TOP 30 Best luxury inns in Massachusetts

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Holiday Inn Express & Suites Great Barrington - Lenox Area is a modern and comfortable lodging option located at 415 Stockbridge Road in the charming town of Great Barrington, Massachusetts. Situated in the heart of the picturesque Lenox Area, this hotel offers guests a convenient and relaxing stay with easy access to a variety of attractions and activities. The hotel features spacious and well-appointed guest rooms and suites, each equipped with modern amenities such as flat-screen TVs, free Wi-Fi, and comfortable bedding. Guests can also enjoy complimentary breakfast each morning, as well as access to a fitness center and indoor pool.

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires is a cozy and modern lodging option located at 249 Stockbridge Road in the charming town of Great Barrington, Massachusetts. Situated in the heart of the picturesque Berkshires region, this hotel offers guests a convenient and comfortable stay with close proximity to popular attractions such as Tanglewood, Norman Rockwell Museum, and Ski Butternut. The hotel features spacious and well-appointed rooms and suites, a complimentary hot breakfast buffet, a fitness center, an indoor pool, and free Wi-Fi. Whether you are visiting for business or leisure, Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires provides a welcoming and relaxing atmosphere for all guests.

The Wainwright Inn Bed & Breakfast is a charming and historic lodging establishment located at 518 South Main Street in the picturesque town of Great Barrington, Massachusetts, United States. This cozy inn offers comfortable accommodations in a beautiful Victorian-style setting, perfect for a relaxing getaway or romantic retreat. Guests can enjoy a delicious homemade breakfast each morning and explore the nearby attractions, including the Berkshire Mountains and quaint shops and restaurants in the town center. With its warm hospitality and inviting atmosphere, The Wainwright Inn Bed & Breakfast is the perfect choice for a memorable stay in the Berkshires.

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.

Located in the quaint village of New Marlborough in Massachusetts, The Old Inn On The Green is a historic institution offering both bar services and lodging. The inn, originally a stagecoach relay, features beautifully restored guest rooms, fine dining in candlelit rooms, and seasonal outdoor dining on the garden terrace. The Southfield Store, open for takeout daily, is also part of the institution. Whether you are visiting for business or pleasure, for dinner or an overnight stay, The Old Inn On The Green provides a charming and authentic experience in the heart of the Berkshire region. With its picturesque surroundings of rolling fields and meadows, this historic inn is a perfect destination for those seeking a peaceful retreat in New England. Visit us at 134 Hartsville-New Marlborough Rd, New Marlborough, MA 01230 or contact us at 413-229-7924 or info@oldinn.com. Feel the love and experience the best of the oldest at The Old Inn On The Green.

Springfield Inn is a charming lodging establishment located at 1573 Riverdale Street in West Springfield, Massachusetts, United States. Situated in a convenient location, the inn offers comfortable accommodations and excellent amenities for both leisure and business travelers. With its welcoming atmosphere and friendly staff, guests can enjoy a relaxing stay while exploring the nearby attractions and activities. Whether you are visiting for a weekend getaway or a business trip, Springfield Inn provides a cozy and convenient home away from home.

Bel Air Inn is a cozy lodging facility located at 387 Riverdale Street in West Springfield, Massachusetts. This charming inn offers comfortable accommodations and a welcoming atmosphere for guests looking for a relaxing stay. Conveniently situated in a prime location, Bel Air Inn is the perfect choice for travelers visiting the area for business or pleasure. With its friendly staff, clean rooms, and affordable rates, Bel Air Inn is a top choice for those seeking a comfortable and convenient place to stay in West Springfield.

Riverdale Inn is a charming lodging located at 1500 Riverdale Street in West Springfield, Massachusetts. Situated in a picturesque setting, this cozy inn offers a relaxing and comfortable stay for guests visiting the area. The rooms are tastefully decorated and equipped with modern amenities to ensure a pleasant stay. The friendly staff at Riverdale Inn are dedicated to providing exceptional service and making guests feel right at home. Whether you are in town for business or leisure, this welcoming inn is the perfect place to unwind and enjoy a peaceful retreat.

Hilton Garden Inn Springfield, MA offers comfortable and modern lodging accommodations in the heart of Springfield, Massachusetts. Conveniently located at 800 Hall of Fame Avenue, this hotel is perfect for both business and leisure travelers. The hotel features spacious rooms with amenities such as free Wi-Fi, a fitness center, a restaurant serving delicious meals, and a bar for relaxing after a long day. With its convenient location near popular attractions like the Basketball Hall of Fame and Six Flags New England, Hilton Garden Inn Springfield is the perfect choice for your stay in the area.

Naomi's Inn Bed and Breakfast is a charming and cozy lodging located at 20 Springfield Street in Springfield, Massachusetts, United States. This historic inn offers comfortable accommodations with a personal touch, making guests feel right at home. The beautifully decorated rooms, delicious homemade breakfast, and warm hospitality create a welcoming atmosphere for travelers looking for a relaxing stay. Conveniently situated near local attractions and amenities, Naomi's Inn Bed and Breakfast is the perfect choice for a memorable and enjoyable getaway in Springfield.

The Trainmaster's Inn, located at 1292 South Main Street in Palmer, Massachusetts, offers a unique and high-end lodging experience. From the same team behind The Steaming Tender Restaurant, this inn allows guests to immerse themselves in the architectural beauty of the 19th century while enjoying modern comforts. Guests can choose to stay in the Inn itself or in one of the unique properties offered, such as the 1946 Bangor Aroostook Caboose overlooking the New England Central Railroad Railyard. The caboose has been meticulously restored to maintain its authentic charm.

City Place Inn & Suites is a cozy and convenient lodging option located at 711 Dwight Street in Springfield, Massachusetts. This institution offers comfortable accommodations for travelers looking to explore the vibrant city of Springfield. With its central location, guests can easily access nearby attractions, restaurants, and shopping centers. The inn provides well-appointed rooms and suites, along with modern amenities to ensure a pleasant stay for guests. Whether visiting for business or leisure, City Place Inn & Suites is the perfect choice for a memorable stay in Springfield.

The Hampton Inn Sturbridge is a cozy and inviting lodging option located at 328 Main Street in Sturbridge, Massachusetts. Situated in the heart of this historic town, guests can enjoy easy access to local attractions such as Old Sturbridge Village and the Sturbridge Antique Shops. The hotel offers comfortable rooms, complimentary breakfast, an indoor pool, and a fitness center for guests to enjoy during their stay. Whether you are visiting for business or pleasure, the Hampton Inn Sturbridge provides a convenient and relaxing place to rest and recharge.

Hamilton Inn is a charming lodging establishment located at 172 Main Street in the heart of Sturbridge, Massachusetts. This cozy inn offers comfortable accommodations and a warm, inviting atmosphere for guests looking to relax and unwind. With its convenient location, guests can easily explore the nearby attractions, shops, and restaurants in the area. Whether you are visiting for business or pleasure, Hamilton Inn provides a peaceful retreat for travelers seeking a home away from home.

The Woof and Whisker Inn, located at 265 Dudley River Road in Southbridge, Massachusetts, offers a range of services including dog boarding, cat boarding, doggie daycare, and full-service grooming. With over 15 years of experience, we are dedicated to providing the highest quality care for your pets. Our team loves animals and strives to create lasting relationships with both pets and their owners. Don't feel guilty about leaving your furry friend at home all day - bring them to our daycare where they can socialize and have fun with other animals. Our professional groomers are experienced with all dog breeds and will ensure your companion looks and feels their best. Trust us to care for your pets while you're at work, and give them the attention and love they deserve.

River Inn is a charming lodging establishment nestled in the heart of Springfield, Massachusetts. Located in the United States, this cozy inn offers comfortable accommodations and a warm, inviting atmosphere for guests to relax and unwind. With a picturesque setting along the river, guests can enjoy scenic views and a peaceful environment. Whether you are traveling for business or leisure, River Inn provides a convenient and welcoming place to stay during your time in Springfield.

The Old Inn On The Green Restaurant is a charming dining establishment located at 134 Hartsville-New Marlborough Road in New Marlborough, Massachusetts, United States. The dining rooms are beautifully illuminated by candlelight and feature cozy fireplaces in each room. The restaurant boasts an award-winning wine list curated by General Manager Eric Goulange. The decor includes comfortable windsor chairs, mahogany tavern tables, iron chandeliers, and wall sconces that reflect the inn's early history. During the summer months, guests can enjoy dinner on the garden terrace under a white canopy with views of the dome steepled 19th-century Meeting House and the surrounding wooded country road. After dinner, patrons can relax in the taproom with a glass of port or retire to one of the historic bedrooms upstairs for an overnight stay.

Old Inn Associates is a charming establishment located at 100 Stone Manor Dr in New Marlborough, Massachusetts. As a renowned food, lodging, and restaurant institution, we pride ourselves on providing top-notch service and comfortable accommodations for our guests. Whether you're looking for a delicious meal at our restaurant, a cozy stay in our well-appointed rooms, or a relaxing retreat in the beautiful Massachusetts countryside, Old Inn Associates has everything you need for a memorable experience. Come visit us and experience the warm hospitality and exceptional amenities that have made us a favorite destination for travelers near and far.

The Barkwood Inn Pet Resort is a luxurious retreat for your furry friends, located at 462 Worcester Road in Charlton, Massachusetts, United States. Our facility offers top-notch accommodations and amenities for dogs and cats, including spacious suites, indoor and outdoor play areas, grooming services, and personalized care from our experienced staff. Whether your pet is staying with us for a day of play or an extended stay, they will be treated like royalty at The Barkwood Inn Pet Resort. Book your pet's stay with us today and give them a vacation of their own!

Comfort Inn Hyannis - Cape Cod is a cozy and inviting lodging option located at 259 Main Street in Barnstable, Massachusetts. Situated in the heart of Cape Cod, this hotel offers comfortable accommodations and convenient amenities for both leisure and business travelers. Guests can enjoy a complimentary breakfast, free wifi, a fitness center, and a seasonal outdoor pool. The hotel's central location provides easy access to nearby attractions such as beaches, shopping, dining, and entertainment options. Whether you are visiting for a weekend getaway or an extended stay, Comfort Inn Hyannis - Cape Cod is the perfect choice for a relaxing and enjoyable stay on the beautiful Cape Cod peninsula.

Located in the picturesque town of Pittsfield, Massachusetts, the Best Western Plus Berkshire Hills Inn & Suites offers comfortable and modern lodging for travelers looking to explore the beautiful Berkshires region. Situated at 1350 West Housatonic Street, this hotel provides guests with a convenient location near popular attractions such as Tanglewood, Hancock Shaker Village, and the Norman Rockwell Museum. The hotel features spacious rooms and suites equipped with amenities such as free Wi-Fi, flat-screen TVs, and mini fridges. Guests can also enjoy a complimentary hot breakfast, a fitness center, and an indoor pool. Whether visiting for business or leisure, the Best Western Plus Berkshire Hills Inn & Suites provides a welcoming and relaxing atmosphere for all guests.

The Inn At Richmond is a charming lodging establishment located at 802 State Road in the picturesque town of Richmond, Massachusetts, United States. Nestled in the heart of the Berkshires, this historic inn offers a peaceful retreat for guests seeking a relaxing getaway. With cozy rooms, elegant decor, and modern amenities, The Inn At Richmond provides a comfortable and inviting atmosphere for visitors to enjoy. Whether you're looking to explore the nearby attractions or simply unwind in a tranquil setting, this institution is the perfect choice for your stay in the Berkshires.

Located at 10 Richmond Mountain Road in Lenox, Massachusetts, the Apple Tree Inn is a charming lodging option that serves as the perfect retreat for those looking to nurture their creativity. Surrounded by the natural beauty of the Berkshires, this institution offers a peaceful escape from the ordinary where guests can unlock new ideas and inspiration. The inn features a picturesque 1885 Victorian main house with 13 rooms that blend historic charm with modern amenities such as Frette linens. Additionally, there is a rustic Lodge with 21 rooms that provide a cozy and tranquil setting overlooking the lush green forests and rolling hills of the Berkshires.

The Chesapeake Inn of Lenox is a charming lodging establishment located at 210 West Street in the picturesque town of Lenox, Massachusetts. This cozy inn offers comfortable accommodations and a warm, welcoming atmosphere for guests looking to relax and unwind in the heart of the Berkshires. With its convenient location near historic sites, cultural attractions, and outdoor activities, the Chesapeake Inn of Lenox is the perfect destination for a peaceful getaway or romantic retreat. Experience the beauty and hospitality of Lenox at this charming inn.

The Inn at Kenmore Hall is a charming lodging located at 1385 State Road in Richmond, Massachusetts. Nestled in the beautiful countryside of the United States, this institution offers a peaceful and relaxing retreat for guests looking to escape the hustle and bustle of everyday life. With comfortable accommodations and attentive staff, visitors can enjoy a restful stay surrounded by scenic views and serene surroundings. Whether you're looking for a romantic getaway or a quiet weekend retreat, The Inn at Kenmore Hall is the perfect destination for a memorable stay.

Located in the charming town of Lenox, Massachusetts, the Eastgate Inn Bed & Breakfast offers a cozy and welcoming atmosphere for travelers looking for a peaceful retreat. Situated at 207 West Street, this quaint lodging establishment provides comfortable accommodations with a personal touch. Guests can enjoy a delicious homemade breakfast each morning before exploring the nearby attractions such as Tanglewood, The Mount, and the shops and restaurants of Lenox. Whether you are visiting for a romantic getaway or a relaxing vacation, the Eastgate Inn Bed & Breakfast is the perfect place to stay in the heart of the Berkshires.

Located at 30 Main Street in Stockbridge, Massachusetts, The Red Lion Inn is a historic landmark of hospitality that has been welcoming guests for 250 years. The property includes the original Main Inn, a contemporary guest house, and unique lodging options like the turn-of-the-century Firehouse. Enjoy the heated outdoor pool, Hot Tub, and Pool House stocked with fresh towels and games. The culinary experience at The Red Lion Inn is top-notch, with seasonal menu items sourced from local farmers, craft cocktails, and an award-winning wine selection. Live music at The Lion’s Den adds to the vibrant atmosphere. Guests rave about the cozy rooms, delicious food, and exceptional service. Don't miss out on the curated packages and experiences to make the most of your stay in the Berkshires. The Red Lion Inn is a proud member of Historic Hotels of America and the National Trust for Historic Preservation. Come experience the charm and history of The Red Lion Inn for yourself.

Located in the charming town of West Stockbridge, Massachusetts, the Shaker Mill Inn offers a cozy and comfortable lodging experience. Situated at 2 Oak Street, this historic inn provides a peaceful retreat for guests looking to relax and unwind. The beautifully decorated rooms and friendly staff make for a memorable stay. With its convenient location and warm hospitality, the Shaker Mill Inn is the perfect choice for travelers visiting the Berkshires region.

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.

Berkshire Valley Inn is a charming lodging located at 2541 Hancock Road in the picturesque town of Williamstown, Massachusetts. Surrounded by the stunning Berkshire Mountains, this cozy inn offers a peaceful retreat for guests looking to relax and unwind. The well-appointed rooms provide a comfortable and inviting atmosphere, perfect for a weekend getaway or a longer stay. Guests can enjoy the beautiful surroundings, explore nearby hiking trails, or visit the many attractions in the area. Whether you're seeking a quiet escape or an adventurous vacation, Berkshire Valley Inn is the perfect destination for your next trip to the Berkshires.