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
Jul 31 - Aug 2
In two weeks
Aug 7 - Aug 9
In one month
Aug 21 - Aug 23
In two months
Sep 18 - Sep 20
No exact matches found, but these alternatives could be just right

Recommended hotels in Pittsfield

Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (1,004 reviews)
"Staff was fabulous and extremely helpful and friendly. Valey parking was terrific!!! and FREE Great to have since we had to park at the bank next to the hotel while there was construction in front of the building. Rooms were tidy and very clean Breakfast was excellent with a large variety of offerings"
United States
Margaret
$130 nightly
The price is $145
Jul 26 - Jul 27
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, desk, laptop workspace, blackout drapes

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, (1,001 reviews)
"Hotel was clean and staff helpful and courteous. Hotel is a little tired (showing it's age) but I would certainly not hesitate to book a future stay."
United States
Andrew
$118 nightly
The price is $132
Jul 26 - Jul 27
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
Indoor pool

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, (137 reviews)
"Breakfast was good, good location, friendly staff."
United States
Courtney
$145 nightly
The price is $162
Jul 26 - Jul 27
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Property entrance

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (877 reviews)
"Beautiful room with an amazing lobby."
United States
Dragana
$249 nightly
The price is $278
Jul 29 - Jul 30
Total with taxes and fees
Hotel On North
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,015 reviews)
"Great location too"
United States
judith
$155 nightly
The price is $173
Aug 19 - Aug 20
Total with taxes and fees
Berkshire Mountain Lodge
Desk, iron/ironing board, WiFi (free), bed sheets

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (887 reviews)
"Clean, quiet, friendly, no frills but everything needed. Mattresses were very good."
United States
James
$90 nightly
The price is $101
Jul 21 - Jul 22
Total with taxes and fees
Berkshire Inn
Exterior

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (379 reviews)
"Central location!"
United States
Brenda
$107 nightly
The price is $120
Jul 21 - Jul 22
Total with taxes and fees
The Central Downtown Inn & Suites
Breakfast, lunch and dinner served

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (697 reviews)
"Five Star stay!"
United States
Adeline
$209 nightly
The price is $233
Jul 22 - Jul 23
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
Desk, iron/ironing board, WiFi (free), bed sheets

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (857 reviews)
"Some of the furniture and rugs show age. The bed was comfortable and the staff was always available to help!"
United States
DAVID
$63 nightly
The price is $70
Jul 27 - Jul 28
Total with taxes and fees
FairBridge Inn Express
Outdoor dining

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.
$493 nightly
The price is $551
Jul 26 - Jul 27
Total with taxes and fees
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Outdoor dining

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.
$983 nightly
The price is $1,064
Jul 21 - Jul 22
Total with taxes and fees
Hancock Village Inn Near Jiminy Peak
Superior Room, 1 King Bed, Jetted Tub | Jetted tub

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,008 reviews)
"A comfortable, clean place with good breakfast, good amenities, and a good hot tub."
United States
Michael
$169 nightly
The price is $189
Jul 22 - Jul 23
Total with taxes and fees
The Yankee Inn
In-room safe, desk, laptop workspace, iron/ironing board

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (885 reviews)
"Great place"
United States
Luciane
$99 nightly
The price is $111
Jul 21 - Jul 22
Total with taxes and fees
Howard Johnson by Wyndham Lenox
Free daily buffet breakfast

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,003 reviews)
"Perfect place to stay if going to Tanglewood or Stockbridge."
United States
Barry
$188 nightly
The price is $210
Aug 19 - Aug 20
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,005 reviews)
"Nice place to stay."
United States
Debra
$165 nightly
The price is $184
Jul 23 - Jul 24
Total with taxes and fees
Berkshires Untold
Lobby

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)
"Great place"
United States
Michelle
$135 nightly
The price is $151
Aug 10 - Aug 11
Total with taxes and fees
Quality Inn Lee - Lenox South
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (464 reviews)
"Wonderful place to stay!"
United States
Mervin
$165 nightly
The price is $181
Jul 22 - Jul 23
Total with taxes and fees
Shaker Mill Inn
Lobby

Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (28 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
$229 nightly
The price is $256
Jul 27 - Jul 28
Total with taxes and fees
Element by Marriott Lenox Berkshires
Lake

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
$168 nightly
The price is $188
Jul 23 - Jul 24
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Property amenity

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (639 reviews)
"I usually stay here when I'm going to a concert at Tanglewood, it's comfortable, quiet, and convenient. The staff are really friendly. There's a Tesla EV charging station directly across Route 20 from the hotel."
United States
Michael
$220 nightly
The price is $246
Jul 26 - Jul 27
Total with taxes and fees
Courtyard 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

Berkshire Inn

Berkshire Inn

10/10 Excellent
"At a good price, it offered a pleasant stay."
Mary Louise 1-night trip
Posted less than an hour ago
Berkshire Inn

Find out more about Pittsfield

Pittsfield Resorts information

Number of reviews
10,567
Accommodation
28 Resorts
Lowest Price
$70
Highest Price
$1,064

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 resort near Pittsfield: Holiday Inn Club Vacations Oak 'n Spruce Resort - Ski resort. 12 mi (19.4 km) from Pittsfield. Enjoy the sauna, fitness center, and terrace.
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 Housatonic River.
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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