Holiday rentals with a fireplace in Oak Bluffs

Vineyard Haven Escape

This Vineyard Haven property offers an open concept floor plan with a renovated kitchen, dining area, living room with a gas fireplace, den, along with a half bathroom and laundry. There are french doors that lead to the large mahogany deck / yard. The second floor features a spacious primary bedroom with an on-suite bathroom, two large bedrooms, a reading nook, and a full hallway bath. There is central air conditioning and heat. The outside offers a large yard and outdoor shower. Come enjoy.

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.

The Island Collection MV: The Hideaway

This beautiful 3 bedroom home is located in a quiet area on Martha’s Vineyard by Lagoon Pond. When you walk inside, you will be delighted by the stone fireplace and the comforting ambience. It presents gorgeous “costa esmeralda” granite counter tops with solid cherry cabinets, stainless steel appliances, and a kitchen which integrates to the dining area. From there, the french doors invite you to a patio surrounded by artisan landscaping. Tenant brings own linens/sheets/towels/beach towels.

WATERFRONT Cottage, Downtown w/ Beach

DIRECT WATERFRONT in-town beach house with walk-out beach and onsite private parking. This recently renovated 1 bedroom, 1.5 bath, 2-story house is located directly across the street from the famous Black Dog Tavern, right on the bustling year-round Vineyard Haven harbor. This property is no doubt one of the most unique residential properties on Martha’s Vineyard given its proximity to the harbor, ferry terminal, stores, restaurants, bike rentals, beaches & so much more. You will love it!

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!

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.

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.

Valentine's Retreat Hot Tub Fire Pit Trails Beach

LOCATION LOCATION ✅ Rated Top 5% of Homes ✅Cleanliness, Fully stocked kitchen ✅Pet-Friendly, Minutes from ferry & beaches ✅ Peaceful & private neighborhood ✅ HotTub, Fire Pit, Trails at your door step, perfect for peaceful strolls or energetic hikes through lush landscapes. AND Flexibility, with Every detail curated for comfort and style, you'll feel at home the moment you step inside. Located with the island's natural beauty around you, unwind and reconnect with nature.

Chappaquiddick Island - Whispering Pines

Peace and quiet, and access to fabulous East Beach, Mytoy, Wasque and the many wonderful walking trails of Chappaquiddick, this lovely home among "whispering Pines" will be your warm welcoming retreat after a day at the beach, exploring Chappy by bike or fishing to your hearts delight. We provide a comfy, well furnished and beautifully decorated home outfitted with all cotton bedding, linens and fresh pillows, and lovely quilts, wool and cotton rugs, and so much more.

NEW Beautiful Waterfront, Firepit & Private Dock

Welcome to Weather Permitting, a relaxing Cape Cod retreat perfect for families and groups. Enjoy beautiful water views, cozy gathering spaces, and direct pond access from the private dock. Spend your days relaxing by the water, lounging on the deck, or exploring nearby beaches and local attractions. - 6 min drive to Seconsett Beach - 10 min drive to South Cape Beach - 15 min drive to Mashpee Commons shopping & dining Experience Mashpee with us & learn more below!

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!