TOP 30 Guest house lodging in Oak Bluffs, Massachusetts

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JADE House Bed and Breakfast, located at 1 Rustling Oaks Road in West Tisbury, Massachusetts, invites you to experience the beauty of Martha's Vineyard in a comfortable and welcoming setting. Joy and Alan, your friendly hosts, are dedicated to providing a safe and enjoyable stay for all guests. Our spacious rooms feature queen size beds with memory foam mattresses, private en-suite bathrooms, and individually controlled temperature settings. You can choose to book one, two, or all three of our private guest rooms for your stay.

The Oak Bluffs Inn is a charming lodging establishment located at 64 Circuit Avenue in the picturesque town of Oak Bluffs, Massachusetts. This historic inn offers comfortable accommodations and personalized service to all guests. With its convenient location near shops, restaurants, and the beach, The Oak Bluffs Inn is the perfect choice for a relaxing getaway on Martha's Vineyard. Experience the warmth and hospitality of this quaint inn during your stay in this beautiful coastal town.

Isabelle's Beach House is a charming lodging institution located at 83 Seaview Avenue in Oak Bluffs, Massachusetts, United States. Our family-owned B&B was founded on the principles of hospitality, warmth, and community, making every guest feel like part of our inclusive community. As a gift of Island Joy, we offer 2024 Gift Certificates for a memorable stay at our beach house. Our newly opened boutique in Oak Bluffs, launched in August 2023, serves as a platform for mission-driven businesses and conscious consumers. Summer boutique hours are from May to October, or shop online 24/7 at www.jubileemv.com.

Narragansett House is a charming lodging establishment located at 46 Narragansett Avenue in Oak Bluffs, Massachusetts, United States. This cozy inn offers comfortable and well-appointed rooms for guests looking to enjoy a relaxing stay on Martha's Vineyard. The institution's convenient location allows visitors to easily explore the island's attractions, including beaches, shops, and restaurants. With its warm hospitality and inviting atmosphere, Narragansett House is the perfect choice for a peaceful getaway in this picturesque New England town.

Capricorn House is a charming lodging establishment located at 79 Seaview Avenue in Oak Bluffs, Massachusetts. Situated in the picturesque town of Oak Bluffs, this cozy inn offers comfortable accommodations for travelers looking to relax and unwind on Martha's Vineyard. With its convenient location near the beach and other attractions, Capricorn House is the perfect place to stay for a memorable vacation experience. Whether you're visiting for a weekend getaway or an extended stay, you'll feel right at home at Capricorn House.

The Attleboro House is a charming lodging establishment located at 42 Lake Avenue in Oak Bluffs, Massachusetts, United States. This quaint and cozy inn offers comfortable accommodations for guests looking to relax and unwind in the picturesque surroundings of Martha's Vineyard. With its convenient location near the waterfront and local attractions, The Attleboro House is the perfect choice for a peaceful and enjoyable getaway. Whether you're seeking a romantic retreat or a family vacation, this welcoming institution provides a warm and inviting atmosphere for all guests to enjoy.

The Walker House is a charming lodging establishment located at 27 Huntington Avenue in Oak Bluffs, Massachusetts, United States. This historic building offers a cozy and comfortable retreat for guests visiting the area. With its convenient location and welcoming atmosphere, The Walker House is the perfect place to stay while exploring all that Oak Bluffs has to offer. Whether you're in town for a weekend getaway or an extended vacation, you'll feel right at home at The Walker House.

Kelley House is a charming lodging option located at 79 Circuit Avenue in the picturesque town of Oak Bluffs, Massachusetts. This historic establishment offers comfortable accommodations in a quaint and welcoming atmosphere. Guests can enjoy the convenience of being within walking distance to the town's shops, restaurants, and attractions, as well as the nearby beaches. With its prime location and cozy accommodations, Kelley House is the perfect choice for visitors looking to experience the charm of Martha's Vineyard.

Vineyard Square Hotel & Suites is a charming lodging institution located at 38 North Water Street in Edgartown, Massachusetts, United States. Situated in the heart of downtown Edgartown, this boutique hotel offers warm hospitality and comfortable accommodations for a relaxing Martha's Vineyard getaway. Guests can enjoy easy access to gourmet restaurants, quaint shops, and a vibrant arts scene just steps away from the hotel. With luxury amenities, a variety of lodging options, and affordable prices, Vineyard Square Hotel & Suites is the perfect gateway to the island. Guests rave about the excellent service and convenient location of the hotel. The staff is friendly and accommodating, and the homemade breakfast is delicious. Guests can also enjoy access to complimentary bikes for exploring the area. Whether staying in a cozy room or a beautiful suite, visitors appreciate the attention to detail and the overall experience at Vineyard Square Hotel & Suites. With free parking nearby and a variety of nearby restaurants and shops, guests can easily explore all that Martha's Vineyard has to offer. Whether relaxing on the spacious porch or taking a bike ride to Oak Bluffs, guests can make the most of their stay at this highly recommended hotel.

The Island Inn on Martha's Vineyard by Vacasa is a charming vacation destination located at 30 Island Inn Road in Oak Bluffs, Massachusetts, United States. This condominium resort sits on five acres of beautiful land and is open year-round, offering a perfect New England getaway. The Island Inn on Martha's Vineyard offers a variety of vacation rentals to suit every traveler's needs. Whether you're looking for a cozy retreat for two or a spacious home for the whole family, there is something for everyone. The property boasts 51 vacation rentals with internet access, allowing guests to stay connected during their stay.

The Tivoli Inn, located at 125 Circuit Avenue in Oak Bluffs, Massachusetts, is a charming gingerbread house that offers clean and friendly lodging. Situated within walking distance to numerous restaurants, shops, nightlife, beaches, hiking trails, public transportation, and seasonal ferry terminals, the inn is in a prime location for visitors to explore the area. With reasonable rates, the Tivoli Inn provides a comfortable and convenient stay for guests looking to experience the beauty and attractions of Martha's Vineyard.

The Pequot Hotel, located at 19 Pequot Avenue in Oak Bluffs, Massachusetts, is a charming lodging establishment nestled among the historic "Gingerbread" cottages of the area. With a prime location just one block from the beach, four blocks from the ferry, and a short walk to Circuit Avenue, the hotel offers convenience and comfort to its guests. Closed for the winter season, the Pequot Hotel will reopen in early May for the 2024 season, with reservations becoming available starting January 2, 2024. The 32-room hotel features classic cottage décor, decorative lattice porches, and modern amenities such as private baths, air conditioning, and free wifi.

Inkwell Beach Cottage is a charming lodging located at 83 Seaview Avenue in Oak Bluffs, Massachusetts, United States. Nestled in a picturesque seaside town, this cozy cottage offers a relaxing and comfortable retreat for guests looking to unwind and enjoy the beauty of Martha's Vineyard. Just steps away from the sandy shores of Inkwell Beach, guests can enjoy stunning ocean views and easy access to swimming, sunbathing, and beachcombing. The cottage features well-appointed rooms, a fully equipped kitchen, and a spacious living area, making it the perfect home-away-from-home for a seaside getaway. Whether you're looking for a romantic escape or a fun-filled family vacation, Inkwell Beach Cottage provides a peaceful and idyllic setting for your next trip to the Cape Cod area.