Search for Cheap Deals on
Hotels in Pittsfield

Choose from 1266 Pittsfield Hotel Deals

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
3 out of 5
One West Street, Pittsfield, MA
  • 6 min drive from Bousquet Ski Area
The price is $111 per night from Jan 5 to Jan 6
$111
includes taxes & fees
Jan 5 - Jan 6, 2025
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
7.8/10 Good! (701 reviews)
"Staff was very accommodating. The pool area was quite nice and it was deep"

Reviewed on Dec 16, 2024

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites
2.5 out of 5
1350 W Housatonic St, Pittsfield, MA
  • 26 min walk from Bousquet Ski Area
The price is $105 per night from Jan 5 to Jan 6
$105
includes taxes & fees
Jan 5 - Jan 6, 2025
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (1,000 reviews)
"The bed was comfortable and room was nice."

Reviewed on Dec 10, 2024

Best Western Plus Berkshire Hills Inn & Suites
Berkshire Mountain Lodge
Berkshire Mountain Lodge
3 out of 5
8 Dan Fox Dr, Pittsfield, MA
  • 4 min walk from Bousquet Ski Area
The price is $204 per night from Jan 1 to Jan 2
$204
includes taxes & fees
Jan 1 - Jan 2, 2025
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (417 reviews)
"Good"

Reviewed on Dec 21, 2024

Berkshire Mountain Lodge
Hilton Garden Inn Lenox Pittsfield
Hilton Garden Inn Lenox Pittsfield
3 out of 5
1032 South Street, Pittsfield, MA
  • 10 min walk from Bousquet Ski Area
The price is $162 per night from Dec 31 to Jan 1
$162
includes taxes & fees
Dec 31 - Jan 1, 2025
Stay at this 3-star hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ...
9.2/10 Wonderful! (619 reviews)
"Check in and check out where quick and easy. The room was comfortable and clean. The staff were nice and accommodating. Central location to surrounding attractions."

Reviewed on Nov 10, 2024

Hilton Garden Inn Lenox Pittsfield
Berkshire Inn
Berkshire Inn
2 out of 5
150 W Housatonic St, Pittsfield, MA
  • 5 min drive from Bousquet Ski Area
The price is $96 per night from Dec 24 to Dec 25
$96
includes taxes & fees
Dec 24 - Dec 25
Stay at this motel in Pittsfield. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.6/10 Good! (751 reviews)
Nice Motel, No Breakfast
"This is a nice motel, though there is no continental breakfast. There is a pot of coffee made at 7am. The rooms are clean and updated, the mattress is good, airconditioner in back wall, simple round thermostat for hot water radiator heating, mini-fridge is compressor type, microwave."

Reviewed on Nov 27, 2024

Berkshire Inn
Hotel Downstreet
Hotel Downstreet
3 out of 5
40 Main St, North Adams, MA
  • 48 min drive from Bousquet Ski Area
The price is $144 per night from Dec 24 to Dec 25
$144
includes taxes & fees
Dec 24 - Dec 25
Stay at this 3-star hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (1,000 reviews)
"Stayed for a weekend wedding and it was a great location. Room was large"

Reviewed on Dec 19, 2024

Hotel Downstreet
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 out of 5
461 Pittsfield Rd, Lenox, MA
  • 16 min walk from Bousquet Ski Area
The price is $108 per night from Jan 1 to Jan 2
$108
includes taxes & fees
Jan 1 - Jan 2, 2025
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
9/10 Wonderful! (1,001 reviews)
"This hotel was awesome! We enjoyed the hot tub along with the fireplace in our room!"

Reviewed on Dec 15, 2024

The Yankee, Trademark Collection by Wyndham
Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
  • 5 min drive from Bousquet Ski Area
The price is $99 per night from Jan 5 to Jan 6
$99
includes taxes & fees
Jan 5 - Jan 6, 2025
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
9/10 Wonderful! (455 reviews)
"The coziest best hotel in area! Staff was so wonderful, room was perfect! Lobby bar and lounge is so great."

Reviewed on Dec 19, 2024

Life House Berkshires
The Red Lion Inn
The Red Lion Inn
3.5 out of 5
30 Main Street, Stockbridge, MA
  • 22 min drive from Bousquet Ski Area
The price is $144 per night from Jan 6 to Jan 7
$144
includes taxes & fees
Jan 6 - Jan 7, 2025
Stay at this 3.5-star historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
8.8/10 Excellent! (1,000 reviews)
Heritage stay at an old Inn
"It is one of the oldest inns in America - so it creaks a lot, uneven floors, and for sure that look of old.. not necessarily bad... just a heritage property that has its quirks. We liked it.. the bed could be better for sure... I think that's the main fault.. the restaurant and pub were wonderful, ..."

Reviewed on Dec 16, 2024

The Red Lion Inn
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Black Swan Lee - Lenox, Ascend Hotel Collection
3 out of 5
435 Laurel St, Lee, MA
  • 16 min drive from Bousquet Ski Area
The price is $113 per night from Dec 30 to Dec 31
$113
includes taxes & fees
Dec 30 - Dec 31
Stay at this 3-star hotel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular ...
8.8/10 Excellent! (1,000 reviews)
"Good"

Reviewed on Dec 9, 2024

The Black Swan Lee - Lenox, Ascend Hotel Collection
Quality Inn
Quality Inn
2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
  • 37 min drive from Bousquet Ski Area
The price is $94 per night from Dec 29 to Dec 30
$94
includes taxes & fees
Dec 29 - Dec 30
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8/10 Very Good! (1,000 reviews)
"Friendly staff"

Reviewed on Dec 16, 2024

Quality Inn
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
3.5 out of 5
190 Meadow Street, South Lee, MA
  • 24 min drive from Bousquet Ski Area
The price is $158 per night from Jan 6 to Jan 7
$158
includes taxes & fees
Jan 6 - Jan 7, 2025
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff in our ...
8.8/10 Excellent! (571 reviews)
"Westayed at the resort for the Stockbridge Christmas weekend location was so convenient to town, dining and events, Resort facilities were extra special pool movie theatre and resort Christmas themed activities would recommend."

Reviewed on Dec 9, 2024

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
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.

Find cheap hotels in Pittsfield

You’re not an average traveler—and Hotwire knows it. Your wanderlust takes you off the beaten path to discover unique adventures and every travel destination’s lesser-known tourist scenes. Hotwire has the hookup! Book your Pittsfield hotel with Hotwire to complete your one-of-a-kind travel checklist.

For you, intrepid voyager, Hotwire has a large selection of the best hotels in Pittsfield.

Choosing the right hotel in Massachusetts has everything to do with the way you want your trip to go. If you’ve scribbled a few obscure destinations on your itinerary, you probably already have a good sense of how your getaway is taking shape. Lean into that by booking one of Pittsfield’s 1,266 hotels. Choose the one that best catches your trip’s tourist drift.

If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as $94. In town for pleasure? Hotwire still has you covered. If you’re in the mood for a quick last-minute weekend getaway or spa retreat, you can get great Pittsfield hotel deals at the last minute.

While traveling, where you stay plays a major role in your overall vacation enjoyment. Choosing the right hotel is just as important as making sure you book the right flight and car rental. If you’re traveling with family or friends, you may need to book a hotel with connecting rooms. If you enjoy an elegant and relaxing hotel ambiance, opt for one of Hotwire’s luxury hotels in Pittsfield. No matter your reason for visiting Pittsfield, with Hotwire’s large selection of hotels in the area, you’re sure to book a hotel that meets all your accommodation needs.

Frequently Asked Questions About Pittsfield hotels

Where can I find the best last-minute travel deals?

If you’re traveling in the spirit of spontaneity, you’ll love the idea of leaving your exact hotel choice up to chance. With Hotwire Hot Rates, you can unlock great deals on your next flight, hotel, or car rental. Just plug in your general preferences and let Hotwire choose last-minute hotel deals in Pittsfield for as low as $94.

How many hotels are there in Pittsfield?

With over 1,266 hotels in Pittsfield, you’re sure to find one that best matches your travel mood. When you book with Hotwire, you can score a stellar home away from home for as low as $94.

How to find cheap car rentals in Pittsfield?

Finding a cheap car rental deal in Pittsfield is as easy as scoring cheap hotels in Pittsfield. Hotwire partners with top-of-the-line car rental companies to bring you a large selection of affordable options. Whether you’re in need of a large SUV for the entire family or a more compact but stylish vehicle, Hotwire has you covered. You can unlock great car rental deals if you book a Hotwire Hot Rate at the last minute.