TOP 30 Berkshires getaway in Massachusetts

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Located in the charming town of West Stockbridge, Massachusetts, the Pleasant Valley Motel offers comfortable and affordable lodging for those looking to explore the beautiful Berkshires region. Situated at 42 West Stockbridge Road, this cozy motel provides a peaceful retreat for visitors seeking a relaxing getaway. With its convenient location and friendly staff, Pleasant Valley Motel is the perfect choice for travelers looking for a comfortable stay in West Stockbridge.

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.

Wheatleigh is a luxurious lodging institution located on Hawthorne Road in Lenox, Massachusetts, United States. This grand estate offers a unique and elegant experience for guests looking to immerse themselves in opulence and sophistication. With its stunning architecture, lush gardens, and impeccable service, Wheatleigh provides a truly unforgettable stay for those seeking a refined retreat in the heart of the Berkshires. Whether you are looking for a romantic getaway, a peaceful escape, or a lavish event venue, Wheatleigh promises to exceed your expectations and create lasting memories.

Holiday Inn Club Vacations Oak n’ Spruce Resort - Tour Reception is a welcoming lodging institution located in Lee, Massachusetts, United States. Situated at 165 Meadow Street, this resort offers a relaxing and comfortable environment for guests to enjoy during their vacation. The tour reception area provides guests with information about the resort's amenities and activities, ensuring a memorable stay for all visitors. With its convenient location and friendly staff, Holiday Inn Club Vacations Oak n’ Spruce Resort - Tour Reception is the perfect choice for those seeking a peaceful getaway in the beautiful Berkshires region.

The Black Swan Lee - Lenox, Ascend Hotel Collection is a charming lodging institution located at 435 Laurel Street in Lee, Massachusetts, United States. This unique hotel offers a cozy and inviting atmosphere for guests to relax and unwind during their stay. With comfortable accommodations and top-notch amenities, The Black Swan Lee is the perfect choice for travelers looking for a memorable experience in the heart of the Berkshires. Whether you are visiting for business or pleasure, this hotel is sure to exceed your expectations with its exceptional service and convenient location. Book your stay at The Black Swan Lee - Lenox, Ascend Hotel Collection for a truly unforgettable experience.

Devonfield Inn is a charming lodging establishment located at 85 Stockbridge Road in Lee, Massachusetts, United States. Nestled in the picturesque Berkshire Mountains, this cozy inn offers a peaceful and serene retreat for guests seeking a relaxing getaway. The beautifully appointed rooms and suites are tastefully decorated and provide all the comforts of home. Guests can enjoy a delicious homemade breakfast each morning, as well as afternoon tea and snacks. The inn also features a lovely garden area, perfect for unwinding and taking in the natural beauty of the surrounding landscape. Whether you're looking for a romantic escape or a peaceful retreat, Devonfield Inn is the perfect destination for your next vacation.

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.

33 Main offers a luxurious lodging experience curated by renowned designer Annie Selke. Located in the charming town of Lenox, Massachusetts, this upscale accommodation combines modern amenities with classic New England charm. Each room is elegantly decorated with Selke's signature style, creating a cozy and inviting atmosphere for guests to relax and unwind. With its prime location on Main Street, guests can easily explore the local shops, restaurants, and cultural attractions that Lenox has to offer. Whether you're visiting for a romantic getaway or a weekend retreat, 33 Main promises a memorable and indulgent stay in the heart of the Berkshires.

Located at 91 Walker Street in Lenox, Massachusetts, the Hampton Terrace Inn is a historic bed and breakfast that has been rated the #1 place to stay in Lenox on Tripadvisor. Originally built in 1897, this inn was once owned by some of the wealthiest families in the country and was among the first of the "Berkshire cottages" to welcome guests. Today, the inn offers romantic cottages and suites that have been updated with modern amenities while still preserving the property's rich history. Just a 5-minute walk from downtown Lenox, Hampton Terrace Inn is the perfect location for a Berkshires getaway. Guests can enjoy private baths, air conditioning, HDTVs, free Wi-Fi, complimentary cognac and liqueurs, and a full breakfast buffet included in their room rate. The inn also features a heated pool, jetted tubs, and fireplaces for guests to relax and unwind after a day of exploring the Berkshires.

The Ponds at Foxhollow is a secluded resort located in the heart of the Berkshire Mountains at 3 Fox Hollow Drive, Lenox, Massachusetts. The resort offers one and two bedroom condominiums for timesharing or rental purposes, each with a master bedroom, fully equipped kitchen, living area with a double sleeper sofa, and a deck overlooking a picturesque pond. The property spans 223 acres, perfect for hiking in the warmer months and cross country skiing in the winter. The resort also offers outdoor activity equipment and canoes for guests to use. With breathtaking mountain views and a variety of recreational and cultural activities nearby, The Ponds at Foxhollow is the perfect destination for a relaxing getaway. Please note that the hot tub is temporarily out of service, but a new one is on the way.

Blantyre is a luxurious lodging institution located at 16 Blantyre Road in the picturesque town of Lenox, Massachusetts, United States. This historic property offers elegant accommodations, impeccable service, and stunning views of the surrounding Berkshire Mountains. Guests can enjoy fine dining, relaxing spa treatments, and a variety of outdoor activities on the expansive grounds. Blantyre is the perfect destination for a romantic getaway, a special occasion, or a relaxing retreat in a beautiful New England setting.

Welcome to Brook Farm Inn, a charming lodging establishment located at 15 Hawthorne Street in Lenox, Massachusetts. Our Victorian Inn offers 15 guest rooms, including a carriage house with three luxury accommodations, perfect for a relaxing getaway in the beautiful Berkshires. Surrounded by trees and award-winning gardens, our inn provides a serene and secluded atmosphere, while still being just a short walk from historic Lenox village. Built in 1882 and furnished with antiques, our elegant inn features a library filled with poetry, history, and literature, where guests can enjoy the soothing sounds of classical music. Each room at Brook Farm Inn includes a full plated breakfast, providing a perfect start to the day before exploring all that the Berkshires have to offer. From skiing and hiking to theater and antiquing, there is something for everyone to enjoy in the area.

The Dewey is a charming lodging establishment located at 7 Hubbard Street in Lenox, Massachusetts. This cozy inn offers comfortable accommodations in a picturesque setting, perfect for those looking to relax and unwind in the heart of the Berkshires. The Dewey's convenient location allows guests to easily explore the many attractions and activities in the area, including historic sites, art galleries, and outdoor adventures. With its warm hospitality and inviting atmosphere, The Dewey is the ideal destination for a peaceful getaway in the beautiful New England countryside.

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.

Howard Johnson by Wyndham Lenox is a charming lodging facility located at 462 Pittsfield Road in Lenox, Massachusetts. Situated in the beautiful Berkshires region, this hotel offers comfortable and affordable accommodations for travelers looking to explore the area. Guests can enjoy spacious rooms, complimentary breakfast, free Wi-Fi, and a seasonal outdoor pool. With its convenient location near popular attractions such as Tanglewood and the Norman Rockwell Museum, Howard Johnson by Wyndham Lenox is the perfect choice for a relaxing getaway in Massachusetts.

Wagon Wheel Inn is a charming lodging located at 484 Pittsfield Road in Lenox, Massachusetts. Nestled in the heart of the beautiful Berkshire Mountains, this cozy inn offers comfortable accommodations and a warm, welcoming atmosphere. Guests can relax in well-appointed rooms, enjoy a delicious complimentary breakfast, and take advantage of convenient amenities such as free Wi-Fi and onsite parking. Whether you're visiting for a weekend getaway or a longer stay, Wagon Wheel Inn is the perfect home base for exploring all that Lenox has to offer.

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.

Jiminy Peak Mountain Resort is a premier destination located at 37 Corey Road in Hancock, Massachusetts, United States. This institution offers a wide range of activities for visitors, including skiing and snowboarding in the winter, as well as hiking, biking, and zip-lining in the summer. With on-site lodging options, dining establishments, and a variety of recreational amenities, Jiminy Peak Mountain Resort is the perfect destination for a family vacation or weekend getaway. Experience the beauty of the Berkshire Mountains while enjoying all that this top-rated tourist attraction has to offer.

Club Wyndham Bentley Brook is a premier lodging destination nestled in the picturesque town of Hancock, Massachusetts. As a part of the renowned Wyndham vacation ownership network, this institution offers luxurious accommodations, top-notch amenities, and exceptional service. Whether you're looking for a relaxing getaway or an adventurous vacation, Club Wyndham Bentley Brook has something for everyone. With its prime location near ski slopes, hiking trails, and other outdoor activities, guests can enjoy a truly unforgettable experience. Plan your next vacation with Club Wyndham Bentley Brook and create lasting memories in the beautiful Berkshires region of Massachusetts.

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.

Sunset Inn is a charming lodging facility located at 150 Housatonic Street in the picturesque town of Lee, Massachusetts, United States. This cozy inn offers comfortable accommodations and a warm, welcoming atmosphere for guests looking to relax and unwind. With its convenient location near popular attractions and scenic views, Sunset Inn is the perfect choice for a peaceful getaway in the heart of the Berkshires. Whether you're visiting for business or pleasure, you'll find everything you need for a comfortable stay at Sunset Inn.

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.

Chambery Inn is a charming lodging and spa located at 199 Main Street in Lee, Massachusetts. This historic inn offers a tranquil and luxurious retreat for guests seeking a peaceful getaway in the heart of the Berkshires. The beautifully appointed rooms feature elegant decor and modern amenities, creating a cozy and inviting atmosphere for relaxation. Guests can indulge in rejuvenating spa treatments, unwind in the serene garden courtyard, or explore the nearby attractions and activities in the picturesque town of Lee. With its convenient location and exceptional service, Chambery Inn is the perfect destination for a memorable and rejuvenating stay.

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.

Lanesborough Country Inn is a charming lodging located at 499 South Main Street in Lanesborough, Massachusetts, United States. This cozy inn offers a peaceful retreat in the picturesque Berkshire Mountains, surrounded by beautiful nature and just a short drive from cultural attractions such as Tanglewood and the Norman Rockwell Museum. Guests can relax in comfortable rooms, enjoy delicious breakfasts, and unwind in the serene setting of the inn's grounds. Whether you're looking for a romantic getaway or a relaxing escape, Lanesborough Country Inn provides a warm and welcoming atmosphere for your stay.

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.