Hotels with Bars in The Berkshires, MA
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Featured The Berkshires Hotels with Bar

Hotel On North
297 North Street Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$149 nightly
The price is $166 total per night
$166 total
Dec 29 - Dec 30
Total with taxes and fees
Hotel On North features free WiFi in public areas, meeting rooms, and a business center. There's free parking if you drive. Front-desk staff can answer questions 24/7, and assist with tours or tickets, securing valuables, and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include coffee/tea in a common area, a banquet hall, and an ATM.
Pet friendly
Parking included

The Black Swan Lee - Lenox, an Ascend Collection Hotel
435 Laurel St Lee MA
Free Cancellation
$104 nightly
The price is $116 total per night
$116 total
Jan 5 - Jan 6, 2026
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

The Cornell Inn, Lenox & The Berkshires
203 Main St Lenox MA
Free Cancellation
Reserve now, pay when you stay
$148 nightly
The price is $165 total per night
$165 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Cornell Inn, Lenox & The Berkshires features free WiFi in public areas, coffee in a common area, and microwave in a common area. If you drive, put free parking to good use. The 24-hour front desk has staff standing by to help with luggage storage and concierge services. Additional amenities include a refrigerator in a common area, a computer station, and a library.
Breakfast included
Parking included

Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Free Cancellation
$124 nightly
The price is $138 total per night
$138 total
Jan 27 - Jan 28, 2026
Total with taxes and fees
Guests of Hotel Downstreet, an Ascend Collection Hotel have access to an indoor pool, a 24-hour gym, and free WiFi in public areas. There's free parking if you drive. The front desk is staffed 24 hours a day to help with securing valuables and luggage storage. Additional amenities include a hot tub, express check-out, and laundry facilities.
Pool
Hot Tub

The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $103 total per night
$103 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Guests staying at The Yankee, Trademark Collection by Wyndham enjoy an indoor pool, a 24-hour gym, and free WiFi in public areas. Free parking is available if you drive. The 24-hour front desk has multilingual staff ready to help with concierge services, and answer any questions about the area. Additional amenities include a hot tub, a seasonal outdoor pool, and coffee/tea in a common area.
Pool
Hot Tub

Gateways Inn & Restaurant
51 Walker St Lenox MA
$167 nightly
The price is $186 total per night
$186 total
Jan 12 - Jan 13, 2026
Total with taxes and fees
Gateways Inn & Restaurant features free WiFi in public areas, conference space, and a business center. If you drive, put free parking to good use. Staff members can answer questions about accommodations, and also provide front-desk service during limited hours. Additional amenities include a library, a terrace, and wedding services.
Parking included
Free WiFi

Jiminy Peak Mountain Resort
37 Corey Rd Hancock MA
Free Cancellation
Reserve now, pay when you stay
$212 nightly
The price is $237 total per night
$237 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
At Jiminy Peak Mountain Resort, guests enjoy ski-in/ski-out access, an outdoor pool, and a gym. You can put free parking to good use if you drive. Front-desk staff can answer questions 24/7, and assist with concierge services, securing valuables, and luggage storage. Other amenities at this ski condominium resort include 2 hot tubs, outdoor tennis courts, and free WiFi in public areas.
Pool
Hot Tub

The Red Lion Inn
30 Main Street Stockbridge MA
Free Cancellation
Reserve now, pay when you stay
$177 nightly
The price is $198 total per night
$198 total
Jan 14 - Jan 15, 2026
Total with taxes and fees
Guests of The Red Lion Inn have access to an outdoor pool, a gym, and free WiFi in public areas. The 24-hour front desk has multilingual staff ready to assist with tours or tickets, luggage storage, and dry cleaning/laundry. Other amenities at this historic hotel include meeting rooms, a 24-hour business center, and coffee/tea in a common area.
Pool
Spa

The Porches Inn at Mass MoCA
231 River Street North Adams MA
Free Cancellation
Reserve now, pay when you stay
$164 nightly
The price is $183 total per night
$183 total
Jan 26 - Jan 27, 2026
Total with taxes and fees
Guests staying at The Porches Inn at Mass MoCA enjoy an outdoor pool, a 24-hour gym, and a sauna. If you drive, put free parking to good use. The front desk is staffed 24 hours a day to help with tours/tickets and securing valuables. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include free WiFi in public areas, a hot tub, and a business center.
Pool
Hot Tub

The Orchards Hotel
222 Adams Rd Williamstown MA
Guests of The Orchards Hotel enjoy a gym, free WiFi in public areas, and meeting rooms. You can put free parking to good use if you drive. The 24-hour front desk has staff standing by to help with securing valuables, dry cleaning/laundry, and concierge services. Additional amenities include conference space, a business center, and a seasonal outdoor pool.
Pool
Breakfast included

Courtyard by Marriott Lenox Berkshires
70 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$139 nightly
The price is $155 total per night
$155 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
Guests staying at Courtyard by Marriott Lenox Berkshires enjoy an indoor pool, a gym, and free WiFi in public areas. 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. Additional amenities include a 24-hour business center, a meeting room, and express check-in.
Pool
Parking included

Cozy Corner Motel
284 Sand Springs Rd. Rte 7 Williamstown MA
Free Cancellation
Reserve now, pay when you stay
$75 nightly
The price is $84 total per night
$84 total
Jan 19 - Jan 20, 2026
Total with taxes and fees
Guests of Cozy Corner Motel enjoy a lazy river, free WiFi in public areas, and a business center. If you drive, take advantage of free parking. Front-desk staff can assist with luggage storage and securing valuables. Other amenities at this family-friendly motel include coffee/tea in a common area, free newspapers, and laundry facilities.
Breakfast included
Parking included

Hampton Terrace Inn
91 Walker Street Lenox MA
$219 nightly
The price is $245 total per night
$245 total
Jan 15 - Jan 16, 2026
Total with taxes and fees
Guests of Hampton Terrace Inn enjoy free WiFi in public areas, an outdoor tennis court, and a seasonal outdoor pool. Free parking is included with your stay. Front-desk staff can assist with concierge services and luggage storage. Additional amenities include a library, express check-in, and express check-out.
Pool
Parking included

Hilton Garden Inn Lenox Pittsfield
1032 South Street Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$128 nightly
The price is $143 total per night
$143 total
Jan 2 - Jan 3, 2026
Total with taxes and fees
At Hilton Garden Inn Lenox Pittsfield, guests enjoy an indoor pool, a gym, and free WiFi in public areas. Free parking is available if you drive. Multilingual staff at the front desk are standing by 24/7 to help with dry cleaning/laundry, luggage storage, and securing valuables. Additional amenities include a terrace, laundry facilities, and a convenience store.
Pool
Pet friendly

Holiday Inn Club Vacations Oak 'n Spruce Resort
190 Meadow Street South Lee MA
Holiday Inn Club Vacations Oak 'n Spruce Resort features a gym, a sauna, and a business center. Staff members are on hand to provide dry cleaning/laundry services and a safe deposit box at the front desk. Other amenities at this ski resort include an arcade/game room, a terrace, and laundry facilities.
Gym
Business services
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 | 1,084 hotels |
|---|---|
Lowest Price | $84 |
Highest Price | $245 |
Popular hotels | Hotel On North, The Black Swan Lee - Lenox, an Ascend Collection Hotel, The Cornell Inn, Lenox & The Berkshires, Hotel Downstreet, an Ascend Collection Hotel, The Yankee, Trademark Collection by Wyndham, Gateways Inn & Restaurant, Jiminy Peak Mountain Resort, The Red Lion Inn, The Porches Inn at Mass MoCA, The Orchards Hotel, Courtyard by Marriott Lenox Berkshires, Cozy Corner Motel, Hampton Terrace Inn, Hilton Garden Inn Lenox Pittsfield, Holiday Inn Club Vacations Oak 'n Spruce Resort |
Recent Hotels with Bar Reviews

Berkshire Mountain Lodge
5/5 Excellent
"Clean and warm, very spacious and cozy. People here are very nice too! Very good experience here. "
A verified traveler stayed at Berkshire Mountain Lodge
Posted 1 day ago
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