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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

1. 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, (1,004 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
$119 nightly
The price is $133
Aug 30 - Aug 31
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

2. 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, (1,000 reviews)
"Quite comfortable Beds"
United States
Jermaine
$102 nightly
The price is $114
Aug 3 - Aug 4
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
Lobby

3. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,034 reviews)
"Clean room, friendly staff, nice property"
United States
Joseph
$121 nightly
The price is $136
Aug 31 - Sep 1
Total with taxes and fees
Berkshire Mountain Lodge
Desk, iron/ironing board, WiFi (free), bed sheets

4. Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (901 reviews)
"Very clean and updated simple motel."
United States
christopher
$88 nightly
The price is $98
Aug 12 - Aug 13
Total with taxes and fees
Berkshire Inn
Desk, iron/ironing board, WiFi (free), bed sheets

5. 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 11 - Aug 12
Total with taxes and fees
FairBridge Inn Express
Property entrance

6. 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
$199 nightly
The price is $222
Aug 31 - Sep 1
Total with taxes and fees
Hotel On North
Exterior

7. 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
$116 nightly
The price is $130
Aug 2 - Aug 3
Total with taxes and fees
The Central Downtown Inn & Suites
Indoor pool

8. 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, (147 reviews)
"Breakfast was good, good location, friendly staff."
United States
Courtney
$151 nightly
The price is $169
Aug 31 - Sep 1
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
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
$192 nightly
The price is $215
Aug 9 - Aug 10
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.
$486 nightly
The price is $543
Aug 2 - Aug 3
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.
$1,180 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

12. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
"First class staff and wonderful breakfast."
United States
Larry
$142 nightly
The price is $159
Aug 2 - Aug 3
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, (891 reviews)
"Great place"
United States
Luciane
$79 nightly
The price is $88
Aug 30 - Aug 31
Total with taxes and fees
Howard Johnson by Wyndham Lenox
Lobby lounge

14. Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,000 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

15. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
"Great comfortable beds Good breakfast"
United States
Nancy
$147 nightly
The price is $164
Aug 31 - Sep 1
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
Lobby

16. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,487 reviews)
"Great and tranquil location, good sleeps, friendly and helpful staff, would do it again."
United States
Melanie
$128 nightly
The price is $143
Aug 31 - Sep 1
Total with taxes and fees
Vacation Village in the Berkshires
BBQ/picnic area

17. Hideaway Inn Lenox

Hideaway Inn Lenox
2.0 star property
Lenox
8.0 out of 10, Very Good, (28 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
Aug 2 - Aug 3
Total with taxes and fees
Hideaway Inn Lenox
Lobby

18. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (31 reviews)
"Great staff very friendly rooms very clezn"
United States
Lawrence
$220 nightly
The price is $246
Aug 13 - Aug 14
Total with taxes and fees
Element by Marriott Lenox Berkshires
Lobby

19. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,001 reviews)
"great location very clean friendly staff"
United States
Jeanne
$120 nightly
The price is $134
Aug 24 - Aug 25
Total with taxes and fees
Quality Inn Lee - Lenox South
Property amenity

20. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (643 reviews)
"Helpful staff, clean room and great facilities."
United Kingdom
Laura
$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

Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent
"Always enjoy the quietness and the delicious coffee and breakfast. The new upgraded bathrooms are beautiful. Staff always helpful and friendly."
Theresa 1-night trip
Posted 12 hours ago
Comfort Inn & Suites East Greenbush - Albany

Find out more about Pittsfield

Pittsfield Resorts information

Number of reviews
10,508
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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