Holiday rentals with outdoor seating in Tisbury

Arrowsmith Cottage-Oak Bluffs Near Eastville Beach

Welcome to Arrowsmith Cottage! If you are considering bringing your pet, please note - 1 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. Hosts are not responsible for listing inaccuracies due to Airbnb's own input or AI.

Value · Location · Beach

Harbor view apartment, a quick walk from the ferry

This is a great one bedroom apartment on the second floor of a house. My place is close to the beach, public transport, the Steamship Authority ferry, Black Dog Tavern, Main Street Vineyard Haven, Stop & Shop grocery, and lots of great shopping. You’ll love the convenience! Walk to the apartment right off the ferry boat. Lots to do in walking distance, and onsite parking. The Martha's Vineyard Museum is a 5 minute walk, down the same street. My place is great for couples and solo adventurers.

Outdoor spaces · Value · Cleanliness

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!

Outdoor spaces · Location · Walkability

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!

Outdoor spaces · Location · TV

East Chop Cottage - walk to lighthouse & beach!

This quaint little cottage is located in the heart of East Chop, a neighborhood of Oak Bluffs. East Chop features the high, prominent bluffs that gave Oak Bluffs its name. A lighthouse, East Chop Light, stands at the north end of the chop on Telegraph Hill- only a five minute walk from the cottage. The cottage is a twelve minute walk to the harbor, and about a mile from the Oak Bluffs ferry! There is a public beach about 1/2 mile down the road. ***This space is not suitable for children

Location · Outdoor spaces · Layout

West Chop Cottage + Beach Access

Sweet, rustic, and tiny - yet comfortable with all the amenities - the cottage is a short walk to the town center, lighthouse, landmarks, and lovely harbor beaches on desirable West Chop. The private yard with harbor view allows for sunbathing and stargazing, lounging and lawn games, grilling and campfires. With access to spectacular private association ocean beach, Hancock Beach, on the island's south shore in Chilmark, this rental offers a complete Vineyard experience.

Value · Outdoor spaces · Air conditioning

Cottage suite between the harbors: no minimum stay

Nestled between Oak Bluffs and Vineyard Haven harbors, our relaxing suite is a perfect way to extend your weekly rental, or to enjoy a day or two on this special island we call The Rock. Our cozy guest suite, newly renovated has two bedrooms, living space, kitchenette, full bath, deck with grill, outdoor shower, and footwash (hot H20), W/D (in unit) and a private entrance. An easy walk to town and beaches. Parking is available in our driveway. Enjoy our historic home!

Location · Outdoor spaces · Check-in

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!

Outdoor spaces · Location · Bathroom

MV King bed, Water Views, Near Bike Path- Bus stop

Have your morning coffee looking out at the sunrise and sailboats from your living room or bedroom windows. This modern studio feels secluded while only a mile and a half from Main Street Vineyard Haven, four miles from Oak Bluffs, and eight miles to Edgartown. This is the perfect place to unplug but does come equipped with everything you need, including wifi, smart tv, fully equipped kitchen, beach towels, linens, and bath towels for your stay. :)

Location · Value · View

Central location for your vacation

An apartment in a peaceful Raised Ranch! Your Martha’s Vineyard sanctuary. Centrally located from nearby Vineyard Haven, Oak Bluffs, Edgartown and West Tisbury. Beaches and trails in close proximity. 8 minutes away from ferry. Great for family vacation, Island explorations, work trips, hosting wedding guests, wellness retreat, or just a simple gateway, this home will compliment your Martha’s Vineyard experience.

Value · Outdoor spaces · Nearby

Quiet Hide Away

Lovely efficiency suite with private entrance in a quiet neighborhood. Private space located over attached garage. Plenty of space for two guests. Comfortably appointed with queen bed, dining set, living area with tv and full bath. Enjoy a coffee or cocktail on the private deck. Toaster oven, refrigerator and coffee maker will start your day right before heading to nearby beaches, golf courses or shopping.

Outdoor spaces · Location · Layout

Not Your Great Aunt's Island Cottage

In the heart Vineyard, 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 • Easily walkable 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

Outdoor spaces · Location · Quiet