Historical Hotels in The Berkshires, MA
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 Historic Hotels

The Red Lion Inn
30 Main Street, Stockbridge, MA
Free Cancellation
Reserve now, pay when you stay
$229 nightly
The price is $256 total per night
$256 total
Aug 27 - Aug 28
Total includes 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 securing valuables, 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
$195 nightly
The price is $214 total per night
$214 total
Aug 4 - Aug 5
Total includes 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
At this apartment, guests have access to features like laundry facilities.
Kitchen
Washer

Chambery Inn
199 Main St, Lee, MA
$250 nightly
The price is $279 total per night
$279 total
Aug 6 - Aug 7
Total includes 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
$168 nightly
The price is $188 total per night
$188 total
Aug 27 - Aug 28
Total includes 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
$189 nightly
The price is $211 total per night
$211 total
Aug 3 - Aug 4
Total includes 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 concierge services, 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, an ATM, and a banquet hall.
Pet friendly
Parking included

Whistler's Inn Bed & Breakfast
5 Greenwood Street, Lenox, MA
$193 nightly
The price is $215 total per night
$215 total
Aug 3 - Aug 4
Total includes taxes and fees
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 fireplace in the lobby.
Breakfast included
Pet friendly

The Porches Inn at Mass MoCA
231 River Street, North Adams, MA
Free Cancellation
Reserve now, pay when you stay
$240 nightly
The price is $268 total per night
$268 total
Sep 1 - Sep 2
Total includes 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 securing valuables and concierge services. 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
$309 nightly
The price is $345 total per night
$345 total
Sep 1 - Sep 2
Total includes 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 tours/tickets. 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
$144 nightly
The price is $160 total per night
$160 total
Sep 1 - Sep 2
Total includes 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 | 1,113 hotels |
---|---|
Lowest Price | $160 |
Highest Price | $345 |
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

Hotel Downstreet, Ascend Hotel Collection
5/5 Excellent
"Clean,friendly staff and great location."
A verified traveler stayed at Hotel Downstreet, Ascend Hotel Collection
Posted 2 days ago
Other Historic Hotels
Areas Of The Berkshires
Hotels Near
Hotel Themes
Flights To
Top Trending
Hotels
- Cape Cod Romantic Getaways & Hotels
- Central Massachusetts Luxury Hotels
- Cape Cod Pet Friendly Hotels
- North Shore Hotels with Hot Tubs
- Martha's Vineyard Hotel Deals
- Cape Cod Oceanfront Hotels
- Cape Cod Kid Friendly Hotels
- Cape Cod Hotels with an Indoor Pool
- Cape Cod Hotels with Balconies
- Nantucket Island Hotel Deals
- Cape Cod Beach Resorts & Hotels
- Cape Cod All Inclusive Resorts & Hotels
- Cape Cod Spa Resorts & Hotels
- Western Massachusetts Romantic Getaways & Hotels
- Cape Cod Hotel Deals
- Cape Cod Cheap Hotels
- Cape Cod Hotels with Hot Tubs
- Western Massachusetts Hotels with Hot Tubs
- Cape Cod Casino Resorts & Hotels
- Cape Cod Hotels with Kitchenettes
- Cape Cod Waterpark Hotels & Resorts
Flights