Search Pittsfield hotels

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Pittsfield hotels

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1,002 reviews)
"Room was clean. Breakfast was fresh and the area was pristine. All staff was pleasant. "
United States
Melinda
The price is NZ$210
includes taxes & fees
26 May - 27 May
Best Western Plus Berkshire Hills Inn & Suites

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (96 reviews)
"This is a great hotel-super clean, nice breakfast, staff very pleasant and helpful. Close to Pittsfield but quieter. Pool and hot tub were great. Highly recommend staying here if you’re in the area."
United States
Kathleen
The price is NZ$243
includes taxes & fees
28 May - 29 May
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (946 reviews)
"Really clean, great staff. Pool & hot tub A+"
United States
Daniel
The price is NZ$206
includes taxes & fees
26 May - 27 May
Berkshire Mountain Lodge

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (856 reviews)
"Clean comfortable room. Very nice staff. Close to everything in downtown Pittsfield. This is the only place I stay when I’m in Pittsfield. Very peaceful. Excellent place to relax. "
United States
Jennifer
The price is NZ$147
includes taxes & fees
25 May - 26 May
Berkshire Inn

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (678 reviews)
"Clean room, staff was friendly and efficient. Great breakfast"
United States
Donna
The price is NZ$274
includes taxes & fees
31 May - 1 June
Hilton Garden Inn Lenox Pittsfield

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (859 reviews)
"Very nice clean hotel. Close to Colonial theater. Would definitely stay there again."
United States
KEITH AND SHIRLEY
The price is NZ$246
includes taxes & fees
27 May - 28 May
Hotel On North

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very good, (1,001 reviews)
"The room was comfortable, and clean. The staff was very courteous and helpful. Breakfast was adequate. Check in and check out went smoothly."
United States
Sharon
The price is NZ$233
includes taxes & fees
31 May - 1 June
Holiday Inn & Suites Pittsfield-Berkshires by IHG

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (367 reviews)
The price is NZ$225
includes taxes & fees
31 May - 1 June
The Central Downtown Inn & Suites

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (819 reviews)
"Scammers!! I booked a night just to shower and refresh. An abandoned public bathroom is 100 times cleaner than their room"
United States
Elie
The price is NZ$131
includes taxes & fees
7 June - 8 June
FairBridge Inn Express

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,004 reviews)
"Breakfast ok, coffee good, staff great"
United States
Peter
The price is NZ$208
includes taxes & fees
28 May - 29 May
The Yankee Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (457 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is NZ$186
includes taxes & fees
25 May - 26 May
Shaker Mill Inn

Gregory House Country Inn

Gregory House Country Inn
3.0 star property
Averill Park
9.0 out of 10, Wonderful, (95 reviews)
"Comfy, cozy, quiet stay in this lovely property full of character! Thank you, hard-working staff."
United States
Leslieann H
The price is NZ$196
includes taxes & fees
26 May - 27 May
Gregory House Country Inn

The Revival House

The Revival House
3.0 star property
Adams
9.2 out of 10, Wonderful, (29 reviews)
"Great place. Large rooms amazing common areas super fun w friends. "
United States
James
The price is NZ$297
includes taxes & fees
25 May - 26 May
The Revival House

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.6 out of 10, Excellent, (1,002 reviews)
The price is NZ$161
includes taxes & fees
27 May - 28 May
Quality Inn Great Barrington

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (856 reviews)
"Very clean and cozy in a great location! "
United States
Lidia
The price is NZ$131
includes taxes & fees
26 May - 27 May
Monument Mountain Motel

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (606 reviews)
"Very clean and comfortable room and grounds, pleasant and helpful hosts, relaxing setting. Highly recommended."
United States
David J.
The price is NZ$208
includes taxes & fees
27 May - 28 May
Maple Terrace Motel

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (958 reviews)
"Great stay!"
United States
Aditya
The price is NZ$205
includes taxes & fees
8 June - 9 June
Berkshires Untold

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (766 reviews)
"Above average hotel breakfast. Very clean hotel."
United States
Helen
The price is NZ$237
includes taxes & fees
1 June - 2 June
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Hideaway Inn Lenox

Hideaway Inn Lenox
2.0 star property
Lenox
8.0 out of 10, Very good, (2 reviews)
"After a little snafu with check-in (we had completed the form in advance and never received the room number text), we were able to get checked in with the virtual front desk. The inn was clean and well appointed and centrally located. The common areas felt inviting and useful for both the adults and kids. We would stay again."
United States
Samantha
The price is NZ$219
includes taxes & fees
25 May - 26 May
Hideaway Inn Lenox

The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (785 reviews)
"The room was comfortable and clean, I will stay there again"
United States
Monica
The price is NZ$151
includes taxes & fees
26 May - 27 May
The Villager Motel
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.
Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Pittsfield attractions

Learn more about Pittsfield

Nestled in the heart of the Berkshires, this cultural hub boasts the renowned Berkshire Museum and historic Colonial Theatre. Outdoor enthusiasts can hike nearby Pittsfield State Forest trails before exploring the vibrant downtown's farm-to-table restaurants and local art galleries.

Top Pittsfield Hotel Reviews

More cheap accommodation in Pittsfield

Frequently asked questions

Where is the best place for a stay in Pittsfield?
Berkshire Mountain Lodge is one of the top choices for your stay based on our traveller data. This lodge offers an indoor pool and free parking. Other good choices for your visit include Hotel On North and Holiday Inn & Suites Pittsfield-Berkshires by IHG. See all available top hotels, or vacation rentals in Pittsfield.
What are some of the best holiday rentals that Pittsfield has to offer?
Peace and quiet on the lake: This holiday home rental outside of Pittsfield is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind. See all vacation rentals in Pittsfield.
If I need to cancel my hotel reservation in Pittsfield, will I receive a refund?
Yes! You'll find that most hotel room reservations are fully refundable if cancelled before the hotel's cancellation deadline, which is usually within 24-48 hours of your scheduled arrival. If your reservation is non-refundable, it may still be possible to cancel it and get a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Pittsfield.
What's the best budget-friendly hotel in Pittsfield?
Based on our traveller reviews, Berkshire Inn is a top choice for a less expensive stay. View all budget hotels in Pittsfield.
What's the best family accommodation in Pittsfield?
Holiday Inn & Suites Pittsfield-Berkshires by IHG is a hotel with an indoor pool and a restaurant, and it's a top choice on Expedia for families. Other options for your child-friendly holiday include Holiday Inn Express & Suites Pittsfield - Berkshires by IHG and Best Western Plus Berkshire Hills Inn & Suites. Also, attractions such as Berkshire Museum and Bousquet Ski Area are fun for children of all ages. Find more child-friendly accommodations in Pittsfield.
What is the top LGBTQ-friendly place to stay in Pittsfield?
Holiday Inn & Suites Pittsfield-Berkshires by IHG is a top LGBTQ-friendly hotel, and features free Wi-Fi and free Internet. Hilton Garden Inn Lenox Pittsfield is another good option for your trip. See all available hotels listed as LGBTQ-friendly in Pittsfield.
What's the best dog-friendly accommodation option in Pittsfield?
Hotel On North is a top hotel for people travelling with their pets, and offers a bar/lounge and concierge services for its human guests. Other good choices for you and your pet's trip include Holiday Inn & Suites Pittsfield-Berkshires by IHG and Best Western Plus Berkshire Hills Inn & Suites. See more pet-friendly hotel accommodations in Pittsfield.
What are some accommodation options with pools in Pittsfield?
Hilton Garden Inn Lenox Pittsfield is a top hotel with a pool, free WiFi and free self-parking. Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more! is an additional hotel with an on-site pool. View all hotels with pools in Pittsfield.
What is staying in Pittsfield like?
Visitors to Pittsfield will definitely enjoy the sporting events, entertainment and theatres. Tourists can also enjoy the city's museums, lake views and ski areas. In Pittsfield, there are 73 hotels and other accommodation options to choose from. Find out more about Pittsfield.
What should I do while I'm visiting Pittsfield?
Cultural venues include Berkshire Museum, Barrington Stage Company and Hancock Shaker Village. Landmarks like Colonial Theater and Herman Melville's Arrowhead might be worth a visit. A couple of additional sights to add to your itinerary are Bousquet Ski Area and Housatonic River. Take a look at what more there is to see and do in Expedia's Pittsfield guide.
How should I get around Pittsfield?
To see more of the surrounding area, ride one of the trains from Pittsfield Intermodal Transportation Center or Pittsfield Station. If you want to venture out around the area, you may want a rental car in Pittsfield for your journey.
What's the seasonal weather like in Pittsfield?
The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Pittsfield are January, March, February and November, with each month seeing an average of 18 cm of snowfall.

Explore a world of travel with Expedia