Holiday rentals with a fireplace in Oak Bluffs

Lambert's Cove Retreat, Water view, Beach pass

Enjoy stunning views of Vineyard Sound from this cozy three bedroom two bath home in a quiet neighborhood just minutes from Lambert's Cove Beach. This upside down house has one bedroom on the main level along with a full bath and open kitchen, dining, and family room. The downstairs has another living space, two bedrooms, laundry room, and full bath. Enjoy family time in the open upstairs with water views, or retreat to the lower level living room for some separation, quiet time, or work space.

Charming 3-Bedrm w/Loft.New Construct! Walk 2 town

A stylish place to stay, perfect for group trips. 15min walk from town and Inkwell beach. NEW construct, beautiful open layout home is just what you have been looking for. Every bedrm has its OWN full bath. The kitchen is modern and stylish. The open layout design, leads outside to the deck, to a peaceful yet fun backyard. As you sit on the mahogany deck, you will smell the tasty delights coming from the grill of the outdoor kitchen. This home is my home and I want to share it with you.

Oak Bluffs Renovated Retreat

Fully renovated for 2025, this 3-bed, 2.5-bath townhome invites you to unwind with a community pool, tennis courts, and direct access to Sengekontacket Pond. Inside, a custom chef’s kitchen, new baths, and luxury furnishings set an upscale coastal tone. The main level flows from a sun-lit living room to dining area / deck, and powder room. The entire second floor is reserved for the primary suite. The walk-out lower level offers two guest bedrooms, a full bath, laundry, and a private patio.

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!

4-Season Guest House on Historic Chilmark Estate

Beautiful private guest house in Chilmark on Martha's Vineyard. Secluded yet convenient. Drive on pass to spectacular Chilmark beaches! Newly renovated and gorgeous. Great location - 10 minute walk to Chilmark Store. Full kitchen, living area, kitchen island/dining table, queen bed, day bed (not for sleeping), fireplace/heater, private outdoor shower, deck and picnic table, full bath inside. Keurig machine. 2 friendly labs/2 chickens on premises. Easy bus access. Old-style MV charm.

A Nostalgic Space: Your Martha's Vineyard Getaway!

Our amazing property is a perfect place to spend with family and friends! The property is wonderful for everything from a memorable family vacation to a serene couples retreat. You and your guests will begin to enjoy the feeling of privacy the minute you arrive. The home was completely updated in 2019, with an all new interior that is bright and fresh! It features an open floor plan, with a bright kitchen, all new appliances and new finishes. You can't beat the location of this home!

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.

Cozy garden retreat close to it all! Pet friendly

Come enjoy the cape from a private, dead-end road off Rt 28. 10-15 mins to beaches, 15 to Hyannis or Falmouth, 5 to Mashpee commons. Or, relax in a hammock in the privacy of the fully-fenced in wooded yard or by the fire pit. Family and dog friendly! 2 desks for WFH in separate rooms. -Heat/AC in every room -High speed Wifi : 200+ Mbps in all areas inside, 30+ Mbps from hammock -Smart speakers for in/outdoor use -Fire TV w/ Netflix, Disney+, etc -Working fireplace (in Winter)

The Driftwood Home, 5 min from Mashpee Commons, AC

- NOW PET FRIENDLY! - 15 min to Old Silver, South Cape, and Falmouth Heights beaches - 5 min to Mashpee Commons - 15 min to Falmouth Main St - 1600 square feet, built in 2014, w/ central AC - Large kitchen w/ all cookware and utensils - Outdoor deck with seating, fire pit, and grill - 55” Smart TV - 10 min to Shining Sea Bike Trail - Less than 10 min to Falmouth, Cape Cod, and Quashnet Valley Country Clubs - Centrally located to all of the Upper Cape - No parties or events!

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

Custom-build home with beautiful water views of Lagoon Pond. Surrounded by Land Bank and Sheriff's Meadow, this property is extremely private and 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

Martha's Vineyard Cottage: Walk to Town and Beach

Updated 1920s Cottage in Edgartown Village – Walk to Beach, Harbor and Main Street Step into classic Vineyard charm at this fully updated 4-bed, 3-bath craftsman cottage in the heart of Edgartown. Two blocks from Main Street’s restaurants, galleries, and harbor and a quick walk to Fuller St Beach & Lighthouse Beach. Fully winterized + AC, high-speed Wi-Fi, three workstations. Ideal for families, bachelorette parties or anyone craving a New England coastal escape.

Cape Cod Cotuit Cottage, 3 Bed Near Beaches

5 star rental Cottage in the beautiful village of Cotuit! This quaint 3-bedroom cottage is perfect for a getaway for friends and family. It is just a short distance to nearby beaches, local market, walking trails, Cape Cod league baseball stadium, shopping and restaurants. Relax on the private patio area and enjoy the peaceful, natural setting. Bring along your dog too!