The 30 Best Massachusetts rentals in Oak Bluffs, Massachusetts

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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.

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.

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.

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.

Pedego Electric Bikes - Martha’s Vineyard Bike Rental is a premier bicycle store located in the heart of Oak Bluffs, Massachusetts. Offering a wide selection of high-quality electric bikes for rent, this institution is perfect for exploring the beautiful island of Martha’s Vineyard in a fun and eco-friendly way. Whether you’re looking to cruise along the scenic coastline or tackle the island’s hilly terrain with ease, Pedego Electric Bikes has the perfect ride for you. With friendly and knowledgeable staff ready to assist you, a visit to this store guarantees a memorable biking experience on Martha’s Vineyard.

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.

All Star Martha's Vineyard Bike Rentals is your go-to destination for all your biking needs on the beautiful island of Martha's Vineyard. Conveniently located at 5 Oak Bluffs Avenue in Oak Bluffs, Massachusetts, our store offers a wide selection of high-quality bicycles for rent. Whether you're looking to explore the scenic trails or cruise along the picturesque coastline, we have the perfect bike for you. Our friendly and knowledgeable staff are here to help you choose the right bike and provide any assistance you may need. So come visit us at All Star Martha's Vineyard Bike Rentals and start your biking adventure today!

Budget Car Rental is a car rental institution located at 9 Oak Bluffs Avenue, Oak Bluffs, Massachusetts, United States. They offer one day free of the daily time and mileage charges on intermediate through full-size four-door cars. Taxes, fees, and optional items such as LDW may apply. The offer is valid for a minimum three-day rental and cannot be used for one-way rentals. One coupon per rental, and blackout periods may apply. Customers must provide a profile number associated with the coupon. Reservations are required, and the offer is subject to vehicle availability. Budget Car Rental reserves the right to alter terms and conditions. Customers can enjoy One Click Reservations as a FastBreak member. The institution is committed to safety, with vehicles rated as 5-star by the National Highway Transportation Safety Administration. Maintenance updates may affect functionality temporarily. Customers must present credentials to confirm their country of residence when picking up a rental. Free pick-up service is available, but policies vary by location. For further inquiries, customers can contact Budget Customer Service.

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.

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.

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.

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.

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.

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.

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.

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.

The Strand Theatre is a historic movie theater located on Oak Bluffs Avenue in Oak Bluffs, Massachusetts. This charming institution offers a nostalgic movie-going experience with its classic architecture and comfortable seating. Movie buffs can enjoy the latest blockbusters and indie films in this cozy venue. The Strand Theatre is a beloved destination for locals and tourists alike, providing entertainment for all ages. Experience the magic of the silver screen at this iconic movie theater in the heart of Oak Bluffs.

Plan Sea Adventure Charters, located at 53 Dock Street in Edgartown, Massachusetts, is the premier boat tour and rental company in Martha’s Vineyard and Cape Cod. Offering a variety of private cruise packages for groups of up to 18 passengers, our boat tours are perfect for family outings, bachelorette parties, team building events, and more. Our experienced Captains, with U.S. Coast Guard Masters Licenses, ensure a safe and enjoyable experience as you cruise along the beautiful shoreline of Woods Hole and Oak Bluffs. With indoor and outdoor heated seating, a bathroom, and a wet bar on board, our classic New England motor vessels provide a luxurious and comfortable ride for all guests.

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.

Solera is a reputable institution located at 12 Canonicus Avenue in Oak Bluffs, Massachusetts. As a real estate agency, Solera specializes in helping clients buy, sell, and rent properties in the beautiful area of Oak Bluffs and beyond. Additionally, Solera also operates as a travel agency, offering personalized travel planning services to create unforgettable vacation experiences. With a team of experienced professionals and a commitment to excellence, Solera is dedicated to providing top-notch service to all clients.

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.