A person snowboarding down a snowy slope.

The Berkshires hotel rooms a the Wyndham Extra Holidays

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Aug 30 - Aug 31
Tomorrow
Aug 31 - Sep 1
Next weekend
Sep 4 - Sep 6
In two weeks
Sep 11 - Sep 13
Save an average of 15% on thousands of hotels when you're signed in

Top The Berkshires Hotel Reviews

The Yankee Inn

The Yankee Inn

8/10 Good
"Independent option convenient to Tanglewood. Spacious room and facility. Breakfast included but needs better coffee and some other tweaks."
Francis 1-night trip
Posted 1 hour ago
The Yankee Inn
Berkshires Untold

Berkshires Untold

10/10 Excellent
"Although an excellent 2-night stay, our comments are intended to make future stays even better. Room temperature: virtually impossible to maintain a comfort level. Basically it was too cold in spite of raising the thermostat temp. At 80 when the heat came on, it was much too hot! Room lighting: too dark; only the bathroom was well lit. Bathroom moisture: in the absence of a ventilation or fan, the bathroom remained damp after a shower and keeping the door open resulted in everything in the bedroom becoming damp. But the positives far outweigh these few items."
Naomi 2-night trip
Posted 17 hours ago
Berkshires Untold
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Friendly and professional staff. Check in quick and easy. Will definitely stay again"
abdoul kader 1-night trip
Posted 18 hours ago
Vacation Village in the Berkshires
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"Location"
patricia 2-night trip
Posted 18 hours ago
Quality Inn Great Barrington
Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent
"Amazing time. Stayed in the Presidential units. Worth it."
Marsha 5-night trip
Posted 1 day ago
Holiday Inn Club Vacations Oak 'n Spruce Resort
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Having stayed at the Red Lion over forty times since 1979, when we were pleasantly snowed in and obliged to spend an extra night whilst the roads were plowed, I have watched the inn evolve. The beds were as comfy as always, the pool a delight under the moon, still the delicious Bloody Marys to sip in a rocking chair on the wide, wooden porch, an idyllic perch to chat and watch the town’s visitors to-ing and fro-ing and the small - and not so small-ones riding the lions that frame the entrance. Long carpeted, bumpy hallways framed with an eclectic array of deeds, art, china-stuffed cupboards and dresses still charm and enlighten the journey to one’s room. Contemporary sophistication and New England history blend. Over doors, painted horizontal windows that once served to cool a room, and pre electrified gas switches that controlled the lights allow the guest to transcend time. The food is delicious, as always, the menus having broaden to reflect contemporary tastes. Love the small bar and was pleased to see there was sometimes entertainment in The Lion’s Den. The upstairs gift shop carries an imaginative collection of Red Lion and New England sundries, whilst another shop holds varied treasures, including clothing. Of note, I noticed that that the porch rattan needed repair, the dining area has shrunk to accommodate more seating and the porch table overflowed with empty glasses. Still the rocking steed sits proudly in the back room!"
Dorothy 1-night trip
Posted 2 days ago
The Red Lion Inn
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent
"Nice, well-maintained property, everything was very clean. The breakfast nook was not overly crazy crowded, which is really good traveling with young children. The staff even apologized for not having the waffle maker as a new one was being delivered. The hot tub was also a plus!"
Corinne 1-night trip
Posted 3 days ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Nice place"
Peter 1-night trip
Posted 4 days ago
Hotel Downstreet, an Ascend Collection Hotel
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

10/10 Excellent
"Fine place to stay in the Lenox area."
Anthony 1-night trip
Posted 5 days ago
Best Western Plus Berkshire Hills Inn & Suites

Explore a world of travel with Expedia