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
Aug 21 - Aug 23
In two weeks
Aug 28 - Aug 30
In one month
Sep 11 - Sep 13
In two months
Oct 9 - Oct 11
No exact matches found, but these alternatives could be just right

Recommended hotels in Pittsfield

Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, desk, laptop workspace, blackout drapes

1. 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, (1,005 reviews)
"Quite comfortable Beds"
United States
Jermaine
$114 nightly
The price is $127
Aug 30 - Aug 31
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
Restaurant

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)
"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 13 - Sep 14
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, (1,068 reviews)
"A beautiful, spacious and conveniently located suite just a few minutes away that everything the Berkshires have to offer. I really love this place!"
United States
Karilyn
$125 nightly
The price is $139
Aug 31 - Sep 1
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, (889 reviews)
"Beautiful room with an amazing lobby."
United States
Dragana
$179 nightly
The price is $200
Sep 7 - Sep 8
Total with taxes and fees
Hotel On North
Desk, iron/ironing board, WiFi (free), bed sheets

5. Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (907 reviews)
"Very clean and updated simple motel."
United States
christopher
$90 nightly
The price is $101
Aug 17 - Aug 18
Total with taxes and fees
Berkshire Inn
Exterior

6. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (388 reviews)
"Large, clean, comfortable suite."
United States
Rena
$91 nightly
The price is $102
Sep 3 - Sep 4
Total with taxes and fees
The Central Downtown Inn & Suites
Breakfast, lunch and dinner served

7. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (699 reviews)
"Five Star stay!"
United States
Adeline
$146 nightly
The price is $163
Sep 13 - Sep 14
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
Indoor pool

8. 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, (158 reviews)
"A clean pleasant place to stay"
United States
Ken
$131 nightly
The price is $146
Sep 7 - Sep 8
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Desk, iron/ironing board, WiFi (free), bed sheets

9. FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (870 reviews)
"Some of the furniture and rugs show age. The bed was comfortable and the staff was always available to help!"
United States
DAVID
$61 nightly
The price is $68
Aug 18 - Aug 19
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.
$482 nightly
The price is $539
Aug 15 - Aug 16
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 9 - Sep 10
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, (1,000 reviews)
"Very nice and convenient hotel."
United States
Karen
$165 nightly
The price is $184
Sep 7 - Sep 8
Total with taxes and fees
The Yankee Inn
In-room safe, desk, laptop workspace, iron/ironing board

13. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (893 reviews)
"Great place"
United States
Luciane
$79 nightly
The price is $88
Aug 31 - Sep 1
Total with taxes and fees
Howard Johnson by Wyndham Lenox
Free daily buffet breakfast

14. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
"Great comfortable beds Good breakfast"
United States
Nancy
$130 nightly
The price is $146
Sep 13 - Sep 14
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, (1,027 reviews)
"Clean and modern hotel close to the center part of Lenox."
United States
Ivana
$145 nightly
The price is $162
Sep 8 - Sep 9
Total with taxes and fees
Berkshires Untold
Property amenity

16. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (648 reviews)
"Helpful staff, clean room and great facilities."
United Kingdom
Laura
$186 nightly
The price is $208
Aug 19 - Aug 20
Total with taxes and fees
Courtyard by Marriott Lenox Berkshires
Lobby

17. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,000 reviews)
"Very nice stay"
United States
Christine
$107 nightly
The price is $120
Aug 31 - Sep 1
Total with taxes and fees
Quality Inn Lee - Lenox South
Lake

18. 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, (1,002 reviews)
"enjoyable stay"
United States
James
$134 nightly
The price is $150
Sep 7 - Sep 8
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lobby

19. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,525 reviews)
"Pool and staff was great"
United States
peter
$128 nightly
The price is $142
Aug 27 - Aug 28
Total with taxes and fees
Vacation Village in the Berkshires
Lobby

20. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (32 reviews)
"Great staff very friendly rooms very clezn"
United States
Lawrence
$203 nightly
The price is $227
Sep 7 - Sep 8
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

Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent
"Perfect for our needs , excellent location"
Alex 1-night trip
Posted 2 hours ago
Comfort Inn & Suites East Greenbush - Albany

Find out more about Pittsfield

Pittsfield Resorts information

Number of reviews
12,470
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: 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. In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants - Ski resort steps from Jiminy Peak Mountain Resort. 7.6 mi (12.3 km) from Pittsfield. Access to ski-in/ski-out access, a fitness center, 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 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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