TOP 30 Best Vacation getaway in Massachusetts

Thornewood Inn is a charming and historic lodging located at 453 Stockbridge Road in the picturesque town of Great Barrington, Massachusetts. Nestled in the heart of the Berkshires, this cozy inn offers a tranquil escape for guests looking to relax and unwind. The beautifully appointed rooms are elegantly furnished and offer modern amenities for a comfortable stay. Guests can enjoy a delicious breakfast each morning and explore the surrounding area, which is known for its scenic beauty and cultural attractions. Whether you are seeking a romantic getaway or a peaceful retreat, Thornewood Inn is the perfect destination for your next vacation.

The Stockbridge Country Inn is a charming bed and breakfast located at 26 Glendale Road in Stockbridge, Massachusetts. Nestled in the heart of the picturesque Berkshires, this cozy inn offers beautifully appointed guest accommodations, each with its own unique character and style. Guests can enjoy a peaceful and relaxing atmosphere, surrounded by stunning gardens and a cozy fireplace room. Conveniently located just 1 mile away from the Norman Rockwell Museum and Chesterwood, The Stockbridge Country Inn is the #1 closest Berkshires Bed and Breakfast to these popular attractions. This makes it an ideal choice for visitors looking to explore the museum while enjoying the serene surroundings of the Berkshires.

Located at 30 East Street in Stockbridge, Massachusetts, The Inn at Stockbridge is a charming Georgian-style bed and breakfast nestled on six beautifully landscaped acres in the tranquil Berkshires. Offering three distinct lodging options to cater to every traveler's preferences, guests can choose between the elegant Main House, the cozy Cottage House, or the rustic-chic Barn. Immerse yourself in the thriving arts and culture scene of the Berkshires, with world-class museums and entertainment venues just minutes away. Explore attractions like the Norman Rockwell Museum, MASS MoCA, and Tanglewood, or enjoy exclusive offerings such as tee times at Stockbridge Golf Club and deals at local ski resorts.

The Goldenrod Country Inn is a charming bar and lodging establishment located at 144 Huntington Road in the picturesque town of Worthington, Massachusetts. Nestled in the heart of the countryside, this cozy inn offers a warm and inviting atmosphere for guests looking to relax and unwind. With comfortable accommodations, a well-stocked bar, and friendly staff, The Goldenrod Country Inn is the perfect destination for a weekend getaway or a peaceful retreat in the New England countryside.

On Cranberry Pond Bed & Breakfast is a charming lodging establishment located at 43 Fuller Street in Middleborough, Massachusetts. Situated on the picturesque Cranberry Pond, guests can enjoy a peaceful and relaxing stay in the heart of nature. The cozy rooms are tastefully decorated and offer all the comforts of home. Guests can start their day with a delicious homemade breakfast served in the dining area overlooking the pond. With friendly and attentive staff, On Cranberry Pond Bed & Breakfast is the perfect retreat for those looking to unwind and rejuvenate in a serene setting.

Boston Yacht Haven Inn & Marina is a luxurious lodging option located at 87 Commercial Wharf in the heart of Boston, Massachusetts. This waterfront institution offers unparalleled views of the harbor and easy access to the city's top attractions. Guests can relax in elegantly appointed rooms, enjoy delicious dining options, and take advantage of the marina facilities for those arriving by boat. Whether you're visiting for business or pleasure, Boston Yacht Haven Inn & Marina provides a comfortable and convenient stay in one of America's most historic cities.

The Woods Hole Inn is a charming and historic lodging establishment located at 28 Water Street in Falmouth, Massachusetts, United States. This cozy inn offers a unique blend of modern amenities and old-world charm, making it the perfect destination for travelers looking for a relaxing and comfortable stay. In addition to providing lodging accommodations, the Woods Hole Inn also operates as a real estate agency, helping visitors find their dream vacation home in the beautiful Cape Cod area. With its convenient location near the water and close proximity to local attractions, this institution is also a great resource for travelers looking to book tours and plan their itinerary through its travel agency services. Whether you're looking for a place to stay, a property to buy, or assistance with planning your trip, the Woods Hole Inn is the ideal destination for all your lodging, real estate, and travel needs.

The Daniels House Inn is a charming bed and breakfast located at 1 Daniels Street in historic Salem, Massachusetts. This quaint inn offers cozy accommodations and a warm, inviting atmosphere for guests to relax and unwind. With its convenient location near popular tourist attractions, including the Salem Witch Trials Memorial and the Peabody Essex Museum, The Daniels House Inn is the perfect place to stay while exploring all that Salem has to offer. Whether you're visiting for a weekend getaway or a longer vacation, you'll feel right at home at this charming inn.

The Palmer House Inn is a charming and historic lodging establishment located at 81 Palmer Avenue in Falmouth, Massachusetts. This elegant inn offers a cozy and welcoming atmosphere, perfect for a relaxing getaway on Cape Cod. The beautifully decorated rooms and suites feature luxurious amenities and thoughtful touches to ensure a comfortable stay. Guests can enjoy a delicious homemade breakfast each morning and unwind in the peaceful garden or cozy common areas. Conveniently located near the beach, shopping, and dining options, the Palmer House Inn is the ideal choice for a memorable stay in Falmouth.

Frederick William House is a charming lodging located at 594 Palmer Avenue in Falmouth, Massachusetts, United States. This historic institution offers a cozy and welcoming atmosphere for guests looking to explore the beautiful Cape Cod area. The house boasts comfortable accommodations, friendly staff, and convenient access to local attractions such as beaches, restaurants, and shopping. Whether you are seeking a relaxing getaway or an adventurous vacation, Frederick William House is the perfect place to stay during your visit to Falmouth.

The Cove At Rockport is a charming lodging located at 1 King Street in the picturesque town of Rockport, Massachusetts. Situated in the United States, this institution offers cozy accommodations with stunning views of the surrounding area. Guests can enjoy a peaceful retreat by the sea, with easy access to local attractions, shops, and restaurants. Whether you're looking for a romantic getaway or a family vacation, The Cove At Rockport provides a comfortable and welcoming atmosphere for all travelers.

Thomas Sea Suites is a charming lodging establishment located at 150 Water Street in the historic town of Plymouth, Massachusetts. Situated just steps away from the picturesque waterfront, our suites offer a comfortable and relaxing retreat for visitors to the area. Each suite is tastefully decorated and equipped with modern amenities to ensure a pleasant stay. Guests can enjoy stunning views of the ocean and easy access to local attractions, restaurants, and shops. Whether you are visiting for business or pleasure, Thomas Sea Suites provides a welcoming atmosphere for all travelers.

Located at 321 Shore Street in Falmouth, Massachusetts, the Beach Breeze Inn offers a variety of accommodations including guest rooms, suites, efficiency apartments, and studio apartments. Whether you're looking for a quick getaway or a week-long family vacation, the Beach Breeze Inn has something for everyone. This casual Cape Cod Inn has a 5-star review rating on TripAdvisor and is the perfect place to stay in Falmouth. Just a half mile stroll away, guests can enjoy shopping and dining options, while also being just steps away from the beach, the ferry to Martha's Vineyard, and the Shining Sea Bikeway.

Sand Dollar Bed & Breakfast is a charming lodging establishment located at 8 Indian Trail in Bourne, Massachusetts, United States. Nestled in a peaceful and scenic setting, this cozy B&B offers guests a relaxing and comfortable stay. The rooms are beautifully decorated and equipped with modern amenities to ensure a pleasant experience. Guests can enjoy a delicious breakfast each morning and unwind in the serene surroundings of the property. Whether you are looking for a romantic getaway or a peaceful retreat, Sand Dollar Bed & Breakfast is the perfect choice for your next vacation.

Bearskin Neck Motor Lodge is an ocean front lodging located at 64 Bearskin Neck in Rockport, Massachusetts. Despite the term "motor lodge," our rooms are clean and provide a pleasant atmosphere for your stay. Enjoy a bottle of wine and some steamed lobsters on the back deck while watching the sunset. Our friendly staff is always available to provide restaurant recommendations or trip ideas. Each room is equipped with air conditioning, refrigerators, cable TV, and free WiFi. All rooms have ocean front views and a shared balcony with chairs right outside your door. Additional deck tables are available adjacent to the hotel. Free parking is available on Bearskin Neck, with one parking spot per room. We also offer Express Check-In for your convenience. Our central location allows easy access to shops, restaurants, and Front Beach. The office is open from 9 am to 7 PM daily, and assistance is available after hours by calling (978) 546-6677. The deck behind the main office is currently being renovated to create a new alfresco seating area called The Hideaway, which will offer cocktails, beer, wine, and light bites like charcuterie. We look forward to welcoming you to Bearskin Neck Motor Lodge for a relaxing and enjoyable stay.

Blue Shutters Beachside Inn is a charming lodging located at 1 Nautilus Road in Gloucester, Massachusetts. Situated right by the beach, this inn offers stunning ocean views and a peaceful atmosphere for guests to relax and unwind. The cozy rooms are tastefully decorated and equipped with modern amenities to ensure a comfortable stay. Guests can enjoy a complimentary breakfast each morning and take advantage of the inn's convenient location near local attractions and activities. Whether you're looking for a romantic getaway or a family vacation, Blue Shutters Beachside Inn is the perfect destination for a memorable stay by the sea.

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.

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.

Accommodations At Rocky Neck offers cozy and comfortable lodging in the heart of Gloucester, Massachusetts. Located at 43 Rocky Neck Avenue, this charming institution provides a peaceful retreat for guests looking to relax and unwind by the sea. With its convenient location just steps away from the beach and local shops and restaurants, Accommodations At Rocky Neck is the perfect choice for travelers seeking a tranquil getaway. The well-appointed rooms and friendly staff ensure a pleasant stay for all visitors. Whether you're exploring the historic sights of Gloucester or simply enjoying a leisurely day at the beach, Accommodations At Rocky Neck is the ideal place to call home during your stay in this picturesque coastal town.

The Lamb and Lion Inn, located at 2504 Main Street in Barnstable, Massachusetts, is a classic Cape Cod inn with the spirit of a small luxury hotel. It has been recognized as one of the top 12 pet-friendly properties in the world, making it the perfect destination for travelers with furry friends. The inn offers ultimate guest privacy with multiple separate entrances and exits, ensuring a peaceful and relaxing stay. Situated on 4 acres in historic Cape Cod Bay, the inn is just minutes away from Barnstable Village's shops, restaurants, waterfront dining, and whale watch boat. Guests can also enjoy a short walk to a sunset beach and hiking trails, as well as a ten-minute drive to the island ferries and Hyannis' nightlife. The inn dates back to a 1740 farmhouse with horse stables that have been converted into suites, and features the original 1740 Barn and a central courtyard for a fun and relaxed atmosphere.

Captains Bounty Beach View is a charming lodging institution located at 10 Beach Street in the picturesque town of Rockport, Massachusetts, United States. The property offers stunning views of the beach and ocean, providing guests with a truly relaxing and serene atmosphere. The rooms are tastefully decorated and equipped with modern amenities to ensure a comfortable stay. Guests can enjoy the beautiful surroundings, take a leisurely stroll along the beach, or explore the nearby attractions. Captains Bounty Beach View is the perfect destination for those looking for a peaceful and idyllic getaway by the sea.

Sesuit Harbor House is a charming lodging institution located in Dennis, Massachusetts, along Massachusetts 6A. Nestled in the heart of Cape Cod, this quaint bed and breakfast offers cozy and comfortable accommodations for guests looking to relax and unwind by the sea. With its picturesque surroundings and warm hospitality, Sesuit Harbor House provides the perfect retreat for those seeking a peaceful getaway in the beautiful coastal town of Dennis, Massachusetts.

Aerie House is a charming lodging facility located at 184 Bradford Street in the picturesque town of Provincetown, Massachusetts. Nestled in a serene and scenic setting, Aerie House offers a tranquil retreat for guests looking to escape the hustle and bustle of everyday life. The property features comfortable accommodations, friendly service, and stunning views of the surrounding natural beauty. Whether you're seeking a romantic getaway, a family vacation, or a solo adventure, Aerie House provides the perfect home base for exploring all that Provincetown has to offer. Experience warm hospitality and a relaxing atmosphere at this inviting institution in the heart of Cape Cod.

Prince Albert Guest House is a charming lodging establishment located at 164 Commercial Street in the picturesque town of Provincetown, Massachusetts. This historic guest house offers comfortable accommodations and personalized service to enhance your stay in this beautiful coastal town. Whether you are looking for a relaxing getaway or a fun-filled adventure, Prince Albert Guest House is the perfect choice for your next vacation. In addition to providing lodging services, the guest house also operates as a real estate agency and travel agency, helping guests find their dream vacation home or plan the perfect itinerary for their trip. Experience the warm hospitality and inviting atmosphere of Prince Albert Guest House during your visit to Provincetown.

The Brass Key Guesthouse is a charming lodging establishment located at 67 Bradford Street in the picturesque town of Provincetown, Massachusetts, United States. This cozy guesthouse offers a unique and inviting atmosphere for guests looking for a comfortable and relaxing stay. With well-appointed rooms, friendly staff, and a convenient location near local attractions, The Brass Key Guesthouse is the perfect choice for a memorable getaway on Cape Cod.

John Randall House B&B and Condos is a charming lodging institution located at 140 Bradford Street in the picturesque town of Provincetown, Massachusetts. Situated in the United States, this cozy establishment offers a unique blend of bed and breakfast accommodations as well as condominium rentals. Guests can enjoy comfortable and stylish rooms, delicious breakfast options, and a convenient location near the town's attractions and amenities. Whether you are looking for a relaxing getaway or a fun-filled vacation, John Randall House B&B and Condos provides the perfect home away from home in Provincetown.

Revere Guest House is a charming lodging located at 14 Court Street in the picturesque town of Provincetown, Massachusetts, United States. This cozy guest house offers a warm and welcoming atmosphere, perfect for a relaxing getaway. The rooms are tastefully decorated and equipped with modern amenities to ensure a comfortable stay. Guests can enjoy the beautiful surroundings and explore the nearby attractions such as beaches, shops, and restaurants. Whether you are looking for a romantic retreat or a fun-filled vacation, Revere Guest House is the perfect choice for your accommodation needs.

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.

Cliffside Beach Club is a luxurious lodging institution located at 46 Jefferson Avenue in the picturesque town of Nantucket, Massachusetts. Situated right on the beach, guests can enjoy stunning ocean views and easy access to the sandy shores. The club offers a range of upscale accommodations, from elegant rooms to spacious suites, all designed to provide a comfortable and relaxing stay. Guests can also take advantage of the on-site amenities, including a swimming pool, fitness center, and fine dining restaurant. Whether you're looking for a romantic getaway or a family vacation, Cliffside Beach Club provides the perfect retreat for those seeking a peaceful and rejuvenating experience by the sea.

21 Broad is a chic and stylish lodging institution located at 21 Broad Street in Nantucket, Massachusetts. This urban-inspired hotel seamlessly blends the vibrant energy of Nantucket's historic neighborhood with modern interior design, offering guests a unique and luxurious escape. From spinning tunes on the turntable to relaxing on the back deck around the fire pit, 21 Broad pampers guests with unexpected luxuries. The newly renovated Swain House at 21 Broad offers five distinct rooms and suites, providing a private and exclusive retreat for families and friends. With 27 modern accommodations featuring luxury linens and a range of amenities, 21 Broad is the perfect choice for discerning travelers looking to stay in the heart of Nantucket. Just two blocks from the Steamship Authority ferry terminal, this hotel is conveniently located in the bustling center of town.