Cherry Plain Holiday Rentals, New York: Private House Rentals

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Our top choices for Cherry Plain hotels

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Hotel

Breakfast included

Heated pool

Balcony or patio

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

Nyra

2.268.629 ₫

2.820.552 ₫ total

includes taxes & fees

31 Aug - 1 Sept

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

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

2. Willows Motel Williamstown

Williamstown

Richard

2.704.312 ₫

3.020.577 ₫ total

includes taxes & fees

25 Aug - 26 Aug

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

A swimming pool with lounge chairs and a fence.

3. Maple Terrace Motel

Williamstown

Annette

3.264.500 ₫

3.646.577 ₫ total

includes taxes & fees

9 Sept - 10 Sept

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

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

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

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

4. Hotel Downstreet, an Ascend Collection Hotel

North Adams

Victoria

3.884.755 ₫

4.339.272 ₫ total

includes taxes & fees

1 Sept - 2 Sept

An outdoor seating area with Adirondack chairs and potted plants.

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.

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

5. Cozy Corner Motel

Williamstown

Jeremy

2.303.431 ₫

2.707.446 ₫ total

includes taxes & fees

9 Sept - 10 Sept

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

A swimming pool with a surrounding deck, a stone wall, and a building 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 hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

6. The Yankee Inn

Lenox

Karen

4.126.328 ₫

4.609.108 ₫ total

includes taxes & fees

14 Sept - 15 Sept

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

A rectangular swimming pool with a wooden deck surrounding it.

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.

7. Howard Johnson by Wyndham Williamstown

Williamstown

Donna

2.872.499 ₫

3.208.612 ₫ total

includes taxes & fees

25 Aug - 26 Aug

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.

8. Gregory House Country Inn

Averill Park

Raghvendra

2.938.050 ₫

3.261.235 ₫ total

includes taxes & fees

25 Aug - 26 Aug

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

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

9. Hilton Garden Inn Troy

Troy

Gary

2.952.414 ₫

3.277.180 ₫ total

includes taxes & fees

31 Aug - 1 Sept

A modern bar area with a central island, multiple bar stools, and a seating area with tables and chairs.

A Holiday Inn & Suites hotel with a modern design, featuring a prominent sign and a well-lit entrance.

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

10. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

Myrna

3.107.804 ₫

3.471.417 ₫ total

includes taxes & fees

21 Sept - 22 Sept

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

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

A hotel lobby with a snow-covered entrance and a sign reading "Lobby".

An indoor swimming pool with a high ceiling, multiple windows, and seating areas.

11. Berkshire Mountain Lodge

Pittsfield

Robert

2.470.473 ₫

3.342.949 ₫ total

includes taxes & fees

31 Aug - 1 Sept

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

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.

12. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

Jermaine

2.976.702 ₫

3.324.976 ₫ total

includes taxes & fees

1 Sept - 2 Sept

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

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

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.

13. The Williams Inn

Williamstown

John

6.859.367 ₫

7.661.913 ₫ total

includes taxes & fees

14 Sept - 15 Sept

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

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 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.

14. Comfort Inn & Suites East Greenbush - Albany

Castleton-on-Hudson

Michael

3.149.590 ₫

3.496.046 ₫ total

includes taxes & fees

7 Sept - 8 Sept

A hotel lobby with leather armchairs, a blue sofa, a white coffee table, and a stone fireplace.

A hotel reception area with a modern design, featuring a reception desk, a wall-mounted TV, and a shelf with snacks.

A modern living room with leather armchairs, a blue sofa, and a patterned ottoman.

A Fairfield Inn & Suites Marriott hotel with a covered entrance, stone facade, and multiple floors.

15. Fairfield Inn & Suites Albany East Greenbush

East Greenbush

Luis

3.085.605 ₫

3.425.021 ₫ total

includes taxes & fees

7 Sept - 8 Sept

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

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

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.

16. Jiminy Peak Mountain Resort

Hancock

Sandy

3.737.200 ₫

4.174.452 ₫ total

includes taxes & fees

30 Aug - 31 Aug

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

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

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

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

17. The Villager Motel

Williamstown

Rebecca

2.324.324 ₫

2.596.192 ₫ total

includes taxes & fees

1 Sept - 2 Sept

A hotel room with a large bed, two bedside lamps, a chair, and a window with curtains.

A swimming pool with lounge chairs and umbrellas, surrounded by trees and buildings.

A motel with a parking lot, a swimming pool, and outdoor seating.

A residential street with a paved road, a lamp post, and flowering trees.

18. Berkshire Inn

Pittsfield

Adriana

2.350.179 ₫

2.625.150 ₫ total

includes taxes & fees

25 Aug - 26 Aug

A greenhouse with a transparent roof, a seating area with cushions, and a potted plant.

A living room with a fireplace, sofa, armchair, and a TV.

A living room with a grey sectional sofa, a small round coffee table, a brown leather armchair, and a window with curtains.

A dining table with plates of food, a coffee cup, and a plant.

19. Berkshire Valley Inn

Williamstown

4.348.314 ₫

4.857.067 ₫ total

includes taxes & fees

7 Sept - 8 Sept

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, 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.

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

20. Williamstown Motel

Williamstown

Matthew

2.846.644 ₫

3.179.702 ₫ total

includes taxes & fees

7 Sept - 8 Sept

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Top Cherry Plain Hotel Reviews

Berkshires Untold

10/10 Excellent

"Very comfortable stay due in large part to the attention paid to guests. You never had to go far to get a question answered or help. I also value being recognized and therefore not feeling like just another anonymous visitor. A real bonus was the quality and outright deliciousness of the food- there was no reason to wander and look for any other meal option- you could stay "home" and be completely satisfied. Bravo, Bershires Untold!"

Hotel On North

8/10 Good

"It’s a good place to stay. The rooms are but dark and could you add more lamps to the room?"

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent

"Nice place"

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

10/10 Excellent

"Our entire stay was exemplary!"

Hilton Garden Inn Troy

8/10 Good

"Nice"

The Yankee Inn

8/10 Good

"the room smelled like marijuana and cigarettes at initial arrival. I was in the 2nd bldg. and not able to get fresh coffee in the morning. overall, our stay was well worth it."

FairBridge Inn Express

10/10 Excellent

"It was very nice and everyone was extremely helpful"

Howard Johnson by Wyndham Lenox

8/10 Good

"Room was clean and comfortable. Always nice to have a frig and microwave."

More cheap stays in Cherry Plain

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

1.621.804 ₫

1.811.555 ₫ total

25 Aug - 26 Aug

includes taxes & fees

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA

2.063.164 ₫

2.304.553 ₫ total

31 Aug - 1 Sept

includes taxes & fees

7.6/10 Good! (903 reviews)

Comfort Inn & Suites East Greenbush - Albany

99 Miller Rd Castleton-on-Hudson NY

3.149.590 ₫

3.496.046 ₫ total

7 Sept - 8 Sept

includes taxes & fees

8.8/10 Excellent! (1,005 reviews)

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

1055 South Street Pittsfield MA

3.186.152 ₫

3.558.827 ₫ total

7 Sept - 8 Sept

includes taxes & fees

9.4/10 Exceptional! (171 reviews)

Best Western Plus Franklin Square Inn Troy/Albany

One Fourth Street Troy NY

3.424.330 ₫

3.801.008 ₫ total

1 Sept - 2 Sept

includes taxes & fees

8.8/10 Excellent! (1,005 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

4.126.328 ₫

4.609.108 ₫ total

14 Sept - 15 Sept

includes taxes & fees

9.2/10 Wonderful! (1,019 reviews)

Frequently asked questions

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 1.811.555 ₫

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. Willows Motel Williamstown

3. Maple Terrace Motel

4. Hotel Downstreet, an Ascend Collection Hotel

5. Cozy Corner Motel

6. The Yankee Inn

7. Howard Johnson by Wyndham Williamstown

8. Gregory House Country Inn

9. Hilton Garden Inn Troy

10. Holiday Inn & Suites Pittsfield-Berkshires by IHG

11. Berkshire Mountain Lodge

12. Best Western Plus Berkshire Hills Inn & Suites

13. The Williams Inn

14. Comfort Inn & Suites East Greenbush - Albany

15. Fairfield Inn & Suites Albany East Greenbush

16. Jiminy Peak Mountain Resort

17. The Villager Motel

18. Berkshire Inn

19. Berkshire Valley Inn

20. Williamstown Motel

Top Cherry Plain Hotel Reviews

Berkshires Untold

Hotel On North

Comfort Inn & Suites East Greenbush - Albany

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

Hilton Garden Inn Troy

The Yankee Inn

FairBridge Inn Express

Howard Johnson by Wyndham Lenox

More cheap stays in Cherry Plain

FairBridge Inn Express

Howard Johnson by Wyndham Lenox

Comfort Inn & Suites East Greenbush - Albany

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

Best Western Plus Franklin Square Inn Troy/Albany

The Yankee Inn

Frequently asked questions

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