𝗧𝗢𝗣 𝟭𝟬 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Cherry Plain (2026)

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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.

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

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

1. Vacation Village in the Berkshires

Williamstown

Denton

S$129

includes taxes & fees

1 Nov - 2 Nov

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

2. The Springs Motel

New Ashford

Elizabeth

S$156

includes taxes & fees

4 Nov - 5 Nov

An outdoor seating area with Adirondack chairs and potted plants.

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

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

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

3. Cozy Corner Motel

Williamstown

Jonathan

S$113

includes taxes & fees

3 Nov - 4 Nov

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.

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

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

4. Williamstown Motel

Williamstown

Ahmet

S$102

includes taxes & fees

8 Nov - 9 Nov

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

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

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.

5. Willows Motel Williamstown

Williamstown

S$121

includes taxes & fees

1 Nov - 2 Nov

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

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

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.

6. The Villager Motel

Williamstown

DONNA

S$113

includes taxes & fees

1 Nov - 2 Nov

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

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.

7. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

Joe

S$134

includes taxes & fees

1 Nov - 2 Nov

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 swimming pool with lounge chairs and a fence.

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

8. Maple Terrace Motel

Williamstown

Deborah

S$142

includes taxes & fees

1 Nov - 2 Nov

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

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

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

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

9. Jiminy Peak Mountain Resort

Hancock

Jeffrey

S$192

includes taxes & fees

18 Oct - 19 Oct

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 blue sofa, yellow armchair, and a coffee table. A staircase leads to an upper level with a balcony.

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

10. Comfort Inn & Suites East Greenbush - Albany

Castleton-on-Hudson

Sean

S$162

includes taxes & fees

29 Oct - 30 Oct

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

A modern interior with a large window, a wooden table, and bar stools.

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

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

11. Hotel Downstreet, an Ascend Collection Hotel

North Adams

Julia

S$171

includes taxes & fees

1 Nov - 2 Nov

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.

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

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

12. Howard Johnson by Wyndham Williamstown

Williamstown

S$157

includes taxes & fees

12 Oct - 13 Oct

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

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

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

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

13. Fairfield Inn & Suites by Marriott Williamstown

Williamstown

S$218

includes taxes & fees

1 Nov - 2 Nov

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.

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

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

14. The Yankee Inn

Lenox

S$152

includes taxes & fees

1 Nov - 2 Nov

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

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 wooden sign for The Gregory House, County Inn and Restaurant, with a rustic design and a natural backdrop.

15. Gregory House Country Inn

Averill Park

DONNA

S$160

includes taxes & fees

13 Oct - 14 Oct

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

A gym with exercise equipment including treadmills, a stationary bike, and free weights.

A conference room with multiple tables and chairs, a flat-screen TV mounted on the wall, and a carpeted floor.

A large indoor swimming pool with clear water, surrounded by tiled walls and a tiled floor.

16. Hampton Inn & Suites Berkshires-Lenox

Lenox

S$163

includes taxes & fees

7 Nov - 8 Nov

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

A library with bookshelves, a television, and two armchairs.

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.

17. Hotel On North

Pittsfield

Lawrence

S$192

includes taxes & fees

2 Nov - 3 Nov

A modern hotel room with a sofa, a TV, a kitchen area with bar stools, and a patterned floor.

A hotel room with a large bed, a desk with a lamp, a television, and a view of the city.

A conference room with a whiteboard, tables, and chairs.

18. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

S$140

includes taxes & fees

7 Nov - 8 Nov

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

A snack bar with shelves of snacks and a refrigerated display.

A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.

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

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

Pittsfield

Sheldon

S$142

includes taxes & fees

9 Nov - 10 Nov

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

A hotel room with a fitness center including a weight machine, an elliptical, and a treadmill.

A hotel room with a desk, computer, TV, and a chair.

A hotel room with a TV, microwave, mini-fridge, desk, chair, mirror, and a coat rack.

20. FairBridge Inn Express

Pittsfield

William

S$85

includes taxes & fees

22 Oct - 23 Oct

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Top Cherry Plain Hotel Reviews

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent

"Property was clean, staff was knowledgeable and cordial. Parking was very easy."

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

10/10 Excellent

"Very nice rooms, staff friendly."

Hotel On North

10/10 Excellent

"This is a great hotel. Large rooms, great amenities and a steak house restaurant that is superb. We like it so much we are staying an extra night."

The Yankee Inn

10/10 Excellent

"Not enough bath clothes towels not enough outlets around the bed for people who have cpap or breathing problems."

The Cornell Inn, Lenox & The Berkshires

8/10 Good

"Nice Inn/B&B in Lenox MA, about a mile from downtown."

Hilton Garden Inn Troy

8/10 Good

"No curtains to pull shut at night. Blind but you could see out through( not sure if could see in from outside. When went to check out no one at front desk. Waited for awhile and finally a person working in restaurant come over took key cards."

Courtyard by Marriott Albany Troy/Waterfront

10/10 Excellent

"Very nice"

Courtyard by Marriott Lenox Berkshires

10/10 Excellent

"I was only there to sleep for a few hours"

More cheap stays in Cherry Plain

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

S$85

22 Oct - 23 Oct

includes taxes & fees

5.4/10 (919 reviews)

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA

S$113

18 Oct - 19 Oct

includes taxes & fees

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

1055 South Street Pittsfield MA

S$142

9 Nov - 10 Nov

includes taxes & fees

9.2/10 Wonderful! (231 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

S$152

1 Nov - 2 Nov

includes taxes & fees

9.2/10 Wonderful! (1,000 reviews)

Comfort Inn & Suites East Greenbush - Albany

99 Miller Rd Castleton-on-Hudson NY

S$162

29 Oct - 30 Oct

includes taxes & fees

Best Western Plus Franklin Square Inn Troy/Albany

One Fourth Street Troy NY

S$199

18 Oct - 19 Oct

includes taxes & fees

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 traveller data. Two other choices for your stay in 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, you'll find most room reservations are fully refundable if cancelled before the hotel's cancellation deadline, which often is within 24-48 hours of check in. If your reservation is non-refundable, you might still have the option to cancel and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Cherry Plain.

What is staying in Cherry Plain like?

Visitors to Cherry Plain will definitely find plenty to explore and enjoy. There are 630 hotels and other accommodation options in the surrounding area. Find out more about Cherry Plain.

What should I do while I'm visiting 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. Take a look at what more there is 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 temperature of 18°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Cherry Plain are January, March, February and November, with each month seeing an average of 18 cm of snowfall.

Cherry Plain Hotels from S$85

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. The Springs Motel

3. Cozy Corner Motel

4. Williamstown Motel

5. Willows Motel Williamstown

6. The Villager Motel

7. Best Western Plus Berkshire Hills Inn & Suites

8. Maple Terrace Motel

9. Jiminy Peak Mountain Resort

10. Comfort Inn & Suites East Greenbush - Albany

11. Hotel Downstreet, an Ascend Collection Hotel

12. Howard Johnson by Wyndham Williamstown

13. Fairfield Inn & Suites by Marriott Williamstown

14. The Yankee Inn

15. Gregory House Country Inn

16. Hampton Inn & Suites Berkshires-Lenox

17. Hotel On North

18. Holiday Inn & Suites Pittsfield-Berkshires by IHG

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

20. FairBridge Inn Express

Top Cherry Plain Hotel Reviews

Hotel Downstreet, an Ascend Collection Hotel

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

Hotel On North

The Yankee Inn

The Cornell Inn, Lenox & The Berkshires

Hilton Garden Inn Troy

Courtyard by Marriott Albany Troy/Waterfront

Courtyard by Marriott Lenox Berkshires

More cheap stays in Cherry Plain

FairBridge Inn Express

Howard Johnson by Wyndham Lenox

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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