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 7 - Aug 9
In two weeks
Aug 14 - Aug 16
In one month
Aug 28 - Aug 30
In two months
Sep 25 - Sep 27
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
7.8 out of 10, Good, (1,005 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
$111 nightly
The price is $124
Aug 2 - Aug 3
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, (1,010 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
$99 nightly
The price is $110
Aug 5 - Aug 6
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,030 reviews)
"Clean room, friendly staff, nice property"
United States
Joseph
$142 nightly
The price is $158
Aug 27 - Aug 28
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, (900 reviews)
"Very clean and updated simple motel."
United States
christopher
$90 nightly
The price is $101
Jul 30 - Jul 31
Total with taxes and fees
Berkshire Inn
Desk, iron/ironing board, WiFi (free), bed sheets

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (861 reviews)
"Some of the furniture and rugs show age. The bed was comfortable and the staff was always available to help!"
United States
DAVID
$62 nightly
The price is $69
Aug 5 - Aug 6
Total with taxes and fees
FairBridge Inn Express
Property entrance

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (881 reviews)
"Beautiful room with an amazing lobby."
United States
Dragana
$219 nightly
The price is $245
Aug 2 - Aug 3
Total with taxes and fees
Hotel On North
Exterior

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (381 reviews)
"Large, clean, comfortable suite."
United States
Rena
$104 nightly
The price is $117
Aug 5 - Aug 6
Total with taxes and fees
The Central Downtown 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, (145 reviews)
"Breakfast was good, good location, friendly staff."
United States
Courtney
$145 nightly
The price is $162
Aug 2 - Aug 3
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
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, (698 reviews)
"Five Star stay!"
United States
Adeline
$192 nightly
The price is $215
Aug 9 - Aug 10
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
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 30 - Jul 31
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.
$1,180 nightly
The price is $1,283
Aug 3 - Aug 4
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, (1,028 reviews)
"The breakfast buffet is wonderfully extensive."
United States
Stephanie
$156 nightly
The price is $174
Aug 4 - Aug 5
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, (890 reviews)
"Great place"
United States
Luciane
$99 nightly
The price is $111
Jul 30 - Jul 31
Total with taxes and fees
Howard Johnson by Wyndham Lenox
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,022 reviews)
"Nice place to stay."
United States
Debra
$154 nightly
The price is $172
Aug 23 - Aug 24
Total with taxes and fees
Berkshires Untold
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, (1,005 reviews)
"Perfect place to stay if going to Tanglewood or Stockbridge."
United States
Barry
$163 nightly
The price is $182
Aug 23 - Aug 24
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
Lobby

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,483 reviews)
"Great and tranquil location, good sleeps, friendly and helpful staff, would do it again."
United States
Melanie
$134 nightly
The price is $150
Aug 11 - Aug 12
Total with taxes and fees
Vacation Village in the Berkshires
BBQ/picnic area

Hideaway Inn Lenox

Hideaway Inn Lenox
2.0 star property
Lenox
7.8 out of 10, Good, (27 reviews)
"Wonderful pet-friendly property in a fantastic location. Everything in the village is just a short walk away, making it easy to enjoy local shops, restaurants, and attractions."
United States
Leonardo
$151 nightly
The price is $169
Jul 30 - Jul 31
Total with taxes and fees
Hideaway Inn Lenox
Lobby

Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (31 reviews)
"Great hotel- clean, spacious and the most friendly, helpful staff"
United States
Bruce
$212 nightly
The price is $237
Aug 13 - Aug 14
Total with taxes and fees
Element by Marriott Lenox Berkshires
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,010 reviews)
"great location very clean friendly staff"
United States
Jeanne
$127 nightly
The price is $142
Aug 24 - Aug 25
Total with taxes and fees
Quality Inn Lee - Lenox South
Property amenity

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (642 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
$212 nightly
The price is $236
Aug 19 - Aug 20
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

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"It turned out to be a great choice. Staff were present twenty-four hours a day and were very friendly. The breakfast was excellent, and everything was well-maintained."
Dennis 4-night trip
Posted less than an hour ago
Quality Inn Great Barrington

Find out more about Pittsfield

Pittsfield Resorts information

Number of reviews
7,973
Accommodation
28 Resorts
Lowest Price
$69
Highest Price
$1,283

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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