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

Villas in Pittsfield

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21
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, (967 reviews)
"Very nice hotel"
United States
Philip
$128 nightly
The price is $143
Nov 8 - Nov 9
Total with taxes and fees
Hotel On North
A multi-story hotel with a prominent entrance, a parking lot, and a flagpole.

2. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (715 reviews)
"Great place to stay. Great staff and convenient location. Nice restaurant as well."
United States
James
$119 nightly
The price is $133
Nov 15 - Nov 16
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
Exterior

3. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,239 reviews)
"beautiful location, giant suite room for incredible value"
United States
Michael
$118 nightly
The price is $132
Nov 11 - Nov 12
Total with taxes and fees
Berkshire Mountain Lodge
A Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.

4. 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, (1,001 reviews)
"Room was spacious and clean"
United States
James
$93 nightly
The price is $104
Nov 2 - Nov 3
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
A modern hotel with a large entrance, multiple floors, and a well-lit facade.

5. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (250 reviews)
"This a much better Holiday Inn than the one at Saugerties that we went one day before."
United States
Yuguo
$101 nightly
The price is $113
Nov 15 - Nov 16
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A covered porch with a wooden floor and white railing, overlooking a green lawn and a clear blue sky.

6. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.4 out of 10, Very good, (431 reviews)
"Consistently, a clean, quiet, convenient location and comfortable stay."
United States
Debra
$93 nightly
The price is $104
Nov 6 - Nov 7
Total with taxes and fees
The Central Downtown Inn & Suites
A hotel room with a large bed, two bedside lamps, a chair, and a window with curtains.

7. Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (940 reviews)
"It was an ok place to stay for 2 nights"
United States
cheryl
$83 nightly
The price is $92
Nov 28 - Nov 29
Total with taxes and fees
Berkshire Inn
A multi-story hotel with a prominent sign for Holiday Inn & Suites.

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
$103 nightly
The price is $115
Nov 28 - Nov 29
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
A hotel room with a large bed, a separate sitting area, a bathtub, and a large mirror.

9. FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (928 reviews)
"This motel was well-cared for and a good value compared to anywhere close boy on our early-October Saturday night in the busy Berkshires!"
United States
Richard
$65 nightly
The price is $72
Nov 12 - Nov 13
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.
$441 nightly
The price is $493
Oct 30 - Oct 31
Total with taxes and fees
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
A large white house with black shutters, surrounded by snow-covered trees and a fence.

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.
$1,000 nightly
The price is $1,083
Nov 3 - Nov 4
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, (1,011 reviews)
"The location was good for our trip."
United States
Basil
$100 nightly
The price is $112
Nov 3 - Nov 4
Total with taxes and fees
The Yankee Inn
A multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.

13. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (930 reviews)
"Really enjoyed our one night stay in this hotel"
United States
Aleksandr
$79 nightly
The price is $88
Oct 29 - Oct 30
Total with taxes and fees
Howard Johnson by Wyndham Lenox
Exterior

14. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.0 out of 10, Wonderful, (1,000 reviews)
"Breakfast was great"
United States
Thomas
$110 nightly
The price is $122
Nov 4 - Nov 5
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
A covered outdoor area with stone pillars and a view of a road and green hills.

15. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (683 reviews)
"Great stay!"
United States
Vandhana
$126 nightly
The price is $140
Nov 8 - Nov 9
Total with taxes and fees
Courtyard by Marriott Lenox Berkshires
A large, modern two-story house with a prominent gable roof, large windows, and a covered porch area.

16. Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,055 reviews)
"A very good place to stay"
United States
Madhavi R
$144 nightly
The price is $161
Nov 18 - Nov 19
Total with taxes and fees
Berkshires Untold
A lodge with a large building and a dock by a lake, surrounded by forest.

17. 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, (1,000 reviews)
"Amazing place, clean, staff is awesome , amazing location , amazing views! Free breakfast, free coffee bar , free gym and the best it’s pet friendly !"
United States
Gustavo
$110 nightly
The price is $122
Nov 22 - Nov 23
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Dining

18. Garden Gables

Garden Gables
4.0 star property
Lenox
10.0 out of 10, Exceptional, (1 review)
"Lovely place!"
United States
Eyee
$210 nightly
The price is $235
Oct 29 - Oct 30
Total with taxes and fees
Garden Gables
A Super 8 motel with a two-story building, a parking lot, and a picnic table.

19. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.6 out of 10, Excellent, (1,006 reviews)
"Perfect for a travel stop-over."
United States
James
$93 nightly
The price is $103
Nov 18 - Nov 19
Total with taxes and fees
Quality Inn Lee - Lenox South
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

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

8/10 Good
"The room was clean and the staff was friendly and helpful. Lots of parking . The hot tub was nice after a day of biking."
Kathleen 2-night trip
Posted 1 hour ago
Hotel Downstreet, an Ascend Collection Hotel

Find out more about Pittsfield

Pittsfield Villas information

Number of reviews
11,579
Accommodation
4 Villas
Lowest Price
$72
Highest Price
$1,083

Frequently asked questions

Why book your villa in Pittsfield with Expedia?
Reserving a villa in Pittsfield is as easy as deciding on your travel dates and selecting an option that suits your style. Looking for something luxurious or low cost, or a stay that also includes a laundry and kitchen? Use Expedia's search filters to narrow your results and find your ideal pad.
How can I find cheap villas in Pittsfield?
Expedia is here to help you easily source cheap villas in Pittsfield. Use our convenient filter tool to choose star rating, amenities and budget to refine your search and find a perfect stay in a few quick keystrokes.
What is there to do near my villa in Pittsfield?
Pittsfield has enough experiences to keep you going for weeks, starting with Hancock Shaker Village. Pittsfield State Forest, Arrowhead Museum and Bousquet Ski Area are other fantastic attractions. If you're in town for longer, Barrington Stage Company and Berkshire Museum will round off your itinerary nicely.

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