Condo Rentals in Cherry Plain
New York
United States of America
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Search Condos Rentals in Cherry Plain from CA $438

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your current months are November, 2026 and December, 2026.

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Our top choices for Cherry Plain condo rentals

A spacious living area with a stone fireplace, comfortable seating, and a view of the kitchen.

A Country Inn with a covered entrance, stone foundation, and a white fence.

A spa area with a hot tub, wooden panel walls, and wall-mounted lights.

A television on a wooden stand with a fire feature below it, a small gnome figurine, and a framed picture on the wall.

1. UNIQUE - 1BR Country Condo @ Jiminy Peak

UNIQUE - 1BR Country Condo @ Jiminy Peak

Hancock

9.8 out of 10, Exceptional, (18 reviews)

9.8/10

Exceptional

(18 reviews)

"lovely place to stay"

Nancy P.

The price is CA $439

CA $439

CA $781 total

includes taxes & fees

Nov 6 - Nov 7

UNIQUE - 1BR Country Condo @ Jiminy Peak

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

View all properties

Top reviews in Cherry Plain

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

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

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

Vacation Village in the Berkshires

Williamstown

10/10 Excellent

We enjoyed our stay. Aspects of it

Kiril

Reviewed October 25, 2026Reviewed October 25, 2026

Vacation Village in the Berkshires

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.

Willows Motel Williamstown

Williamstown

10/10 Excellent

The owners are really generous and friendly! The Breakfast is the best I ever had anywhere I have ever been! All sorts of fruits, yogurts, all kinds of spreads, different types of bread, and all organic. Amazing generosity!

Alexander

Reviewed September 20, 2023Reviewed September 20, 2023

Willows Motel Williamstown

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

Maple Terrace Motel

Williamstown

10/10 Excellent

The room is clean, well stocked and spacious. Check in was smooth oth and the front desk staff was warm and helpful.

Tanya

Reviewed January 2, 2026Reviewed January 2, 2026

Maple Terrace Motel

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

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

Cozy Corner Motel

Williamstown

10/10 Excellent

Pour le prix, c'est imbattable. Super service, bon petit déjeuner. Je considère le meilleur motel a ce prix.

alain

Reviewed August 6, 2024Reviewed August 6, 2024

Cozy Corner Motel

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

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.

Williamstown Motel

Williamstown

10/10 Excellent

A pleasant surprise. The staff was very friendly and even accepted to change my reservation day. The service at the counter was exceptional. The room was clean, nice bathroom, AC. No complaints.

Guy

Reviewed July 16, 2024Reviewed July 16, 2024

Williamstown Motel

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

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

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

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

The Villager Motel

Williamstown

10/10 Excellent

Great service, great price.

Nicolas

Reviewed January 5, 2025Reviewed January 5, 2025

The Villager Motel

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 library with bookshelves, a television, and two armchairs.

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

Hotel On North

Pittsfield

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.

alan

Reviewed October 8, 2026Reviewed October 8, 2026

Hotel On North

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 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.

The Williams Inn

Williamstown

10/10 Excellent

Nice hotel, good location Large rooms But noisy aircon

peter

Reviewed September 4, 2025Reviewed September 4, 2025

The Williams Inn

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.

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

Jiminy Peak Mountain Resort

Hancock

10/10 Excellent

Belle chambre de style condo avec chambre fermée, salon, cuisinette, salle de bain. Télé dans la chambre et de le salon. Tout ce qu'il faut pour faire la cuisine. Lit confortable et tout les équipements était fonctionnel.

Rémi

Reviewed October 6, 2024Reviewed October 6, 2024

Jiminy Peak Mountain Resort

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

A room with large windows, a red patterned rug, a wooden table with benches, and shelves with figurines.

An indoor swimming pool with a colorful mural on the wall, a lifeguard station, and clear pool rules posted.

Hotel Downstreet, an Ascend Collection Hotel

North Adams

10/10 Excellent

it was beautiful, centrally located, perfect getaway

Tara

Reviewed October 9, 2026Reviewed October 9, 2026

Hotel Downstreet, an Ascend Collection Hotel

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

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.

A hotel room with a fireplace, a desk, a television, and a poster of a lake scene.

The Yankee Inn

Lenox

10/10 Excellent

Really clean and quiet.. Love!!

Gilles

Reviewed November 1, 2026Reviewed November 1, 2026

The Yankee Inn

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 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.

Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

10/10 Excellent

Wonderful reception staff and housekeeping. beautiful very large rooms. will stay here again.

Lorraine

Reviewed July 3, 2021Reviewed July 3, 2021

Best Western Plus Berkshire Hills Inn & Suites

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

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

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.

Fairfield Inn & Suites by Marriott Williamstown

Williamstown

10/10 Excellent

The property was excellent. They are just finishing renovations so it did quite work for breakfast. But overall when renovations are finished it will be great.loved the coffee

Brian

Reviewed August 14, 2026Reviewed August 14, 2026

Fairfield Inn & Suites by Marriott Williamstown

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

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

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.

Comfort Inn & Suites East Greenbush - Albany

Castleton-on-Hudson

10/10 Excellent

Clean room. Plenty of parking. Convenient breakfast

Mateo

Reviewed October 7, 2026Reviewed October 7, 2026

Comfort Inn & Suites East Greenbush - Albany

A bedroom with a large bed, a chandelier, a dresser, and a nightstand with a lamp.

A garden with a stone wall, various plants, and a small shed.

A spacious living room with a fireplace, elegant furniture, and a chandelier.

A room with a large window, a statue, and a small table with various items.

Gardner Farm Inn

Troy

10/10 Excellent

This is a fantastic B&B. John is the ultimate host. He keeps very stringent Covid practices yet the inn is still warm and inviting. Breakfast was a treasure. We will return!

Katharine

Reviewed November 15, 2020Reviewed November 15, 2020

Gardner Farm Inn

A spacious living room with high ceilings, exposed wooden beams, a fireplace, and comfortable seating.

A spacious living room with a high ceiling, wooden beams, a fireplace, and a bookshelf filled with books.

A spacious kitchen with wooden beams, a dining area with a large table and chairs, and a view of the outdoors through large windows.

A wooden interior with a table, chair, and a view of a red barn through an open door.

Inn at Silver Maple Farm

East Chatham

10/10 Excellent

The property itself is wonderful. Chloe and Sean are delightful hosts. A great breakfast is icing on the cake.

Timothy

Reviewed June 22, 2023Reviewed June 22, 2023

Inn at Silver Maple Farm

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

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

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.

Hilton Garden Inn Troy

Troy

10/10 Excellent

Great room and experience overall!

Brad

Reviewed September 28, 2026Reviewed September 28, 2026

Hilton Garden Inn Troy

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Search Condos Rentals in Cherry Plain from CA $438

Change your mind

Treat yourself

Be picky

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Cherry Plain condo rentals

1. UNIQUE - 1BR Country Condo @ Jiminy Peak

Top reviews in Cherry Plain

Vacation Village in the Berkshires

10/10 Excellent

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