A historic building with classical architecture, a traffic light, and a yellow taxi.

Best Resorts in Pittsfield

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Check prices for these dates

Next weekend
Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18
In one month
Oct 30 - Nov 1
In two months
Nov 27 - Nov 29
No exact matches found, but these alternatives could be just right

Recommended hotels in Pittsfield

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,170 reviews)
"Absolutely wonderful room with many amenities with short drive to Tanglewood and restaurant options."
United States
Jay
$111 nightly
The price is $124
Nov 2 - Nov 3
Total with taxes and fees
Berkshire Mountain Lodge
A building entrance with a large planter with purple flowers and a small tree.

2. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (934 reviews)
"Great place!"
United States
Lawrence
$127 nightly
The price is $141
Nov 1 - Nov 2
Total with taxes and fees
Hotel On North
An indoor swimming pool with clear water, tiled floors, and a blue wall.

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (225 reviews)
"Most helpful staff, very clean and best breakfast around"
United States
Sheldon
$99 nightly
The price is $111
Nov 1 - Nov 2
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

4. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.4 out of 10, Very good, (1,000 reviews)
"Friendly staff. Good location."
United States
Joe
$93 nightly
The price is $104
Nov 1 - Nov 2
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.

5. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (710 reviews)
"Great place to stay. Great staff and convenient location. Nice restaurant as well."
United States
James
$128 nightly
The price is $143
Nov 1 - Nov 2
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

6. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.4 out of 10, Very good, (420 reviews)
"Large, clean, comfortable suite."
United States
Rena
$99 nightly
The price is $111
Oct 5 - Oct 6
Total with taxes and fees
The Central Downtown Inn & Suites
A hotel room with a large bed, two bedside lamps, a chair, and a window with curtains.

7. Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (931 reviews)
"Very well maintained and clean for an older looking property. I stayed here twice now."
United States
Kristina
$79 nightly
The price is $88
Nov 2 - Nov 3
Total with taxes and fees
Berkshire Inn
A hotel room with a large bed, a separate sitting area, a bathtub, and a large mirror.

8. FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (911 reviews)
"Parking and staff were good"
United States
William
$69 nightly
The price is $77
Oct 4 - Oct 5
Total with taxes and fees
FairBridge Inn Express
A wooden deck with a table and chairs, surrounded by a white railing.

9. 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
8.4 out of 10, Very good, (10 reviews)
"Very comfortable and clean accommodations in a nice neighborhood, and a great deck to appreciate the view."
United States
Stephen L.
$441 nightly
The price is $493
Oct 13 - Oct 14
Total with taxes and fees
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
A wooden deck with outdoor furniture, including chairs and a table, surrounded by a lush garden and trees.

10. Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (22 reviews)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
$1,059 nightly
The price is $1,148
Oct 6 - Oct 7
Total with taxes and fees
Hancock Village Inn Near Jiminy Peak
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

11. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,003 reviews)
"The room was spacious, clean and comfortable. I will definitely stay there again."
United States
William
$106 nightly
The price is $118
Nov 1 - Nov 2
Total with taxes and fees
The Yankee Inn
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

12. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (920 reviews)
"Clean, big rooms!"
United States
Mark
$79 nightly
The price is $88
Oct 4 - Oct 5
Total with taxes and fees
Howard Johnson by Wyndham Lenox
A spacious hotel lobby with multiple seating areas, large windows, and a television.

13. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.0 out of 10, Wonderful, (1,001 reviews)
"Breakfast was great"
United States
Thomas
$115 nightly
The price is $129
Nov 3 - Nov 4
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

14. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (662 reviews)
"Nice hotel."
United States
Tracy
$126 nightly
The price is $140
Nov 1 - Nov 2
Total with taxes and fees
Courtyard by Marriott Lenox Berkshires
A reception area with a fireplace, seating, and a doormat with the logo "Quality".

15. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.6 out of 10, Excellent, (1,002 reviews)
"Very nice stay"
United States
Christine
$110 nightly
The price is $122
Oct 25 - Oct 26
Total with taxes and fees
Quality Inn Lee - Lenox South
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

16. Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,028 reviews)
"A very good place to stay"
United States
Madhavi R
$135 nightly
The price is $151
Nov 1 - Nov 2
Total with taxes and fees
Berkshires Untold
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

17. The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.2 out of 10, Wonderful, (1,002 reviews)
"Beautiful setting, clean facilities. Thoroughly enjoyed my stay."
United States
Bob
$116 nightly
The price is $129
Nov 1 - Nov 2
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

18. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,695 reviews)
"Very pleased with our stay -great place for the family we will G-d willing return"
United States
Denton
$110 nightly
The price is $123
Nov 1 - Nov 2
Total with taxes and fees
Vacation Village in the Berkshires
A snow-covered outdoor area with a patio, seating, and a covered dining area.

19. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
"Convenient location for Tanglewood and other Berkshire sights. Nice complimentary breakfast and arrival cocktail."
United States
Rosann
$160 nightly
The price is $179
Oct 27 - Oct 28
Total with taxes and fees
The Cornell Inn, Lenox & The Berkshires
A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.

20. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (41 reviews)
"Stay was nice"
United States
Kirsty
$151 nightly
The price is $169
Nov 1 - Nov 2
Total with taxes and fees
Element by Marriott Lenox Berkshires
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

8/10 Good
"I have stayed here multiple times. My unit this trip was very clean, well equipped and comfortable. The check in process and front desk staff were terrific. My only issue was a strong smell of marijuana coming through the slider and bedroom window . The staff gave me a fan to blow the smell back out however it was an issue throughout my stay."
Susan 7-night trip
Posted 8 hours ago
Berkshire Mountain Lodge

Find out more about Pittsfield

Pittsfield Resorts information

Number of reviews
6,170
Accommodation
12 Resorts
Lowest Price
$77
Highest Price
$1,148

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 highest-rated resorts near Pittsfield: 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. Has ski-in/ski-out access, a fitness center, and a garden. COZY CABIN IN BERKSHIRES RESORT. - Ski resort right by Jiminy Peak Mountain Resort. 7.7 mi (12.4 km) from Pittsfield. Enjoy the ski-in/ski-out access, fitness center, and beach sun loungers. Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out - Ski resort, 5-minute walk from Jiminy Peak Mountain Resort. 7.7 mi (12.4 km) from Pittsfield. Access to ski-in/ski-out access, a fitness center, and an indoor pool.
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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