

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

Little Miss Sunshine: cozy New England cottage

Little Miss Sunshine is a cozy and cheerful 600 square foot cottage located in South Westport. This classic New England cottage is located in a small coastal neighborhood and is within walking distance to the Bayside Restaurant, Westport's East Beach, and the beautiful walking trails of Allens Pond Wildlife Sanctuary. Our cottage is also within short driving distances of great Westport beaches, breweries, wineries, and restaurants.

The Blue Lagoon, Oak Bluffs

Come enjoy this beautifully designed, brand new home. With 3 bedrooms and 3 full bathrooms you will have all the space you need. An outdoor patio with gas grill is the perfect spot to relax after a day at the beach. Just a few steps away is the lagoon where you can paddle board, kayak, dig clams, or just take in the amazing sunsets! Summer rentals are Saturday to Saturday. Please send a message if you have any questions.

Sweet Cottage w/ yard, 1.5BR, Walk to Town & Water

Lovely 500 sq. ft. guest cottage on peaceful, residential hilltop near town & water. Open kitchen & living area; bedroom with double bed; sweet office accessed only thru BR with twin-sized couch; queen sofabed in LR. Walkable to parks, beach and town for kids and adults! Fenced in yard w bbq, outdoor shower and a brand new fire pit. A true pleasure. Read more below!