Historical Hotels in Pittsfield, MA
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Featured Pittsfield Historic Hotels

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 30 - Dec 31
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.

Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$98 nightly
The price is $109 total per night
$109 total
Jan 2 - Jan 3, 2026
Total with taxes and fees
Guests of Holiday Inn & Suites Pittsfield-Berkshires by IHG have access to an indoor pool, a gym, and free WiFi in public areas. If you decide to drive, there's free parking. The 24-hour front desk has multilingual staff ready to assist with securing valuables, luggage storage, and dry cleaning/laundry. Additional amenities include a conference center, a 24-hour business center, and a computer station.

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.

Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St Pittsfield MA
Free Cancellation
$76 nightly
The price is $85 total per night
$85 total
Jan 4 - Jan 5, 2026
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 securing valuables, luggage storage, and tours or tickets. 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.

Berkshire Inn
150 W Housatonic St Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$79 nightly
The price is $89 total per night
$89 total
Dec 30 - Dec 31
Total with taxes and fees
Guests of Berkshire Inn enjoy free WiFi in public areas, a seasonal outdoor pool, and a TV in a common 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 picnic area.
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.
Pittsfield hotels essential information
Accommodation | 1,338 hotels |
|---|---|
Lowest Price | $85 |
Highest Price | $166 |
Popular hotels | Hotel On North, Holiday Inn & Suites Pittsfield-Berkshires by IHG, Hilton Garden Inn Lenox Pittsfield, Best Western Plus Berkshire Hills Inn & Suites, Berkshire Inn |
Recent Historic Hotels Reviews

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
5/5 Excellent
"Everything was great. Very. Clean and check in simple. "
A verified traveler stayed at Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Posted 4 days ago
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