Pittsfield Condominium Resorts

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

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Recommended hotels in Pittsfield

A building entrance with a large planter with purple flowers and a small tree.

1. Hotel On North

Pittsfield

Lawrence

HK$1,175 total

includes taxes & fees

1 Nov - 2 Nov

A hotel patio with outdoor seating and a fire pit.

2. Hilton Garden Inn Lenox Pittsfield

Pittsfield

James

HK$1,121 total

includes taxes & fees

1 Nov - 2 Nov

An indoor swimming pool with clear water, tiled floors, and a blue wall.

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

Pittsfield

HK$868 total

includes taxes & fees

11 Nov - 12 Nov

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

4. Berkshire Mountain Lodge

Pittsfield

Kathleen

HK$927 total

includes taxes & fees

9 Nov - 10 Nov

A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

5. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

James

HK$819 total

includes taxes & fees

1 Nov - 2 Nov

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

6. Berkshire Inn

Pittsfield

Linda

HK$754 total

includes taxes & fees

19 Oct - 20 Oct

A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

7. The Central Downtown Inn & Suites

Pittsfield

Rena

HK$868 total

includes taxes & fees

15 Oct - 16 Oct

8. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

Mark

HK$903 total

includes taxes & fees

13 Nov - 14 Nov

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

9. FairBridge Inn Express

Pittsfield

William

HK$544 total

includes taxes & fees

15 Oct - 16 Oct

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.

HK$3,867 total

includes taxes & fees

19 Oct - 20 Oct

A wooden deck with outdoor furniture, including chairs and a table, surrounded by a lush garden and trees.

11. Hancock Village Inn Near Jiminy Peak

Hancock

Price F.

HK$9,017 total

includes taxes & fees

20 Oct - 21 Oct

A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

12. The Yankee Inn

Lenox

Basil

HK$929 total

includes taxes & fees

1 Nov - 2 Nov

A spacious hotel lobby with multiple seating areas, large windows, and a television.

13. Hampton Inn & Suites Berkshires-Lenox

Lenox

Thomas

HK$961 total

includes taxes & fees

1 Nov - 2 Nov

A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

14. Howard Johnson by Wyndham Lenox

Lenox

Aleksandr

HK$692 total

includes taxes & fees

18 Oct - 19 Oct

A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

15. Courtyard by Marriott Lenox Berkshires

Lenox

Tracy

HK$1,101 total

includes taxes & fees

1 Nov - 2 Nov

A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

16. Berkshires Untold

Lenox

Madhavi R

HK$1,141 total

includes taxes & fees

1 Nov - 2 Nov

A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

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

Lee

Gustavo

HK$1,006 total

includes taxes & fees

8 Nov - 9 Nov

18. Quality Inn Lee - Lenox South

Lee

Christine

HK$812 total

includes taxes & fees

3 Nov - 4 Nov

A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.

19. Element by Marriott Lenox Berkshires

Lenox

Kirsty

HK$1,253 total

includes taxes & fees

8 Nov - 9 Nov

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

Williamstown

Pofen

HK$790 total

includes taxes & fees

1 Nov - 2 Nov

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Top Pittsfield Hotel Reviews

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

10/10 Excellent

"Very clean and nice options for breakfast. Helpful staff."

Vacation Village in the Berkshires

10/10 Excellent

"We had a wonderful family stay at Vacation Village in the Berkshires! We traveled with our children and their grandmothers, and it was such a special opportunity to make memories together. Our accommodation felt like two apartments in one, with plenty of space for everyone. We loved the layout and the beautiful views, especially with the fall colors surrounding us. It was lovely to enjoy the scenery right where we were staying. The location was a great base for exploring the Berkshires, and we felt we got excellent value for the price. This trip was very special for our family, and we would love to come back. Highly recommend it for a family getaway!"

Berkshire Mountain Lodge

10/10 Excellent

"Great to have a whole suite not just a room. Even though a little outdated still very nice. Downsides were an absence of food vending machines for when you need a quick snack and don’t want to leave, and hot tub was under renovations which we weren’t made aware of until online check in. Overall very happy."

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