Hotels in Cherry Plain from P5,031 for 2026 - Fully Refundable Options

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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.

A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.

1. Vacation Village in the Berkshires

Williamstown

Luke

P5,103

P6,397 total

includes taxes & fees

Nov 1 - Nov 2

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

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

2. Jiminy Peak Mountain Resort

Hancock

Olga

P8,496

P9,489 total

includes taxes & fees

Nov 7 - Nov 8

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 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.

3. Fairfield Inn & Suites by Marriott Williamstown

Williamstown

Josh

P9,167

P10,240 total

includes taxes & fees

Nov 15 - Nov 16

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".

4. The Springs Motel

New Ashford

Elizabeth

P6,717

P7,369 total

includes taxes & fees

Nov 1 - Nov 2

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

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

5. The Williams Inn

Williamstown

Pete

P12,904

P14,414 total

includes taxes & fees

Nov 8 - Nov 9

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

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

6. Hotel Downstreet, an Ascend Collection Hotel

North Adams

mary ellen

P7,572

P8,458 total

includes taxes & fees

Nov 15 - Nov 16

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

7. Willows Motel Williamstown

Williamstown

David

P5,371

P5,999 total

includes taxes & fees

Nov 1 - Nov 2

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

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

8. Howard Johnson by Wyndham Williamstown

Williamstown

Barbara

P6,351

P7,095 total

includes taxes & fees

Nov 22 - Nov 23

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

9. Cozy Corner Motel

Williamstown

Frank

P4,745

P5,601 total

includes taxes & fees

Nov 2 - Nov 3

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

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

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.

10. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

James

P6,198

P6,924 total

includes taxes & fees

Nov 15 - Nov 16

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

A swimming pool with lounge chairs and a fence.

11. Maple Terrace Motel

Williamstown

yeraldine

P6,289

P7,024 total

includes taxes & fees

Nov 1 - Nov 2

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

12. The Villager Motel

Williamstown

DONNA

P4,764

P5,322 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.

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

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

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

13. The Porches Inn at Mass MoCA

North Adams

Ram

P9,965

P12,549 total

includes taxes & fees

Nov 22 - Nov 23

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

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

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

14. The Yankee Inn

Lenox

Basil

P6,733

P7,521 total

includes taxes & fees

Nov 1 - Nov 2

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 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 living room with a sofa, chairs, a coffee table, and a rug. There is a kitchen area with a refrigerator and a water dispenser.

15. Williamstown Motel

Williamstown

Ahmet

P5,088

P5,683 total

includes taxes & fees

Nov 1 - Nov 2

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

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.

16. Hotel On North

Pittsfield

Devon

P7,925

P8,853 total

includes taxes & fees

Nov 8 - Nov 9

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

A wooden cabinet with a coffee maker and a white container.

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

A hotel room with a bed, a nightstand with a lamp and phone, a chair, and framed pictures on the wall.

17. Hampton Inn & Suites Berkshires-Lenox

Lenox

Thomas

P6,947

P7,759 total

includes taxes & fees

Oct 30 - Oct 31

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

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

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

18. Comfort Inn & Suites East Greenbush - Albany

Castleton-on-Hudson

barbara

P6,965

P7,731 total

includes taxes & fees

Nov 12 - Nov 13

A modern hotel lobby with a dining area, a reception desk, and a bar.

A snack and treat section with shelves stocked with various snacks and beverages, a microwave, and a refrigerator.

An indoor swimming pool with clear blue water, surrounded by lounge chairs and a tiled deck.

An outdoor seating area with blue sofas and a stone fire pit.

19. Hampton Inn & Suites Albany-East Greenbush

East Greenbush

Donald

P8,862

P10,059 total

includes taxes & fees

Oct 30 - Oct 31

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

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

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

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

20. Hilton Garden Inn Troy

Troy

Cameron

P7,401

P8,216 total

includes taxes & fees

Nov 16 - Nov 17

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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!"

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 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!"

Best Western Plus Franklin Square Inn Troy/Albany

10/10 Excellent

"We reserved a room who has trouble with stairs, and this hotel is perfect. It has ample parking, it is clean, and is located right in the downtown area. Our friend was very happy."

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent

"Clean room. Comfortable beds. Good breakfast. Staff were nice and professional."

More cheap stays in Cherry Plain

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

P4,504

P5,031 total

Nov 5 - Nov 6

includes taxes & fees

5.4/10 (925 reviews)

Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St Pittsfield MA

P6,198

P6,924 total

Nov 15 - Nov 16

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

P6,289

P7,024 total

Nov 22 - Nov 23

includes taxes & fees

The Yankee Inn

461 Pittsfield Rd Lenox MA

P6,733

P7,521 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

P6,965

P7,731 total

Nov 12 - Nov 13

includes taxes & fees

Best Western Plus Franklin Square Inn Troy/Albany

One Fourth Street Troy NY

P8,888

P9,866 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.

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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Cherry Plain Hotels

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. Fairfield Inn & Suites by Marriott Williamstown

4. The Springs Motel

5. The Williams Inn

6. Hotel Downstreet, an Ascend Collection Hotel

7. Willows Motel Williamstown

8. Howard Johnson by Wyndham Williamstown

9. Cozy Corner Motel

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. Hotel On North

17. Hampton Inn & Suites Berkshires-Lenox

18. Comfort Inn & Suites East Greenbush - Albany

19. Hampton Inn & Suites Albany-East Greenbush

20. Hilton Garden Inn Troy

Top Cherry Plain Hotel Reviews

Jiminy Peak Mountain Resort

Berkshires Untold

The Yankee Inn

The Williams Inn

Best Western Plus Berkshire Hills Inn & Suites

Courtyard by Marriott Albany Troy/Waterfront

Hilton Garden Inn Troy

Best Western Plus Franklin Square Inn Troy/Albany

Hampton Inn & Suites Berkshires-Lenox

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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