Hotels in Windsor

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.

This hotel puts you close to Yankee Candle Village and Mount Sugarloaf State Reservation. Enjoy clean rooms with free WiFi and parking, plus attentive 24-hour staff to assist throughout your stay. UMass Amherst is just a short drive 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.

Immerse yourself in the tranquility of Shelburne Falls at this welcoming guesthouse. Free WiFi and daily housekeeping provide essential comforts, while snowmobiling, snowshoeing, and sledding await right outside. Popular attractions like Glacial Potholes are nearby.

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.

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 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.

Wake up to a complimentary self-serve breakfast at this charming Adams guesthouse. Enjoy free WiFi and parking while exploring nearby Adams Theater and Berkshire Scenic Railway Museum. Just a 22-minute drive from Pittsfield Station.

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.

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.

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.

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.

Tucked away in Becket, this motel offers convenient perks like free WiFi, complimentary parking, and room service. Hiking enthusiasts can explore nearby trails and visit the historic Becket Land Trust Quarry for outdoor adventures.

Experience tranquility at this West Stockbridge B&B where hiking, biking, and kayaking adventures await. Enjoy free breakfast, complimentary parking, and daily housekeeping while exploring Ebenezer II Gifts and nearby cultural attractions.

Escape to this Williamstown motel in the entertainment district with a seasonal pool. Clean rooms await after exploring nearby Linear Park. Friendly staff, free breakfast, WiFi and parking enhance your value-packed stay.