Pittsfield, MA Villas Rentals

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Recommended hotels in Pittsfield

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

1. Hotel On North

Pittsfield

Philip

$112 nightly

Nov 29 - Nov 30

Total with taxes and fees

2. Berkshire Mountain Lodge

Pittsfield

Susan J

$108 nightly

Dec 10 - Dec 11

Total with taxes and fees

A multi-story hotel with a prominent entrance, a parking lot, and a flagpole.

3. Hilton Garden Inn Lenox Pittsfield

Pittsfield

James

$119 nightly

Nov 15 - Nov 16

Total with taxes and fees

A modern hotel with a large entrance, multiple floors, and a well-lit facade.

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

Pittsfield

Ruth

$110 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

Pittsfield

James

$93 nightly

Dec 1 - Dec 2

Total with taxes and fees

A hotel room with a large bed, two bedside lamps, a chair, and a window with curtains.

6. Berkshire Inn

Pittsfield

cheryl

$85 nightly

Dec 11 - Dec 12

Total with taxes and fees

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

Pittsfield

Debra

$93 nightly

Nov 13 - Nov 14

Total with taxes and fees

A multi-story hotel with a prominent sign for Holiday Inn & Suites.

8. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

Mark

$98 nightly

Dec 11 - Dec 12

Total with taxes and fees

A hotel room with a large bed, a separate sitting area, a bathtub, and a large mirror.

9. FairBridge Inn Express

Pittsfield

William

$79 nightly

Nov 11 - Nov 12

Total with taxes and fees

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!

Pittsfield

Stephen L.

$421 nightly

Nov 12 - Nov 13

Total with taxes and fees

A large white house with black shutters, surrounded by snow-covered trees and a fence.

11. Hancock Village Inn Near Jiminy Peak

Hancock

Price F.

$1,008 nightly

Nov 17 - Nov 18

Total with taxes and fees

Two Adirondack chairs facing a river with a forested hill in the background.

12. The Yankee Inn

Lenox

Stephanie

$113 nightly

Nov 15 - Nov 16

Total with taxes and fees

A hotel entrance with a covered driveway, a sign for Hampton Inn & Suites by Hilton, and a brick building with multiple windows.

13. Hampton Inn & Suites Berkshires-Lenox

Lenox

Thomas

$110 nightly

Nov 17 - Nov 18

Total with taxes and fees

A multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.

14. Howard Johnson by Wyndham Lenox

Lenox

Aleksandr

$79 nightly

Nov 11 - Nov 12

Total with taxes and fees

A hotel room with a bed, a television, a wardrobe, and a bathroom visible through an open door.

15. Garden Gables

Lenox

Eyee

$188 nightly

Nov 23 - Nov 24

Total with taxes and fees

A covered outdoor area with stone pillars and a view of a road and green hills.

16. Courtyard by Marriott Lenox Berkshires

Lenox

Vandhana

$126 nightly

Nov 15 - Nov 16

Total with taxes and fees

A large, modern two-story house with a prominent gable roof, large windows, and a covered porch area.

17. Berkshires Untold

Lenox

Brian

$118 nightly

Nov 17 - Nov 18

Total with taxes and fees

A lodge with a large building and a dock by a lake, surrounded by forest.

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

Lee

Gustavo

$107 nightly

Dec 6 - Dec 7

Total with taxes and fees

A hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.

19. Element by Marriott Lenox Berkshires

Lenox

Francis

$135 nightly

Nov 29 - Nov 30

Total with taxes and fees

A Super 8 motel with a two-story building, a parking lot, and a picnic table.

20. Quality Inn Lee - Lenox South

Lee

Bernardo Jr

$86 nightly

Dec 6 - Dec 7

Total with taxes and fees

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Learn more about Pittsfield

Nestled in the heart of the Berkshires, this cultural hub boasts the renowned Berkshire Museum and historic Colonial Theatre. Outdoor enthusiasts can hike nearby Pittsfield State Forest trails before exploring the vibrant downtown's farm-to-table restaurants and local art galleries.

See all hotels in Pittsfield

A historic building with a clock, a flag, and a street lamp.

Top reviews in Pittsfield

Hotel On North

Pittsfield

10/10 Excellent

The Hotel on North is a thoughtful and beautiful transformation of 2 old contiguous buildings, a store and factory, into a hip and fun hotel. The spaces are extremely large and open from the common spaces to the guest rooms, including the bathrooms. The aesthetic is colorful and friendly rather than the cookie cutter faux luxury I usually find in expensive hotels. The quirky design features such as vintage furniture and painted floors are a great juxtaposition to the perfect bed linens and...

Steve

Hilton Garden Inn Lenox Pittsfield

Pittsfield

10/10 Excellent

t

The Yankee Inn

Lenox

10/10 Excellent

We had a fantastic stay at the Yankee! Our adjoining rooms were clean, large and comfortable. We loved that the rooms had a fireplace and balcony! All the amenities were appreciated. The breakfast had so many offerings, including fresh fruit and two kinds of eggs. The front desk staff (especially George) were professional, helpful and friendly. This was our first stay at the Yankee, but it won't be the last!

Colleen

Berkshire Mountain Lodge

Pittsfield

10/10 Excellent

Elliott

Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

10/10 Excellent

Gregory

The Central Downtown Inn & Suites

Pittsfield

10/10 Excellent

Beautiful room, very conveniently located right next to a main strip of little shops, theaters and restaurants. We brought all of our own food and were able to store it safely, roomy refrigerator provided- and all cooking utensils, pots, pans, plates... Everything provided. There was a dvd player, and we were able to have movie nights, and a back balcony to enjoy coffee on the porch or read a book in a heavily wooded area which provided a nice shady view to block the parking lot. The front desk...

Anonymous traveler

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

10/10 Excellent

Gipsy

An aerial view of a large estate with multiple buildings, surrounded by dense greenery and trees.

Inn at Silver Maple Farm

East Chatham

10/10 Excellent

Michelle

A large, two-story house with a well-maintained lawn and a fence.

Devonfield Inn B&B

Lee

10/10 Excellent

Anonymous traveler

Courtyard by Marriott Lenox Berkshires

Lenox

10/10 Excellent

Alyssa

Shaker Mill Inn

West Stockbridge

10/10 Excellent

This was the most comfortable B&B I have every heard of let alone stayed at. It does not have the awkwardness of eating breakfast in a community room of strangers. All the breakfast amenities are in you room, including the food that is stock daily by the inn keepers, so you get to enjoy in the comforts of your room (which is a cozy as home). The room was so spacious and well kept. Every detail is thought of by the innkeepers and if they forgot something they are accessible and gracious to...

Joe

A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

Brook Farm Inn

Lenox

10/10 Excellent

roberta

A large, two-story building with a symmetrical facade, multiple windows, and a central entrance with a covered porch.

Harbour House Inn

Cheshire

10/10 Excellent

Anonymous traveler

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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Pittsfield Vacation Rentals
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Villas in Pittsfield

Bundle & Save

OneKeyCash

Upfront pricing

Find vacation rentals that suit your style

Check prices for these dates

Recommended hotels in Pittsfield

1. Hotel On North

2. Berkshire Mountain Lodge

3. Hilton Garden Inn Lenox Pittsfield

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

5. Best Western Plus Berkshire Hills Inn & Suites

6. Berkshire Inn

7. The Central Downtown Inn & Suites

8. Holiday Inn & Suites Pittsfield-Berkshires by IHG

9. FairBridge Inn Express

10. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

11. Hancock Village Inn Near Jiminy Peak

12. The Yankee Inn

13. Hampton Inn & Suites Berkshires-Lenox

14. Howard Johnson by Wyndham Lenox

15. Garden Gables

16. Courtyard by Marriott Lenox Berkshires

17. Berkshires Untold

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

19. Element by Marriott Lenox Berkshires

20. Quality Inn Lee - Lenox South

Learn more about Pittsfield

Top reviews in Pittsfield

Hotel On North

10/10 Excellent

Frequently Asked Questions

Why book your villa in Pittsfield with Expedia?

How can I find cheap villas in Pittsfield?

What is there to do near my villa in Pittsfield?

Explore a world of travel with Expedia