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Top Pittsfield hotels 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
Free Cancellation
The price is $106 per night
$106
includes taxes & fees
$95 per night
Nov 30 - Dec 1
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Pool
Pet friendly
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Free Cancellation
The price is $204 per night
$204
includes taxes & fees
$185 per night
Nov 23 - Nov 24
This lodge features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the spa tub and perks like free self parking.
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
Reserve now, pay when you stay
The price is $101 per night
$101
includes taxes & fees
$90 per night
Dec 1 - Dec 2
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling for business? Take advantage of the 24-hour business center, express check-out, and conference space. There's a gym on site, and a 24-hour front desk and a snack bar/deli are also provided.
Berkshire Inn

Berkshire Inn

2 out of 5
150 W Housatonic St, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
The price is $87 per night
$87
includes taxes & fees
$77 per night
Nov 24 - Nov 25
A seasonal outdoor pool is featured at this motel, along with free self parking. WiFi in public areas is free. A picnic area is provided and the front desk is staffed around-the-clock.
Hotel On North

Hotel On North

3.5 out of 5
297 North Street, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
The price is $162 per night
$162
includes taxes & fees
$145 per night
Nov 25 - Nov 26
This hotel features a gym and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, dry cleaning, and luggage storage are also offered.
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
The price is $153 per night
$153
includes taxes & fees
$137 per night
Dec 22 - Dec 23
This hotel features an indoor pool, a gym, and a restaurant. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi. A terrace, a snack bar/deli, and a grocery/convenience store are also on offer.
Pool
Pet friendly
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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.

Popular places to visit

Hardly anyone here! Great way to spend a week day, skiing and tubing!

Bousquet Ski Area

4/5(9 reviews)

Hit the slopes at Bousquet Ski Area during your trip to Pittsfield. Wander the lakeside in this family-friendly area.

Bousquet Ski Area
View of peak foliage in the Berkshires.

Berkshire Museum

You can spend an afternoon exploring the galleries in Berkshire Museum during your trip to Pittsfield. Wander the lakeside in this family-friendly area.

Berkshire Museum

Colonial Theater

3.5/5(3 reviews)

You can make plans for a show at Colonial Theater during your trip to Pittsfield. Wander the lakeside in this family-friendly area.

Colonial Theater

Frequently asked questions

How much are vacation packages to Pittsfield?
With a Travelocity vacation package, you can live it up in Pittsfield for as low as . Flights, hotels and experiences — we’ve got you. You can save some cash just for combining your bookings. With all of that taken care of before you even set off, you won’t have to worry about a thing.
How long should my Pittsfield vacation be?
Your Pittsfield break can be as short or as long as you’d like it to be, but the majority of travelers stay roughly 2 nights. Hoping to veer off the beaten path and discover some hidden gems? Book a couple more nights and see another side of this place.
Where can I get the best vacation package deals for Pittsfield?
It’s hard to beat Travelocity when it comes to putting together your Pittsfield package deal. There are at least 400 airlines and 1,000,000 properties worldwide to select from. Book your trip now and get ready to tick another exciting place off your to-do list.
Why should I book my Pittsfield vacation bundle with Travelocity?
From our 24/7 support to our range of exhilarating destinations, we are dedicated to fulfilling your vacation dreams. All you’ll have to do is click and book — our Price Match Guarantee will ensure you get the best deal.
Can I save money on my Pittsfield car rental if I combine it with hotels and flights?
With a Pittsfield vacation package, you can bundle your hotel, car and flight bookings and save a ton. If you want to uncover the best of this fantastic area, why not start with Times Square? This renowned sight is 120 mi from Pittsfield. With your own rental car, you’ll be there in no time.
Which airport is best for Pittsfield?
Bradley Intl. Airport (BDL) is 45 mi from the city center and is the starting point for many exciting adventures. Alternatively, Albany Intl. Airport (ALB) is 35 mi away from central Pittsfield and Hartford, CT (HFD-Hartford - Brainard) is 60 mi away from central Pittsfield.
What is there to do in Pittsfield?
Pittsfield has plenty of places to explore, such as Bousquet Ski Area and Barrington Stage Company. These two impressive attractions top most travelers’ itineraries.
Where should I stay when visiting Pittsfield?
Many travelers opt to spend their nights at the Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel. It’s the perfect base for your Pittsfield vacation.

Photos of local treasures

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Pittsfield featuring a city
Pittsfield featuring flowers and heritage elements
Pittsfield
Pittsfield featuring a church or cathedral
Pittsfield showing fall colors