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8 Aug - 9 Aug
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8 Aug - 10 Aug
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Top hotels and accommodation in Cherry Plain

Blue Vista Motor Lodge
Single Room

Blue Vista Motor Lodge

2.0 star property
9.8 out of 10, Exceptional, (179)
"Clean, beautiful view wonderful service"
The price is NZ$429
includes taxes & fees
1 Sept - 2 Sept
Blue Vista Motor Lodge
The Trail in Adams - Berkshires’ Art Hotel
Terrace/patio

The Trail in Adams - Berkshires’ Art Hotel

2.5 star property
8.8 out of 10, Excellent, (132)
"Stayed only one night Very cosy, quiet place "
The price is NZ$356
includes taxes & fees
12 Aug - 13 Aug
The Trail in Adams - Berkshires’ Art Hotel
The Revival House
Romantic Room, 1 King Bed (Room 4)

The Revival House

3.0 star property
9.6 out of 10, Exceptional, (8)
"Beautifully renovated historical bed and breakfast that offers historical details along with modern touches. Our room was spacious and very clean and common areas are appointed with great attention to detail. "
The price is NZ$337
includes taxes & fees
10 Aug - 11 Aug
The Revival House
Hotel Downstreet, Ascend Hotel Collection
Hypo-allergenic bedding, laptop workspace, blackout curtains

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.8 out of 10, Excellent, (1000)
"Clean,friendly staff and great location."
The price is NZ$269
includes taxes & fees
7 Sept - 8 Sept
Hotel Downstreet, Ascend Hotel Collection
The Porches Inn at Mass MoCA
Suite, 2 Bedrooms

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (405)
"Very comfortable room that worked great for our family. "
The price is NZ$370
includes taxes & fees
8 Sept - 9 Sept
The Porches Inn at Mass MoCA
Harbour House Inn
Exterior

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (51)
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! "
The price is NZ$421
includes taxes & fees
14 Aug - 15 Aug
Harbour House Inn
FairBridge Inn Express
1 bedroom, desk, iron/ironing board, free WiFi

FairBridge Inn Express

2.5 star property
5.4 out of 10, (763)
"Close to our target event a plus"
The price is NZ$133
includes taxes & fees
27 Aug - 28 Aug
FairBridge Inn Express
Holiday Inn Express & Suites Pittsfield - Berkshires
Free daily buffet breakfast

Holiday Inn Express & Suites Pittsfield - Berkshires

2.5 star property
9.4 out of 10, Exceptional, (12)
"Really enjoyed my stay here, definitely need a car to get around"
The price is NZ$285
includes taxes & fees
10 Aug - 11 Aug
Holiday Inn Express & Suites Pittsfield - Berkshires
Hilton Garden Inn Lenox Pittsfield
Terrace/patio

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (637)
"Very comfortable, VERY spacious rooms, friendly, helpful staff, very comfortable beds, being renovated, June 2025 so will be even better. AND Jae's Restaurant on property is very good, with great service. "
The price is NZ$294
includes taxes & fees
7 Sept - 8 Sept
Hilton Garden Inn Lenox Pittsfield
Wagon Wheel Inn
Property grounds

Wagon Wheel Inn

2.0 star property
7.0 out of 10, Good, (617)
"Convenient location for my trip"
The price is NZ$223
includes taxes & fees
11 Aug - 12 Aug
Wagon Wheel Inn
Howard Johnson by Wyndham Lenox
Exterior

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (778)
"My stay was perfect. I can't wait to stay there again. "
The price is NZ$148
includes taxes & fees
1 Sept - 2 Sept
Howard Johnson by Wyndham Lenox
Howard Johnson by Wyndham Williamstown
Pool

Howard Johnson by Wyndham Williamstown

2.0 star property
6.4 out of 10, (862)
"Humble little hotel. Ideal for a visit to nearby Mass MOCA."
The price is NZ$206
includes taxes & fees
10 Aug - 11 Aug
Howard Johnson by Wyndham Williamstown
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (546)
"Excellent stay!"
Berkshire Mountain Lodge
Hampton Inn & Suites Berkshires-Lenox
Exterior

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1002)
"Great staff! Comfortable bed! "
The price is NZ$269
includes taxes & fees
1 Sept - 2 Sept
Hampton Inn & Suites Berkshires-Lenox
Hotel On North
Food and drink

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (752)
"Staff were excellent and welcoming."
The price is NZ$335
includes taxes & fees
8 Sept - 9 Sept
Hotel On North
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.2 out of 10, Wonderful, (1001)
"Wonderful place to stay"
The price is NZ$251
includes taxes & fees
8 Sept - 9 Sept
The Yankee, Trademark Collection by Wyndham
The Central Downtown Inn & Suites
Microwave, oven, stovetop, dishwasher

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (299)
"Friendly staff, clean and perfect for a trip with the pups! "
The price is NZ$215
includes taxes & fees
7 Sept - 8 Sept
The Central Downtown Inn & Suites
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (852)
"Consistently a clean room with welcoming staff."
The price is NZ$215
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.2 out of 10, Wonderful, (664)
"Fun place and very clean. Friendly staff and an amazing outdoor area to hang out."
The price is NZ$301
includes taxes & fees
7 Sept - 8 Sept
Berkshires Untold
Courtyard by Marriott Lenox Berkshires
Property amenity

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (567)
"After coming to Lenox for 15 years, I can easily say this is the best in town. "
The price is NZ$285
includes taxes & fees
1 Sept - 2 Sept
Courtyard by Marriott Lenox Berkshires
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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Learn more about Cherry Plain

Head to Cherry Plain State Park and Brodie Mountain—just two of the sights around Cherry Plain.

See all hotels in Cherry Plain

Top Cherry Plain Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"A very clean and friendly environment. Staff were efficient and knowledgeable. Would appreciate two more handcap parking spaces at front of hotel. Thank you."
Susan 1-night trip
Posted 1 day ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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 Berkshire Mountain Lodge and FairBridge Inn Express. 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?

Contemporary Berkshire Home with Views of Taconic Golf Course: 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 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games. 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 are some hotels with pools in Cherry Plain?

Vacation Village in the Berkshires: 3-star condo, 2-minute walk from Jiminy Peak Mountain Resort. Features a children's pool, an indoor pool and a health club. Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel and Hilton Garden Inn Lenox Pittsfield are a couple of other choices that offer an on-site pool. View all hotels with pools in Cherry Plain.

What is staying in Cherry Plain like?

Visitors to Cherry Plain will definitely find plenty to explore and enjoy. There are 661 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 Mountain Coaster 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.