TOP 30 Best Hotel in Oak Bluffs, Massachusetts

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.

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 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.

Inn 38 Oak Bluff Circle is a charming and cozy lodging establishment located at 38 Oak Bluff Circle in Plymouth, Massachusetts, United States. Nestled in a picturesque setting, this inn offers comfortable accommodations and a warm, welcoming atmosphere for guests to relax and unwind. With its convenient location near popular attractions and scenic landmarks, guests can easily explore all that Plymouth has to offer. Whether you're visiting for business or pleasure, Inn 38 Oak Bluff Circle provides a peaceful retreat for a memorable stay.

The Morgan Hotel, located at 9 Healy Way in Oak Bluffs, Massachusetts, offers comfortable and stylish lodging for guests visiting the area. With its convenient location in the heart of Oak Bluffs, guests can easily explore the charming town and enjoy all it has to offer. The hotel features modern amenities, cozy rooms, and friendly staff to ensure a pleasant stay for every guest. Whether you're visiting for business or pleasure, the Morgan Hotel is the perfect choice for your accommodations in Oak Bluffs.

The Island Inn Hotel is a charming lodging establishment located at 15 Island Inn Road in Oak Bluffs, Massachusetts, United States. Nestled on the picturesque Martha's Vineyard, this hotel offers a relaxing and comfortable stay for guests looking to unwind and enjoy the beauty of the island. The hotel features cozy rooms, stunning views, and top-notch amenities such as a swimming pool, tennis courts, and a fitness center. Whether you're visiting for a romantic getaway, family vacation, or business trip, the Island Inn Hotel is the perfect place to stay. Experience the warmth and hospitality of this lovely hotel during your next visit to Martha's Vineyard.

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.

Ocean Park Realty Inc is a reputable real estate agency that has been serving sellers and buyers island wide for over 47 years. Located at 69 Circuit Avenue in Oak Bluffs, Massachusetts, this institution is known for its expertise in the local market and dedication to providing top-notch service to clients. Whether you are looking to sell your property or find your dream home, Ocean Park Realty Inc is the go-to agency for all your real estate needs. With a proven track record of success and a team of experienced professionals, you can trust that you are in good hands with Ocean Park Realty Inc.

Madison Inn is a charming lodging option located at 18 Kennebec Avenue in Oak Bluffs, Massachusetts. This quaint inn offers comfortable accommodations and a warm, welcoming atmosphere for guests looking to enjoy a relaxing stay on Martha's Vineyard. With its convenient location and cozy rooms, Madison Inn is the perfect choice for travelers seeking a peaceful retreat in the heart of this picturesque seaside town. Enjoy a comfortable stay at Madison Inn and experience the beauty and charm of Oak Bluffs, Massachusetts.

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.

The Dockside Inn is a charming and cozy lodging located at 9 Circuit Avenue Extension in Oak Bluffs, Massachusetts. Situated in the heart of this picturesque seaside town, the inn offers comfortable accommodations and a warm, welcoming atmosphere. Guests can enjoy easy access to the nearby shops, restaurants, and attractions, as well as stunning views of the harbor. Whether you're looking for a relaxing getaway or a fun-filled vacation, The Dockside Inn is the perfect place to stay.

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.

Martha's Vineyard Resort is a charming lodging destination located at 117 New York Avenue in Oak Bluffs, Massachusetts, United States. Nestled in the heart of the picturesque Martha's Vineyard, this resort offers a tranquil and relaxing atmosphere for guests to unwind and enjoy a peaceful getaway. With comfortable accommodations, top-notch amenities, and impeccable service, Martha's Vineyard Resort is the perfect choice for travelers looking for a memorable stay on this beautiful island. Whether you're seeking a romantic retreat, a family vacation, or a weekend escape with friends, this resort has everything you need to make your stay unforgettable.

Summercamp is a charming lodging institution located at 70 Lake Avenue in Oak Bluffs, Massachusetts, United States. This unique establishment offers a fun and relaxing atmosphere perfect for those looking to escape the hustle and bustle of everyday life. With comfortable accommodations and a range of exciting activities, Summercamp is the ideal destination for a memorable summer getaway. Whether you're looking to unwind by the lake, explore the local shops and restaurants, or participate in organized events and excursions, Summercamp has something for everyone. Come experience the magic of summer at this one-of-a-kind institution.

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.

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 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.

East Chop Harbor Front Apartments is a charming waterfront accommodation located at 47 East Chop Drive in Oak Bluffs, Massachusetts. Situated on the picturesque East Chop Harbor, this institution offers stunning views of the water and easy access to the beach. The apartments are spacious and well-appointed, perfect for a relaxing getaway or a longer stay on Martha's Vineyard. Guests can enjoy the peaceful atmosphere and convenient location, with shops, restaurants, and attractions just a short drive away. Whether you're looking for a weekend retreat or a summer escape, East Chop Harbor Front Apartments is the perfect choice for your next vacation.

Vineyard Dream Realty is a premier real estate agency located at 26 Winne Avenue in Oak Bluffs, Massachusetts. With a deep love for Martha's Vineyard, our team of experienced professionals is dedicated to helping you find your dream home on this magical island. Founded over a decade ago by a family who fell in love with Martha's Vineyard and decided to make it their permanent home, Vineyard Dream Realty offers personalized service tailored to your individual needs and desires. Our team's extensive background in real estate, combined with our intimate knowledge of the island and its vibrant community, ensures that we can help you find the perfect property to fulfill your Vineyard dream.

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.

Martha's Vineyard Real Estate, located at 63 Winter Street in Edgartown, Massachusetts, is a reputable real estate agency with a rich history dating back to 1972. Originally a peaceful retreat for families to escape to, Martha's Vineyard has since evolved into a bustling community with diverse real estate transactions. Despite the changes over the years, Martha's Vineyard Real Estate still prides itself on building personal connections with clients that last long after the transaction is complete. The agency's agents have a strong working knowledge of the island's real estate market and are committed to providing individual attention to each client.

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 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.

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.

The Overton House is a historic landmark and popular tourist attraction located on Narragansett Avenue in Oak Bluffs, Massachusetts, United States. This beautiful and well-preserved house offers visitors a glimpse into the past with its unique architecture and rich history. Explore the grounds and learn about the fascinating stories behind this iconic building, making it a must-see destination for history enthusiasts and tourists alike.

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.