Hotels in Chester

Discover this Lenox retreat with stunning mountain views, year-round swimming options, and fireplaces in select rooms. Just minutes from Bousquet Ski Area and local attractions, enjoy free breakfast and helpful staff after a day exploring.

Escape to this Pittsfield hotel near the train station, with Tanglewood Music Center nearby. After enjoying the complimentary breakfast, explore local skiing trails or workout in the fitness center. Clean rooms and attentive staff create a welcoming mountain getaway.

Dive into Berkshires charm at this centrally located Lenox motel, where you'll enjoy the refreshing outdoor pool and free parking. Near Guido's Marketplace and Bousquet Ski Area, with clean rooms and exceptionally helpful staff to enhance your stay.

This welcoming country inn features a bar, café, and terrace surrounded by beautiful gardens. Located near Porter Phelps Huntington Museum, guests enjoy complimentary breakfast, WiFi, and parking while praising the helpful staff.

This business-friendly hotel is near University of Massachusetts Amherst, offering free breakfast, WiFi, and parking. Travelers will appreciate the indoor pool and 24-hour fitness center after exploring Central Rock Climbing Center and Hadley Farm Museum.

Discover West Hatfield from this welcoming motel with 24-hour reception and complimentary WiFi. Explore nearby Pioneer Valley Indoor Karting or Connecticut River Greenway State Park, then return to hassle-free accommodations with free parking.

Just 15 minutes from Springfield, this welcoming hotel offers an indoor pool for year-round relaxation and a fitness center for active travelers. Guests rave about the complimentary breakfast, free WiFi, and convenient parking, plus the exceptionally helpful staff.

Escape to the heart of Pittsfield where this hotel offers an indoor pool and relaxing hot tub after exploring Tanglewood. Free breakfast, WiFi, and parking enhance your stay while nearby Guido's Marketplace awaits your discovery.

Escape to this golf course adjacent hotel with 2 restaurants and a relaxing spa offering deep-tissue massages. The pool and fitness center enhance your stay, while Mount Tom State Reservation provides nearby adventure opportunities.

This peaceful Lee hotel offers free daily continental breakfast near local restaurants and shopping. Just minutes from Lee Library and Animagic Museum, guests praise the helpful staff. Enjoy convenient access to cultural attractions during your Berkshires stay.

Escape to the heart of the Berkshires in this well-maintained motel close to Tanglewood Music Center. Free WiFi and parking make exploring local attractions like Hoffman's Pottery and Charles H. Baldwin & Sons effortless. Clean rooms and daily housekeeping ensure a comfortable stay.

Close to Chicopee Falls Dam, this hotel offers free breakfast, WiFi, and parking that guests consistently praise. Splash in the indoor pool or work out at the fitness center after enjoying in-room conveniences like refrigerators and microwaves.

Wake to tranquility at this quiet Westfield hotel near General Wareham Park. Enjoy free buffet breakfast, WiFi, and parking while friendly staff ensure a comfortable stay in clean rooms. Springfield Union Station is just an 18-minute drive away.

Immerse yourself in this charming landmark hotel with peaceful accommodations and an on-site fitness center. Located near Calvin Theater and UMass Amherst, the hotel offers two restaurants including the Historic Wiggins Tavern serving American cuisine.

Enjoy a serene retreat in Pittsfield with a seasonal outdoor pool and proximity to Colonial Theater and Berkshire Museum. This motel offers clean rooms, free WiFi, and parking. Just a 2-minute drive from the transportation hub for your Tanglewood adventures.

Refresh in the indoor pool at this welcoming Great Barrington hotel. The fitness center adds value to each stay, while free breakfast fuels adventures to nearby Lake Mansfield Park and Housatonic River. Guests rave about the clean rooms and helpful staff.

This Chicopee hotel offers an indoor pool and bar just 10 minutes from MGM Springfield and the Basketball Hall of Fame. Enjoy complimentary breakfast, WiFi, and parking, plus 24-hour fitness center access. Guests praise the helpful staff and convenient location near restaurants and shopping.

Nestled in Lenox, this lodge offers easy access to Kennedy Park and Pleasant Valley Wilderness Sanctuary. The Club Room serves American cuisine, while the terrace provides a perfect spot to unwind after exploring local attractions.