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Check prices for these dates

Next weekend
22 May - 24 May
In two weeks
29 May - 31 May
In one month
12 Jun - 14 Jun
In two months
10 Jul - 12 Jul
No exact matches found, but these alternatives could be just right

Recommended hotels in Pittsfield

Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk

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, (1,003 reviews)
"Room was clean. Breakfast was fresh and the area was pristine. All staff was pleasant. "
United States
Melinda
The price is £92
includes taxes & fees
20 May - 21 May
Best Western Plus Berkshire Hills Inn & Suites
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (936 reviews)
"Clean and great job staffing "
United States
Pedro
The price is £90
includes taxes & fees
24 May - 25 May
Berkshire Mountain Lodge
Indoor pool

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (94 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 £106
includes taxes & fees
28 May - 29 May
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Desk, iron/ironing board, free WiFi, bed sheets

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (855 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 £66
includes taxes & fees
28 May - 29 May
Berkshire Inn
Breakfast, lunch and dinner served

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (677 reviews)
"Clean room, staff was friendly and efficient. Great breakfast"
United States
Donna
The price is £106
includes taxes & fees
28 May - 29 May
Hilton Garden Inn Lenox Pittsfield
Property entrance

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (854 reviews)
"It was an absolute pleasure to stay! We enjoyed ourselves and felt very comfortable"
United States
philip
The price is £133
includes taxes & fees
16 Jun - 17 Jun
Hotel On North
Exterior

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (365 reviews)
"Easy access to parking, nearby everything and room was very clean. Definitely will come back here to stay again! "
United States
Aisha
The price is £96
includes taxes & fees
1 Jun - 2 Jun
The Central Downtown Inn & Suites
Exterior

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, (1,000 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 £99
includes taxes & fees
25 May - 26 May
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Outdoor dining

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
7.8 out of 10, Good, (7 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is £372
includes taxes & fees
19 May - 20 May
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Outdoor dining

Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (19 reviews)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is £814
includes taxes & fees
19 May - 20 May
Hancock Village Inn Near Jiminy Peak
Desk, iron/ironing board, free WiFi, bed sheets

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 £60
includes taxes & fees
31 May - 1 Jun
FairBridge Inn Express
Indoor pool, outdoor pool, open 8:00 AM to 10:00 PM, pool loungers

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,003 reviews)
"Great place to stay and close to shops and restaurants will be back!"
United States
Marie-Pascale
The price is £91
includes taxes & fees
19 May - 20 May
The Yankee Inn
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (454 reviews)
"Everything was excellent"
United States
Barbara
The price is £83
includes taxes & fees
25 May - 26 May
Shaker Mill Inn
Dining room

Gregory House Country Inn

Gregory House Country Inn
3.0 star property
Averill Park
9.0 out of 10, Wonderful, (94 reviews)
"Comfy, cozy, quiet stay in this lovely property full of character! Thank you, hard-working staff."
United States
Leslieann H
The price is £85
includes taxes & fees
18 May - 19 May
Gregory House Country Inn
Lobby sitting area

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 £96
includes taxes & fees
19 May - 20 May
Hideaway Inn Lenox
Room, 2 Queen Beds, Non Smoking | Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (854 reviews)
"Very clean and cozy in a great location! "
United States
Lidia
The price is £57
includes taxes & fees
18 May - 19 May
Monument Mountain Motel
Lobby

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.6 out of 10, Excellent, (1,006 reviews)
"Great staff breakfast was good location was close enough to walk but far enough from the noise "
United States
Braynd
The price is £71
includes taxes & fees
25 May - 26 May
Quality Inn Great Barrington
Gazebo

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (905 reviews)
"Facilities were excellent. Staff was very helpful and very efficient & courteous in taking care of any concerns I had."
United States
Barbara J
The price is £70
includes taxes & fees
31 May - 1 Jun
Cozy Corner Motel
55-inch LCD TV with digital channels, printers

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 £145
includes taxes & fees
18 May - 19 May
The Revival House
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (948 reviews)
"Great stay!"
United States
Aditya
The price is £96
includes taxes & fees
26 May - 27 May
Berkshires Untold
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.
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Top Pittsfield Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Not gonna lie, I had very low expectations based on the price, but needed a long-ish term place to stay. This lodge blew all my expectations away and it was actually an amazing place."
Paul 12-night trip
Posted 4 hours ago
Berkshire Mountain Lodge

Find out more about Pittsfield

Pittsfield Resorts information

Number of reviews
9,205
Accommodation
30 Resorts
Lowest Price
£57
Highest Price
£814

Frequently asked questions

What can I expect from a resort holiday in Pittsfield?
You deserve some time off, and a resort is just the place to pamper yourself with the amenities and services you need for a relaxing time in Pittsfield. One of the comfortable resort hotels in the surrounding area could be just what you're looking for, whether you want an amazing pool, shopping possibilities or nightly entertainment options.
What's the best resort for my stay in Pittsfield?
Our top-rated resorts near Pittsfield: Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more! - 2.6 mi (4.1 km) from Pittsfield. Features a fitness centre, an indoor pool and an outdoor pool. Berkshire Mountain Lodge - 2.6 mi (4.1 km) from Pittsfield. In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants - Ski resort. 7.6 mi (12.3 km) from Pittsfield. Amenities include ski-in/ski-out access, a fitness centre and a garden. COZY CABIN IN BERKSHIRES RESORT. SKI IN AND OUT. PET FRIENDLY. - Ski resort. 7.7 mi (12.4 km) from Pittsfield. Access to ski-in/ski-out access, a fitness centre and beach sunloungers.
What can I do in Pittsfield?
Travellers enjoy the cultural offerings in Pittsfield, and have good things to say about its entertainment choices and theatres. Explore the interesting exhibits at Berkshire Museum and Hancock Shaker Village, or catch the latest production at Barrington Stage Company or Colonial Theater. A few other attractions you may want to see are Bousquet Ski Area and Housatonic River.
What's the 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.
What's the best way to get to and around Pittsfield?
Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 2.5 mi (4 km) away from the heart of the city. You can also search for flights into Hudson, NY (HCC-Columbia County), which is 25.7 mi (41.4 km) away. To venture out into the surrounding area, hop aboard a train at Pittsfield Intermodal Transportation Center or Pittsfield Station.