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
Sep 4 - Sep 6
In two weeks
Sep 11 - Sep 13
In one month
Sep 25 - Sep 27
In two months
Oct 23 - Oct 25
No exact matches found, but these alternatives could be just right

Recommended hotels in Pittsfield

A modern bar area with a central island, multiple bar stools, and a seating area with tables and chairs.

1. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
7.8 out of 10, Good, (1,017 reviews)
"Hotel is currently under renovation which impacted parking and only 1 elevator available. Hotel staff, cleanliness and location excellent."
United States
Myrna
$119 nightly
The price is $133
Sep 23 - Sep 24
Total with taxes and fees
Holiday Inn & Suites Pittsfield-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.

2. 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, (1,012 reviews)
"Quite comfortable Beds"
United States
Jermaine
$110 nightly
The price is $123
Sep 1 - Sep 2
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

3. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,091 reviews)
"A nice place to stay in the Berkshires."
United States
Robert
$138 nightly
The price is $155
Aug 30 - Aug 31
Total with taxes and fees
Berkshire Mountain Lodge
A building entrance with a large planter with purple flowers and a small tree.

4. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (902 reviews)
"Very nice and reasonably priced hotel for the region."
United States
Drew
$179 nightly
The price is $200
Sep 7 - Sep 8
Total with taxes and fees
Hotel On North
A hotel room with a large bed, two bedside lamps, a chair, and a window with curtains.

5. Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (914 reviews)
"Excellent room super clean!"
United States
Adriana
$90 nightly
The price is $101
Aug 26 - Aug 27
Total with taxes and fees
Berkshire Inn
A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.

6. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (704 reviews)
"Great place to stay. Great staff and convenient location. Nice restaurant as well."
United States
James
$149 nightly
The price is $166
Sep 13 - Sep 14
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
An indoor swimming pool with clear water, tiled floors, and a blue wall.

7. 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, (173 reviews)
"A clean pleasant place to stay"
United States
Ken
$119 nightly
The price is $133
Sep 24 - Sep 25
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

8. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.4 out of 10, Very Good, (397 reviews)
"Large, clean, comfortable suite."
United States
Rena
$89 nightly
The price is $100
Sep 1 - Sep 2
Total with taxes and fees
The Central Downtown Inn & Suites
A hotel room with a large bed, a separate sitting area, a bathtub, and a large mirror.

9. FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (886 reviews)
"It was very nice and everyone was extremely helpful"
United States
ERICIA
$61 nightly
The price is $68
Aug 27 - Aug 28
Total with taxes and fees
FairBridge Inn Express
A wooden deck with a table and chairs, surrounded by a white railing.

10. 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 clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
$496 nightly
The price is $554
Aug 27 - Aug 28
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.

11. 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.
$1,060 nightly
The price is $1,149
Sep 9 - Sep 10
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.

12. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,021 reviews)
"Very nice and convenient hotel."
United States
Karen
$158 nightly
The price is $176
Sep 14 - Sep 15
Total with taxes and fees
The Yankee Inn
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
9.2 out of 10, Wonderful, (1,008 reviews)
"Great comfortable beds Good breakfast"
United States
Nancy
$127 nightly
The price is $142
Sep 9 - Sep 10
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

14. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (903 reviews)
"Great hotel for a reasonable price. The only drawback is that they didn’t offer shampoos and body wash like most hotels but otherwise a great value."
United States
Sheila
$78 nightly
The price is $87
Sep 8 - Sep 9
Total with taxes and fees
Howard Johnson by Wyndham Lenox
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

15. Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,020 reviews)
"Great hotel with fabulous outdoor sitting space"
United States
Christine
$141 nightly
The price is $157
Sep 8 - Sep 9
Total with taxes and fees
Berkshires Untold
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

16. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,561 reviews)
"Place was clean and well equipped, pool and amenities were great too !"
United States
Nyra
$139 nightly
The price is $156
Sep 2 - Sep 3
Total with taxes and fees
Vacation Village in the Berkshires
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
9.0 out of 10, Wonderful, (1,010 reviews)
"I liked the balcony overlooking the lake"
United States
Rinat
$128 nightly
The price is $142
Sep 15 - Sep 16
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

18. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (650 reviews)
"Helpful staff, clean room and great facilities."
United Kingdom
Laura
$178 nightly
The price is $198
Sep 7 - Sep 8
Total with taxes and fees
Courtyard by Marriott Lenox Berkshires
A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.

19. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (35 reviews)
"Great staff very friendly rooms very clezn"
United States
Lawrence
$195 nightly
The price is $218
Sep 3 - Sep 4
Total with taxes and fees
Element by Marriott Lenox Berkshires
A reception area with a fireplace, seating, and a doormat with the logo "Quality".

20. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,009 reviews)
"Very nice stay"
United States
Christine
$110 nightly
The price is $122
Sep 15 - Sep 16
Total with taxes and fees
Quality Inn Lee - Lenox South
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

Hotel On North

Hotel On North

10/10 Excellent
"Great hotel, rooms spacious and clean. Had a lovely lunch in the dining room. Easy parking, would stay again."
Cindy 1-night trip
Posted 3 hours ago
Hotel On North

Find out more about Pittsfield

Pittsfield Resorts information

Number of reviews
10,038
Accommodation
12 Resorts
Lowest Price
$68
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 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. Enjoy the ski-in/ski-out access, fitness center, and garden. COZY CABIN IN BERKSHIRES RESORT. - 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.
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 Pontoosuc Lake.
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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