Hotels with Air Conditioning in The Berkshires
Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels
Save 10% or more on select hotels with Insider Prices
Book on the app to instantly earn 5% on 350,000+ hotels
Featured The Berkshires Hotels with Air Conditioning

Monument Mountain Motel
247 Stockbridge Rd, Great Barrington, MA
$105 nightly
The price is $117 total per night
$117 total
Jul 30 - Jul 31
Total includes taxes and fees
Monument Mountain Motel features free WiFi in public areas and barbecue grills. If you decide to drive, there's free parking. Staff members can answer questions about accommodations, and also provide front-desk service during limited hours. This smoke-free motel also has a picnic area.
Parking included
Free WiFi

The Weathervane Motel
475 South Main St. Route 7, Lanesborough, MA
The Weathervane Motel features free WiFi in public areas and a garden. You can put free parking to good use if you drive.
Parking included
Free WiFi

Northside Motel
45 North St, Williamstown, MA
Guests of Northside Motel enjoy access to free WiFi in public areas, a business center, and a seasonal outdoor pool. There's free parking if you drive. Front-desk staff can help with luggage storage, and provide local restaurant recommendations. Additional amenities include a meeting room, a computer station, and a library.
Pool
Parking included

Econo Lodge Lee - Great Barrington
980 Pleasant Street, Lee, MA
Free Cancellation
Reserve now, pay when you stay
$64 nightly
The price is $71 total per night
$71 total
Aug 11 - Aug 12
Total includes taxes and fees
Econo Lodge Lee - Great Barrington features free WiFi in public areas and a vending machine. Free parking is available if you drive. The 24-hour front desk has multilingual staff ready to help with tours or tickets, and answer any questions about the area.
Breakfast included
Pet friendly

Wagon Wheel Inn
484 Pittsfield Rd, PO Box 808, Lenox, MA
$69 nightly
The price is $77 total per night
$77 total
Jul 30 - Jul 31
Total includes taxes and fees
Guests of Wagon Wheel Inn enjoy free WiFi in public areas, a hot tub, and coffee in a common area. Free parking is available if you drive. Staff members can help with accommodation requests, and provide front-desk service during limited hours. This motel also has express check-out.
Hot Tub
Parking included

Lenox Inn
Pittsfield Road,525, Lenox, Massachusetts
Guests of Lenox Inn enjoy free WiFi in public areas, a seasonal outdoor pool, and a garden. You can put free parking to good use if you drive. Staff members can help with accommodation requests, and provide front-desk service during limited hours. This hotel also has a picnic area.
Pool
Parking included

Travelodge by Wyndham Great Barrington Berkshires
400 Stockbridge Rd, Great Barrington, MA
Free Cancellation
Reserve now, pay when you stay
$89 nightly
The price is $99 total per night
$99 total
Jul 31 - Aug 1
Total includes taxes and fees
Guests staying at Travelodge by Wyndham Great Barrington Berkshires enjoy free WiFi in public areas, laundry facilities, and a garden. If you decide to drive, there's free parking. The front desk has multilingual staff that can help with dry cleaning/laundry and securing valuables. Additional amenities include a picnic area, a vending machine, and barbecue grills.
Pet friendly
Parking included

Pleasant Valley Motel West Stockbridge
42 Stockbridge Rd, West Stockbridge, MA
$70 nightly
The price is $76 total per night
$76 total
Aug 3 - Aug 4
Total includes taxes and fees
Guests of Pleasant Valley Motel West Stockbridge enjoy features like free WiFi in public areas. If you drive, put free parking to good use. Staff members can help with accommodation requests, and provide front-desk service during limited hours.
Parking included
Free WiFi

Stay Berkshires
1146 Cold Spring Road, Williamstown, MA
Guests of Stay Berkshires enjoy free WiFi in public areas, a seasonal outdoor pool, and a fireplace in the lobby. Free parking is included with your stay. This smoke-free hotel also has a vending machine.
Pool
Breakfast included

Berkshire Inn
150 W Housatonic St, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
$94 nightly
The price is $105 total per night
$105 total
Jul 30 - Jul 31
Total includes taxes and fees
Guests of Berkshire Inn enjoy free WiFi in public areas, a seasonal outdoor pool, and a picnic area. You can put free parking to good use if you drive. The 24-hour front desk has staff always at the ready. This smoke-free motel also has a TV in a common area.
Pool
Parking included

Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
$127 nightly
The price is $141 total per night
$141 total
Jul 31 - Aug 1
Total includes taxes and fees
Guests of Best Western Plus Berkshire Hills Inn & Suites enjoy a gym, free WiFi in public areas, and conference space. A stay here includes free parking. The 24-hour front desk has multilingual staff ready to assist with tours or tickets, dry cleaning/laundry, and securing valuables. If you like to take your furry friend along on your adventures, this pet-friendly property offers an off-leash area. Additional amenities include a 24-hour business center, coffee/tea in a common area, and a computer station.
Breakfast included
Pet friendly

The Dewey
7 Hubbard Street, Lenox, MA
$204 nightly
The price is $228 total per night
$228 total
Aug 25 - Aug 26
Total includes taxes and fees
At The Dewey, guests have access to free WiFi in public areas, a meeting room, and a library. If you plan to drive, free parking is available. Staff members can help with accommodation requests, and provide concierge services. Additional amenities include express check-out, free newspapers, and a terrace.
Parking included
Free WiFi

The Black Swan Lee - Lenox, Ascend Hotel Collection
435 Laurel St, Lee, MA
$195 nightly
The price is $217 total per night
$217 total
Aug 6 - Aug 7
Total includes taxes and fees
Guests of The Black Swan Lee - Lenox, Ascend Hotel Collection enjoy a 24-hour gym, free WiFi in public areas, and a 24-hour business center. If you plan to drive, free parking is available. Front-desk staff are standing by 24/7 to assist with any requests. Additional amenities include coffee/tea in a common area, a microwave in a common area, and a meeting room.
Breakfast included
Pet friendly
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 | 1,113 hotels |
---|---|
Lowest Price | $71 |
Highest Price | $228 |
Popular hotels | Monument Mountain Motel, The Weathervane Motel, Northside Motel, Econo Lodge Lee - Great Barrington, Wagon Wheel Inn, Lenox Inn, Travelodge by Wyndham Great Barrington Berkshires, Pleasant Valley Motel West Stockbridge, Stay Berkshires, Berkshire Inn, Best Western Plus Berkshire Hills Inn & Suites, The Dewey, The Black Swan Lee - Lenox, Ascend Hotel Collection |
Recent Hotels with Air Conditioning Reviews

Hotel Downstreet, Ascend Hotel Collection
5/5 Excellent
"Loved the staff and art centric area. "
A verified traveler stayed at Hotel Downstreet, Ascend Hotel Collection
Posted 1 day ago
Areas Of The Berkshires
Hotels Near
Hotel Themes
Flights To
Top Trending
Hotels
- Romantic Getaways & Hotels in Cape Cod
- Luxury Hotels in Central Massachusetts
- Pet Friendly Hotels in Cape Cod
- Hotels with Hot Tubs in North Shore
- Hotels in Martha's Vineyard
- Oceanfront Hotels in Cape Cod
- Kid Friendly Hotels in Cape Cod
- Hotels with an Indoor Pool in Cape Cod
- Hotels with Balconies in Cape Cod
- Hotels in Nantucket Island
- Beach Resorts & Hotels in Cape Cod
- All Inclusive Resorts & Hotels in Cape Cod
- Spa Resorts & Hotels in Cape Cod
- Romantic Getaways & Hotels in Western Massachusetts
- Hotels in Cape Cod
- Cheap Hotels in Cape Cod
- Hotels with Hot Tubs in Cape Cod
- Hotels with Hot Tubs in Western Massachusetts
- Casino Resorts & Hotels in Cape Cod
- Hotels with Kitchenettes in Cape Cod
- Waterpark Hotels & Resorts in Cape Cod
Flights