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

Villas in Pittsfield

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

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, (961 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
$132 nightly
The price is $148
Nov 10 - Nov 11
Total with taxes and fees
Hotel On North
A hotel lobby with a snow-covered entrance and a sign reading "Lobby".

2. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,226 reviews)
"Beautiful location. Easy access to local restaurants and hiking trails."
United States
Joel
$115 nightly
The price is $128
Nov 22 - Nov 23
Total with taxes and fees
Berkshire Mountain Lodge
A multi-story hotel with a clear entrance, a covered waiting area, and a landscaped front yard.

3. 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
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, (1,000 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 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, (244 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 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
$86 nightly
The price is $96
Oct 25 - Oct 26
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, (428 reviews)
"Consistently, a clean, quiet, convenient location and comfortable stay."
United States
Debra
$99 nightly
The price is $111
Oct 25 - Oct 26
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, (926 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
8.4 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.
$444 nightly
The price is $496
Oct 26 - Oct 27
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 27 - Oct 28
Total with taxes and fees
Hancock Village Inn Near Jiminy Peak
Exterior

11. 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 31 - Nov 1
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
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)
"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
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, (1,048 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 Super 8 motel with a two-story building, a parking lot, and a picnic table.

16. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.6 out of 10, Excellent, (1,005 reviews)
"Perfect for a travel stop-over."
United States
James
$83 nightly
The price is $93
Nov 19 - Nov 20
Total with taxes and fees
Quality Inn Lee - Lenox South
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, (1,009 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
$109 nightly
The price is $122
Nov 22 - Nov 23
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.

18. 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.

19. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,004 reviews)
"Wonderful staff , great location ! Fresh brownies offered at check in , specialty cocktails in the evening , lovely breakfast in the morning:)"
United States
Sandra
$160 nightly
The price is $179
Oct 27 - Oct 28
Total with taxes and fees
The Cornell Inn, Lenox & The Berkshires
Exterior

20. Garden Gables

Garden Gables
4.0 star property
Lenox
$184 nightly
The price is $205
Nov 2 - Nov 3
Total with taxes and fees
Garden Gables
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pittsfield Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"beautiful location, giant suite room for incredible value"
Michael 4-night trip
Posted 1 hour ago
Berkshire Mountain Lodge

Find out more about Pittsfield

Pittsfield Villas information

Number of reviews
10,256
Accommodation
4 Villas
Lowest Price
$72
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.

Explore a world of travel with Expedia