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Aug 5 - Aug 6
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Compare 663 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

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 CA $333
CA $352 total
includes taxes & fees
Aug 6 - Aug 7
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 CA $269
CA $300 total
includes taxes & fees
Aug 12 - Aug 13
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 CA $248
CA $277 total
includes taxes & fees
Aug 6 - Aug 7
The Revival House
Hotel Downstreet, Ascend Hotel Collection
Hypo-allergenic bedding, laptop workspace, blackout drapes

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.8 out of 10, Excellent, (1006)
"Clean,friendly staff and great location."
The price is CA $198
CA $221 total
includes taxes & fees
Sep 4 - Sep 5
Hotel Downstreet, Ascend Hotel Collection
The Porches Inn at Mass MoCA
Exterior

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 CA $259
CA $320 total
includes taxes & fees
Sep 2 - Sep 3
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 CA $325
CA $344 total
includes taxes & fees
Aug 14 - Aug 15
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, (761)
"Close to our target event a plus"
The price is CA $98
CA $109 total
includes taxes & fees
Aug 6 - Aug 7
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, (10)
"Really enjoyed my stay here, definitely need a car to get around"
The price is CA $221
CA $247 total
includes taxes & fees
Sep 1 - Sep 2
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 CA $219
CA $244 total
includes taxes & fees
Sep 2 - Sep 3
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 CA $95
CA $106 total
includes taxes & fees
Aug 6 - Aug 7
Wagon Wheel Inn
Howard Johnson by Wyndham Lenox
Exterior

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (775)
"My stay was perfect. I can't wait to stay there again. "
The price is CA $109
CA $122 total
includes taxes & fees
Sep 1 - Sep 2
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, (861)
"Humble little hotel. Ideal for a visit to nearby Mass MOCA."
The price is CA $151
CA $169 total
includes taxes & fees
Aug 6 - Aug 7
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, (542)
"Excellent stay!"
The price is CA $152
CA $201 total
includes taxes & fees
Aug 24 - Aug 25
Berkshire Mountain Lodge
Hampton Inn & Suites Berkshires-Lenox
Exterior

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1004)
"The breakfast."
The price is CA $198
CA $221 total
includes taxes & fees
Sep 1 - Sep 2
Hampton Inn & Suites Berkshires-Lenox
Hotel On North
Food and drink

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (750)
"Staff were excellent and welcoming."
The price is CA $252
CA $281 total
includes taxes & fees
Aug 6 - Aug 7
Hotel On North
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1002)
"Loved the Yankee Inn!"
The price is CA $210
CA $234 total
includes taxes & fees
Aug 17 - Aug 18
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 CA $158
CA $177 total
includes taxes & fees
Sep 1 - Sep 2
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, (847)
"I like this place a lot and have stayed here many times over the years. Comfortable stay at a reasonable price at a convenient location in Pittsfield. "
The price is CA $158
CA $177 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.2 out of 10, Wonderful, (659)
"It's a clean, nice place. And easy to get to the surrounding towns."
The price is CA $177
CA $198 total
includes taxes & fees
Sep 1 - Sep 2
Berkshires Untold
Courtyard by Marriott Lenox Berkshires
Property amenity

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (566)
"After coming to Lenox for 15 years, I can easily say this is the best in town. "
The price is CA $209
CA $234 total
includes taxes & fees
Sep 1 - Sep 2
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

Check out Brodie Mountain and Williamstown Theatre Festival—just a couple of the sights around Cherry Plain.

See all hotels in Cherry Plain

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 traveler data. Two other choices for your visit to the area are Hotel Downstreet, Ascend Hotel Collection and The Williams Inn. See all available top hotels, or vacation rentals in Cherry Plain.

What's the top vacation rental in Cherry Plain?

Contemporary Berkshire Home with Views of Taconic Golf Course: This vacation home rental outside of Cherry Plain offers a fireplace, a patio, and a barbecue grill 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 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! Most room reservations are refundable if you cancel before the hotel’s cancellation deadline, which often is within 24-48 hours of your arrival date. If you have a non-refundable reservation, you might be able to still cancel and receive a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Cherry Plain.

Where can I learn more about changing or cancelling my trip to Cherry Plain?

To access more information about rescheduling or cancelling your trip to Cherry Plain, go to https://www.expedia.com/service/.

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 with an onsite pool. View all hotels with pools in Cherry Plain.

What is staying in Cherry Plain like?

Visitors to Cherry Plain are sure to find plenty to explore and enjoy. There are 665 hotels and other accommodations in the surrounding area. Find out more about Cherry Plain.

What should I see while I'm in Cherry Plain?

Places to visit in the wider area include Brodie Mountain, Williamstown Theatre Festival, and Jiminy Peak Mountain Resort. You'll also find Mountain Coaster and Waubeeka Golf Links in the area. Check out what more 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 temp of 65°F, while the coldest months are January and February with an average of 26°F. The snowiest months in Cherry Plain are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.