Hotels in Cherry Plain

Q: What hotels do travelers recommend in Cherry Plain?

Guests like Vacation Village in the Berkshires , The Williams Inn and Jiminy Peak Mountain Resort .

Where to?

Dates

November 2026

December 2026

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Where to stay in Cherry Plain?

A kitchen with a countertop, a refrigerator, and a window.

1. The Villager Motel

Williamstown

$77 total

includes taxes & fees

Dec 1 - Dec 2

An outdoor seating area with Adirondack chairs and potted plants.

2. Cozy Corner Motel

Williamstown

$88 total

includes taxes & fees

Nov 3 - Nov 4

A patio area with outdoor furniture, a fire pit, and potted plants.

3. The Springs Motel

New Ashford

$117 total

includes taxes & fees

Nov 4 - Nov 5

A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

4. Vacation Village in the Berkshires

Williamstown

$117 total

includes taxes & fees

Nov 3 - Nov 4

A patio area with wooden chairs and tables, surrounded by dense greenery and trees.

5. Willows Motel Williamstown

Williamstown

$99 total

includes taxes & fees

Nov 3 - Nov 4

A small, single-story building with a green roof and a white exterior. There are two large trees in front of the building, each with a flower pot on top. The surrounding area has grass, a few pumpkins, and a small garden with red flowers.

6. Williamstown Motel

Williamstown

$99 total

includes taxes & fees

Nov 8 - Nov 9

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

7. The Yankee Inn

Lenox

$128 total

includes taxes & fees

Nov 20 - Nov 21

A resort with multiple buildings, a parking area, and a mountainous backdrop.

8. Jiminy Peak Mountain Resort

Hancock

$150 total

includes taxes & fees

Nov 3 - Nov 4

9. Hotel Downstreet, an Ascend Collection Hotel

North Adams

$133 total

includes taxes & fees

Nov 23 - Nov 24

A building with a covered parking area and a grassy front yard.

10. Howard Johnson by Wyndham Williamstown

Williamstown

$112 total

includes taxes & fees

Nov 22 - Nov 23

A garden with a swing set, a blue chair, and a flower bed.

11. Maple Terrace Motel

Williamstown

$111 total

includes taxes & fees

Nov 3 - Nov 4

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

12. Hotel On North

Pittsfield

$130 total

includes taxes & fees

Nov 29 - Nov 30

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

13. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

$104 total

includes taxes & fees

Dec 1 - Dec 2

A hotel room with a bed, two bedside lamps, a chair, a dresser, a mirror, and a painting on the wall.

14. Rodeway Inn

Adams

$75 total

includes taxes & fees

Dec 2 - Dec 3

A dining table set for two with red plates, silverware, and a wine glass, viewed through a window overlooking a red building.

15. Gregory House Country Inn

Averill Park

$139 total

includes taxes & fees

Nov 4 - Nov 5

A hotel with a covered entrance, stone facade, and arched windows.

16. Comfort Inn & Suites East Greenbush - Albany

Castleton-on-Hudson

$126 total

includes taxes & fees

Nov 23 - Nov 24

A fire feature with a metal frame and a brick wall in the background.

17. Fairfield Inn & Suites by Marriott Williamstown

Williamstown

$171 total

includes taxes & fees

Nov 8 - Nov 9

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

18. Berkshire Inn

Pittsfield

$92 total

includes taxes & fees

Nov 28 - Nov 29

A large, multi-story building with a prominent stone facade and a metal roof, surrounded by landscaped gardens and a pedestrian bridge.

19. The Williams Inn

Williamstown

$240 total

includes taxes & fees

Nov 8 - Nov 9

20. Berkshire Mountain Lodge

Pittsfield

$128 total

includes taxes & fees

Nov 8 - Nov 9

View all properties

Go beyond your typical stay in Cherry Plain

Check out reviews of Cherry Plain hotels guests love

Cozy Corner Motel

Williamstown

10/10 Exceptional

Henry

Willows Motel Williamstown

Williamstown

10/10 Exceptional

Sandra

Maple Terrace Motel

Williamstown

10/10 Exceptional

Eric

Vacation Village in the Berkshires

Williamstown

10/10 Exceptional

Anonymous traveler

The Villager Motel

Williamstown

10/10 Exceptional

Anonymous traveler

Hotel On North

Pittsfield

10/10 Exceptional

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

Williamstown Motel

Williamstown

10/10 Exceptional

Douglas

The Yankee Inn

Lenox

10/10 Exceptional

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

Hotel Downstreet, an Ascend Collection Hotel

North Adams

10/10 Exceptional

Ann

Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

10/10 Exceptional

Gregory

Jiminy Peak Mountain Resort

Hancock

10/10 Exceptional

Lloyd A.

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

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

Pittsfield

10/10 Exceptional

William

A garden with a stone wall, various plants, and a small shed.

Gardner Farm Inn

Troy

10/10 Exceptional

My daughter and I were in town for one night to tour RPI. We certainly chose well with our overnight accommodations. Although the house is quaint, extra clean, and decorated perfectly, the star of our stay was the innkeeper, John. From the moment we walked in, it was like seeing an old friend. John was friendly, kind and took excellent care of us. His hospitality made us want to come back again....very soon.

Victoria

Two people relaxing by a poolside with drinks, a building in the background, and a clear sky.

The Porches Inn at Mass MoCA

North Adams

10/10 Exceptional

Stacey

Berkshire Mountain Lodge

Pittsfield

10/10 Exceptional

Elliott

Fairfield Inn & Suites by Marriott Williamstown

Williamstown

10/10 Exceptional

Diane

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 Exceptional

Michelle

Frequently Asked Questions

What hotels do travelers recommend in Cherry Plain?

Guests like Vacation Village in the Berkshires, The Williams Inn and Jiminy Peak Mountain Resort.

Can I book a refundable hotel in Cherry Plain?

If you want the flexibility to change your travel plans to Cherry Plain, most properties offer refundable* bookable rates. You can see these properties by searching our site and using the "fully refundable" filter to narrow down the results.

What will the weather in Cherry Plain be like during my vacation?

July and August are typically the warmest months in Cherry Plain when the average temp is 65°F. January and February are the coldest months when the average temperature is 26°F. October and December are the months with the most rain.

Why should I book my Cherry Plain hotel through Hotels.com?

There are lots of reasons to book your Cherry Plain trip with us: our free cancellations on selected hotels* gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.