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.
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.
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.
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.
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.
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 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.
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.
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 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.
Embrace comfort at this Pittsfield retreat with an indoor pool and fitness center. Jae's Asian Fusion restaurant serves three daily meals, while rooms offer convenient refrigerators and microwaves. Guido's Marketplace and literary landmarks await nearby.
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.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Zema's Nursery is 2 mi (3.1 km) from central Stephentown, why not stop by during your stay. If you have fun at Zema's Nursery, you'll love Alpine Super Slide, located nearby.
The Hotel on North is a thoughtful and beautiful transformation of 2 old contiguous buildings, a store and factory, into a hip and fun hotel. The spaces are extremely large and open from the common spaces to the guest rooms, including the bathrooms. The aesthetic is colorful and friendly rather than the cookie cutter faux luxury I usually find in expensive hotels. The quirky design features such as vintage furniture and painted floors are a great juxtaposition to the perfect bed linens and...
We had a fantastic stay at the Yankee! Our adjoining rooms were clean, large and comfortable. We loved that the rooms had a fireplace and balcony! All the amenities were appreciated. The breakfast had so many offerings, including fresh fruit and two kinds of eggs. The front desk staff (especially George) were professional, helpful and friendly. This was our first stay at the Yankee, but it won't be the last!
This is a super clean, comfortable, and relaxing Inn. The Inn-keepers, Chloe and Shawn are wonderful. I could not have been happier with the service, the level of cleanliness, and the comfort of my room and common areas. Breakfast was delicious!
It was very conveniently located to the activities we were doing on our mini-vacation. There were a couple of issues that developed during our stay, but the staff did an excellent job of dealing with the issues.
Arrived late after office closed. Easy arrangements for check in made with no issues. Light in room was on to welcome me. Room was very clean with nice appointments of water, coffee, tea, chocolates.
Beautiful room, very conveniently located right next to a main strip of little shops, theaters and restaurants. We brought all of our own food and were able to store it safely, roomy refrigerator provided- and all cooking utensils, pots, pans, plates... Everything provided. There was a dvd player, and we were able to have movie nights, and a back balcony to enjoy coffee on the porch or read a book in a heavily wooded area which provided a nice shady view to block the parking lot. The front desk...
Stayed end of Sept 2026 for 3 nights. Booked the standard room with 2 queen beds. Very clean, spacious, great amenities (microwave, mini fridge, dishes, utensils and sink), spacious closet with drawers and closet rod & hangers. EV charging in parking lot. Breakfast included. Convenient location. Friendly & helpful staff. Would stay there again.
Everything there was great except Christiansens taver. The service was ok but the food was terrible. I would not recommend this place for dining. I would go to McDonalds before I ate there again. We do however recommend Powder Hounds Tavern at the entrance, The service and the food were excellent and affordable.
This motel is in a convenient location for visiting Williams College. Rooms are clean and the mattresses are very comfortable. They have the largest TV screens I've seen in any motel. Their Continental breakfast is extensive with a variety of pastries, breads, and beverages. The staff is kind, caring, helpful, and accommodating.
Can I book a refundable accommodation in Stephentown?
If you're looking for the flexibility to change your travel plans to Stephentown, most properties offer refundable* rates you can book. You can find these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.
Where can I stay in Stephentown if I want a vacation home instead of a traditional hotel?
If you want to find a good alternative to a hotel, look over our selection of 7 vacation homes.
What will the weather in Stephentown be like during my trip?
The warmest months in Stephentown are usually July and August with an average temp of 65°F. January and February are the chilliest months when the average temp is 26°F. The rainiest months are October and December.
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