Vacation homes in Oak Bluffs, Massachusetts

Martha's Vineyard Island Home Realty is a premier real estate agency located at 97 Circuit Avenue in Oak Bluffs, Massachusetts. Specializing in properties on beautiful Martha's Vineyard, our team of experienced agents is dedicated to helping clients find their dream island home. Whether you're looking for a cozy cottage, a waterfront estate, or a charming vacation rental, we have the expertise to guide you through the buying or selling process. Trust Martha's Vineyard Island Home Realty to make your island living dreams a reality.

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 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.

Martha's Vineyard Surfside Hotel, located at 7 Oak Bluffs Avenue in Oak Bluffs, Massachusetts, is a premier lodging option on the beautiful island of Martha's Vineyard. This family-owned and operated hotel has been welcoming guests since 1987, offering a cozy and comfortable stay for visitors looking to explore all that the island has to offer. Situated in the heart of Oak Bluffs, Martha's Vineyard Surfside Hotel is the perfect home base for exploring the six charming towns, stunning beaches, and delicious farm-to-table restaurants that make up the island. Whether you're interested in biking, hiking, fishing, or sailing, there is something for everyone to enjoy on Martha's Vineyard.

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.

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.

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.

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.

Seacoast Properties is a premier real estate agency and travel agency located at 31 North Summer Street in Edgartown, Massachusetts. Specializing in Martha's Vineyard properties, we offer a wide selection of vacation rentals and homes for sale, from charming cottages to luxurious estates. Our experienced agents are experts in the local market and are dedicated to helping you maximize your sales and rental profits. Martha's Vineyard is a unique resort island known for its rich history, arts, music, and culture. With outstanding restaurants, shops, galleries, and beautiful beaches, there is something for everyone to enjoy. Whether you are looking to buy, sell, or rent a property on the island, Seacoast Properties is here to make your Martha's Vineyard dreams a reality.

Anchor Realty of Martha's Vineyard is a premier real estate and travel agency located in the charming town of Oak Bluffs, Massachusetts. Our dedicated team of professionals specializes in helping clients buy, sell, and rent properties on the beautiful island of Martha's Vineyard. Whether you are looking for a vacation rental or a permanent home, we are here to assist you every step of the way. With our extensive knowledge of the local real estate market and our personalized approach to customer service, Anchor Realty is the perfect choice for all your real estate needs on Martha's Vineyard. Visit us at 41 Circuit Avenue to start your journey towards finding your dream property on this picturesque island.

Viewpoints Real Estate Martha's Vineyard is a premier real estate and travel agency located at 79 Beach Road in Tisbury, Massachusetts, United States. Specializing in Martha's Vineyard real estate sales and vacation rentals, our team of experienced agents and brokers are dedicated to providing top-notch service to clients looking to buy, sell, or rent properties on this beautiful island off the coast of New England. Whether you're searching for a primary home, luxury vacation getaway, waterfront property, historic antique, new construction, or vacant land, Viewpoints Real Estate has the expertise to assist you every step of the way. Our knowledge of the island is extensive, covering all towns from Chilmark to Oak Bluffs, ensuring that our clients have access to the most comprehensive information when making real estate decisions.

Martha's Vineyard Island-Wide Realty and Island-Life Studio is a unique institution located in the heart of Oak Bluffs, Massachusetts. Combining a clothing store with a real estate agency, this one-of-a-kind establishment offers a diverse range of products and services to cater to the needs of both locals and tourists. Whether you're looking for stylish apparel or searching for your dream home on Martha's Vineyard, this institution has you covered. Visit us at 61 Circuit Avenue to experience the best of island living at Martha's Vineyard Island-Wide Realty and Island-Life Studio.

Grace Hagerty Real Estate Inc. is a reputable real estate agency located at 2 Wing Road in Oak Bluffs, Massachusetts, United States. With years of experience in the industry, our dedicated team of professionals is committed to helping clients find their dream homes or sell their properties quickly and efficiently. Whether you are looking to buy, sell, or rent, we provide personalized service and expert guidance every step of the way. Trust Grace Hagerty Real Estate Inc. to make your real estate goals a reality.

The Island Collection MV is a premier real estate and travel agency located at 53 Ocean Avenue in Oak Bluffs, Massachusetts. Specializing in luxury properties and vacation rentals on Martha's Vineyard, our experienced team offers personalized service to help clients find their dream island getaway. Whether you're looking to buy a waterfront home or book a relaxing vacation rental, The Island Collection MV is your go-to destination for all things Martha's Vineyard. Explore the beauty of the island with us and let us help you create unforgettable memories on this picturesque New England gem.