A historic building with classical architecture, a traffic light, and a yellow taxi.

Pittsfield Condominium Resorts to Rent

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7
No exact matches found, but these alternatives could be just right

Recommended hotels in Pittsfield

A multi-story hotel with a classic facade, large windows, and a prominent entrance.

1. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (985 reviews)
"Staff very pleasant and accommodating."
United States
Rosemarie
$112 nightly
The price is $125
Nov 29 - Nov 30
Total with taxes and fees
Hotel On North
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

2. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,273 reviews)
"Excellent stay!!!!"
United States
Susan J
$107 nightly
The price is $119
Dec 16 - Dec 17
Total with taxes and fees
Berkshire Mountain Lodge
A restaurant with multiple dining tables, chairs, and a large Buddha statue centerpiece.

3. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (718 reviews)
"Great place to stay. Great staff and convenient location. Nice restaurant as well."
United States
James
$120 nightly
The price is $134
Nov 22 - Nov 23
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
An indoor swimming pool with clear water, tiled floors, and a blue wall.

4. 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, (260 reviews)
"The room was clean and well kept, breakfast was amazing!"
United States
Ruth
$110 nightly
The price is $123
Nov 20 - Nov 21
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A reception area with a wooden reception desk, a seating area with sofas, a colorful stained glass window, a mounted television, and various potted plants.

5. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.4 out of 10, Very good, (1,002 reviews)
"Room was spacious and clean"
United States
James
$93 nightly
The price is $104
Dec 1 - Dec 2
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
A rectangular pool with a blue interior, surrounded by a grey deck. There are lounge chairs and umbrellas in the background.

6. Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (944 reviews)
"It was an ok place to stay for 2 nights"
United States
cheryl
$81 nightly
The price is $90
Dec 16 - Dec 17
Total with taxes and fees
Berkshire Inn
A covered porch with a wooden floor and white railing, overlooking a green lawn and a clear blue sky.

7. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.4 out of 10, Very good, (436 reviews)
"Consistently, a clean, quiet, convenient location and comfortable stay."
United States
Debra
$91 nightly
The price is $102
Dec 1 - Dec 2
Total with taxes and fees
The Central Downtown Inn & Suites
A large indoor swimming pool with multiple levels of balconies, surrounded by tables and chairs.

8. 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, (1,000 reviews)
"enjoyed our stay"
United States
Mark
$105 nightly
The price is $117
Dec 11 - Dec 12
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
A hotel room with a large bed, a separate bathroom with a bathtub, a large mirror, and a painting on the wall.

9. FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (937 reviews)
"Friendly staff"
United States
William
$79 nightly
The price is $88
Nov 16 - Nov 17
Total with taxes and fees
FairBridge Inn Express
A wooden deck with a table and chairs, surrounded by a white railing.

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
8.6 out of 10, Excellent, (11 reviews)
"Very comfortable and clean accommodations in a nice neighborhood, and a great deck to appreciate the view."
United States
Stephen L.
$423 nightly
The price is $473
Nov 18 - Nov 19
Total with taxes and fees
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
A wooden deck with outdoor furniture, including chairs and a table, surrounded by a lush garden and trees.

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.
$1,008 nightly
The price is $1,091
Nov 17 - Nov 18
Total with taxes and fees
Hancock Village Inn Near Jiminy Peak
Two Adirondack chairs facing a river with a forested hill in the background.

12. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,004 reviews)
"What a beautiful stay. Room was so clean ! Great food selection for breakfast."
United States
Stephanie
$126 nightly
The price is $141
Dec 12 - Dec 13
Total with taxes and fees
The Yankee Inn
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

13. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (938 reviews)
"Really enjoyed our one night stay in this hotel"
United States
Aleksandr
$79 nightly
The price is $88
Nov 16 - Nov 17
Total with taxes and fees
Howard Johnson by Wyndham Lenox
A spacious hotel lobby with multiple seating areas, large windows, and a television.

14. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.0 out of 10, Wonderful, (1,002 reviews)
"Breakfast was great"
United States
Thomas
$108 nightly
The price is $121
Dec 15 - Dec 16
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
A modern bedroom with a four-poster bed, a fireplace, and a large floral mural on the wall.

15. Garden Gables

Garden Gables
4.0 star property
Lenox
10.0 out of 10, Exceptional, (2 reviews)
"Lovely place!"
United States
Eyee
$188 nightly
The price is $210
Nov 23 - Nov 24
Total with taxes and fees
Garden Gables
An outdoor patio area with a circular fire pit surrounded by wicker furniture and a stone fire table.

16. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (690 reviews)
"Great stay!"
United States
Vandhana
$114 nightly
The price is $127
Dec 13 - Dec 14
Total with taxes and fees
Courtyard by Marriott Lenox Berkshires
A spacious bar area with a long counter and multiple stools, a seating area with a sofa and chairs, and a view through large windows to the outdoors.

17. Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,074 reviews)
"Nice Hotel"
United States
Juan
$106 nightly
The price is $119
Nov 17 - Nov 18
Total with taxes and fees
Berkshires Untold
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

18. The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.2 out of 10, Wonderful, (1,002 reviews)
"clean room - pleasant staff"
United States
Tina
$107 nightly
The price is $120
Dec 6 - Dec 7
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A modern living room with a fireplace, two blue armchairs, and decorative vases on the mantel.

19. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.6 out of 10, Excellent, (1,000 reviews)
"Just perfect lodging place for short time travelers"
United States
Bernardo Jr
$85 nightly
The price is $95
Dec 6 - Dec 7
Total with taxes and fees
Quality Inn Lee - Lenox South
A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.

20. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (52 reviews)
"Clean, spacious room Accommodating staff especially Shawn and Jennifer at the front desk. Very nice pool and gym Definitely coming back"
United States
Francis
$135 nightly
The price is $151
Nov 29 - Nov 30
Total with taxes and fees
Element 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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Big place,nice indoor pool with arcade. Fireplace in the suite and nice balcony on 2nd floor units. Really close to Jimney Peak"
John 1-night trip
Posted 13 hours ago
Vacation Village in the Berkshires

Find out more about Pittsfield

Pittsfield Condo Resorts information

Number of reviews
4,204
Accommodation
0 Condo Resorts
Lowest Price
$88
Highest Price
$1,091

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