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 11 - Sep 13
In two weeks
Sep 18 - Sep 20
In one month
Oct 2 - Oct 4
In two months
Oct 30 - Nov 1
No exact matches found, but these alternatives could be just right

Recommended hotels in Pittsfield

Room

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, (1,009 reviews)
"Look good for being under constructikn"
United States
Debra
$118 nightly
The price is $132
Sep 7 - Sep 8
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)

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, (1,006 reviews)
"Quite comfortable Beds"
United States
Jermaine
$106 nightly
The price is $118
Sep 7 - Sep 8
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
Lobby

3. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,107 reviews)
"A nice place to stay in the Berkshires."
United States
Robert
$108 nightly
The price is $120
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, (906 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
Exterior

5. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.4 out of 10, Very Good, (403 reviews)
"Large, clean, comfortable suite."
United States
Rena
$89 nightly
The price is $100
Sep 22 - Sep 23
Total with taxes and fees
The Central Downtown Inn & Suites
Room

6. Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (915 reviews)
"Excellent room super clean!"
United States
Adriana
$86 nightly
The price is $96
Sep 1 - Sep 2
Total with taxes and fees
Berkshire Inn
Pool

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (181 reviews)
"Clean & easy to stay there"
United States
Steve
$118 nightly
The price is $132
Sep 8 - Sep 9
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Restaurant

8. 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
$148 nightly
The price is $165
Sep 13 - Sep 14
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
Room

9. FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (889 reviews)
"It was very nice and everyone was extremely helpful"
United States
ERICIA
$61 nightly
The price is $68
Sep 1 - Sep 2
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.
$496 nightly
The price is $554
Sep 2 - Sep 3
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, (1,004 reviews)
"Very nice and convenient hotel."
United States
Karen
$100 nightly
The price is $112
Sep 28 - Sep 29
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, (907 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
$79 nightly
The price is $88
Sep 1 - Sep 2
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
9.2 out of 10, Wonderful, (1,001 reviews)
"Great comfortable beds Good breakfast"
United States
Nancy
$121 nightly
The price is $135
Sep 30 - Oct 1
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, (1,005 reviews)
"Great hotel with fabulous outdoor sitting space"
United States
Christine
$145 nightly
The price is $162
Sep 28 - Sep 29
Total with taxes and fees
Berkshires Untold
Lobby

16. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,595 reviews)
"All the amenities offered are an excellent plus. Good rates for rooms. Good place to stay at, lots to do even around the area"
United States
Alex
$106 nightly
The price is $118
Sep 3 - Sep 4
Total with taxes and fees
Vacation Village in the Berkshires
Lake

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, (1,003 reviews)
"enjoyable stay"
United States
James
$128 nightly
The price is $142
Sep 21 - Sep 22
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Property amenity

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
Lobby

19. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (36 reviews)
"Great staff very friendly rooms very clezn"
United States
Lawrence
$178 nightly
The price is $199
Sep 7 - Sep 8
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
8.4 out of 10, Very Good, (1,006 reviews)
"Very nice stay"
United States
Christine
$110 nightly
The price is $122
Sep 20 - Sep 21
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

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"The Red Lion Inn is always charming and comfortable!"
Maureen R 1-night trip
Posted 1 hour ago
The Red Lion Inn

Find out more about Pittsfield

Pittsfield Resorts information

Number of reviews
11,770
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. Enjoy the ski-in/ski-out access, 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. Amenities include 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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