The 30 Best Charming establishment in Massachusetts

Hotel on North is a charming and sophisticated institution located in the heart of Pittsfield, Massachusetts. Situated at 297 North Street, this unique establishment offers a combination of luxurious lodging, a vibrant bar, and a lively night club all under one roof. Guests can enjoy stylish accommodations, delicious cocktails, and exciting entertainment all in one convenient location. Whether you're looking for a relaxing retreat or a fun night out, Hotel on North has something for everyone. Experience the best of Pittsfield at this one-of-a-kind destination.

The Berkshire Inn is a charming lodging establishment located at 150 West Housatonic Street in the picturesque town of Pittsfield, Massachusetts. This cozy inn offers comfortable accommodations and a warm, welcoming atmosphere for guests to enjoy during their stay. Conveniently situated in the heart of the Berkshires, guests can easily explore the area's many attractions, including cultural venues, outdoor activities, and charming shops and restaurants. Whether visiting for business or pleasure, the Berkshire Inn is the perfect home away from home for travelers seeking a relaxing and enjoyable experience in the beautiful Berkshires region.

Yankee Inn, Trademark Collection by Wyndham is a charming lodging establishment located at 461 Pittsfield Road in Lenox, Massachusetts, United States. This cozy inn offers comfortable accommodations and top-notch amenities, making it the perfect place to relax and unwind during your stay in the beautiful Berkshires. With its convenient location and warm hospitality, Yankee Inn is the ideal choice for travelers looking for a memorable and enjoyable experience in Lenox.

The Cornell Inn is a charming lodging establishment located at 203 Main Street in Lenox, Massachusetts, United States. This historic inn offers cozy accommodations, friendly service, and a convenient location in the heart of the Berkshires. Guests can relax in comfortable rooms, enjoy a delicious breakfast, and explore the nearby shops, restaurants, and attractions. Whether you're visiting for a romantic getaway, a family vacation, or a business trip, the Cornell Inn is the perfect place to stay in Lenox.

Knights Inn Lenox is a charming lodging establishment located at 474 Pittsfield Road in Pittsfield, Massachusetts. This cozy inn offers comfortable accommodations and excellent service to ensure a pleasant stay for guests. Conveniently situated in the heart of the Berkshires, guests can easily explore the area's attractions, including Tanglewood, Norman Rockwell Museum, and the beautiful landscapes of the region. With its affordable rates and welcoming atmosphere, Knights Inn Lenox is the perfect choice for travelers looking for a relaxing retreat in western Massachusetts.

Berkshire Yankee Suites is a charming lodging establishment located at 20 West Housatonic Street in the picturesque city of Pittsfield, Massachusetts. Our suites offer a cozy and comfortable stay for travelers looking to explore the beautiful Berkshire region. Each suite is tastefully decorated and equipped with modern amenities to ensure a relaxing stay. Our convenient location allows guests easy access to local attractions, dining options, and outdoor activities. Whether you are visiting for business or pleasure, Berkshire Yankee Suites is the perfect home away from home in the heart of the Berkshires.

Country Inn is a charming lodging establishment located at 37 Corey Road in Hancock, Massachusetts, United States. Nestled in the picturesque countryside, this quaint inn offers a cozy and inviting atmosphere for guests looking to relax and unwind. With comfortable accommodations, warm hospitality, and beautiful surroundings, Country Inn is the perfect destination for a peaceful getaway in the heart of nature. Whether you are visiting for a romantic weekend escape or a family vacation, you will feel right at home at this idyllic retreat.

Villager Motel is a cozy lodging establishment situated at 953 Simonds Road in the picturesque town of Williamstown, Massachusetts, United States. Nestled in a tranquil setting, this charming motel offers comfortable accommodations for travelers looking for a peaceful retreat. With its convenient location near local attractions and amenities, Villager Motel is the perfect choice for visitors seeking a relaxing stay in the heart of the Berkshires. Experience warm hospitality and excellent service at Villager Motel during your next trip to Williamstown.

The New Ashford Motor Inn is a cozy lodging establishment located at 259 U.S. 7 in the picturesque town of New Ashford, Massachusetts. Situated in a convenient location just off the highway, this charming inn offers comfortable accommodations for travelers looking to explore the beautiful Berkshires region. With its friendly staff, clean rooms, and affordable rates, the New Ashford Motor Inn is the perfect choice for a relaxing getaway in the heart of New England.

The Springs Motel is a charming lodging establishment located at 94 U.S. 7 in the picturesque town of New Ashford, Massachusetts. This cozy motel offers comfortable and affordable accommodations for travelers looking to explore the beauty of the Berkshires region. With its convenient location and friendly staff, The Springs Motel is the perfect choice for a relaxing getaway or a stopover during a road trip. Experience the warmth and hospitality of this family-owned motel during your stay in New Ashford.

Northside Motel is a cozy and welcoming lodging establishment located at 45 North Street in the charming town of Williamstown, Massachusetts. Situated in the heart of the United States, this quaint motel offers comfortable and affordable accommodations for travelers seeking a peaceful retreat. Guests can enjoy spacious rooms, friendly service, and convenient amenities during their stay. Whether you are visiting for business or pleasure, Northside Motel provides a relaxing home away from home in a picturesque New England setting.

Pilgrim Inn is a charming lodging establishment located at 165 Housatonic Street in Lee, Massachusetts, United States. Situated in the heart of the picturesque Berkshires region, this institution offers cozy and comfortable accommodations for travelers seeking a peaceful retreat. The Pilgrim Inn provides a warm and welcoming atmosphere, with well-appointed rooms and friendly staff dedicated to ensuring a pleasant stay for all guests. Whether you are visiting for business or pleasure, Pilgrim Inn is the perfect choice for a relaxing and enjoyable experience in the beautiful town of Lee.

Morgan House Inn & Restaurant is a charming establishment located at 33 Main Street in Lee, Massachusetts, United States. This institution offers a cozy and inviting atmosphere perfect for enjoying a meal or drinks with friends and family. The restaurant serves delicious food made with fresh, locally sourced ingredients, while the bar offers a variety of cocktails, wines, and beers. Whether you're looking for a casual meal or a special occasion dinner, Morgan House Inn & Restaurant is the perfect place to relax and indulge in good food and drinks.

The Jonathan Foote 1778 House Bed & Breakfast is a charming and historic lodging establishment located at 1 East Street in Lee, Massachusetts. This beautiful inn offers cozy and comfortable accommodations in a quaint setting, perfect for a relaxing getaway. Guests can enjoy a delicious homemade breakfast each morning and explore the nearby attractions and activities in the picturesque town of Lee. With its warm hospitality and unique colonial-era charm, the Jonathan Foote 1778 House Bed & Breakfast is the perfect destination for a memorable stay in the United States.

Chez Pet is a charming store located at 55 Pittsfield Road in Lenox, Massachusetts. This pet-friendly establishment offers a wide range of products and services for your beloved furry friends. From premium pet food and toys to stylish accessories and grooming supplies, Chez Pet has everything you need to keep your pets happy and healthy. The knowledgeable and friendly staff are always ready to assist you in finding the perfect items for your pets. Visit Chez Pet today and treat your pets to the best in pet care!

The Weathervane Motel is a charming lodging establishment located at 475 U.S. 7 in Lanesborough, Massachusetts, United States. This cozy motel offers comfortable accommodations for travelers looking to explore the beautiful Berkshires region. With its convenient location and friendly staff, The Weathervane Motel is the perfect choice for a relaxing stay in the area. Whether you're passing through on a road trip or planning a weekend getaway, this quaint motel welcomes guests with its warm hospitality and affordable rates. Experience the charm of New England hospitality at The Weathervane Motel.

The Williams Inn is a charming lodging establishment located at 101 Spring Street in the picturesque town of Williamstown, Massachusetts, United States. This historic inn offers comfortable accommodations and modern amenities for guests looking to explore the beauty of the Berkshires region. With its convenient location near Williams College and the Clark Art Institute, The Williams Inn is the perfect place to stay for visitors seeking a relaxing and memorable experience in this charming New England town.

Willows Motel is a charming lodging establishment located at 480 Main Street in the picturesque town of Williamstown, Massachusetts. Offering comfortable and affordable accommodations, this quaint motel is the perfect choice for travelers looking to explore the beauty of the Berkshires region. With its convenient location and friendly staff, Willows Motel provides a welcoming and relaxing atmosphere for guests to enjoy during their stay. Whether you are visiting for business or pleasure, Willows Motel is the ideal choice for your next trip to Williamstown.

The Williamstown Motel is a cozy and comfortable lodging option located at 295 Main Street in the charming town of Williamstown, Massachusetts. Situated in the heart of the United States, this motel offers a convenient and affordable stay for travelers looking to explore the beautiful Berkshires region. With clean and spacious rooms, friendly staff, and a convenient location near local attractions and restaurants, the Williamstown Motel is the perfect choice for your next getaway. Experience relaxation and hospitality at its finest at this charming establishment.

Ingalls Crossing Farm Bed and Breakfast is a charming lodging establishment located at 175 Blair Road in the picturesque town of Williamstown, Massachusetts, United States. Situated on a beautiful farm with scenic views of the surrounding countryside, this bed and breakfast offers a peaceful and relaxing retreat for guests. The cozy rooms are tastefully decorated and feature modern amenities for a comfortable stay. Guests can enjoy a delicious homemade breakfast each morning made with fresh ingredients from the farm. Whether you are looking for a romantic getaway or a peaceful escape, Ingalls Crossing Farm Bed and Breakfast is the perfect destination.

Welcome to Blackinton Manor, a charming lodging establishment located at 1391 Massachusetts Avenue in North Adams, Massachusetts. This historic manor offers a unique and luxurious experience for guests looking to escape the hustle and bustle of everyday life. With its elegant architecture, beautifully landscaped grounds, and top-notch amenities, Blackinton Manor is the perfect destination for a relaxing getaway. Whether you're looking to explore the nearby attractions or simply unwind in a tranquil setting, our friendly staff is dedicated to ensuring your stay is comfortable and memorable. Experience the timeless elegance of Blackinton Manor during your next visit to Massachusetts.

Thistle & Mirth is a cozy and inviting bar and restaurant located at 44 West Street in Pittsfield, Massachusetts. This charming establishment offers a warm and welcoming atmosphere where guests can enjoy delicious food and drinks in a relaxed setting. With a menu featuring a variety of mouth-watering dishes and a wide selection of craft beers and cocktails, Thistle & Mirth is the perfect spot for a casual meal with friends or a night out on the town. Whether you're looking for a quick bite to eat or a leisurely dinner, this hidden gem in Pittsfield has something for everyone to enjoy.

Shamrock Village Inn is a charming lodging establishment located at 633 Main Street in Dalton, Massachusetts, United States. Nestled in a picturesque village setting, this quaint inn offers comfortable accommodations and personalized service to ensure a memorable stay for guests. With its cozy rooms, convenient location, and warm hospitality, Shamrock Village Inn is the perfect choice for travelers looking for a peaceful retreat in the heart of the Berkshires.

The Becket Motel is a cozy lodging establishment located at 29 Chester Road in Becket, Massachusetts, United States. Nestled in the serene countryside, this charming motel offers comfortable accommodations for travelers seeking a peaceful retreat. With its convenient location and warm hospitality, The Becket Motel is the perfect choice for those looking to relax and unwind in a picturesque setting.

Hotel Downstreet is a charming lodging establishment located at 40 Main Street in the quaint town of North Adams, Massachusetts. Situated in the heart of the United States, this hotel offers a cozy and comfortable stay for guests looking to explore the beauty of the Berkshires region. With its convenient location and warm hospitality, Hotel Downstreet is the perfect choice for travelers seeking a relaxing and enjoyable getaway.

The Trail in Adams is a charming lodging and store located at 10 Pleasant Street in Adams, Massachusetts. This cozy establishment offers comfortable accommodations for travelers exploring the beautiful Berkshire region. Guests can also browse through the store's selection of unique gifts, local crafts, and outdoor gear. Whether you're looking for a place to rest after a day of hiking or shopping for a special souvenir, The Trail in Adams is the perfect destination for your next adventure.

Harbour House Inn B&B is a charming lodging establishment located at 725 North State Road in the picturesque town of Cheshire, Massachusetts, United States. This cozy bed and breakfast offers comfortable accommodations in a historic building, with a warm and inviting atmosphere. Guests can enjoy a delicious homemade breakfast each morning, as well as access to a peaceful garden and relaxing common areas. Whether you are looking for a romantic getaway or a peaceful retreat in the Berkshires, Harbour House Inn B&B is the perfect choice for your stay.

Whistler's Inn is a charming lodging establishment located at 5 Greenwood Street in the picturesque town of Lenox, Massachusetts, United States. This cozy inn offers comfortable accommodations and personalized service to make guests feel right at home. With its convenient location near popular attractions such as Tanglewood and the Norman Rockwell Museum, Whistler's Inn is the perfect choice for travelers looking to experience the beauty and culture of the Berkshires. Whether you're visiting for a romantic getaway or a family vacation, Whistler's Inn provides a peaceful retreat in the heart of Lenox.

67 Church Street is a charming lodging located in the heart of Lenox, Massachusetts. This historic institution offers comfortable accommodations and personalized service in a picturesque setting. Guests can enjoy the convenience of being just steps away from the town's shops, restaurants, and cultural attractions. Whether you are visiting Lenox for business or pleasure, 67 Church Street provides a cozy and welcoming home away from home.

26 Church Street is a charming lodging institution located in the heart of Lenox, Massachusetts. Situated at the address 26 Church Street, this cozy establishment offers a warm and inviting atmosphere for guests looking to experience the beauty of the Berkshires. With comfortable accommodations and a convenient location near local attractions, 26 Church Street is the perfect choice for a relaxing getaway in this picturesque New England town. Whether you're exploring the nearby shops and restaurants or simply unwinding in your well-appointed room, you'll feel right at home at this lovely inn.