Best Resorts in Pittsfield

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Resorts in Pittsfield

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Recommended hotels in Pittsfield

Lobby sitting area
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, (1003)
"I have stayed here many times and it is consistently a comfortable, clean and quiet place."
United States
Jeanine
$93 nightly
The price is $104
Nov 16 - Nov 17
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (58)
"Room was far from spotless but overall good and nice breakfast. "
United States
Hannah
$110 nightly
The price is $122
Dec 4 - Dec 5
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
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, (954)
"Great stay! Nice quiet room for 2 little “alert “ to outside noise pups!! Comfy beds and central location for the day trips we had planned."
United States
Stacey
$88 nightly
The price is $99
Nov 21 - Nov 22
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (753)
"Everything was so perfect for a weekend to just get away and decompress, the staff were great, the room was awesome. "
United States
Jeff
$120 nightly
The price is $135
Nov 16 - Nov 17
Total with taxes and fees
Berkshire Mountain Lodge
Microwave, oven, stovetop, dishwasher
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

4.0 star property
Pittsfield
8.6 out of 10, Excellent, (343)
"The rooms were large and well appointed! You could easily stay for a while and cook in the room. Nice balcony, nice living room area and very comfy bed and pillows. We enjoyed our stay very much"
United States
Candee
$85 nightly
The price is $95
Nov 16 - Nov 17
Total with taxes and fees
The Central Downtown Inn & Suites
Terrace/patio
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (656)
"Lovely hotel, room was great along with the staff and the grounds where beautiful. Thank you."
United States
Vicki
$111 nightly
The price is $124
Nov 23 - Nov 24
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, (838)
"This property has a mid century motel look from the street but the rooms have been recently upgraded and are fully modern inside. A great value and comfortable place to stay"
United States
Phillip
$75 nightly
The price is $84
Nov 24 - Nov 25
Total with taxes and fees
Berkshire Inn
Front of property - evening/night
Hotel On North

Hotel On North

3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (796)
"Clean room and staff was super friendly"
United States
Yuen
$133 nightly
The price is $149
Nov 16 - Nov 17
Total with taxes and fees
Hotel On North
Fridge, microwave, oven, stovetop
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!

2.0 star property
Pittsfield
7.8 out of 10, Good, (6)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
$440 nightly
The price is $492
Nov 15 - Nov 16
Total with taxes and fees
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Exterior
Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak

Hancock
10.0 out of 10, Exceptional, (15)
"Kids will love the fun bunk room setup, millennials will appreciate the big screen TV's and broadband Internet access, while parentals and grandparents enjoy the fully equipped kitchen and space to enjoy dinner together around a table for 12. Hot tub right outside the kitchen door, close proximity to Jiminy Peak makes it a breeze to shuttle the family back and forth . Extremely clean property.. Rent the extra suite if you have difficulty with stairs, and enjoy having the entire inn to...
United States
Jim O.
$1,026 nightly
The price is $1,111
Nov 18 - Nov 19
Total with taxes and fees
Hancock Village Inn Near Jiminy Peak
Desk, iron/ironing board, free WiFi, bed sheets
FairBridge Inn Express

FairBridge Inn Express

2.5 star property
Pittsfield
5.4 out of 10, (809)
"Room spotless and staff helpful."
United States
William
$75 nightly
The price is $84
Nov 16 - Nov 17
Total with taxes and fees
FairBridge Inn Express
Smart TV
Chic corporate apartment in wonderful Pittsfield with AC, WiFi

Chic corporate apartment in wonderful Pittsfield with AC, WiFi

2.0 star property
Pittsfield
2.0 out of 10, (1)
"THIS. PLACE. IS. A. DUMP. Do NOT STAY HERE under any circumstances."
United States
Michael
$200 nightly
The price is $223
Nov 30 - Dec 1
Total with taxes and fees
Chic corporate apartment in wonderful Pittsfield with AC, WiFi
Garden
Shaker Mill Inn

Shaker Mill Inn

2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (435)
"Nice place, easy check in"
United States
Robert
$106 nightly
The price is $117
Nov 19 - Nov 20
Total with taxes and fees
Shaker Mill Inn
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

3.0 star property
Lenox
9.6 out of 10, Exceptional, (10)
"Very friendly with dog. No complaints with accommodations "
United States
Lilian
$135 nightly
The price is $151
Nov 20 - Nov 21
Total with taxes and fees
Element Lenox Berkshires
Exterior
Cozy Corner Motel

Cozy Corner Motel

2.0 star property
Williamstown
9.2 out of 10, Wonderful, (881)
"Clean, Great Staff, Quiet"
United States
john
$79 nightly
The price is $88
Nov 16 - Nov 17
Total with taxes and fees
Cozy Corner Motel
Lobby
Quality Inn

Quality Inn

2.5 star property
Lee
8.4 out of 10, Very Good, (1000)
"Clean room and good breakfast "
United States
Kelly
$87 nightly
The price is $98
Dec 1 - Dec 2
Total with taxes and fees
Quality Inn
Room, 1 Queen Bed, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
Monument Mountain Motel

Monument Mountain Motel

2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (784)
"This was an older property, but room was nice and bathroom was updated. "
United States
Martha
$67 nightly
The price is $74
Nov 16 - Nov 17
Total with taxes and fees
Monument Mountain Motel
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, (692)
"Solid location, great room, good breakfast. Fair Price. Been 3 different times and look forward to returning again "
United States
Jamie
$102 nightly
The price is $114
Nov 16 - Nov 17
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
In-room safe, desk, free cribs/infant beds, free rollaway beds
Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

2.0 star property
Great Barrington
7.6 out of 10, Good, (558)
"I loved the stay people were nice loved the pool and internet was great "
United States
Jennifer
$75 nightly
The price is $84
Nov 14 - Nov 15
Total with taxes and fees
Travelodge by Wyndham Great Barrington Berkshires
Exterior
The Villager Motel

The Villager Motel

2.0 star property
Williamstown
8.8 out of 10, Excellent, (759)
"It's very good for stay over"
United States
Frances
$69 nightly
The price is $77
Dec 1 - Dec 2
Total with taxes and fees
The Villager Motel
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

Berkshires Untold

Berkshires Untold

10/10 Excellent
"Enjoyed the Clubhouse before retiring in for the evening. Cozy, comfortable, and relaxing atmosphere."
Kim 2-night trip
Posted 3 days ago
Berkshires Untold

Find out more about Pittsfield

Pittsfield Resorts information

Number of reviews
11,298
Accommodation
34 Resorts
Lowest Price
$74
Highest Price
$1,111

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 top-rated resorts near Pittsfield: Berkshire Mountain Lodge - 2.6 mi (4.1 km) from Pittsfield. Mountain Lodge Apt! - 2.6 mi (4.1 km) from Pittsfield. Has a fitness center. All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx. - Only a 5-minute walk from Jiminy Peak Mountain Resort. 7.7 mi (12.4 km) from Pittsfield. Amenities include a sauna. 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 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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