Best Resorts in Pittsfield

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Recommended hotels in Pittsfield

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
$110 nightly
The price is $123
May 18 - May 19
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (931 reviews)
"Spacious, clean, and the pool was warm and perfect for family swimming "
United States
Danielle
$113 nightly
The price is $126
May 25 - May 26
Total with taxes and fees
Berkshire Mountain Lodge

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, (93 reviews)
"Room was clean, bed was comfortable, pool was nice, breakfast and coffee were good!"
United States
Haley
$106 nightly
The price is $119
May 17 - May 18
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (854 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
$78 nightly
The price is $87
May 25 - May 26
Total with taxes and fees
Berkshire Inn

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
$131 nightly
The price is $146
May 26 - May 27
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (850 reviews)
"It was an absolute pleasure to stay! We enjoyed ourselves and felt very comfortable"
United States
philip
$159 nightly
The price is $178
May 14 - May 15
Total with taxes and fees
Hotel On North

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.
$440 nightly
The price is $492
May 14 - May 15
Total with taxes and fees
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

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
$118 nightly
The price is $132
May 17 - May 18
Total with taxes and fees
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, (364 reviews)
"Easy access to parking, nearby everything and room was very clean. Definitely will come back here to stay again! "
United States
Aisha
$106 nightly
The price is $118
May 31 - Jun 1
Total with taxes and fees
The Central Downtown Inn & Suites

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.
$1,060 nightly
The price is $1,149
May 19 - May 20
Total with taxes and fees
Hancock Village Inn Near Jiminy Peak

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
$76 nightly
The price is $85
May 25 - May 26
Total with taxes and fees
FairBridge Inn Express

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,007 reviews)
"Great place to stay and close to shops and restaurants will be back!"
United States
Marie-Pascale
$89 nightly
The price is $100
May 17 - May 18
Total with taxes and fees
The Yankee Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (453 reviews)
"Everything was excellent"
United States
Barbara
$102 nightly
The price is $112
May 14 - May 15
Total with taxes and fees
Shaker Mill Inn

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (940 reviews)
"Great stay!"
United States
Aditya
$111 nightly
The price is $124
May 25 - May 26
Total with taxes and fees
Berkshires Untold

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
$155 nightly
The price is $173
May 14 - May 15
Total with taxes and fees
The Revival House

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (851 reviews)
"Very clean and cozy in a great location! "
United States
Lidia
$76 nightly
The price is $85
May 14 - May 15
Total with taxes and fees
Monument Mountain Motel

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (25 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
$167 nightly
The price is $187
May 19 - May 20
Total with taxes and fees
Element Lenox Berkshires

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very Good, (1,000 reviews)
"Great staff breakfast was good location was close enough to walk but far enough from the noise "
United States
Braynd
$85 nightly
The price is $94
May 17 - May 18
Total with taxes and fees
Quality Inn Great Barrington

Rodeway Inn

Rodeway Inn
2.0 star property
Adams
7.4 out of 10, Good, (242 reviews)
"Found dead flies in the beds and the sheets were stained. I would not expect much from an inexpensive room but I do expect it to be clean."
United States
Heidi
$71 nightly
The price is $79
May 19 - May 20
Total with taxes and fees
Rodeway Inn

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
9.8 out of 10, Exceptional, (6 reviews)
"The new owners have done a great job. The place is immaculate, the room was very comfortable and well appointed, the common areas charming. Highly recommended."
United States
Robert
$190 nightly
The price is $212
May 14 - May 15
Total with taxes and fees
The Berkshire Mountain Inn
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Top Pittsfield Hotel Reviews

Find out more about Pittsfield

Pittsfield Resorts information

Number of reviews
10,920
Accommodation
29 Resorts
Lowest Price
$79
Highest Price
$1,149

Frequently asked questions

What can I expect from a resort vacation in Pittsfield?
You deserve a getaway, 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're hoping for an amazing pool, a state-of-the-art fitness center, or fun activities to try.
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 center, 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 center, 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 center, and beach sun loungers.
What can I do in Pittsfield?
Travelers enjoy the cultural offerings in Pittsfield, and have good things to say about its entertainment choices and theaters. Check out the interesting exhibits at Berkshire Museum and Hancock Shaker Village, or catch the latest production at Colonial Theater or Barrington Stage Company. A few other attractions you may want to see are Bousquet Ski Area and Housatonic River.
What's the seasonal weather like in Pittsfield?
The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Pittsfield are January, March, February, and November, with each month seeing an average of 7 inches 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) from the city center. Otherwise, look for flights into Hudson, NY (HCC-Columbia County), which is 25.7 mi (41.4 km) away. To explore the surrounding area, hop aboard a train at Pittsfield Intermodal Transportation Center or Pittsfield Station.

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