TOP 10 Luxury vacation accommodations in Massachusetts

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 Christopher is a charming lodging institution located at 24 South Water Street in the historic town of Edgartown, Massachusetts. This picturesque establishment offers comfortable accommodations in a beautiful setting, just steps away from the waterfront. Guests can enjoy the quaint surroundings of Edgartown while staying at The Christopher, making it the perfect destination for a relaxing getaway. With its cozy rooms and convenient location, The Christopher is the ideal choice for those looking to experience the charm of Martha's Vineyard.

The Ashley Inn is a charming lodging establishment located at 129 Main Street in the picturesque town of Edgartown, Massachusetts. This cozy inn offers a peaceful and comfortable retreat for guests looking to relax and unwind in a beautiful coastal setting. With its convenient location near local attractions, shops, and restaurants, the Ashley Inn is the perfect choice for travelers seeking a memorable stay in Martha's Vineyard. Experience warm hospitality, well-appointed accommodations, and personalized service at this delightful inn.

The Sydney is a charming lodging establishment located at 22 Winter Street in the picturesque town of Edgartown, Massachusetts, United States. This cozy inn offers comfortable accommodations and a warm, welcoming atmosphere for guests looking to relax and unwind during their stay on Martha's Vineyard. With its convenient location near shops, restaurants, and attractions, The Sydney is the perfect home base for exploring all that this beautiful island has to offer. Whether you're seeking a romantic getaway or a family vacation, The Sydney has everything you need for a memorable and enjoyable experience.

Faraway Martha's Vineyard is a unique lodging institution located at 23 Kelly Street in Edgartown, Massachusetts, United States. Embrace the free-spirited elegance of the island at this enchanting escape, which features 6 lodging properties, 3 dining experiences, and a private pool and patio. Stay in the hotel's main guest house or choose from full-floor suites with harbor views and private patios. Retreat to a stand-alone Captain's house or enjoy a full floor-through suite overlooking the hotel grounds. The premium two-level, two-bedroom suite is perfect for families and friends to gather. Guests can enjoy craft coffee at The Strand, shop at the on-site boutique WHEAT, and relax by the exclusive swimming pool or state-of-the-art fitness courtyard. With luxury toiletries, a custom vinyl record library, and designer beach towels, Faraway Martha's Vineyard offers a truly unique experience for guests to enjoy the beauty of Martha's Vineyard.

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 Harborside Inn is a charming lodging establishment located at 3 South Water Street in the picturesque town of Edgartown, Massachusetts, United States. Situated right by the waterfront, this inn offers stunning views of the harbor and a relaxing atmosphere for guests to enjoy. The rooms are cozy and well-appointed, providing a comfortable retreat for visitors exploring Martha's Vineyard. With its convenient location and warm hospitality, The Harborside Inn is the perfect choice for a memorable stay on the island.

The Crocker House Inn is a charming lodging establishment located at 12 Crocker Avenue in the picturesque town of Tisbury, Massachusetts, United States. This historic inn offers guests a cozy and comfortable retreat with beautifully decorated rooms, modern amenities, and warm hospitality. Situated in a convenient location near local attractions, shops, and dining options, the Crocker House Inn is the perfect choice for travelers looking for a relaxing and memorable stay on Martha's Vineyard. Whether you're visiting for a romantic getaway, family vacation, or business trip, the Crocker House Inn provides a welcoming atmosphere and top-notch service for all guests.

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.

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.

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.

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.

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.

Admiralty Inn and Suites is a charming lodging establishment located at 51 Teaticket Highway in beautiful Falmouth, Massachusetts. This cozy inn offers comfortable accommodations and excellent amenities for travelers looking to explore Cape Cod. Whether you're visiting for a weekend getaway or an extended vacation, Admiralty Inn and Suites is the perfect home base for your adventures. With its convenient location, friendly staff, and affordable rates, this institution is the ideal choice for both leisure and business travelers. Book your stay today and experience the warm hospitality of Admiralty Inn and Suites.

InnSeason Resorts Captain's Quarters is a charming lodging establishment located at 241 Grand Avenue in the picturesque town of Falmouth, Massachusetts, United States. This cozy resort offers comfortable accommodations and a warm, welcoming atmosphere for guests looking to relax and unwind by the sea. With its convenient location near the beach and local attractions, guests can enjoy a peaceful getaway while still being close to all the action. Whether you're looking for a romantic escape or a family vacation, InnSeason Resorts Captain's Quarters is the perfect destination for your next trip to Cape Cod.

InnSeason Resorts Surfside is a charming lodging institution located at 134 Menauhant Road in Falmouth, Massachusetts, United States. Situated just steps away from the beach, this resort offers guests a relaxing and peaceful retreat by the sea. The accommodations are comfortable and well-appointed, with modern amenities to ensure a pleasant stay. Guests can enjoy a range of on-site facilities including a swimming pool, fitness center, and outdoor BBQ area. With its convenient location and cozy atmosphere, InnSeason Resorts Surfside is the perfect choice for a memorable vacation on Cape Cod.

The Club at New Seabury is a luxurious lodging institution located at 95 Shore Drive West in Mashpee, Massachusetts, United States. Nestled in the beautiful seaside community of New Seabury, this prestigious club offers upscale accommodations and world-class amenities for guests looking to relax and unwind in style. With stunning views of the ocean and access to private beaches, golf courses, and fine dining options, The Club at New Seabury is the perfect destination for those seeking a truly unforgettable getaway. Whether you're looking to escape for a weekend retreat or plan a special event, this exclusive institution promises a memorable experience in a picturesque setting.

Northey Street House Bed and Breakfast is a charming lodging establishment located at 30 Northey Street in the historic city of Salem, Massachusetts. This cozy bed and breakfast offers comfortable accommodations in a beautiful Victorian-style home. Guests can enjoy a delicious homemade breakfast each morning and relax in the inviting common areas. Whether you are visiting Salem for its rich history, vibrant culture, or stunning waterfront views, Northey Street House Bed and Breakfast is the perfect place to stay. Book your stay today and experience the warmth and hospitality of this lovely establishment.

The South Cape Motel is a charming lodging establishment located at 499 Waquoit Highway in the picturesque town of Falmouth, Massachusetts. Situated in the heart of Cape Cod, this cozy motel offers comfortable accommodations and a warm, welcoming atmosphere for guests looking to relax and unwind. With its convenient location near beautiful beaches, shopping, dining, and outdoor activities, the South Cape Motel is the perfect choice for a memorable stay on the Cape. Whether you're visiting for a weekend getaway or an extended vacation, you'll find everything you need for a comfortable and enjoyable stay at this lovely motel.

Southcape Resort and Club is a lodging institution located at 950 Falmouth Road in Mashpee, Massachusetts, United States. Situated in one of the most beautiful areas in Cape Cod, Mashpee attracts visitors year-round with its stunning beaches and bay access. The town is known for its fishing and boating community, as well as its proximity to Martha's Vineyard and Nantucket. The resort offers two-bedroom accommodations in either a townhouse or ranch style, each equipped with a fully equipped kitchen and spacious living and dining area. Guests can enjoy resort-style amenities such as five tennis courts, shuffleboard courts, indoor and outdoor pools, and a children's playground. With over thirty golf courses, luxury shopping, delicious restaurants, outdoor activities, and nightlife nearby, Southcape Resort and Club is the perfect home base for exploring all that Mashpee has to offer. Visitors can take advantage of special deals when booking directly with the resort. Whether you're looking to relax by the pool or explore the area's attractions, Southcape Resort and Club has something for everyone.

The Courtyard by Marriott Cape Cod Hyannis is a charming lodging destination situated at 707 Iyannough Road in Barnstable, Massachusetts, United States. This hotel offers comfortable and modern accommodations for guests looking to explore the beautiful Cape Cod area. With spacious rooms, a fitness center, indoor pool, and on-site dining options, the Courtyard by Marriott Cape Cod Hyannis provides a relaxing and convenient stay for travelers of all kinds. Whether visiting for business or pleasure, guests can enjoy the hotel's close proximity to local attractions, shopping, and dining options. Experience comfort and hospitality at its finest at the Courtyard by Marriott Cape Cod Hyannis.

Sea Mist Resort is a charming lodging institution located at 141 Great Neck Road South in the picturesque town of Mashpee, Massachusetts. Nestled in a serene coastal setting, this resort offers guests a peaceful retreat with easy access to the beautiful beaches and attractions of Cape Cod. The resort features comfortable accommodations, a variety of amenities including a pool and fitness center, and friendly staff dedicated to ensuring a memorable stay for all guests. Whether you're looking for a relaxing vacation or an adventurous getaway, Sea Mist Resort is the perfect destination for your next trip to Cape Cod.

The Cape Codder Resort & Spa is a luxurious lodging and spa facility located at 1225 Iyannough Road in Barnstable, Massachusetts. Nestled in the heart of Cape Cod, this resort offers a tranquil escape for guests looking to relax and rejuvenate. With elegant accommodations, top-notch amenities, and a full-service spa, guests can unwind in style. The resort also features indoor and outdoor pools, a water park, on-site dining options, and event spaces for weddings and special occasions. Whether you're seeking a romantic getaway, a family vacation, or a weekend retreat, the Cape Codder Resort & Spa has something for everyone.

Fairfield Inn & Suites by Marriott Cape Cod Hyannis is a charming lodging establishment located at 867 Iyannough Road in Barnstable, Massachusetts, United States. Situated in the heart of Cape Cod, this hotel offers comfortable accommodations and modern amenities for travelers looking to explore the beautiful surroundings. The hotel features spacious rooms and suites, a complimentary breakfast buffet, a fitness center, an indoor pool, and free Wi-Fi. With its convenient location and friendly staff, Fairfield Inn & Suites by Marriott Cape Cod Hyannis is the perfect choice for a relaxing stay on the Cape.

The Animal Inn, located at 2 Massachusetts 130 in Sandwich, Massachusetts, is a premier full service boarding facility for pets. Whether you need veterinary care or a peaceful resting place for your beloved pet, The Animal Inn is dedicated to providing the highest level of care and comfort. Our experienced team treats your pet like family, ensuring their enjoyment and well-being during their stay. With spacious accommodations and a range of amenities, The Animal Inn is the perfect choice for your pet's holiday or vacation needs. Make a reservation for Thanksgiving, Christmas, or winter vacation season, or simply stop by for a tour to see why we are Cape Cod's finest pet hotel. Visit us at 2 Route 130 in Forestdale, Massachusetts to experience the exceptional care and attention to detail that sets The Animal Inn apart.