Hotel holiday rentals in Berkshire County

Prime Berkshires Studio|WiFi|Sleeps 4|Pet-friendly

Perfect for a family or friend getaway with or without your dog in tow, this unit features two luxury pillow-top queen beds, premium linens, a dining table and chairs for work or eating, a sparkling clean bathroom with a shower and a separate sink/vanity area, Roku Smart TV, and individually controlled AC and heat. Quiet, comfy, and comes with full access to East Rock Inn's outdoor dining tables and Adirondack chairs for lounging or enjoying your morning coffee while listening to birdsong.

Spencertown Inn Suite 4

The Spencertown Inn is Columbia County’s newest all-suite luxury Inn. With just 5 suites in total, the Inn offers quiet and private accommodations in a country setting, yet is just minutes away from local restaurants and attractions. The Spencertown Inn is located in the historic town of Spencertown, New York, just minutes from Chatham, New York’s charming downtown Main Street and a short drive to the Cultural Berkshires of Massachusetts. (Room furniture and décor may differ from photos.)

Great place for family |2 BD|Kitchen| Pool

After a day of mountain adventures , our Resort in the Berkshires is the perfect New England-y place to unwind and kick off those hiking boots. Take the whole family for a relaxing indoor swim, enjoy a flick at our onsite movie theater, and end your evening with a toast at the Beartree Bar. • Pools, Gym, Movie Theater and mini golf  • Accommodate up to 6 people  • One guest in the party, must be at least 21 y/o or older.    * U$10 PER NIGHT OF RESORT FEE.  **Additional charge 

Great Place |2 BD|Kitchen| Pool 

After a day of mountain adventures , our Resort in the Berkshires is the perfect New England-y place to unwind and kick off those hiking boots. Take the whole family for a relaxing indoor swim, enjoy a flick at our onsite movie theater, and end your evening with a toast at the Beartree Bar. • Pools, Gym, Movie Theater and mini golf  • Accommodate up to 6 people  • One guest in the party, must be at least 21 y/o or older.    * U$10 PER NIGHT OF RESORT FEE.  **Additional charge 

Great place|2 BD|Kitchen| Pool 

After a day of mountain adventures , our Resort in the Berkshires is the perfect New England-y place to unwind and kick off those hiking boots. Take the whole family for a relaxing indoor swim, enjoy a flick at our onsite movie theater, and end your evening with a toast at the Beartree Bar. • Pools, Gym, Movie Theater and mini golf  • Accommodate up to 6 people  • One guest in the party, must be at least 21 y/o or older.    * U$10 PER NIGHT OF RESORT FEE.  **Additional charge 

★ Vintage Romance with Fireplace & Spa Tub

The Spencer Room is a romantic corner retreat located in the main building, a historic Gilded Age mansion now operating as a boutique inn. It features a Queen bed with a net canopy, vintage throw pillows, antique furniture, leaded glass windows, a corner fireplace, and a private bath with a 72" Ultra spa tub/shower. Enjoy daily full breakfast, A/C, HDTV, Wi-Fi, and access to our heated pool (seasonal, Memorial Day - Labor Day). Professionally managed by Hampton Terrace Inn.

Springs Motel Honeymoon Suite

Experience retro charm and modern comfort in our Honeymoon Suite at The Springs Motel. This beautifully designed suite features a spacious king bedroom, a cozy living area with a pull-out couch, and a dining space, all adorned with unique vintage decor. Enjoy the convenience of two full retro-tiled bathrooms, a private patio, and access to our seasonal front lawn lounge. You’ll love the stylish decor of this charming place to stay.

Hidden Gem Next Door to Catamount - Ski In/Out

Welcome to Catamount! Just steps away from the slopes, our rooms feature exceptional views, unparalleled access, and ideal privacy. You'll also be in the perfect jumping off point for further adventures in Hudson, NY and the rest of the Hudson Valley, or to Great Barrington, MA and the Berkshires beyond. Welcome to the best kept secret in the New York Berkshires!

Little Cat Lodge - Double Double

Merging the rustic charm of an alpine lodge with the magic of mid-century Berkshires, our 400 sq.ft. Double rooms are lined in mushroom wood and accented by original artwork. Built in storage and a private terrace or patio ensure you can make the most of your mountain stay. Mini fridge and Keurig included!