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, (1,001 reviews)
"Very friendly and good Breakfast."
United States
Jesse
$90 nightly
The price is $101
Feb 8 - Feb 9
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites

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)
"Staff was very courteous and rooms clean."
United States
Steven
$102 nightly
The price is $114
Mar 7 - Mar 8
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (665 reviews)
" Nice staff - beautiful hotel!"
United States
MARY
$136 nightly
The price is $152
Mar 8 - Mar 9
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (827 reviews)
"Very comfortable and very close to ski slope and restaurants"
United States
Frederick
$121 nightly
The price is $136
Mar 8 - Mar 9
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, (81 reviews)
"it was a lovely hotel, hot tub was perfect after the day of skiing, everything very clean and new and lovely breakfast. All staff were very nice."
United States
Laura Pearson
$132 nightly
The price is $148
Feb 26 - Feb 27
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, (842 reviews)
"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."
United States
MARIA J
$84 nightly
The price is $94
Feb 8 - Feb 9
Total with taxes and fees
Berkshire Inn

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (355 reviews)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
$101 nightly
The price is $113
Mar 1 - Mar 2
Total with taxes and fees
The Central Downtown Inn & Suites

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (821 reviews)
"Great staff, beautiful hotel. Would definitely recommend "
United States
Shawn
$149 nightly
The price is $166
Feb 8 - Feb 9
Total with taxes and fees
Hotel On North

3-bedroom house in beautiful Berkshires, close to amenities!

3-bedroom house in beautiful Berkshires, close to amenities!
Pittsfield
$274 nightly
The price is $306
Mar 4 - Mar 5
Total with taxes and fees
3-bedroom house in beautiful Berkshires, close to amenities!

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.
$442 nightly
The price is $494
Feb 16 - Feb 17
Total with taxes and fees
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (16 reviews)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
$1,048 nightly
The price is $1,136
Feb 9 - Feb 10
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, (811 reviews)
"Room spotless and staff helpful."
United States
William
$89 nightly
The price is $99
Feb 6 - Feb 7
Total with taxes and fees
FairBridge Inn Express

Chic corporate apartment in wonderful Pittsfield with AC, WiFi

Chic corporate apartment in wonderful Pittsfield with AC, WiFi
Pittsfield
2.0 out of 10, (1 review)
"THIS. PLACE. IS. A. DUMP. Do NOT STAY HERE under any circumstances."
United States
Michael
$183 nightly
The price is $204
Feb 6 - Feb 7
Total with taxes and fees
Chic corporate apartment in wonderful Pittsfield with AC, WiFi

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (18 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
$139 nightly
The price is $155
Feb 22 - Feb 23
Total with taxes and fees
Element Lenox Berkshires

Rodeway Inn

Rodeway Inn
2.0 star property
Adams
7.6 out of 10, Good, (235 reviews)
"The room was clean and nice but i was confusing about the abandoned vehicles directly behind the hotel."
United States
Anonymous traveler
$76 nightly
The price is $85
Mar 8 - Mar 9
Total with taxes and fees
Rodeway Inn

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,008 reviews)
"Very friendly staff comfy beds!"
United States
Giselle
$98 nightly
The price is $110
Feb 8 - Feb 9
Total with taxes and fees
The Yankee, Trademark Collection by Wyndham

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, (731 reviews)
"Great property, very accommodating. "
United States
Shanice
$107 nightly
The price is $120
Feb 11 - Feb 12
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1,000 reviews)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
$98 nightly
The price is $109
Feb 26 - Feb 27
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (445 reviews)
"The large kitchen and sitting/living with gas fireplace, with adjacent separate bedroom was very clean and cozy. Thank you to Meg and Dan for providing a nice holiday stay!!!"
United States
Carin
$113 nightly
The price is $125
Feb 8 - Feb 9
Total with taxes and fees
Shaker Mill Inn

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (567 reviews)
"Excellent location!!"
United States
Abdul Samad
$75 nightly
The price is $84
Feb 8 - Feb 9
Total with taxes and fees
Travelodge by Wyndham Great Barrington Berkshires
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Top Pittsfield Hotel Reviews

Find out more about Pittsfield

Pittsfield Resorts information

Number of reviews
10,156
Accommodation
33 Resorts
Lowest Price
$84
Highest Price
$1,136

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. In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants - Ski resort right by Jiminy Peak Mountain Resort. 7.6 mi (12.3 km) from Pittsfield. Enjoy the ski-in/ski-out access, fitness center, and garden. COZY CABIN IN BERKSHIRES RESORT. SKI IN AND OUT. PET FRIENDLY. - Ski resort right by Jiminy Peak Mountain Resort. 7.7 mi (12.4 km) from Pittsfield. Amenities include ski-in/ski-out access, a fitness center, and beach sun loungers. Vacation Village In The Berkshires 5 Star Resort - Suite B - Family-friendly resort, 5-minute walk from Jiminy Peak Mountain Resort. 8 mi (12.9 km) from Pittsfield. Access to a fitness center, a car charging station, and a garden.
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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