TOP 10 Massachusetts beach vacation 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.

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.

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.

East Chop Beach Club is a prestigious and exclusive private beach club located at 75 East Chop Drive in Oak Bluffs, Massachusetts, United States. With stunning views of the ocean and a pristine sandy beach, members can enjoy a luxurious and relaxing atmosphere. The club offers a range of amenities including beachfront access, swimming pools, dining options, and social events. Whether you're looking to relax in the sun or participate in activities, East Chop Beach Club provides a perfect escape for its members.

South Beach Apparel is a trendy clothing store located in Oak Bluffs, Massachusetts. Offering a wide selection of stylish and fashionable apparel, this store is a must-visit destination for those looking to update their wardrobe with the latest trends. From casual beachwear to chic evening attire, South Beach Apparel has something for every fashionista. Stop by 1 Circuit Avenue Edit to browse their collection and find the perfect outfit for any occasion.

MVeBike- Oak Bluffs Bike Rental is a premier bicycle store located at 15 Circuit Avenue Extension in Oak Bluffs, Massachusetts. We offer a wide range of high-quality bikes for rent, perfect for exploring the beautiful island of Martha's Vineyard. Whether you're looking to cruise along the scenic coastline or tackle the island's many trails, our knowledgeable staff is here to help you find the perfect bike for your adventure. Visit us today and experience the convenience and thrill of exploring Martha's Vineyard on two wheels.

Inkwell Beach, located at 83 Seaview Avenue in Oak Bluffs, Massachusetts, is a picturesque natural feature that offers visitors a serene and beautiful setting for relaxation and recreation. This sandy beach is known for its clear waters, gentle waves, and stunning views of the Atlantic Ocean. Whether you're looking to sunbathe, swim, or simply take a leisurely stroll along the shore, Inkwell Beach is the perfect destination for a day of fun in the sun. With its convenient location and tranquil atmosphere, this beach is a popular spot for locals and tourists alike to unwind and enjoy the beauty of the Massachusetts coastline.

Eastville Point Beach is a stunning tourist attraction located at 351 Beach Road in Oak Bluffs, Massachusetts, United States. This picturesque beach offers visitors a peaceful and serene escape from the hustle and bustle of everyday life. With its soft sand, gentle waves, and beautiful views of the ocean, Eastville Point Beach is the perfect spot for a relaxing day by the water. Whether you're looking to swim, sunbathe, or simply take a leisurely stroll along the shore, this beach has something for everyone. Come and experience the beauty of Eastville Point Beach for yourself.

Circuit Ave Oak Bluffs Stores is a charming retail destination located at 19 Circuit Avenue in Oak Bluffs, Massachusetts. This institution offers a variety of unique and trendy stores for visitors to explore and shop. From fashion boutiques to gift shops, there is something for everyone at Circuit Ave Oak Bluffs Stores. Come and discover the latest trends and must-have items in this vibrant shopping district in the heart of 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 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.

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.

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.

The Beachfront Inn on Martha's Vineyard is a charming lodging establishment located at 65 Seaview Avenue in Oak Bluffs, Massachusetts. Situated right on the beach, guests can enjoy stunning views of the ocean and easy access to the sandy shoreline. The inn offers comfortable accommodations and a warm, welcoming atmosphere for visitors looking to relax and unwind. With its prime location on Martha's Vineyard, guests can explore the island's attractions and enjoy a peaceful retreat by the sea. Whether you're looking for a romantic getaway or a family vacation, the Beachfront Inn is the perfect destination for your 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.

Sand Bar is a popular establishment located at 6 Circuit Avenue Extension in Oak Bluffs, Massachusetts. This vibrant bar and restaurant offers a laid-back atmosphere with delicious food and drinks. Whether you're looking to enjoy a casual meal with friends or grab a drink at the bar, Sand Bar has something for everyone. With its prime location on Martha's Vineyard, this is the perfect spot to unwind and relax while taking in the beautiful surroundings. Come visit Sand Bar for a memorable dining experience in a charming coastal town.

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.

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.

Martha's Vineyard Properties For Rent is a reputable real estate agency located at 89 East Chop Drive in Oak Bluffs, Massachusetts. Specializing in rental properties on the beautiful Martha's Vineyard island, our agency offers a wide range of options to suit every budget and preference. Whether you are looking for a cozy cottage by the beach or a luxurious estate with stunning views, our team of experienced agents is here to help you find the perfect rental property for your stay on Martha's Vineyard. Contact us today to start your search for the ideal vacation rental on this idyllic island destination.

Ocean Park Realty Rentals is a reputable real estate agency located at 69 Circuit Avenue in the charming town of Oak Bluffs, Massachusetts. Specializing in vacation rentals, they offer a wide range of properties to suit every taste and budget. Whether you are looking for a cozy cottage by the sea or a luxurious beachfront villa, their dedicated team of professionals is committed to helping you find the perfect vacation rental for your needs. With their extensive knowledge of the local real estate market and personalized service, Ocean Park Realty Rentals is the go-to agency for all your rental needs on 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.

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.

Our room and cottage rental institution is nestled in the charming town of Oak Bluffs, Massachusetts, just a stone's throw away from the beautiful shores of Martha's Vineyard. Located at 145 Circuit Avenue, our lodging offers a cozy and comfortable retreat for visitors looking to explore the island. Whether you're looking for a quaint room for a weekend getaway or a spacious cottage for a family vacation, we have a variety of accommodations to suit your needs. Enjoy the convenience of being within walking distance to shops, restaurants, and local attractions while also being able to relax in a peaceful and serene setting. Book your stay with us today and experience the beauty and tranquility of Martha's Vineyard.

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.

HomeGrown Tours is a premier travel agency located at 1 Seaview Avenue in Oak Bluffs, Massachusetts, United States. We specialize in providing personalized and unique travel experiences for our clients, showcasing the best that the local area has to offer. Our team of experienced travel experts are dedicated to creating unforgettable vacations, whether you're looking for a relaxing beach getaway, a cultural exploration, or an adventure-filled excursion. Let HomeGrown Tours help you plan your next dream vacation and make memories that will last a lifetime.

The Flying Seahorse offers charming summer cottage rentals in the picturesque town of Oak Bluffs, Massachusetts. Nestled at 8 Pennacook Avenue, our real estate and travel agency specializes in providing cozy accommodations for your summer getaway. With a prime location near the beach and local attractions, our cottages are perfect for families, couples, and solo travelers looking to relax and unwind. Book your stay with The Flying Seahorse for a memorable summer retreat on Martha's Vineyard.

Martha's Vineyard Sightseeing offers unique and exciting tours of the picturesque island of Martha's Vineyard, located at 23 Lake Avenue in Oak Bluffs, Massachusetts. Our experienced guides will take you on a journey to explore the island's stunning natural beauty, charming towns, and rich history. Whether you're interested in visiting the famous lighthouses, pristine beaches, or quaint shops and restaurants, our tours are sure to provide an unforgettable experience. Join us at Martha's Vineyard Sightseeing for a truly memorable adventure on this enchanting island.

Ocean Park is a picturesque and popular tourist attraction located at 2 Seaview Avenue in Oak Bluffs, Massachusetts, United States. This charming park offers stunning views of the Atlantic Ocean and features lush greenery, walking paths, and a gazebo perfect for relaxing and enjoying the ocean breeze. Visitors can also enjoy picnics, sunbathing, and various events and performances held at the park throughout the year. Whether you're looking for a peaceful retreat or a fun day out with family and friends, Ocean Park is the perfect destination for nature lovers and outdoor enthusiasts alike.