TOP 30 Luxury island vacation in Oak Bluffs, Massachusetts

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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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

Coblyn Realty: Martha's Vineyard is a premier real estate and travel agency located at 5 Peter Williamson Boulevard in Oak Bluffs, Massachusetts. Specializing in luxury properties and vacation rentals on the beautiful island of Martha's Vineyard, our experienced team is dedicated to providing exceptional service to both buyers and sellers. Whether you are looking to invest in a waterfront property or plan your dream vacation, Coblyn Realty is here to help you every step of the way. Contact us today to discover the perfect property or vacation rental for you on Martha's Vineyard.

Corbin Norton House is a charming bed and breakfast located at 87 Ocean Avenue in Oak Bluffs, Massachusetts. This historic institution offers comfortable accommodations in a picturesque setting just steps away from the beach. Guests can enjoy beautifully decorated rooms, delicious breakfasts, and personalized service during their stay. With its convenient location and warm hospitality, Corbin Norton House is the perfect destination for a relaxing getaway on Martha's Vineyard.