Experience tranquil moments at this countryside retreat near Undermountain Golf Course and Copake Town Park. North Star restaurant serves American cuisine for dinner, while free WiFi and parking add convenience. Guests consistently praise the attentive staff who enhance every stay.
Tucked in Hillsdale, this cozy motel offers premium bedding for après-ski relaxation, plus free WiFi and parking. Adventure awaits at nearby Catamount Aerial Adventure Park, with cross-country and downhill skiing just moments away.
Escape to this mountain lodge near Catamount Ski Area, featuring a seasonal outdoor pool and relaxing sauna. After alpine adventures, savor complimentary breakfast before unwinding at the bar. Free WiFi and parking round out this Copake Falls retreat.
This peaceful hotel offers complimentary breakfast, WiFi, and parking, with Mahaiwe Performing Arts Center just moments away. Fitness enthusiasts will appreciate the on-site gym and outdoor activities, while the helpful staff ensures a comfortable stay.
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.
Escape to this serene country lodging in Craryville with free WiFi and parking. Explore nearby hiking trails, go kayaking, or visit West Beach. Lake Taghkanic State Park awaits close by, with Hudson station just a 15-minute drive away.
Wake up to a complimentary full breakfast at this cozy East Canaan B&B. Located near Land of Nod Vineyard and Winery, the inn offers free parking and daily housekeeping. Guests consistently praise the helpful staff for making stays memorable.
This tranquil hotel offers sound-insulated accommodations near Housatonic River and River Walk. Guests love the helpful staff, clean rooms, indoor pool, and 24-hour fitness center. Enjoy free breakfast, WiFi, and parking while exploring Great Barrington's nearby restaurants.
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 up to a continental breakfast at this charming Pine Plains B&B, just minutes from the local library and The Stissing Center. Visitors praise the attentive staff, while free parking and daily housekeeping ensure a hassle-free Hudson Valley escape.
Escape to the Berkshires in this inviting Sheffield accommodation with complimentary WiFi and parking. Start your day with cooked-to-order weekend breakfast before exploring nearby Thom Reed UFO Monument Park and Lime Kiln Farm Wildlife Sanctuary.
Nestled beside a golf course in Lakeville, this resort offers a seasonal outdoor pool and rejuvenating deep-tissue massages at the spa. Unwind at the bar after dining at the on-site restaurant, or maintain your routine in the fitness center, all while enjoying free WiFi and parking.
Relish free breakfast before exploring the Harlem Valley Rail Trail and Yoakum Preserve. This hotel offers complimentary WiFi and parking, with the on-site restaurant serving Mediterranean dishes for lunch and dinner in charming surroundings.
Tucked near Hudson Station, this cozy hotel offers free WiFi and parking for stress-free adventures. Explore Hudson Opera House and Area Library on foot, then return for daily housekeeping service. Convenient transit puts the best of Hudson at your fingertips.
Scenic Berkshires escape featuring an outdoor pool and rejuvenating sauna. Enjoy local flavors at The Cliff House restaurant after exploring nearby Catamount attractions. Free WiFi and parking make this wooded sanctuary even more appealing.
Escape to Jenny's Country Manor in Red Hook, where cozy accommodations meet countryside charm. Enjoy complimentary WiFi and parking while exploring nearby Lake Carvel and Stissing Lake Park. Daily housekeeping ensures a fresh, comfortable stay.
This cozy motel offers complimentary WiFi and parking, making outdoor adventures hassle-free. Explore the nearby Housatonic River and River Walk, or try kayaking and mountain biking. Garden views provide a serene backdrop for your Berkshires escape.
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.
Kunal and his family were very hospitable and helpful, making my stay very comfortable in Great Barrington in the heart of Berkshire County!
Their accommodations are quite clean and truly have all you might need for your stay and the price was also the best I found with good quality! They also have a nice continental breakfast...where I met a number of families...traveling for the school vacation week...to be close to the mountains and skiing.
I was traveling for business so Great Barrington...
The Harlow House is a unique, modern hotel. The room was clean, beautiful, and thoughtfully designed. We really enjoyed the king bed and spacious bathroom. Air conditioning worked great and kept us comfortable. Check in was easy. The owner was attentive and quick to respond. The hotel is stunning, situated in the middle of the woods on a quiet, and well kept plot of land. We awoke to a serene setting featuring a family of deer grazing in the nearby woods. It’s only a few minutes drive to...
They have a restaurant and it is amazing. If you find yourself in this direction go to the restaurant. It is worth the extra time. It’s worth the extra drive and it’s worth staying there for the restaurant. It was amazing food I will be coming back.
Our second time staying here was even more lovely than the first! We brought more family members after our great experience last year. We love the easy check in, cozy comfortable rooms, lots of extras (books and DVDs in the hallway, sweet treats downstairs and in the rooms) and Loretta is the BEST host! She makes an exquisite breakfast and accommodates our early start time. Can’t wait to stay here again.
Our second time visiting the Inn. Such a cute and cozy spot, real hidden gem if you're looking for a weekend escape from the city. The inn keeper Patti is super helpful and always makes sure we have the best plans while in town! Rooms are clean with a homey feel and the beds are dreamy. We'll def be back for our now annual visit to Pine Plains.
We were greeted by extremely friendly staff. Check in and check out was seamless. Room was very nice and immaculate. We especially liked the bathroom design - didn't have to trip over the toilet to get in the shower as in most hotels! Free breakfast was the usual fare, but in a very pleasant and uncrowded room. Appreciated the free US News and NY Times Beautiful indoor pool - wish we'd brought our bathing suits!
Just a beautiful home with clean, comfortable rooms and an amazing Innkeeper.
Breakfasts are elegant and delicious. We stayed here in 2025 and returned in 2026 for Labor Day weekend. Will hopefully repeat in 2027.
We enjoyed our stay at the White Hart. We got a room in the back of the building overlooking a garden. We loved sitting out there and relaxing. The room was a nice size and comfortable. The complementary breakfast provided a good selection and was tasty. The lobby is a nice place to have coffee or wine. The chairs are everywhere and make it a nice place to relax. Service was friendly and attentive and Provisions provides excellent sandwiches.
We were also able to park right outside our...