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
Free Cancellation
Reserve now, pay when you stay
$67 nightly
The price is $74 total per night
$74 total
Nov 16 - Nov 17
Total with 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
$59 nightly
The price is $66 total per night
$66 total
Nov 30 - Dec 1
Total with 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
Nov 13 - Nov 14
Total with 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

Travelodge by Wyndham Great Barrington Berkshires
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
Nov 13 - Nov 14
Total with taxes and fees
Guests staying at Travelodge by Wyndham Great Barrington Berkshires enjoy free WiFi in public areas, laundry facilities, and a picnic area. If you decide to drive, there's free parking. The front desk has multilingual staff that can help with securing valuables and dry cleaning/laundry. Additional amenities include a garden, barbecue grills, and a vending machine.
Pet friendly
Parking included

Pleasant Valley Motel West Stockbridge
42 Stockbridge Rd, West Stockbridge, MA
Free Cancellation
Reserve now, pay when you stay
$60 nightly
The price is $66 total per night
$66 total
Nov 18 - Nov 19
Total with 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 vending machine. Free parking is included with your stay. This smoke-free hotel also has a fireplace in the lobby.
Pool
Breakfast included

Berkshire Inn
150 W Housatonic St, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
$74 nightly
The price is $83 total per night
$83 total
Nov 23 - Nov 24
Total with 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
$93 nightly
The price is $104 total per night
$104 total
Nov 16 - Nov 17
Total with 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 luggage storage, securing valuables, and dry cleaning/laundry. 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
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, an Ascend Collection Hotel
435 Laurel St, Lee, MA
Free Cancellation
$110 nightly
The price is $122 total per night
$122 total
Dec 2 - Dec 3
Total with taxes and fees
Guests of The Black Swan Lee - Lenox, an Ascend Collection Hotel 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 | 1,097 hotels |
|---|---|
Lowest Price | $66 |
Highest Price | $122 |
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, Berkshire Inn, Best Western Plus Berkshire Hills Inn & Suites, The Dewey, The Black Swan Lee - Lenox, an Ascend Collection Hotel |
Recent Hotels with Air Conditioning Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG
5/5 Excellent
"Great stay! Nice quiet room for 2 little “alert “ to outside noise pups!! Comfy beds and central location for the day trips we had planned."
A verified traveler stayed at Holiday Inn & Suites Pittsfield-Berkshires by IHG
Posted 3 days ago
More to Explore
- Hotels near Ashintully Gardens
- Condo Rentals in Sandisfield
- Sandisfield Hotels
- Inns in Sandisfield
- Hotels near Bidwell House Museum
- Hotels near Ski Butternut
- Hotels near Becket Land Trust Historic Quarry
- Cottages in New Marlborough
- Cheap Hotels in New Marlborough
- Hotels with Pool in New Marlborough
- Hotels with Bar in New Marlborough
- Pet Friendly Hotels in New Marlborough
- Ski Resorts & in New Marlborough
- Inns in New Marlborough
- B&B in Otis
- Cabin Rentals in Otis
- Guest Houses in Otis
- Pet Friendly Hotels in Otis
- Otis Hotels
- Motels in Otis
- Vacation Homes in Otis
- Rv Parks in Otis
- Resorts in Otis
- Hotels near Otis Reservoir
- Adventure Hotels in Lenox
- Boutique Hotels in Great Barrington
- Cheap Hotels in Great Barrington
- Luxury Hotels in Great Barrington
- Spa Resorts & in Great Barrington
- Hotels near Otis Ridge
- Golf Resorts & in South Lee
- Hotels with Bar in South Lee
- Hotels with Hot Tubs in South Lee
- Hotels with a Wedding Venue in South Lee
- 3 Star Hotels in Monterey
- Apartments in Monterey
- B&B in Monterey
- Monterey Hotels
- Lodges in Monterey
- Motels in Monterey
- Vacation Homes in Monterey
- Rv Parks in Monterey
- Cheap Hotels in Lee
- Business Hotels in Lee
- Kid Friendly Hotels in Lee
- Hotels with Pool in Lee
- Hotels with Balconies in Lee
- Hotels with Bar in Lee
- Hotels with Hot Tubs in Lee
- Hotels with Restaurants in Lee
- Oceanfront Hotels in Lee
- Pet Friendly Hotels in Lee
- Romantic Getaways & Hotels in Lee
- Hotels with Shopping in Lee
- Ski Resorts & in Lee
- Spa Resorts & in Lee
- Hotels with a Wedding Venue in Lee
- Adventure Hotels in Massachusetts
- Business Hotels in Massachusetts
- Hotels with WiFi in Massachusetts
- Hotels with Air Conditioning in Massachusetts
- Hotels with Balconies in Massachusetts
- Hotels with Childcare in Massachusetts
- Hotels with Free Airport Shuttle in Massachusetts
- Hotels with Free Parking in Massachusetts
- Hotels with Restaurants in Massachusetts
- Hotels with Tennis Courts in Massachusetts
- Hotels on the River in Massachusetts
- Hotels near Les Trois Emme Winery
- Hotels near Jacob's Pillow
- Hotels near Pyramid Lake
- Apartments in Mill River
- Motels in Mill River
- Town Houses in Mill River
- 4 Star Hotels in Southfield
- B&B in Southfield
- Inns in Southfield
- Motels in Southfield
- Resorts in Southfield
- Villas in Southfield
- 4 Star Hotels in Tyringham
- 5 Star Hotels in Tyringham
- B&B in Tyringham
- Cabin Rentals in Tyringham
- Cottages in Tyringham
- Hotels with Pool in Tyringham
- Lodges in Tyringham
- Rv Parks in Tyringham
- Resorts in Tyringham


