Cherry Plain Hotels from S$99

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Check prices for these dates

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18 Jul - 19 Jul
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19 Jul - 20 Jul
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18 Jul - 20 Jul
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25 Jul - 27 Jul

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Top 10 trending Cherry Plain hotels

Blue Vista Motor Lodge
1 bedroom, in-room safe, desk, free WiFi

Blue Vista Motor Lodge

2.0 star property
9.8 out of 10, Exceptional, (175)
"Lovely stay!"
The price is S$285
includes taxes & fees
30 Jul - 31 Jul
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, (131)
"Stayed only one night Very cosy, quiet place "
The price is S$267
includes taxes & fees
21 Jul - 22 Jul
The Trail in Adams - Berkshires’ Art Hotel
The Revival House
1 bedroom, desk, iron/ironing board, free WiFi

The Revival House

3.0 star property
9.6 out of 10, Exceptional, (4)
"The Revival House was charming and quiet. It had everything we needed for our short stay. It's only a 6 minute drive to the Bellows Pipe Trail/Mount Greylock, which was a huge plus for us. Wishing all the best for this newly opened hotel!"
The price is S$258
includes taxes & fees
20 Jul - 21 Jul
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, (1002)
"Great place"
The price is S$231
includes taxes & fees
17 Aug - 18 Aug
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, (395)
"Beautiful and peaceful property. Perfect for our last minute mother daughter get away. The staff was friendly and helpful. "
The price is S$320
includes taxes & fees
18 Aug - 19 Aug
The Porches Inn at Mass MoCA
Harbour House Inn
Exterior

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (50)
"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 S$320
includes taxes & fees
23 Jul - 24 Jul
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, (743)
"Close to our target event a plus"
The price is S$102
includes taxes & fees
31 Jul - 1 Aug
FairBridge Inn Express
Holiday Inn Express & Suites Pittsfield - Berkshires
Free daily buffet breakfast

Holiday Inn Express & Suites Pittsfield - Berkshires

2.5 star property
10.0 out of 10, Exceptional, (3)
"Our stay was terrific, and we appreciated the staff's attentiveness, especially Anthony's."
The price is S$255
includes taxes & fees
30 Jul - 31 Jul
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 S$282
includes taxes & fees
27 Jul - 28 Jul
Hilton Garden Inn Lenox Pittsfield
Wagon Wheel Inn
Property grounds

Wagon Wheel Inn

2.0 star property
7.0 out of 10, Good, (611)
"Convenient location for my trip"
The price is S$99
includes taxes & fees
27 Jul - 28 Jul
Wagon Wheel Inn
Howard Johnson by Wyndham Lenox
Exterior

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (761)
"Was great loved the jacuzzi tub "
The price is S$142
includes taxes & fees
27 Jul - 28 Jul
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, (852)
"The rooms were tasteful, cheerful and emaculate. We have been searching for lovely, reasonably priced accommodations for our annual trips to Williamstown and we have definitely found them here. The beds were so comfortable, the room felt spacious and the bathroom had extra perks. We will return , highly recommend!"
The price is S$158
includes taxes & fees
20 Jul - 21 Jul
Howard Johnson by Wyndham Williamstown
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (519)
"Clean, comfortable and great staff. Highly recommend and will be staying there again in the future."
Berkshire Mountain Lodge
Hampton Inn & Suites Berkshires-Lenox
Exterior

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1000)
"Good lodgings in a great area to visit."
The price is S$230
includes taxes & fees
31 Jul - 1 Aug
Hampton Inn & Suites Berkshires-Lenox
Hotel On North
Food and drink

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (744)
"Great boutique hotel"
The price is S$271
includes taxes & fees
12 Aug - 13 Aug
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, (1002)
"Loved the Yankee Inn!"
The price is S$194
includes taxes & fees
31 Jul - 1 Aug
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, (298)
"Friendly staff, clean and perfect for a trip with the pups! "
The price is S$185
includes taxes & fees
27 Jul - 28 Jul
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, (823)
"Very convenient location, downtown, short drive to local attractions "
The price is S$185
includes taxes & fees
31 Jul - 1 Aug
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.2 out of 10, Wonderful, (637)
"Great place stay after an evening at Tanglewood!"
The price is S$619
includes taxes & fees
25 Jul - 26 Jul
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 S$304
includes taxes & fees
24 Jul - 25 Jul
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 Brodie Mountain and Williamstown Theatre Festival—just two of the sights around Cherry Plain.

See all hotels in Cherry Plain

Top Cherry Plain Hotel Reviews

Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent
"When I first walked in to check in this place made me feel very welcome and such an open lobby. The rooms look fairly new. The beds were a little hard and the pool was very cold however I felt very refreshing due to the heat outside during my time there. Both afternoon and morning staff were very wonderful and respectful. If I drive through there I probably will stay there as it's right off the 90. "
Trisha 1-night trip
Posted 3 days ago
Comfort Inn & Suites East Greenbush - Albany

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 The Williams Inn and Hotel Downstreet, Ascend Hotel Collection. See all available top hotels, or 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 674 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 Brodie Mountain, Williamstown Theatre Festival and Jiminy Peak Mountain Resort. You'll also find Mountain Coaster 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.