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 18 - Sep 20
In two weeks
Sep 25 - Sep 27
In one month
Oct 9 - Oct 11
In two months
Nov 6 - Nov 8
No exact matches found, but these alternatives could be just right

Recommended hotels in Pittsfield

Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)

1. 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, (1,002 reviews)
"Friendly staff. Good location."
United States
Joe
$110 nightly
The price is $123
Sep 16 - Sep 17
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
Room

2. 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, (1,001 reviews)
"Look good for being under constructikn"
United States
Debra
$115 nightly
The price is $128
Oct 12 - Oct 13
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Lobby

3. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,143 reviews)
"Clean & comfortable stay"
United States
Robert
$109 nightly
The price is $121
Oct 1 - Oct 2
Total with taxes and fees
Berkshire Mountain Lodge
Property entrance

4. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (915 reviews)
"Very nice and reasonably priced hotel for the region."
United States
Drew
$152 nightly
The price is $170
Sep 14 - Sep 15
Total with taxes and fees
Hotel On North
Restaurant

5. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (706 reviews)
"Great place to stay. Great staff and convenient location. Nice restaurant as well."
United States
James
$146 nightly
The price is $163
Sep 20 - Sep 21
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
Pool

6. 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, (206 reviews)
"Clean & easy to stay there"
United States
Steve
$127 nightly
The price is $142
Sep 20 - Sep 21
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Exterior

7. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.4 out of 10, Very Good, (410 reviews)
"Large, clean, comfortable suite."
United States
Rena
$98 nightly
The price is $110
Oct 5 - Oct 6
Total with taxes and fees
The Central Downtown Inn & Suites
Room

8. Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (925 reviews)
"Quiet location set back from road, comfortable beds and nice shower. Located right on Rt. 20 and near downtown."
United States
Ellen
$85 nightly
The price is $95
Oct 13 - Oct 14
Total with taxes and fees
Berkshire Inn
Room

9. FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (904 reviews)
"great value"
United States
Horace
$69 nightly
The price is $77
Sep 14 - Sep 15
Total with taxes and fees
FairBridge Inn Express
Outdoor dining

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.
$454 nightly
The price is $507
Oct 13 - Oct 14
Total with taxes and fees
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Outdoor dining

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 15 - Sep 16
Total with taxes and fees
Hancock Village Inn Near Jiminy Peak
Superior Room, 1 King Bed, Jetted Tub | Jetted tub

12. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,003 reviews)
"Very nice and convenient hotel."
United States
Karen
$116 nightly
The price is $130
Sep 22 - Sep 23
Total with taxes and fees
The Yankee Inn
Room

13. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (914 reviews)
"We were in town for a concert and skeptical at first but when we arrived at our room it was very clean, the front desk was quick and pleasant, would definitely recommend as a nice place to stay!"
United States
COLLEEN
$79 nightly
The price is $88
Sep 14 - Sep 15
Total with taxes and fees
Howard Johnson by Wyndham Lenox
Breakfast area

14. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.0 out of 10, Wonderful, (1,000 reviews)
"Great comfortable beds Good breakfast"
United States
Nancy
$133 nightly
The price is $149
Sep 23 - Sep 24
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
Lobby lounge

15. Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,007 reviews)
"It"s a very nice small Hotel- nicely appointed"
United States
Drue
$136 nightly
The price is $152
Sep 14 - Sep 15
Total with taxes and fees
Berkshires Untold
Lake

16. 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, (1,006 reviews)
"Excellent staff and excellent Indian restaurant!!! Hotel a little dated, but beds were comfortable and staff was great!"
United States
Susan
$125 nightly
The price is $140
Sep 21 - Sep 22
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Property amenity

17. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (655 reviews)
"Nice hotel."
United States
Tracy
$196 nightly
The price is $219
Sep 20 - Sep 21
Total with taxes and fees
Courtyard by Marriott Lenox Berkshires
Lobby

18. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,636 reviews)
"Great all around stay and lots for the kids to do"
United States
Sarah
$122 nightly
The price is $136
Sep 14 - Sep 15
Total with taxes and fees
Vacation Village in the Berkshires
Lobby

19. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (38 reviews)
"Stay was nice"
United States
Kirsty
$178 nightly
The price is $199
Sep 20 - Sep 21
Total with taxes and fees
Element by Marriott Lenox Berkshires
Lobby

20. 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
$107 nightly
The price is $120
Sep 27 - Sep 28
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"My go-to place for visiting NW MA."
David 1-night trip
Posted 5 hours ago
Vacation Village in the Berkshires

Find out more about Pittsfield

Pittsfield Resorts information

Number of reviews
11,429
Accommodation
12 Resorts
Lowest Price
$77
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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