Hotel vacation rentals in Berkshire County

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 

Beautiful 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 

Singing Bridge Harmony Room

Great views of the Berkshire hilly forests, and hiking trails along a scenic river. Couples, families, and pets feel right at home in our recently renovated kitchen and warm, and friendly lodge with four bedrooms, electric baseboard heat and queen-sized beds. The sunny loft has a comfy queen. Gas heat. Call an hour before arrival if you don't have AT&T or Verizon cell service- other carriers may be inconsistent in the area. Wifi enabled. Pets are welcome for a $25 fee.

★ Romantic Room with Jacuzzi Tub & Fireplace

Known as the Rarus Room, this moody and romantic second-floor space features a Queen bed, corner gas fireplace, and private bath with a Jacuzzi tub. Located in the Carriage House of our historic property, it offers privacy and is a short walk to downtown Lenox. 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.

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!

Standard King in Boutique Lenox Hotel

Designed to relax and inspire, our Standard King guest room is furnished with a writer's desk and harmonious color tones drawn from the seasonal hues of the Berkshires. As always, stocked with luxe touches such as plush linens and terry robes from Revival New York and Le Labo shower amenities.

Wyndham Bentley Brook ** 2BR Deluxe

Ski-In/Ski-Out Plus Year-Round Mountainside Fun. The Wyndham Bentley Brook is situated right at the base of Jiminy Peak ski mountain, making this resort an exceptional choice for mountainside play. In winter, ski out your door and onto the lifts.