Want travel alerts for this area?

Enter your name and email to receive alerts when new vacation deals are added to any property in this region.

By clicking "Submit" you are agreeing to the
Terms of Service.

Alert successfully created!

Go to Map View


Avg. Daily Rate
Resort Type

Showing 16-30 of 66 Resorts and Lodges

Hampton Inn & Suites Berkshires-Lenox

Lenox, Massachusetts, United States
236 Reviews

White Horse Inn

Pittsfield, Massachusetts, United States
46 Reviews

The Morgan House Inn

Lee, Massachusetts, United States
13 Reviews

Kemble Inn

Lenox, Massachusetts, United States
51 Reviews

Four seasons of relaxation and excitement awaits for you at the beautiful Kemble Inn. This Berkshires destination combines the stunning architecture of a 125-year-old Gilded Age mansion with completely modern amenities and furnishings for a one-of-a-kind vacation experience. You'll fall in love with the charming mountain vista scenery, the spacious... more

The 1896 House

Williamstown, Massachusetts, United States

The 1896 House, nestled in Massachusetts' Berkshire Hills, offers its guests natural beauty as well as the cultural activities of the Berkshires. Built in 1896 as a milking barn, complete with bull pen, the house was turned into a famous restaurant in 1939 and continues its reputation seving for wonderful Yankee cuisine to this day.... more

Harbour House Inn

Cheshire, Massachusetts, United States

The Inn at Laurel Lake

Lee, Massachusetts, United States

Federal House Inn

Lee, Massachusetts, United States
92 Reviews

Soon to be listed on the National Register of Historic Buildings, the Federal House is located in the Berkshires close to summer music, drama and dance festivals. Golf and tennis privileges are available at the Stockbridge Country Club, two miles directly down Main Street and in the winter cross-country and downhill ski areas are nearby.... more

Gateways Inn & Restaurant

Lenox, Massachusetts, United States
Very Good
31 Reviews

Red Lion Inn

Stockbridge, Massachusetts, United States
Very Good
285 Reviews

Established as a stage coach stop in 1773 and rebuilt in 1897, The Red Lion Inn is one of the few remaining American inns in continuous use since the 18th century. As immortalized in Norman Rockwell's painting Main Street, Stockbridge, the Inn epitomizes New England tradition. When you step inside The Red Lion Inn, you enter a world full of... more

The Rookwood Inn

Lenox, Massachusetts, United States
42 Reviews

The Rookwood Inn is a restored fairy tale Victorian bed and breakfast in the charming village of Lenox. Peace, seclusion and relaxation are exactly what you will get when you stay at this unique bed and breakfast. Private bathrooms, Wi-Fi, and individual AC are all modern touches that make your stay feel like home. In the morning, a scrumptious... more

The Orchard Hotel

Williamstown, Massachusetts, United States

Wyndham Vacation Resorts - Bentley Brook

Hancock, Massachusetts, United States
118 Reviews

See the mountainside suspended from a chairlift above Jiminy Peak Mountain and discover an unparalleled vacation destination at Wyndham Bentley Brook! This premier Hancock, MA vacation resort is located at the foot of the ski slopes of Jiminy Peak Mountain Resort. After a full day of skiing, snowboarding, hiking and partaking in other seasonal... more

Windflower Inn

Great Barrington, Massachusetts, United States

The Windflower is a classic New England inn, located on a Berkshire County estate dating back to the 1850's. A full breakfast is served daily along with tea and homemade cookies in the afternoon. All rooms have privatebath, AC and many have a working fireplace. The Inn has its own pool and is directly across from a public golf course. The area... more

The Cornell In Lenox

Lenox, Massachusetts, United States
175 Reviews

The Cornell in Lenox offers peaceful Berkshire vacations with the historic charm of New England. This unique bed & breakfast is composed of three historic buildings, dating back as far as 1777! Each guestroom and suite features period-style d├ęcor, with charming touches like print wallpaper, painted cupboards, vintage toys & four poster... more

Showing 16-30 of 66 Resorts and Lodges