Top 10 Hotels in Cherry Plain, NY from ₩105,078 - 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

₩106,299

₩133,250 total

includes taxes & fees

Nov 11 - Nov 12

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

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

A wooden cabin with a porch and steps leading to a door, surrounded by snow.

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

2. Jiminy Peak Mountain Resort

Hancock

Olga

₩177,426

₩198,185 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.

An outdoor seating area with stone fire pit, chairs, and a red building in the background.

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

3. The Williams Inn

Williamstown

Pete

₩268,786

₩300,234 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 reception area with a wooden reception desk, a bar area in the background, and a decorative wall piece.

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

4. Fairfield Inn & Suites by Marriott Williamstown

Williamstown

Josh

₩190,948

₩213,289 total

includes taxes & fees

Nov 16 - Nov 17

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

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

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

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

5. The Springs Motel

New Ashford

Elizabeth

₩140,171

₩153,768 total

includes taxes & fees

Nov 1 - Nov 2

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

A motel with multiple rooms, a parking area, and a large tree in the foreground.

6. Howard Johnson by Wyndham Williamstown

Williamstown

Barbara

₩132,296

₩147,776 total

includes taxes & fees

Nov 22 - Nov 23

A hotel room with a bed, a sofa, a TV, and a desk with a lamp.

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

A bookshelf with various books and pamphlets, including titles like 'JIMINY' and 'Berkshire Landscapes'.

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

7. Hotel Downstreet, an Ascend Collection Hotel

North Adams

mary ellen

₩157,712

₩176,164 total

includes taxes & fees

Nov 22 - Nov 23

An outdoor seating area with Adirondack chairs and potted plants.

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

A reception area with a bulletin board, a 'no smoking' sign, a clock, and a 'STOP' sign.

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

8. Cozy Corner Motel

Williamstown

Frank

₩98,835

₩116,671 total

includes taxes & fees

Nov 12 - Nov 13

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

A hay bale display with pumpkins and scarecrows.

A white two-story building with a porch, labeled as a motel.

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.

9. Willows Motel Williamstown

Williamstown

David

₩111,867

₩124,952 total

includes taxes & fees

Nov 8 - Nov 9

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

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 a coffee machine, a water dispenser, and a sign indicating the fitness center.

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

₩129,107

₩144,212 total

includes taxes & fees

Nov 16 - Nov 17

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

A house with a porch, snow-covered ground, and a Christmas tree with lights.

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

A swimming pool with lounge chairs and a fence.

11. Maple Terrace Motel

Williamstown

yeraldine

₩130,986

₩146,307 total

includes taxes & fees

Nov 9 - Nov 10

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

A kitchen with a refrigerator, a coffee maker, and a microwave.

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

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

12. The Villager Motel

Williamstown

DONNA

₩99,232

₩110,849 total

includes taxes & fees

Nov 16 - Nov 17

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

A cozy living room with a fireplace, a red armchair, a bookshelf, and a coffee table.

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

₩207,553

₩261,394 total

includes taxes & fees

Nov 23 - Nov 24

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

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.

A cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster 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, chairs, a coffee table, and a rug. There is a kitchen area with a refrigerator and a water dispenser.

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

15. Williamstown Motel

Williamstown

Ahmet

₩105,979

₩118,378 total

includes taxes & fees

Nov 8 - Nov 9

A white two-story house with a sloped roof, large windows, and a small porch.

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

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

16. 1896 House Country Inn & Motels

Williamstown

Maryann

₩140,578

₩157,025 total

includes taxes & fees

Nov 14 - Nov 15

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

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

17. Hotel On North

Pittsfield

Devon

₩165,519

₩184,885 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.

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

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

18. Gregory House Country Inn

Averill Park

DONNA

₩148,847

₩165,221 total

includes taxes & fees

Oct 25 - Oct 26

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

A banquet table set for a formal event with candles, glassware, and folded napkins.

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

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

19. Hilton Garden Inn Troy

Troy

Cameron

₩154,140

₩171,095 total

includes taxes & fees

Nov 16 - Nov 17

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

A hotel room with a wooden desk, a flat-screen TV, a coffee maker, a blue chair, and a lamp.

20. Hampton Inn & Suites Berkshires-Lenox

Lenox

Thomas

₩145,077

₩162,050 total

includes taxes & fees

Nov 4 - Nov 5

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Top Cherry Plain Hotel Reviews

The Williams Inn

10/10 Excellent

"The staff and ambience are wonderful!"

Berkshires Untold

10/10 Excellent

"Berkshires Untold is THE PLACE to stay in Lenox. The rooms are terrific. They've been beautifully upgraded and the bathrooms are big and as nice as can be. We were concerned about the noise from the cars on Rte 7 as our room faced the street, but it was not an issue whatsoever. The breakfasts were just right. Coffee was plentiful and ready in the morning when we got up. And the owners (or managers) are suburb; they handled a problem I had with such grace and so generously I was astounded! Bottom line: next time we return for a Foliage experience, we're coming back to the Berkshires Untold!"

Berkshire Mountain Lodge

10/10 Excellent

"Wonderful place to stay for short or long time. Everything is just perfect."

Best Western Plus Franklin Square Inn Troy/Albany

10/10 Excellent

"The hotel was very nice and clean. The free breakfast was great, especially the coffee. It was very conveniently located. Theres no bar or restaurant, but its within walking distance of several. The parking was a little tricky because they had a gate closing off the biggest parking lot which forced us to drive the wrong way around the hotel, but otherwise it was a really good stay for the price and would definitely stay there again if I was visiting Troy."

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent

"The parking lot was being resurfaced and we could not find a handicap spot near the door. It was inconvenient, and one handicap spot was filled by a car without a handicap placard."

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent

"Wonderful staff , great location ! Fresh brownies offered at check in , specialty cocktails in the evening , lovely breakfast in the morning:)"

Vacation Village in the Berkshires

8/10 Good

"Very easy check in. Clean and safe."

The Yankee Inn

10/10 Excellent

"I would prefer more flexibility making reservations. Online and by phone, I wanted two rooms for two people. I was forced to request two rooms for THREE people to work around the algorithm that allowed only one room for two people. Also I was forced to accept two rooms in the same price range, when I wanted one premium king, not two. I left another hotel due to their inflexibility, and I will choose one with a personal approach next time."

Hotel Downstreet, an Ascend Collection Hotel

8/10 Good

"Forgot the woman’s name who checked us in but she was so helpful and friendly with awesome dinner suggestions. Locations was great to walk around town"

More cheap stays in Cherry Plain

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

₩94,072

₩105,078 total

Oct 26 - Oct 27

includes taxes & fees

5.4/10 (926 reviews)

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

1055 South Street Pittsfield MA

₩125,694

₩140,400 total

Nov 24 - Nov 25

includes taxes & fees

Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St Pittsfield MA

₩129,107

₩144,212 total

Nov 16 - Nov 17

includes taxes & fees

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

The Yankee Inn

461 Pittsfield Rd Lenox MA

₩140,503

₩156,942 total

Nov 1 - Nov 2

includes taxes & fees

9.2/10 Wonderful! (1,003 reviews)

Comfort Inn & Suites East Greenbush - Albany

99 Miller Rd Castleton-on-Hudson NY

₩150,700

₩167,277 total

Nov 13 - Nov 14

includes taxes & fees

Best Western Plus Franklin Square Inn Troy/Albany

One Fourth Street Troy NY

₩210,371

₩233,512 total

Oct 26 - Oct 27

includes taxes & fees

8.8/10 Excellent! (1,001 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 ₩105,078

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. Howard Johnson by Wyndham Williamstown

7. Hotel Downstreet, an Ascend Collection Hotel

8. Cozy Corner Motel

9. Willows Motel Williamstown

10. Best Western Plus Berkshire Hills Inn & Suites

11. Maple Terrace Motel

12. The Villager Motel

13. The Porches Inn at Mass MoCA

14. The Yankee Inn

15. Williamstown Motel

16. 1896 House Country Inn & Motels

17. Hotel On North

18. Gregory House Country Inn

19. Hilton Garden Inn Troy

20. Hampton Inn & Suites Berkshires-Lenox

Top Cherry Plain Hotel Reviews

The Williams Inn

Berkshires Untold

Berkshire Mountain Lodge

Best Western Plus Franklin Square Inn Troy/Albany

Hampton Inn & Suites Berkshires-Lenox

The Cornell Inn, Lenox & The Berkshires

Vacation Village in the Berkshires

The Yankee Inn

Hotel Downstreet, an Ascend Collection Hotel

More cheap stays in Cherry Plain

FairBridge Inn Express

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

Best Western Plus Berkshire Hills Inn & Suites

The Yankee Inn

Comfort Inn & Suites East Greenbush - Albany

Best Western Plus Franklin Square Inn Troy/Albany

Frequently asked questions

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