TOP 30 Beautiful island getaway in Massachusetts

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Winnetu Oceanside Resort is a charming lodging institution located at 31 Dunes Road in Edgartown, Massachusetts, United States. This resort is Martha's Vineyard's only resort at iconic South Beach, offering a nostalgic experience reminiscent of carefree childhood days. With various accommodation options ranging from private home rentals to suites and cottages, Winnetu caters to every type of vacationer. Guests can enjoy the stunning beauty of Katama, where farm meets sea at South Beach, just a short distance from historic downtown Edgartown. The resort offers a range of amenities and activities for all ages, including rides in an antique firetruck, weekly clambakes in the summer, an award-winning children's program, and two swimming pools. Guests can also indulge in the flavors of Martha's Vineyard at The Dunes Deck while taking in breathtaking views. For those looking to explore the island, Winnetu provides complimentary shuttles to downtown Edgartown and water taxis to nearby attractions.

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 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 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.

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.

Located at 1 Miller Lane in Nantucket, Massachusetts, the Nantucket Inn offers modern amenities with the charm of a traditional inn. Since 1986, this family-friendly resort has been providing guests with a superior experience at a reasonable value. Enjoy a drink at the bar or take a swim in the island's only hotel with an indoor pool. With complimentary shuttle services to downtown Nantucket, a tennis court, and a fitness center, there are exciting inclusions at every corner. Stay in comfort at this cozy New England hideaway with lower room rates and no resort fees. By booking directly, you'll receive the best available rate guaranteed and access to exclusive packages. Relax by the pool, the island's only hotel with a heated indoor swimming pool, no matter the season.

The Nantucket Hotel & Resort is a historic lodging institution located at 77 Easton Street in Nantucket, Massachusetts, United States. Situated in the charming Brant Point neighborhood, it is just steps away from downtown Nantucket and a short bike ride from the beach. As Nantucket's only year-round hotel, The Nantucket Hotel offers warm hospitality and a range of amenities for guests to enjoy. Guests can choose from elegant 1-4 bedroom suites and cottages with luxurious touches and ocean views. The hotel features two heated pools, a children's program, concierge services, and shuttle service to Jetties Beach and around town. Dining options include Breeze and Sailor’s Valentine, offering a mix of nostalgia and contemporary flair.

The Jared Coffin House is a historic lodging establishment located at 29 Broad Street in the charming town of Nantucket, Massachusetts. This elegant inn offers luxurious accommodations in a beautifully preserved building that dates back to the early 19th century. Guests can enjoy modern amenities while experiencing the rich history and charm of Nantucket. The Jared Coffin House is the perfect destination for those seeking a unique and memorable stay on this picturesque island.

Hotel Pippa is a charming lodging establishment located at 5 Chestnut Street in the picturesque town of Nantucket, Massachusetts. This boutique hotel offers a cozy and inviting atmosphere, with beautifully decorated rooms and top-notch amenities. Guests can enjoy a relaxing stay in the heart of Nantucket, just a short walk away from the island's historic attractions, shops, and restaurants. Whether you are visiting for a romantic getaway or a family vacation, Hotel Pippa provides a comfortable and memorable experience for all guests.

White Elephant Nantucket is a luxurious lodging institution located at 50 Easton Street in the charming island of Nantucket, Massachusetts. This iconic hotel offers elegant accommodations with stunning views of the harbor and easy access to the island's pristine beaches. With its impeccable service, upscale amenities, and beautiful decor, White Elephant Nantucket is the perfect destination for a relaxing getaway or a special occasion. Whether you're looking for a romantic retreat or a family vacation, this renowned institution promises a memorable stay in one of the most picturesque locations in the United States.

The Brass Lantern Inn is a charming lodging located at 11 North Water Street in Nantucket, Massachusetts. This cozy inn offers a welcoming atmosphere and comfortable accommodations for guests visiting the historic island of Nantucket. With its prime location in the heart of downtown Nantucket, guests can easily explore the island's shops, restaurants, and attractions. The Brass Lantern Inn provides a peaceful retreat with beautifully appointed rooms, a delicious breakfast each morning, and friendly staff ready to assist with any needs. Whether you are visiting for a romantic getaway, family vacation, or business trip, the Brass Lantern Inn is the perfect place to stay while experiencing all that Nantucket has to offer.

Located at 9 Cliff Road in Nantucket, Massachusetts, the Cliff Lodge Bed & Breakfast offers a leisurely ambiance and delightful charm to its guests. Originally built in 1771 as a whaling master's home, this historic inn is just a short walk from the ferry and the town, making it a perfect place to experience the beauty and enchantment of Nantucket. Returning visitors often consider Cliff Lodge as their home-away-from-home, appreciating the easy elegance of island life and the exceptional hospitality provided by the hostess and staff. The rooms offer a nice view and the breakfasts, which vary daily, are a highlight for guests. Despite COVID-19 limitations, the inn has managed to maintain its inviting common areas and outdoor spaces.

Faraway Nantucket is a charming lodging institution located at 29 Centre Street in the picturesque island of Nantucket, Massachusetts. This cozy retreat offers a peaceful and tranquil atmosphere, perfect for those looking to escape the hustle and bustle of everyday life. The accommodations at Faraway Nantucket are comfortable and inviting, providing guests with a home away from home during their stay. With its convenient location in the heart of Nantucket, guests can easily explore the island's many attractions, including beautiful beaches, historic sites, and charming shops and restaurants. Whether you're seeking a romantic getaway or a relaxing vacation with family and friends, Faraway Nantucket is the perfect choice for your next escape.

Winthrop Hotels & Resorts is a luxurious lodging institution located at 18 Amelia Drive in the beautiful island of Nantucket, Massachusetts, United States. Offering top-notch hospitality services, exquisite accommodations, and breathtaking views, Winthrop Hotels & Resorts is the perfect destination for those seeking a relaxing and indulgent getaway. With a prime location near the beach and various attractions, guests can enjoy a memorable stay filled with comfort and convenience. Whether you are looking for a romantic retreat, a family vacation, or a weekend escape, Winthrop Hotels & Resorts is the ideal choice for a truly unforgettable experience.

76 Main is a charming lodging institution located on Main Street in the picturesque town of Nantucket, Massachusetts. This cozy retreat offers guests a comfortable and inviting atmosphere, with beautifully decorated rooms and top-notch amenities. Whether you're looking for a relaxing getaway or a romantic escape, 76 Main provides the perfect setting for a memorable stay on the island. Just steps away from shops, restaurants, and the stunning beaches of Nantucket, this institution is the ideal choice for those seeking a quintessential New England experience.

Seven Sea Street Inn is a charming lodging located on Nantucket Island in Massachusetts, United States. Situated at the address 7 Sea Street, this quaint inn offers a cozy and welcoming atmosphere for guests looking to relax and unwind. With comfortable accommodations and personalized service, Seven Sea Street Inn is the perfect home away from home for travelers exploring the historic island of Nantucket. Enjoy a peaceful stay in this beautiful seaside town, just steps away from the beach and local attractions.

The Summer House India Street is a charming lodging institution located at 31 India Street in the picturesque town of Nantucket, Massachusetts. Situated in a historic building, this cozy retreat offers guests a peaceful and relaxing atmosphere for their summer getaway. With comfortable accommodations and a convenient location near the island's attractions, The Summer House India Street is the perfect choice for those looking to experience the beauty of Nantucket. Immerse yourself in the island's rich history and natural beauty while staying at this lovely establishment.

Greydon House, located at 17 Broad Street in Nantucket, Massachusetts, is a unique institution that combines a bar, restaurant, and lodging all in one historic sea captain's house. With 20 beautifully designed rooms by Roman and Williams, known for their work at Ace Hotel New York and The Standard, High Line, Greydon House stands out among Nantucket hotels. Guests can enjoy artworks by Terry Winters, an English garden, and a Venetian-inspired restaurant called Via Mare. The accommodations at Greydon House are stylish and luxurious, with custom-designed beds, block-printed linens by John Robshaw, Waterworks brass fixtures, and Acqua di Parma bath products. The restaurant, Via Mare, offers eclectic cuisine and drinks in a variety of settings, from the dining room to the covered porch to the garden.

Harborview Nantucket is a charming lodging establishment located at 24 Washington Street in the picturesque island of Nantucket, Massachusetts. This cozy inn offers guests a relaxing and comfortable stay in the heart of Nantucket, with easy access to the island's attractions, shops, and restaurants. The rooms at Harborview Nantucket are tastefully decorated and equipped with modern amenities to ensure a pleasant stay. Guests can enjoy the beautiful views of the harbor from the inn's waterfront location. Whether you are visiting Nantucket for a romantic getaway or a family vacation, Harborview Nantucket provides a welcoming and peaceful retreat for all guests.

Located in the heart of Nantucket, Massachusetts, the Regatta Inn offers a unique and luxurious lodging experience. Situated at 78 Centre Street, this iconic Nantucket luxury boutique hotel is part of the Nantucket Resort Collection, along with the Chapman House and Sherburne Inn. The Regatta Inn boasts enchanting gardens, where guests can relax and breathe in the delicious island aroma. Each of the 17th-century buildings has been beautifully restored and furnished with modern coastal design, combining antique charm with modern elegance.

Union Street Inn is a charming and elegant lodging establishment located at 7 Union Street in the heart of Nantucket, Massachusetts. This historic inn offers luxurious accommodations in a quaint and picturesque setting, perfect for a romantic getaway or a relaxing weekend retreat. The beautifully decorated rooms and suites exude a cozy and inviting atmosphere, with modern amenities and thoughtful touches to ensure a comfortable stay. Guests can enjoy a delicious gourmet breakfast each morning, as well as afternoon tea and cookies in the elegant parlor. The inn's central location allows easy access to Nantucket's shops, restaurants, and attractions, making it an ideal choice for travelers looking to experience the charm and beauty of this historic island.

29 Fair Street Inn is a charming and cozy lodging located in the heart of Nantucket, Massachusetts. Situated at the address 29 Fair Street, this historic inn offers a peaceful retreat for guests looking to experience the beauty and charm of Nantucket. With comfortable rooms, friendly staff, and a convenient location near shops, restaurants, and attractions, 29 Fair Street Inn is the perfect place to stay for a relaxing getaway on the island. Whether you are visiting for a weekend getaway or an extended vacation, you will feel right at home at this lovely inn.

The Summer House Fair Street is a charming lodging institution located at 27 Fair Street in the picturesque town of Nantucket, Massachusetts. This historic establishment offers a cozy and inviting atmosphere for guests looking to experience the beauty and tranquility of the island. With comfortable accommodations, friendly staff, and a convenient location near the beach and downtown area, The Summer House Fair Street is the perfect choice for a relaxing getaway on Nantucket. Whether you're looking for a romantic retreat or a family vacation, this charming inn has everything you need for a memorable stay.

The Barnacle Inn is a charming lodging establishment located at 11 Fair Street in Nantucket, Massachusetts. This cozy inn offers a peaceful and relaxing atmosphere for guests to enjoy during their stay on the beautiful island of Nantucket. The Barnacle Inn provides comfortable accommodations, friendly service, and a convenient location near the town center and the island's many attractions. Whether you're looking for a romantic getaway, a family vacation, or a solo retreat, The Barnacle Inn is the perfect choice for a memorable stay in Nantucket.

Nantucket Inns is a charming lodging establishment located at 9 North Water Street in the picturesque island of Nantucket, Massachusetts. As a combination of a lodging, real estate, and travel agency, Nantucket Inns offers a unique experience for guests looking to explore the beauty of the island. With comfortable accommodations, personalized real estate services, and expert travel assistance, Nantucket Inns is the perfect destination for those seeking a memorable stay on Nantucket.

The Manor House Inn is a charming lodging establishment located at 31 Centre Street in the picturesque town of Nantucket, Massachusetts. This historic inn offers a cozy and inviting atmosphere for guests looking to experience the beauty and charm of Nantucket. The Manor House Inn features comfortable rooms, delicious breakfast options, and friendly staff to ensure a memorable stay for all visitors. With its convenient location in the heart of Nantucket, guests can easily explore the island's beaches, shops, and attractions. Whether you're visiting for a weekend getaway or a longer vacation, the Manor House Inn is the perfect place to relax and unwind in Nantucket.

Life House, Nantucket is a charming lodging institution located at 10 Cliff Road in the picturesque island of Nantucket, Massachusetts. This cozy retreat offers guests a peaceful and relaxing getaway in a beautiful seaside setting. With comfortable accommodations, friendly staff, and a convenient location near the island's attractions, Life House is the perfect place to unwind and enjoy all that Nantucket has to offer. Whether you're looking for a romantic escape or a family vacation, Life House provides a welcoming and inviting atmosphere for all guests. Experience the charm and hospitality of Nantucket at Life House.