Top 10 Hotels in Cherry Plain, NY from ₩105,270 - Competitive Prices

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Our top choices for Cherry Plain hotels

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

A spacious living room with large windows, a fireplace, and a variety of seating options.

An outdoor patio area with tables and chairs, green umbrellas, and a building with large windows.

1. Vacation Village in the Berkshires

Williamstown

Luke

₩106,493

₩133,493 total

includes taxes & fees

Nov 11 - Nov 12

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

A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

A restaurant interior with wooden tables and chairs, hanging light fixtures, and large windows allowing natural light.

A cozy living room with a stone fireplace, comfortable seating, and a welcoming sign.

2. Jiminy Peak Mountain Resort

Hancock

Olga

₩177,750

₩198,546 total

includes taxes & fees

Oct 25 - Oct 26

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

A spacious interior with a wooden staircase, a seating area with patterned cushions, and large windows allowing natural light.

A bar area with wooden beams, red chairs, and a long wooden table.

A spacious living area with a fireplace, wooden beams, and a large window.

3. The Williams Inn

Williamstown

Pete

₩269,276

₩300,781 total

includes taxes & fees

Nov 8 - Nov 9

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

A modern restaurant with a long counter, multiple seating areas, and pendant lighting.

A Fairfield Inn & Suites by Marriott hotel with a brick facade, large windows, and a covered outdoor seating area.

A modern living room with a fireplace, comfortable seating, a flat-screen TV, and a stone accent wall.

4. Fairfield Inn & Suites by Marriott Williamstown

Williamstown

Josh

₩191,296

₩213,677 total

includes taxes & fees

Nov 16 - Nov 17

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

A poolside area with lounge chairs, umbrellas, and a swimming pool.

A hotel room with a large bed, a desk, a chair, and a view of the outdoors.

A bar area with stools, a counter displaying fruits and beverages, and a sign reading "Springs".

5. The Springs Motel

New Ashford

Elizabeth

₩140,293

₩153,901 total

includes taxes & fees

Nov 1 - Nov 2

A hotel room with a bed, a sofa, a TV, and a bathroom visible through an open door.

A modern cafe with a wooden accent wall, a coffee machine, and black chairs.

A reception area with a large landscape painting, a dark reception desk, and a potted plant.

A modern hotel building with the name "Hotel Downtown" on the facade.

6. Hotel Downstreet, an Ascend Collection Hotel

North Adams

mary ellen

₩158,000

₩176,486 total

includes taxes & fees

Nov 22 - Nov 23

A hotel room with a large bed, two bedside tables with lamps, a desk with a chair, and a small window.

A rectangular swimming pool with a wooden deck surrounding it.

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

A dining area with wooden chairs and tables, a kitchen counter with appliances, and framed pictures on the wall.

7. Howard Johnson by Wyndham Williamstown

Williamstown

Barbara

₩132,537

₩148,045 total

includes taxes & fees

Nov 22 - Nov 23

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

A hotel room with two blue upholstered chairs, a wooden table with a lamp, a TV mounted on the wall, and a wooden dresser with drawers.

A hay bale display with pumpkins and scarecrows.

A hotel room with a TV, a desk, a chair, a dresser, a bed with a patterned bedspread, and a microwave.

8. Willows Motel Williamstown

Williamstown

David

₩112,071

₩125,180 total

includes taxes & fees

Nov 8 - Nov 9

An outdoor seating area with Adirondack chairs and potted plants.

A building with a double door labeled "WELCOME" and "OFFICE," a "PARKING ONLY" sign, and flower baskets on either side of the entrance.

A sign with the word "CLARM" on a grassy field with a road and trees in the background.

A hotel room with a large bed, two bedside lamps, a nightstand, a framed picture on the wall, and a window with curtains.

9. Cozy Corner Motel

Williamstown

Frank

₩99,015

₩116,883 total

includes taxes & fees

Nov 12 - Nov 13

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

A Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.

A hotel room with a patterned carpet, a sofa, a chair, a small table, a lamp, a television on a cabinet, and two framed pictures on the wall.

A reception area with grey upholstered chairs, a wooden reception desk, and a colorful pear painting on the wall.

10. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

James

₩129,342

₩144,474 total

includes taxes & fees

Nov 16 - Nov 17

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

A motel named 'The Villager Motel' with a 'VACANCY' sign, a picnic table, and a red planter on the lawn.

A park with picnic tables, a playground, and a large coniferous tree.

A hotel room with two beds, a nightstand with a lamp, a television, and framed artwork on the wall.

11. The Villager Motel

Williamstown

DONNA

₩99,413

₩111,051 total

includes taxes & fees

Nov 16 - Nov 17

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

A garden with a wooden pergola, potted plants, and a lawn with chairs.

A swimming pool with lounge chairs and a fence.

A breakfast buffet setup with cereal, milk, juice, and pastries.

12. Maple Terrace Motel

Williamstown

yeraldine

₩131,225

₩146,574 total

includes taxes & fees

Nov 8 - Nov 9

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

A hallway with a collection of plates on the walls, leading to a staircase.

A row of colorful Victorian-style houses with a prominent red one labeled "PORCHES."

Two people sitting by a campfire in a wooded area with benches and a clear view of the surrounding trees.

13. The Porches Inn at Mass MoCA

North Adams

Ram

₩207,932

₩261,872 total

includes taxes & fees

Nov 22 - Nov 23

A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

A swimming pool with a surrounding deck, a stone wall, and a building in the background.

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

14. The Yankee Inn

Lenox

Basil

₩140,503

₩156,942 total

includes taxes & fees

Nov 1 - Nov 2

A blue wooden deck with white picket railings, surrounded by a well-maintained lawn and colorful autumn foliage.

A kitchen with a fireplace, dining area, and a large window with curtains.

A living room with a sofa, coffee table, and fireplace. There is a kitchen area with cabinets and a refrigerator.

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.

15. Williamstown Motel

Williamstown

Marina

₩106,173

₩118,596 total

includes taxes & fees

Nov 8 - Nov 9

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

A lobby with a red sofa, two armchairs, a wooden table with a vase, brick walls, and an ornate ceiling.

A restaurant with a large open dining area, wooden tables and chairs, and a brick wall with a colorful mural.

A spacious room with a large window, a brick wall, a sofa set, and a patterned carpet.

16. Hotel On North

Pittsfield

Devon

₩165,820

₩185,220 total

includes taxes & fees

Nov 8 - Nov 9

A cozy living room with a leather sofa, a wooden coffee table with a vase of flowers, and a staircase leading to an upper level.

An outdoor seating area with tables and chairs covered in beige cloths, connected by a string of lights.

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

17. Gregory House Country Inn

Averill Park

DONNA

₩149,119

₩165,522 total

includes taxes & fees

Oct 24 - Oct 25

A room with plaid wallpaper, a lamp on a table, and a chair.

A covered porch with white furniture and green chairs, surrounded by lush greenery.

A pool area with a white building, a fence, and trees in the background.

18. 1896 House Country Inn & Motels

Williamstown

Maryann

₩140,835

₩157,313 total

includes taxes & fees

Oct 25 - Oct 26

A spacious hotel lobby with a reception desk, seating area, and a large chandelier.

A hotel lobby with a fireplace, seating area, and a bar.

A spacious dining area with a buffet table, multiple dining tables, and chairs.

A hotel room with a bed, a bedside table with a coffee maker, and a lamp.

19. Hilton Garden Inn Troy

Troy

Cameron

₩154,447

₩171,437 total

includes taxes & fees

Nov 16 - Nov 17

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

A hotel room with a bed, a desk, a sofa, a round table, and a large window with curtains.

A spacious living area with a high ceiling, a staircase with a wooden railing, a large blue patterned rug, and a white sofa.

A spacious living room with a stone fireplace, large windows, and modern furniture.

20. Comfort Inn & Suites East Greenbush - Albany

Castleton-on-Hudson

barbara

₩145,341

₩161,327 total

includes taxes & fees

Nov 12 - Nov 13

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Top Cherry Plain Hotel Reviews

Jiminy Peak Mountain Resort

8/10 Good

"The rooms are outdated but they were clean. The hot tubs were down unfortunately which was one reason we booked this resort so that was a bummer but the staff was great and the price was right. The views were gorgeous and it's near hiking trails and a bike trail. Would book it again if they update their rooms and amenities."

Berkshires Untold

10/10 Excellent

"The lobby was absolutely beautiful, aesthetically and structurally! From all the greenery from the plants to the high ceilings, cute seating areas, and nice bar. The outdoor furniture was a plus, especially with the fire pits and the surrounded by the nice view of the berkshires. After an evening out, we came back and played a board game in the lobby and even did a little painting of our own while enjoying some good cocktails…you can definitely create a vibe. The room was clean, and overall it was a great stay if you’re just looking to relax, unwind, and get away for a bit!"

Berkshire Mountain Lodge

10/10 Excellent

"We've stayed at Berkshire Mountain Lodge in October a number of times now, and we really enjoy the property. The rooms are well-appointed, very clean, and quite comfortable. We appreciate the free washers and dryers as well as the many other amenities, and you cannot beat the location. There's a supermarket down the driveway and across the street and an excellent specialty grocer--Guido's Market--just down the road. We highly recommend this property. The District Restaurant in Pittsfield is excellent. We've also seen several great plays at Barrington Theatre Company. The area is loaded with historical and cultural activities. We like the proximity to Lenox and the Edith Wharton mansion as well as The Clark art museum in Williamstown, both of which have lovely grounds/gardens typically exhibiting sculptures. There are also abundant outdoor activities and opportunities for hiking and lovely scenic drives. This was a good year for fall color, and the red maples were glorious! It's a short ride to Vermont where we checked out Mt. Equinox for the first time. Highly recommend the drive to the top on a sunny, clear day."

The Yankee Inn

10/10 Excellent

"This is a five star property. Wonderful breakfast. Indoor pool and hot tub. Convenient free parking. Comfortable bedroom with all the amenities. I recommend to anyone visiting the Lenox/Pittsfield area. Good restaurants nearby."

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent

"Unique and very thoughtfully thought through. Welcome bottle of wine, welcome drink, and breakfast were great! Wish the bar was open later and breakfast started earlier, but this is a minor thing. Would definitely stay there again."

The Williams Inn

10/10 Excellent

"Great location, large room with very comfy bed. Water and coffee every floor by the elevator."

Best Western Plus Berkshire Hills Inn & Suites

8/10 Good

"We had a good stay the staff when I arrived was super nice and personable and we really like the amenities. I really like the water that was filtered in the front and the breakfast was very good choices. Our room was very clean and the TV selection was great."

Courtyard by Marriott Albany Troy/Waterfront

8/10 Good

"We enjoyed our stay at Courtyard by Marriott Albany Troy/Waterfront. As with all Marriott's we've stayed at it was quite clean and the staff was friendly. Our room was nice, with a very comfortable bed, We did not get to partake of many amenities, but the person working reception did offer to light the fire pit for us (we declined, as it was not as enticing at night as it looked in the day pics). Would recommend it, and we will stay there again when visiting Troy again!"

Hilton Garden Inn Troy

10/10 Excellent

"Great place to stay and close to the waterfront!"

More cheap stays in Cherry Plain

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

₩94,243

₩105,270 total

Oct 26 - Oct 27

includes taxes & fees

5.4/10 (925 reviews)

Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St Pittsfield MA

₩129,342

₩144,474 total

Nov 16 - Nov 17

includes taxes & fees

8.4/10 Very Good! (1,000 reviews)

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

1055 South Street Pittsfield MA

₩131,225

₩146,578 total

Nov 22 - Nov 23

includes taxes & fees

The Yankee Inn

461 Pittsfield Rd Lenox MA

₩140,503

₩156,942 total

Nov 1 - Nov 2

includes taxes & fees

9.2/10 Wonderful! (1,002 reviews)

Comfort Inn & Suites East Greenbush - Albany

99 Miller Rd Castleton-on-Hudson NY

₩145,341

₩161,327 total

Nov 12 - Nov 13

includes taxes & fees

Best Western Plus Franklin Square Inn Troy/Albany

One Fourth Street Troy NY

₩185,464

₩205,864 total

Oct 29 - Oct 30

includes taxes & fees

8.8/10 Excellent! (1,000 reviews)

Frequently asked questions

Where is the best place to stay in Cherry Plain?

Vacation Village in the Berkshires, located 5.7 mi (9.2 km) from the heart of Cherry Plain, is a top choice for your stay based on our traveler data. Two other choices for your visit to the area are Berkshire Mountain Lodge and The Yankee Inn. See all available top hotels, or vacation rentals in Cherry Plain.

If I need to cancel my hotel reservation in Cherry Plain, will I receive a refund?

Yes! Most room reservations are refundable if you cancel before the hotel's cancellation deadline, which often is within 24-48 hours of your arrival date. If you have a non-refundable reservation, you might be able to still cancel and receive a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Cherry Plain.

Where can I learn more about changing or cancelling my trip to Cherry Plain?

To access more information about rescheduling or cancelling your trip to Cherry Plain, go to https://www.expedia.com/service/.

What is staying in Cherry Plain like?

Visitors to Cherry Plain are sure to find plenty to explore and enjoy. There are 630 hotels and other accommodations in the surrounding area. Find out more about Cherry Plain.

What should I see while I'm in Cherry Plain?

Places to visit in the wider area include Brodie Mountain, Williamstown Theatre Festival, and Jiminy Peak Mountain Resort. You'll also find Taconic Lake and Mount Greylock State Reservation in the area. Check out what more to see and do in Expedia's Cherry Plain guide.

What's the weather like in Cherry Plain?

The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 26°F. The snowiest months in Cherry Plain are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

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Book Hotels in Cherry Plain on Expedia.com

Find hotels in Cherry Plain, NY from ₩105,270

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Cherry Plain

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Cherry Plain hotels

1. Vacation Village in the Berkshires

2. Jiminy Peak Mountain Resort

3. The Williams Inn

4. Fairfield Inn & Suites by Marriott Williamstown

5. The Springs Motel

6. Hotel Downstreet, an Ascend Collection Hotel

7. Howard Johnson by Wyndham Williamstown

8. Willows Motel Williamstown

9. Cozy Corner Motel

10. Best Western Plus Berkshire Hills Inn & Suites

11. The Villager Motel

12. Maple Terrace Motel

13. The Porches Inn at Mass MoCA

14. The Yankee Inn

15. Williamstown Motel

16. Hotel On North

17. Gregory House Country Inn

18. 1896 House Country Inn & Motels

19. Hilton Garden Inn Troy

20. Comfort Inn & Suites East Greenbush - Albany

Top Cherry Plain Hotel Reviews

Jiminy Peak Mountain Resort

Berkshires Untold

Berkshire Mountain Lodge

The Yankee Inn

The Cornell Inn, Lenox & The Berkshires

The Williams Inn

Best Western Plus Berkshire Hills Inn & Suites

Courtyard by Marriott Albany Troy/Waterfront

Hilton Garden Inn Troy

More cheap stays in Cherry Plain

FairBridge Inn Express

Best Western Plus Berkshire Hills Inn & Suites

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

The Yankee Inn

Comfort Inn & Suites East Greenbush - Albany

Best Western Plus Franklin Square Inn Troy/Albany

Frequently asked questions

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