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 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14
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, (959 reviews)
"This was an excellent hotel. Super convenient right in the middle of town, clean, huge rooms, historic, and comfortable, I would love to stay here again I would recommend it to anyone!"
United States
Devon
$137 nightly
The price is $153
Nov 5 - Nov 6
Total with taxes and fees
Hotel On North
A modern hotel with a large entrance, multiple floors, and a well-lit facade.

2. 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, (244 reviews)
"Very nice rooms, staff friendly."
United States
Ginger
$95 nightly
The price is $106
Nov 19 - Nov 20
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A hotel lobby with a snow-covered entrance and a sign reading "Lobby".

3. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,221 reviews)
"Beautiful location. Easy access to local restaurants and hiking trails."
United States
Joel
$118 nightly
The price is $132
Nov 9 - Nov 10
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, (1,006 reviews)
"Room was spacious and clean"
United States
James
$98 nightly
The price is $109
Nov 15 - Nov 16
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
A multi-story hotel with a clear entrance, a covered waiting area, and a landscaped front yard.

5. 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
$128 nightly
The price is $143
Nov 1 - Nov 2
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
A motel with a parking lot, a swimming pool, and outdoor seating.

6. Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (938 reviews)
"It was an ok place to stay for 2 nights"
United States
cheryl
$83 nightly
The price is $92
Nov 21 - Nov 22
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, (427 reviews)
"Consistently, a clean, quiet, convenient location and comfortable stay."
United States
Debra
$89 nightly
The price is $100
Nov 2 - Nov 3
Total with taxes and fees
The Central Downtown Inn & Suites
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
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, (925 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
$66 nightly
The price is $73
Oct 26 - Oct 27
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
8.4 out of 10, Very good, (10 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 25 - Oct 26
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.
$1,060 nightly
The price is $1,149
Oct 27 - Oct 28
Total with taxes and fees
Hancock Village Inn Near Jiminy Peak
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

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
$101 nightly
The price is $112
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.

13. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (929 reviews)
"Really enjoyed our one night stay in this hotel"
United States
Aleksandr
$79 nightly
The price is $88
Oct 25 - Oct 26
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, (1,002 reviews)
"Breakfast was great"
United States
Thomas
$110 nightly
The price is $122
Oct 30 - Oct 31
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, (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.

16. Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,046 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.

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, (1,003 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
$115 nightly
The price is $128
Nov 15 - Nov 16
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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, (1,003 reviews)
"Had a comfortable stay."
United States
Lucinda
$83 nightly
The price is $93
Nov 17 - Nov 18
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 snow-covered outdoor area with a patio, seating, and a covered dining area.

20. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
"Lovely room, comfortable bed and a nice breakfast."
United Kingdom
judith
$160 nightly
The price is $179
Oct 27 - Oct 28
Total with taxes and fees
The Cornell Inn, Lenox & 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

The Yankee Inn

The Yankee Inn

8/10 Good
"Efficient & comfortable. Very good value."
brian 1-night trip
Posted 1 hour ago
The Yankee Inn

Find out more about Pittsfield

Pittsfield Villas information

Number of reviews
9,997
Accommodation
4 Villas
Lowest Price
$73
Highest Price
$1,149

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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