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 10 - Jul 12
In two weeks
Jul 17 - Jul 19
In one month
Jul 31 - Aug 2
In two months
Aug 28 - Aug 30
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, individually decorated, individually furnished, desk

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)
"clean room, friendly staff, great breakfast"
United States
charles
$136 nightly
The price is $152
Aug 2 - Aug 3
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, (120 reviews)
"Most comfortable hotel bed I've ever slept in"
United States
Matthew
$158 nightly
The price is $176
Jul 8 - Jul 9
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, (687 reviews)
"Five Star stay!"
United States
Adeline
$199 nightly
The price is $222
Jul 6 - Jul 7
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
Desk, iron/ironing board, free WiFi, bed sheets

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (871 reviews)
"I really enjoyed my stay at the Berkshire Inn, it was safe, clean, and in a convenient part of Pittsfield. Parking was a breeze and I was comfortable in my room. I would definitely book again!"
United States
Hannah
$83 nightly
The price is $92
Jul 29 - Jul 30
Total with taxes and fees
Berkshire Inn
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,015 reviews)
"The staff was very helpful. It was very clean and the bed was comfortable. We would stay there again."
United States
Andrew
$155 nightly
The price is $173
Aug 4 - Aug 5
Total with taxes and fees
Berkshire Mountain Lodge
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (841 reviews)
"Plenty of parking. Staff was friendly"
United States
William
$60 nightly
The price is $67
Jul 6 - Jul 7
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, (871 reviews)
"Very nice clean hotel. Close to Colonial theater. Would definitely stay there again."
United States
KEITH AND SHIRLEY
$249 nightly
The price is $278
Jul 7 - Jul 8
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, (373 reviews)
"Easy access to parking, nearby everything and room was very clean. Definitely will come back here to stay again! "
United States
Aisha
$117 nightly
The price is $131
Jul 7 - Jul 8
Total with taxes and fees
The Central Downtown Inn & Suites
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)
"Quiet room. Comfortable bed linens"
United States
Margo
$152 nightly
The price is $170
Aug 3 - Aug 4
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Outdoor dining

Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (20 reviews)
"Really great host - communication was great. House is so close to skiing, can’t beat it "
United States
Stephanie B.
$1,060 nightly
The price is $1,149
Jul 7 - Jul 8
Total with taxes and fees
Hancock Village Inn Near Jiminy Peak
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
8.0 out of 10, Very Good, (8 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.
$536 nightly
The price is $599
Jul 26 - Jul 27
Total with taxes and fees
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
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, (1,002 reviews)
"Great location for sightseeing in the Berkshires. Clean and comfortable room, friendly staff."
Canada
Mark
$124 nightly
The price is $139
Jul 6 - Jul 7
Total with taxes and fees
The Yankee Inn
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (462 reviews)
"Wonderful place to stay!"
United States
Mervin
$156 nightly
The price is $172
Jul 7 - Jul 8
Total with taxes and fees
Shaker Mill Inn
Dining room

Gregory House Country Inn

Gregory House Country Inn
3.0 star property
Averill Park
9.0 out of 10, Wonderful, (110 reviews)
"Wonderful stay! Our room was beautiful - clean and cozy. I had a drink at the outside bar - it was lovely. Highly recommend staying here. It’s a hidden gem."
United States
Michelle
$113 nightly
The price is $125
Jul 6 - Jul 7
Total with taxes and fees
Gregory House Country Inn
Gazebo

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (922 reviews)
"Very clean! Friendly staff! Will stop there again!"
United States
Theresa
$93 nightly
The price is $104
Jul 12 - Jul 13
Total with taxes and fees
Cozy Corner Motel
Lobby lounge

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
$220 nightly
The price is $246
Jul 22 - Jul 23
Total with taxes and fees
Element by Marriott Lenox Berkshires
Restaurant

Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.6 out of 10, Exceptional, (91 reviews)
"Excellent lodge, recommend."
United States
Jason
$169 nightly
The price is $189
Jul 6 - Jul 7
Total with taxes and fees
Little Cat Lodge
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,002 reviews)
$135 nightly
The price is $151
Jul 27 - Jul 28
Total with taxes and fees
Quality Inn Lee - Lenox South
Lobby

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,417 reviews)
"Property is great and stay was great"
United States
Isha
$143 nightly
The price is $159
Jul 6 - Jul 7
Total with taxes and fees
Vacation Village in the Berkshires
Exterior

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (783 reviews)
"very responsive staff excellent check in and check out"
United States
Kathleen
$165 nightly
The price is $184
Jul 27 - Jul 28
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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 Lee - Lenox South

Quality Inn Lee - Lenox South

10/10 Excellent
"Desk staff was impressive."
Joseph 1-night trip
Posted 6 hours ago
Quality Inn Lee - Lenox South

Find out more about Pittsfield

Pittsfield Resorts information

Number of reviews
13,628
Accommodation
28 Resorts
Lowest Price
$67
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 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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