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, (965 reviews)
"Big spacious rooms, great bed, great bath."
United States
John
$124 nightly
The price is $138
Nov 2 - Nov 3
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, (1,233 reviews)
"beautiful location, giant suite room for incredible value"
United States
Michael
$115 nightly
The price is $128
Nov 25 - Nov 26
Total with taxes and fees
Berkshire Mountain Lodge
A modern hotel with a large entrance, multiple floors, and a well-lit facade.

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (247 reviews)
"Very nice rooms, staff friendly."
United States
Ginger
$95 nightly
The price is $106
Nov 24 - Nov 25
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.

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, (1,000 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 hotel room with a large bed, two bedside lamps, a chair, and a window with curtains.

6. Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (939 reviews)
"It was an ok place to stay for 2 nights"
United States
cheryl
$79 nightly
The price is $88
Nov 26 - Nov 27
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, (430 reviews)
"Consistently, a clean, quiet, convenient location and comfortable stay."
United States
Debra
$89 nightly
The price is $100
Nov 24 - Nov 25
Total with taxes and fees
The Central Downtown Inn & Suites
A hotel room with a large bed, a separate sitting area, a bathtub, and a large mirror.

8. FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (927 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 19 - Nov 20
Total with taxes and fees
FairBridge Inn Express
A wooden deck with a table and chairs, surrounded by a white railing.

9. 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 28 - Oct 29
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.

10. 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.
$1,060 nightly
The price is $1,149
Oct 28 - Oct 29
Total with taxes and fees
Hancock Village Inn Near Jiminy Peak
Two Adirondack chairs facing a river with a forested hill in the background.

11. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,006 reviews)
"The location was good for our trip."
United States
Basil
$106 nightly
The price is $118
Nov 1 - Nov 2
Total with taxes and fees
The Yankee Inn
A multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.

12. 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 28 - Oct 29
Total with taxes and fees
Howard Johnson by Wyndham Lenox
Exterior

13. 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
$110 nightly
The price is $122
Nov 2 - Nov 3
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.

14. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (679 reviews)
"Great stay!"
United States
Vandhana
$126 nightly
The price is $140
Nov 1 - Nov 2
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.

15. Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,052 reviews)
"A very good place to stay"
United States
Madhavi R
$133 nightly
The price is $149
Nov 3 - Nov 4
Total with taxes and fees
Berkshires Untold
A lodge with a large building and a dock by a lake, surrounded by forest.

16. 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, (1,013 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

17. Garden Gables

Garden Gables
4.0 star property
Lenox
$184 nightly
The price is $206
Nov 1 - Nov 2
Total with taxes and fees
Garden Gables
A Super 8 motel with a two-story building, a parking lot, and a picnic table.

18. 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 16 - Nov 17
Total with taxes and fees
Quality Inn Lee - Lenox South
A hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.

19. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (47 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 8 - Nov 9
Total with taxes and fees
Element by Marriott Lenox Berkshires
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

20. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,799 reviews)
"We had an amazing stay."
United States
Luke
$128 nightly
The price is $143
Nov 1 - Nov 2
Total with taxes and fees
Vacation Village in the 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
"Great"
Anna 1-night trip
Posted 3 hours ago
Vacation Village in the Berkshires

Find out more about Pittsfield

Pittsfield Villas information

Number of reviews
12,359
Accommodation
4 Villas
Lowest Price
$72
Highest Price
$1,149

Frequently asked questions

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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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