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Arrowsmith Cottage-Oak Bluffs. Aug 15-22 now open!

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.

Vineyard Haven Guest House - A/C, Walk to Town

Queen bed up (large carpeted master suite/living room with vaulted ceiling, ceiling fans, and walk out to deck, This End Up Couch Set), bedroom with 2 twins down, full bathroom (renovated 2023) on first floor, AC throughout the house, washer dryer, 42" flat screen TV with Amazon Firestick and internet based Xfinity cable, grill, outdoor shower and hardwood floors downstairs. Short walk to downtown Vineyard Haven and short drive to many popular beaches! Quiet dead end street with own driveway.

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.

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.

Full 3 bedroom House in Tisbury Woods - Sleeps 8

Our place is close to the bus line and bike paths. The house is in the woods for a private setting. The house is secluded, yet convenient to Vineyard Haven. You can walk to the market through the woods. There is a free bus from the Tisbury Park and Ride (5 minute walk) every 20 minutes to the Steamship dock. Nice place for couples, wedding guests, anglers, fishing, solo adventurers, business travelers, and families with kids. Good location for lots of island events: derby, wedding, road race

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!

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!

Lake Street Haven

Lake Street Haven — Walk to Town, Sleeps 8 | 4BR, 3BA + Outdoor Shower & Firepit Escape to Lake Street Haven, a beautifully decorated 4-bedroom, 3-bathroom private home located in the heart of Vineyard Haven. Just a short walk to town, Owen Park Beach, and the ferry, this coastal retreat blends charm, comfort, and convenience for your Martha’s Vineyard getaway. Whether you’re here for a family vacation, girls’ getaway, or island retreat, Lake Haven offers the perfect home base.

Walk to Town, beach and amazing location 113A

Walk to all Oak Bluffs has to offer. 5-10 mins. to harbor, town, beach and dining. Amazing location! This three unit property offers a shared patio and deck space along with all the amenities. It is private and well appointed. 3 flat screen Televisions, wifi, appliances, tile and wood floors, granite counters, outdoor shower, gas grill and best of all it's all brand new. This 2 bedroom unit will provide you with an excellent home base to explore Oak Bluffs and Martha's Vineyard.

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.

Entire home newly renovated in August 2025

Step into your serene island getaway at 5 Pine Tree Lane, with 4 bedrooms (4 beds) and nestled in the heart of beautiful Martha’s Vineyard. This brand-new home blends modern comfort with Vineyard charm perfect for families, groups of friends, or couples looking for a relaxing escape. Walking distance to a neighborhood beach, year round ferry access (1mi) and shopping. This home was thoughtfully designed and offers everything you need for a peaceful and memorable experience.

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.