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Best Resorts in Pittsfield

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Check prices for these dates

Next weekend
Aug 14 - Aug 16
In two weeks
Aug 21 - Aug 23
In one month
Sep 4 - Sep 6
In two months
Oct 2 - Oct 4
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, (1,003 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, (1,011 reviews)
"Lots of construction going on, but the staff was great. They valet-parked my car and had it waiting for me in the morning. The room was clean and comfortable."
United States
David
$127 nightly
The price is $142
Aug 23 - Aug 24
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, (1,050 reviews)
"Clean room, friendly staff, nice property"
United States
Joseph
$141 nightly
The price is $155
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, (886 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, (904 reviews)
"Very clean and updated simple motel."
United States
christopher
$88 nightly
The price is $98
Aug 11 - Aug 12
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, (387 reviews)
"Large, clean, comfortable suite."
United States
Rena
$100 nightly
The price is $112
Sep 1 - Sep 2
Total with taxes and fees
The Central Downtown Inn & Suites
Indoor 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
9.4 out of 10, Exceptional, (152 reviews)
"Breakfast was good, good location, friendly staff."
United States
Courtney
$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

8. FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (864 reviews)
"Some of the furniture and rugs show age. The bed was comfortable and the staff was always available to help!"
United States
DAVID
$59 nightly
The price is $66
Aug 18 - Aug 19
Total with taxes and fees
FairBridge Inn Express
Breakfast, lunch and dinner served

9. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (698 reviews)
"Five Star stay!"
United States
Adeline
$168 nightly
The price is $188
Sep 7 - Sep 8
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
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, (9 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
$492 nightly
The price is $550
Aug 10 - Aug 11
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.
$1,120 nightly
The price is $1,217
Sep 8 - Sep 9
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, (1,012 reviews)
"First class staff and wonderful breakfast."
United States
Larry
$137 nightly
The price is $153
Aug 9 - Aug 10
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, (892 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, (1,008 reviews)
"Great comfortable beds Good breakfast"
United States
Nancy
$139 nightly
The price is $155
Aug 31 - Sep 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, (1,017 reviews)
"Clean and modern hotel close to the center part of Lenox."
United States
Ivana
$144 nightly
The price is $161
Sep 7 - Sep 8
Total with taxes and fees
Berkshires Untold
Lobby

16. 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)
"great location very clean friendly staff"
United States
Jeanne
$101 nightly
The price is $113
Aug 31 - Sep 1
Total with taxes and fees
Quality Inn Lee - Lenox South
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, (1,005 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

18. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,513 reviews)
"I have been visiting this property for years and it is always great. Can’t beat it after a few days of adventure in the Berkshires"
United States
Brooks
$128 nightly
The price is $143
Aug 31 - Sep 1
Total with taxes and fees
Vacation Village in the Berkshires
Property amenity

19. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (645 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

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
$212 nightly
The price is $237
Aug 19 - Aug 20
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

Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"Evening staff member was very friendly and helpful. Inn located on a Main Street, walking distance to several stores . Refrigerator was not cool enough and no freezer . Breakfast set up was good but a little crowded . Big surprise when train went through at night."
Diane 1-night trip
Posted 10 hours ago
Quality Inn Great Barrington

Find out more about Pittsfield

Pittsfield Resorts information

Number of reviews
8,079
Accommodation
28 Resorts
Lowest Price
$66
Highest Price
$1,217

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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