Hotels with Air Conditioning in The Berkshires from $58

Start date: Check-in selected.
To Date
End date: Check-out

Seize Your Someday with our amazing deals for the whole family!

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Top The Berkshires Hotels with Air Conditioning

Monument Mountain Motel

Monument Mountain Motel

2.5 out of 5
247 Stockbridge Rd Great Barrington MA
Free Cancellation
Reserve now, pay when you stay
$67 nightly
The price is $74 total per night
$74 total
Dec 7 - Dec 8
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A picnic area and barbecue grills are also provided.
Stay Berkshires

Stay Berkshires

2 out of 5
1146 Cold Spring Road Williamstown MA
Get rates
A seasonal outdoor pool is featured at this hotel, along with free self parking. Guests will appreciate free perks like continental breakfast and WiFi in public ...
Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

2 out of 5
400 Stockbridge Rd Great Barrington MA
Free Cancellation
Reserve now, pay when you stay
$75 nightly
The price is $84 total per night
$84 total
Dec 7 - Dec 8
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, a picnic area, and dry cleaning are also on offer.
Wagon Wheel Inn

Wagon Wheel Inn

2 out of 5
484 Pittsfield Rd Lenox MA
$69 nightly
The price is $77 total per night
$77 total
Dec 7 - Dec 8
Total with taxes and fees
A hot tub is featured at this motel, along with free self parking. WiFi in public areas is free. Express check-out is also provided.
Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

2 out of 5
42 Stockbridge Rd West Stockbridge MA
$53 nightly
The price is $58 total per night
$58 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
Free WiFi in public areas is available at this motel. Take advantage of the free self parking.
Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington

2 out of 5
980 Pleasant Street Lee MA
Free Cancellation
Reserve now, pay when you stay
$63 nightly
The price is $70 total per night
$70 total
Dec 18 - Dec 19
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Multilingual staff at the 24-hour front desk ...
The Weathervane Motel

The Weathervane Motel

2 out of 5
475 South Main St. Route 7 Lanesborough MA
Get rates
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden is also provided.
Northside Motel

Northside Motel

2 out of 5
45 North St Williamstown MA
Get rates
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the business center. There's ...
Don't see what you're looking for?
See all available properties in The Berkshires
View all properties
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.

The Berkshires hotels essential information

Accommodation
1,083 hotels
Lowest Price
$58
Highest Price
$84
Popular hotels
Monument Mountain Motel, The Weathervane Motel, Northside Motel, Econo Lodge Lee - Great Barrington, Wagon Wheel Inn, Travelodge by Wyndham Great Barrington Berkshires, Pleasant Valley Motel West Stockbridge, Stay Berkshires

Recent The Berkshires hotel reviews by fellow wanderers

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

5 out of 5
Posted 16 hours ago
Travelocity Verified Review
"I don’t have a single complaint about this hotel! Everything was perfect! Staff was great, parking was easy, everything was clean! My family and I will definitely be staying here again in the future! "
A verified traveler stayed at Hotel Downstreet, an Ascend Collection Hotel
Hotel Downstreet, an Ascend Collection Hotel

Explore More Ways to Travel with Travelocity