Hotels in Stephentown

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.

Experience rustic elegance at this inviting inn, where complimentary WiFi and parking enhance your stay near Pineridge Cross Country Ski Center and Berkshire Retreat Center. Unwind with a cocktail at the bar or savor a meal at the on-site restaurant.

Tucked in New Ashford, this welcoming motel provides a refreshing seasonal outdoor pool, terraced grounds, and garden spaces. Just 15 minutes from skiing at Jiminy Peak and Brodie Mountain with free WiFi and convenient parking.

Surrounded by nature in the Berkshires, this campground offers an outdoor pool and convenient access to hiking and biking trails. Just a short drive from Jiminy Peak Mountain Resort and Mountain Coaster, you'll find the perfect basecamp for outdoor adventures.

Set in Williamstown, this welcoming hotel puts you 10 minutes from Jiminy Peak Mountain Resort and Brodie Mountain. Enjoy a seasonal outdoor pool, free breakfast, and WiFi. Travelers love the helpful staff, clean rooms, and nearby hiking trails.

Slope-side convenience awaits at this mountain resort with direct ski access. After hitting the trails, unwind in 2 hot tubs, grab dinner at John Harvard's, or enjoy the outdoor pool. With ski storage and lessons available, all your winter adventure needs are covered.

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.

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.

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.

Tucked away in East Chatham, this charming B&B offers free daily buffet breakfast, WiFi, and parking. Just moments from Queechy Lake and Hand Hollow State Forest, you'll find a peaceful countryside retreat with easy access to outdoor adventures.

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.

Unwind at this centrally located Pittsfield hotel with an indoor pool and health club. Just 15 minutes from Tanglewood Music Center and a quick 6-minute walk to transportation. Enjoy quiet rooms with microwaves, refrigerators, and a bar on-site.

This boutique hotel combines business-friendly amenities with cozy accommodations near Barrington Stage Company. Enjoy thoughtful perks including complimentary WiFi, free parking, and convenient room service, all while exploring nearby cultural attractions.

Dive into the indoor pool at this Lenox hotel, just 10 minutes from Tanglewood Music Center. Enjoy a complimentary breakfast before exploring nearby attractions like Guido's Marketplace and Bousquet Ski Area. Free WiFi and parking complete your comfortable stay.