Historical Hotels in The Berkshires, MA
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Featured The Berkshires Historic Hotels

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

Shaker Mill Inn
2 Oak Street West Stockbridge MA
$107 nightly
The price is $118 total per night
$118 total
Dec 30 - Dec 31
Total with taxes and fees
Shaker Mill Inn features free WiFi in public areas and a library. There's free parking if you drive.
Breakfast included
Parking included

Heart of Lenox!! - renovated downtown apartment
Lenox MA
At this apartment, guests have access to features like laundry facilities.
Kitchen
Washer

Chambery Inn
199 Main St Lee MA
$190 nightly
The price is $212 total per night
$212 total
Dec 28 - Dec 29
Total with taxes and fees
Guests of Chambery Inn enjoy free WiFi in public areas, a hot tub, and spa services. A stay here includes free parking. Front-desk staff can assist with securing valuables and luggage storage. Additional amenities include express check-in, express check-out, and free newspapers.
Hot Tub
Spa

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 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

Whistler's Inn Bed & Breakfast
5 Greenwood Street Lenox MA
Whistler's Inn Bed & Breakfast features free WiFi in public areas, coffee in a common area, and a meeting room. Free parking is included with your stay. The front desk has multilingual staff that can help with luggage storage, and offer advice about sights and eateries nearby. Additional amenities include a library, a terrace, and a TV in a common area.
Breakfast included
Pet friendly

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 Egremont Village Inn
17 Main Streeet South Egremont MA
At The Egremont Village Inn, guests enjoy features like a nightclub, karaoke, and free WiFi in public areas. There's free parking and an airport shuttle for a fee. Staff members are on hand to provide dry cleaning/laundry services, tour or ticket assistance, and luggage storage. Additional amenities include a meeting room, an arcade/game room, and a library.
Pet friendly
Parking included

Devonfield Inn B&B
85 Stockbridge Rd. Lee MA
$349 nightly
The price is $390 total per night
$390 total
Dec 29 - Dec 30
Total with taxes and fees
At Devonfield Inn B&B, guests have access to an outdoor pool, free WiFi in public areas, and a business center. Free parking is included with your stay. The 24-hour front desk has staff standing by to help with luggage storage and concierge services. Other amenities at this golf bed & breakfast include a meeting room, a library, and free newspapers.
Pool
Breakfast included

Hampton Inn & Suites Berkshires-Lenox
445 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$103 nightly
The price is $115 total per night
$115 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Guests staying at Hampton Inn & Suites Berkshires-Lenox enjoy an indoor pool, a gym, and free WiFi in public areas. If you decide to drive, there's free parking. The front desk has multilingual staff on hand 24/7 to help with luggage storage, dry cleaning/laundry, and securing valuables. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls, an off-leash area, and litter boxes. Additional amenities include conference space, a 24-hour business center, and coffee/tea in a common area.
Pool
Breakfast included
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 | $115 |
Highest Price | $390 |
Popular hotels | The Red Lion Inn, Shaker Mill Inn, Heart of Lenox!! - renovated downtown apartment, Chambery Inn, The Cornell Inn, Lenox & The Berkshires, Hotel On North, Whistler's Inn Bed & Breakfast, The Porches Inn at Mass MoCA, The Egremont Village Inn, Devonfield Inn B&B, Hampton Inn & Suites Berkshires-Lenox |
Recent Historic Hotels Reviews

The Yankee, Trademark Collection by Wyndham
5/5 Excellent
"The room is so spotless, bathroom is so luxurious! The bed is so soft and sleep very quickly! The staffs are so great! Quick to answer to my questions and my needs. Definitely come back again to stay! "
A verified traveler stayed at The Yankee, Trademark Collection by Wyndham
Posted 5 days ago
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