Book Cheap Hotels in Pittsfield

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Most frequently booked Pittsfield hotels

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Free cancellation
Reserve now, pay when you stay
0.11 km from city centre
The price is CA $127 per night
CA $127
CA $142 total
Jan 1 - Jan 2, 2026
includes taxes & fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Berkshire Museum and Colonial Theater are located nearby.
Pool
Pet-friendly
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Free cancellation
Reserve now, pay when you stay
4.09 km from city centre
The price is CA $135 per night
CA $135
CA $181 total
Jan 11 - Jan 12, 2026
includes taxes & fees
Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Guido's Marketplace and Herman Melville's Arrowhead are located nearby.
Pool
Hot tub
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
Free cancellation
5.01 km from city centre
The price is CA $104 per night
CA $104
CA $117 total
Jan 20 - Jan 21, 2026
includes taxes & fees
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 rooms in our reviews. Popular attractions Tracy Brook Wildlife Sanctuary and Hancock Shaker Village are located nearby.
Breakfast included
Pet-friendly
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 out of 5
1055 South Street Pittsfield MA
Free cancellation
4.63 km from city centre
The price is CA $155 per night
CA $155
CA $173 total
Jan 4 - Jan 5, 2026
includes taxes & fees
Stay at this hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Guido's Marketplace and Herman Melville's Arrowhead are located nearby.
Pool
Hot tub
Hotel On North

Hotel On North

3.5 out of 5
297 North Street Pittsfield MA
Free cancellation
Reserve now, pay when you stay
0.48 km from city centre
The price is CA $204 per night
CA $204
CA $228 total
Jan 11 - Jan 12, 2026
includes taxes & fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Barrington Stage Company and Berkshire Athenaeum are located nearby.
Pet-friendly
Parking included
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

3 out of 5
1032 South Street Pittsfield MA
Free cancellation
Reserve now, pay when you stay
4.57 km from city centre
The price is CA $175 per night
CA $175
CA $195 total
Jan 2 - Jan 3, 2026
includes taxes & fees
Stay at this hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Guido's Marketplace and Herman Melville's Arrowhead are located nearby.
Pool
Pet-friendly
Berkshire Inn

Berkshire Inn

2 out of 5
150 W Housatonic St Pittsfield MA
Free cancellation
Reserve now, pay when you stay
0.88 km from city centre
The price is CA $111 per night
CA $111
CA $125 total
Jan 20 - Jan 21, 2026
includes taxes & fees
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. Popular attractions Colonial Theater and Berkshire Museum are located nearby.
Pool
Parking included
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

4 out of 5
20 W Housatonic St. Pittsfield MA
0.37 km from city centre
The price is CA $129 per night
CA $129
CA $144 total
Dec 28 - Dec 29
includes taxes & fees
Stay at this guesthouse in Pittsfield. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Colonial Theater and Berkshire Museum are located nearby.
Pet-friendly
Parking included
Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak

Hancock MA
11.77 km from city centre
The price is CA $820 per night
CA $820
CA $1,437 total
Jan 6 - Jan 7, 2026
includes taxes & fees
Book a stay at this family-friendly vacation home in Pittsfield. Enjoy free WiFi, laundry facilities, and a pool table. Popular attractions Jiminy Peak Mountain Resort and Alpine Super Slide are located nearby.
Hot tub
Kitchen
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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.

Top family friendly Pittsfield hotel deals

Hotel On North

Hotel On North

297 North Street Pittsfield MA
The price is CA $204 per night from Jan 11 to Jan 12
CA $204
CA $228 total
Jan 11 - Jan 12, 2026
includes taxes & fees
9.4/10 Exceptional! (805 reviews)

Top cheap Pittsfield hotel deals

Berkshire Inn

Berkshire Inn

150 W Housatonic St Pittsfield MA
The price is CA $111 per night from Jan 20 to Jan 21
CA $111
CA $125 total
Jan 20 - Jan 21, 2026
includes taxes & fees
7.6/10 Good! (838 reviews)

Top hotels in Pittsfield for Extended Stay

Suite 4 - Quiet and private accommodations in a country setting.

Suite 4 - Quiet and private accommodations in a country setting.

Spencertown NY
10/10 Exceptional! (3 reviews)
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
1,336 hotels
Lowest Price
CA $117
Highest Price
CA $1,437
Popular hotels
Holiday Inn & Suites Pittsfield-Berkshires by IHG, Berkshire Mountain Lodge, Best Western Plus Berkshire Hills Inn & Suites, Holiday Inn Express & Suites Pittsfield - Berkshires by IHG, Hotel On North, Hilton Garden Inn Lenox Pittsfield, Berkshire Inn, The Central Downtown Inn & Suites, Hancock Village Inn Near Jiminy Peak

Frequently asked questions

What are the top kid-friendly hotels in Pittsfield?
From cool amenities to more room to move, kid-friendly hotels come with features that can help turn an everyday family vacation into a fantastic one. These Pittsfield properties make traveling with little ones child's play: The whole team will enjoy their time at Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel. A sauna and a swimming pool are a few of the things that help make this property an appealing option. Alternatively, spend your nights in Pittsfield at The Central Downtown Inn & Suites. Take advantage of pet-friendly facilities, laundry facilities and more here.
Where can I find cheap hotels in Pittsfield?
At Travelocity you'll find really nice hotels in Pittsfield at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Pittsfield rather than in Pittsfield. We may find you even better rates, too.
How do I find the best Pittsfield hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Pittsfield then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Pittsfield?
The cheapest hotel in Pittsfield is CA $117 This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Pittsfield?
There are 1,336 hotels in Pittsfield on Travelocity.
What are the best hotels in Pittsfield?
Pittsfield has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Pittsfield for you!
When is the best time to visit Pittsfield?
If you want the joy of a fun-filled trip in peak season, visit Pittsfield during January, February and July. If you'd prefer the peace of off-season, book a stay during quieter months, such as October, November and December.
When is the cheapest time to stay in Pittsfield?
Based on historic data is usually the cheapest month to visit Pittsfield. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Pittsfield?
There are multiple hotels in Pittsfield that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Pittsfield. We have plenty of kid-friendly hotels in Pittsfield to choose from on Travelocity!
Why book a hotel in Pittsfield through Travelocity?
Because we have the top hotels in Pittsfield! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Pittsfield on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Pittsfield hotel reviews by fellow wanderers

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

5 out of 5
Posted 2 days ago
Travelocity Verified Review
"Clean room, easy checkin, loved the tea kettle. Clean, comfortable, would definitely return. "
A verified traveller stayed at The Central Downtown Inn & Suites
The Central Downtown Inn & Suites

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