Cherry Plain Holiday Rentals, New York: Private House Rentals

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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

Rp1.438.042

Rp1.802.645 total

includes taxes & fees

1 Nov - 2 Nov

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 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

Jeffrey

Rp2.400.256

Rp2.681.086 total

includes taxes & fees

19 Oct - 20 Oct

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

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

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

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

3. The Williams Inn

Williamstown

Soleil

Rp3.636.182

Rp4.061.615 total

includes taxes & fees

8 Nov - 9 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 bar area with stools, a counter displaying fruits and beverages, and a sign reading "Springs".

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

4. The Springs Motel

New Ashford

Elizabeth

Rp1.995.283

Rp2.188.826 total

includes taxes & fees

4 Nov - 5 Nov

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

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

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.

5. Fairfield Inn & Suites by Marriott Williamstown

Williamstown

C. David

Rp2.725.767

Rp3.044.682 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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.

6. Hotel Downstreet, an Ascend Collection Hotel

North Adams

Tara

Rp2.133.561

Rp2.383.187 total

includes taxes & fees

1 Nov - 2 Nov

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

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.

A rectangular swimming pool with a wooden deck surrounding it.

7. Howard Johnson by Wyndham Williamstown

Williamstown

Donna

Rp1.968.711

Rp2.199.051 total

includes taxes & fees

19 Oct - 20 Oct

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

Jonathan

Rp1.337.055

Rp1.578.334 total

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

A hay bale display with pumpkins and scarecrows.

9. Willows Motel Williamstown

Williamstown

Charlene

Rp1.513.360

Rp1.690.382 total

includes taxes & fees

4 Nov - 5 Nov

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

A swimming pool with lounge chairs and a fence.

10. Maple Terrace Motel

Williamstown

Deborah

Rp1.772.001

Rp1.979.271 total

includes taxes & fees

9 Nov - 10 Nov

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

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.

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

11. The Villager Motel

Williamstown

DONNA

Rp1.414.021

Rp1.579.408 total

includes taxes & fees

8 Nov - 9 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 blue wooden deck with white picket railings, surrounded by a well-maintained lawn and colorful autumn foliage.

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.

12. Williamstown Motel

Williamstown

Ahmet

Rp1.433.710

Rp1.601.603 total

includes taxes & fees

8 Nov - 9 Nov

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

Rp2.659.255

Rp3.370.251 total

includes taxes & fees

10 Nov - 11 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 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 Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.

14. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

Joe

Rp1.673.199

Rp1.868.964 total

includes taxes & fees

4 Nov - 5 Nov

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

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

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

15. 1896 House Country Inn & Motels

Williamstown

Maryann

Rp1.903.469

Rp2.126.175 total

includes taxes & fees

11 Oct - 12 Oct

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 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.

16. The Yankee Inn

Lenox

Basil

Rp1.898.990

Rp2.121.172 total

includes taxes & fees

1 Nov - 2 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 lobby with a red sofa, two armchairs, a wooden table with a vase, brick walls, and an ornate ceiling.

17. Hotel On North

Pittsfield

Lawrence

Rp2.400.256

Rp2.681.087 total

includes taxes & fees

8 Nov - 9 Nov

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

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

18. Hilton Garden Inn Troy

Troy

Brad

Rp2.114.767

Rp2.347.392 total

includes taxes & fees

18 Oct - 19 Oct

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.

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

19. Gregory House Country Inn

Averill Park

DONNA

Rp2.013.637

Rp2.235.136 total

includes taxes & fees

11 Oct - 12 Oct

A rooftop terrace with outdoor seating, a fire feature, and a view of a river and buildings.

A hotel room with two beds, a desk, a chair, a TV, and a large window offering a view of greenery.

A modern kitchen with built-in appliances, a refrigerator, and a microwave.

A Courtyard by Marriott hotel with a modern design, featuring a prominent glass facade and a well-lit entrance.

20. Courtyard by Marriott Albany Troy/Waterfront

Troy

Karl

Rp2.421.212

Rp2.687.546 total

includes taxes & fees

18 Oct - 19 Oct

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Top Cherry Plain Hotel Reviews

Berkshire Mountain Lodge

10/10 Excellent

"Service is excellent and the location is so convenient. Rooms have amazing amenities!"

Best Western Plus Berkshire Hills Inn & Suites

8/10 Good

"It was fine. No breakfast that I saw"

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

10/10 Excellent

"The property was very well maintained and the room was very clean. Check in was quick and easy. The included breakfast was satisfying. Would stay here again."

Comfort Inn & Suites East Greenbush - Albany

8/10 Good

"It was fine but not remarkable"

Hotel On North

10/10 Excellent

"The hotel location is very good with convenient parking in the rear. We liked the large room. Lighting was a little dim in our room but it was very comfortable and spacious. The staff were very polite and helpful."

Vacation Village in the Berkshires

10/10 Excellent

"We were surprised by the space that we got!! The lay out of the suite was so pleasant. We enjoyed the stay tremendously."

The Yankee Inn

10/10 Excellent

"Although it's an older hotel, it's well maintained.Clean and updated also very friendly staff."

Jiminy Peak Mountain Resort

8/10 Good

"The pool and hot tub were not heated enough. We didn't plan to use any other amenities so that was a disappointment. We enjoyed our stay. The room was good as we are our breakfast and dinner in the room. The kitchen was great and equipped with everything we needed."

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent

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

More cheap stays in Cherry Plain

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

Rp1.111.528

Rp1.241.577 total

12 Oct - 13 Oct

includes taxes & fees

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA

Rp1.414.021

Rp1.579.461 total

21 Oct - 22 Oct

includes taxes & fees

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

1055 South Street Pittsfield MA

Rp1.772.001

Rp1.979.325 total

9 Nov - 10 Nov

includes taxes & fees

9.2/10 Wonderful! (232 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

Rp1.898.990

Rp2.121.172 total

1 Nov - 2 Nov

includes taxes & fees

9.2/10 Wonderful! (1,001 reviews)

Comfort Inn & Suites East Greenbush - Albany

99 Miller Rd Castleton-on-Hudson NY

Rp1.962.625

Rp2.178.514 total

10 Nov - 11 Nov

includes taxes & fees

8.8/10 Excellent! (1,004 reviews)

Best Western Plus Franklin Square Inn Troy/Albany

One Fourth Street Troy NY

Rp2.504.428

Rp2.779.917 total

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.

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Book Hotels in Cherry Plain on Expedia.com

Find hotels in Cherry Plain, NY from Rp1.241.577

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. The Springs Motel

5. Fairfield Inn & Suites by Marriott Williamstown

6. Hotel Downstreet, an Ascend Collection Hotel

7. Howard Johnson by Wyndham Williamstown

8. Cozy Corner Motel

9. Willows Motel Williamstown

10. Maple Terrace Motel

11. The Villager Motel

12. Williamstown Motel

13. The Porches Inn at Mass MoCA

14. Best Western Plus Berkshire Hills Inn & Suites

15. 1896 House Country Inn & Motels

16. The Yankee Inn

17. Hotel On North

18. Hilton Garden Inn Troy

19. Gregory House Country Inn

20. Courtyard by Marriott Albany Troy/Waterfront

Top Cherry Plain Hotel Reviews

Berkshire Mountain Lodge

Best Western Plus Berkshire Hills Inn & Suites

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

Comfort Inn & Suites East Greenbush - Albany

Hotel On North

Vacation Village in the Berkshires

The Yankee Inn

Jiminy Peak Mountain Resort

Hotel Downstreet, an Ascend Collection Hotel

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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