Hotels in Chester

Wake up to a complimentary continental breakfast at this West Springfield haven. Just a 10-minute drive from thrilling Six Flags New England and MGM Springfield attractions, with hiking trails nearby. Enjoy free WiFi and parking during your adventure-filled stay.

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.

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.

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.

Escape to this comfortable hotel near the train station, featuring plush beds and a complimentary continental breakfast. Explore the nearby Smith College Botanic Garden or catch a train from Northampton Station, just a 4-minute drive away.

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.

Experience comfort and convenience at this motel in Great Barrington, where free WiFi and parking await. Explore nearby Monument Mountain Reservation for hiking, then return to spotless rooms with daily housekeeping and notably helpful staff.

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.

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 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.

Escape the ordinary at this quiet haven with a seasonal outdoor pool and fitness center. Just a 15-minute drive to major attractions and close to Riverdale Shops. The helpful staff and clean rooms earn consistent praise from fellow travelers.

Tucked away in a peaceful corner of Pittsfield, this quiet motel offers free WiFi and parking with a 24-hour front desk. Nearby Crane Museum of Papermaking awaits exploration, while winter enthusiasts will love the downhill skiing options just moments away.

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 peaceful Lenox hotel overlooks a picturesque lake where spectacular sunsets unfold daily. Enjoy Indian cuisine at Mint restaurant, complimentary breakfast, and free WiFi. Just 10 minutes from Tanglewood Music Center with convenient parking.

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 Lee motel offers a playful mini golf course on-site and free continental breakfast to start your day. Located near Greenock Country Club and Lee Premium Outlets, guests praise the helpful staff. Enjoy complimentary WiFi and parking during your stay.

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.

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.