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10 Dec - 11 Dec
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11 Dec - 12 Dec
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12 Dec - 14 Dec
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19 Dec - 21 Dec

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Our top choices for Cherry Plain hotels

Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1008)
"Great stay there!! Very friendly staff"
United States
Ann
The price is AU$126
includes taxes & fees
24 Dec - 25 Dec
The Yankee, Trademark Collection by Wyndham
Interior
Berkshires Untold

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (812)
"Easiest check in and out. Great food in dining room. "
United States
William
The price is AU$184
includes taxes & fees
11 Dec - 12 Dec
Berkshires Untold
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (65)
"Very clean room, courteous staff. "
United States
Jeffrey
The price is AU$182
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very good, (984)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is AU$148
includes taxes & fees
12 Dec - 13 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Front of property
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1000)
"Overall a really fun place to stay. Rooms were good quality and the staff was welcoming and helpful."
United States
Jacob
The price is AU$290
includes taxes & fees
11 Dec - 12 Dec
The Cornell Inn, Lenox & The Berkshires
Lobby
Vacation Village in the Berkshires

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2168)
"Great stay and beautiful scenery close to Jiminy’s Peak Ski slopes. They have a heated pool for winter weather and extra outdoor for the summer plus other family oriented amenities"
United States
Karla
The price is AU$191
includes taxes & fees
11 Dec - 12 Dec
Vacation Village in the Berkshires
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (786)
"This place is so peaceful and the staff is always helpful "
United States
Leona
The price is AU$200
includes taxes & fees
8 Jan - 9 Jan 2026
Berkshire Mountain Lodge
Hypo-allergenic bedding, desk, laptop workspace, blackout curtains
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
8.8 out of 10, Excellent, (1001)
"Great property, nice staff, lovely rooms, awesome location."
Canada
Krysten
The price is AU$181
includes taxes & fees
20 Dec - 21 Dec
Hotel Downstreet, an Ascend Collection Hotel
Front of property – evening/night
Hotel On North

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (805)
"Clean room and staff was super friendly"
United States
Yuen
The price is AU$251
includes taxes & fees
11 Dec - 12 Dec
Hotel On North
Lobby sitting area
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1001)
"I have stayed here many times and it is consistently a comfortable, clean and quiet place."
United States
Jeanine
The price is AU$159
includes taxes & fees
7 Jan - 8 Jan 2026
Best Western Plus Berkshire Hills Inn & Suites
Property amenity
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (589)
"Roomy, clean, the view is fantastic with the foliage, exactly like the photos. "
United States
Mingming
The price is AU$227
includes taxes & fees
14 Dec - 15 Dec
Courtyard by Marriott Lenox Berkshires
Exterior
The Villager Motel

The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (764)
"It's very good for stay over"
United States
Frances
The price is AU$116
includes taxes & fees
11 Dec - 12 Dec
The Villager Motel
Lobby
Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany
2.5 star property
Castleton-on-Hudson
8.4 out of 10, Very good, (1000)
"Great location and easy off/on thruway 90 as well as many food, shopping options."
United States
Gail
The price is AU$158
includes taxes & fees
8 Jan - 9 Jan 2026
Comfort Inn & Suites East Greenbush - Albany
Exterior
Fairfield Inn & Suites by Marriott Williamstown

Fairfield Inn & Suites by Marriott Williamstown

Fairfield Inn & Suites by Marriott Williamstown
2.5 star property
Williamstown
8.8 out of 10, Excellent, (394)
"our stay was great."
United States
nathaniel
The price is AU$264
includes taxes & fees
15 Dec - 16 Dec
Fairfield Inn & Suites by Marriott Williamstown
Free buffet breakfast
Holiday Inn Express & Suites East Greenbush (Albany-Skyline) by IHG

Holiday Inn Express & Suites East Greenbush (Albany-Skyline) by IHG

Holiday Inn Express & Suites East Greenbush (Albany-Skyline) by IHG
2.5 star property
Rensselaer
8.8 out of 10, Excellent, (857)
"Friends visiting our church stayed here -- and they thought it was great! Treated very nicely by the staff; great view of Albany's skyline."
United States
Nicholas
The price is AU$184
includes taxes & fees
19 Dec - 20 Dec
Holiday Inn Express & Suites East Greenbush (Albany-Skyline) by IHG
Suite, 2 Bedrooms
The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA
3.5 star property
North Adams
9.4 out of 10, Exceptional, (445)
"It is the perfect place to stay!"
United States
Darrell
The price is AU$275
includes taxes & fees
8 Jan - 9 Jan 2026
The Porches Inn at Mass MoCA
Microwave, oven, stovetop, dishwasher
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (346)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is AU$150
includes taxes & fees
11 Dec - 12 Dec
The Central Downtown Inn & Suites
Front of property – evening/night
The Williams Inn

The Williams Inn

The Williams Inn
4.0 star property
Williamstown
9.6 out of 10, Exceptional, (548)
"Clean,heating was noisy,bed was to soft,shower head dripped. Very friendly and helpful staff.good breakfast!"
United States
Jon
The price is AU$318
includes taxes & fees
14 Dec - 15 Dec
The Williams Inn
Exterior detail
Williamstown Motel

Williamstown Motel

Williamstown Motel
2.0 star property
Williamstown
9.4 out of 10, Exceptional, (314)
"Was upgraded to a larger room for no special reason. Very nice proprietor. For budget priced accommodations, this is an excellent value. Would definitely stay here again if I am in the area."
United States
DAVID
The price is AU$150
includes taxes & fees
11 Dec - 12 Dec
Williamstown Motel
Exterior detail
Maple Terrace Motel

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (588)
"Reception was great, lovely beds (most important to me), great location, this place is excellent."
United States
William
The price is AU$167
includes taxes & fees
11 Dec - 12 Dec
Maple Terrace Motel
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.
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Top Cherry Plain Hotel Reviews

Recent Reviews in Cherry Plain

Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent
"Clean and perfect."
Allan's 1-night trip
Posted 1 day ago
Comfort Inn & Suites East Greenbush - Albany

More cheap accommodation in Cherry Plain

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

461 Pittsfield Rd Lenox MA
The price is AU$126 per night from 24 Dec to 25 Dec
AU$126
24 Dec - 25 Dec
includes taxes & fees
9/10 Wonderful! (1,008 reviews)

Frequently asked questions

Where is the best place to stay in Cherry Plain?
Vacation Village in the Berkshires, located 5.6 mi (9 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 Hotel Downstreet, an Ascend Collection Hotel and Berkshire Mountain Lodge. See all available top hotels, or vacation rentals in Cherry Plain.
What are some of the best holiday rentals that Cherry Plain has to offer?
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!: This holiday home rental outside of Cherry Plain offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub. See all 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 658 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 Cherry Plain State Park, Brodie Mountain and Williamstown Theatre Festival. You'll also find Jiminy Peak Mountain Resort and Waubeeka Golf Links 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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