Search Resort Hotels in Pittsfield from CA $104

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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)
"Breakfast was reasonable. We had issue with our room and the staff helpfully moved us to another room. Would stay again"
United States
Anandaraja
The price is CA $155
CA $173 total
includes taxes & fees
Jun 9 - Jun 10
Best Western Plus Berkshire Hills Inn & Suites

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (100 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 CA $188
CA $210 total
includes taxes & fees
Jun 14 - Jun 15
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (965 reviews)
"Great location and resort. Very happy with accommodation's"
United States
Robert
The price is CA $170
CA $220 total
includes taxes & fees
Jun 7 - Jun 8
Berkshire Mountain Lodge

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (821 reviews)
"Quiet"
United States
William
The price is CA $93
CA $104 total
includes taxes & fees
Jul 2 - Jul 3
FairBridge Inn Express

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (679 reviews)
"Five Star stay!"
United States
Adeline
The price is CA $204
CA $228 total
includes taxes & fees
Jun 14 - Jun 15
Hilton Garden Inn Lenox Pittsfield

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (859 reviews)
"Great stay "
United States
Brian
The price is CA $109
CA $122 total
includes taxes & fees
Jun 8 - Jun 9
Berkshire Inn

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (863 reviews)
"Very nice clean hotel. Close to Colonial theater. Would definitely stay there again."
United States
KEITH AND SHIRLEY
The price is CA $208
CA $232 total
includes taxes & fees
Jun 9 - Jun 10
Hotel On North

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (368 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 CA $159
CA $177 total
includes taxes & fees
Jun 14 - Jun 15
The Central Downtown 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, (1,002 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 CA $169
CA $188 total
includes taxes & fees
Jun 22 - Jun 23
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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 CA $438
CA $772 total
includes taxes & fees
Jun 8 - Jun 9
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, (19 reviews)
"Really great host - communication was great. House is so close to skiing, can’t beat it "
United States
Stephanie B.
The price is CA $803
CA $1,482 total
includes taxes & fees
Jun 9 - Jun 10
Hancock Village Inn Near Jiminy Peak

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,004 reviews)
"Great location for sightseeing in the Berkshires. Clean and comfortable room, friendly staff."
Canada
Mark
The price is CA $155
CA $173 total
includes taxes & fees
Jun 7 - Jun 8
The Yankee Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (459 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is CA $212
CA $232 total
includes taxes & fees
Jun 8 - Jun 9
Shaker Mill Inn

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (862 reviews)
"This is a great choice for folks traveling on a budget. Clean rooms, friendly owners, and nice retro vibe. Will be staying here again on my trips through the Berkshires."
United States
Mark
The price is CA $107
CA $120 total
includes taxes & fees
Jun 9 - Jun 10
Monument Mountain Motel

Hideaway Inn Lenox

Hideaway Inn Lenox
2.0 star property
Lenox
8.6 out of 10, Excellent, (4 reviews)
"Wonderful pet-friendly property in a fantastic location. Everything in the village is just a short walk away, making it easy to enjoy local shops, restaurants, and attractions."
United States
Leonardo
The price is CA $149
CA $167 total
includes taxes & fees
Jun 9 - Jun 10
Hideaway Inn Lenox

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.6 out of 10, Excellent, (1,001 reviews)
"Great staff breakfast was good location was close enough to walk but far enough from the noise "
United States
Braynd
The price is CA $131
CA $146 total
includes taxes & fees
Jun 9 - Jun 10
Quality Inn Great Barrington

Rodeway Inn

Rodeway Inn
2.0 star property
Adams
7.4 out of 10, Good, (244 reviews)
"Had a great stay."
United States
Trevor
The price is CA $100
CA $112 total
includes taxes & fees
Jun 14 - Jun 15
Rodeway Inn

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (973 reviews)
"Very nice hotel. Highly recommend the restaurant."
United States
Thomas
The price is CA $174
CA $194 total
includes taxes & fees
Jun 8 - Jun 9
Berkshires Untold

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (912 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 CA $118
CA $138 total
includes taxes & fees
Jun 9 - Jun 10
Cozy Corner Motel

Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
The price is CA $176
CA $196 total
includes taxes & fees
Jun 9 - Jun 10
Berkshire Lake Lodge
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

Find out more about Pittsfield

Pittsfield Resorts information

Number of reviews
13,731
Accommodation
30 Resorts
Lowest Price
CA $104
Highest Price
CA $232

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?
Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more! - Features a fitness center, an indoor pool, and an outdoor pool. Mountain Lodge Apt! - Has a fitness center.
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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