Cherry Plain Hotels from S$101

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Check Cherry Plain hotel prices

Tonight
18 Oct - 19 Oct
Tomorrow night
19 Oct - 20 Oct
This weekend
18 Oct - 20 Oct

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Top 10 trending Cherry Plain hotels

The Williams Inn
Front of property – evening/night
The Williams Inn
4.0 star property
9.6 out of 10, Exceptional, (356)
"Very nice. "
The price is S$299
includes taxes & fees
13 Nov - 14 Nov
The Williams Inn
Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1726)
"Friendly staff, clean rooms, and classy crowd"
The price is S$256
includes taxes & fees
27 Oct - 28 Oct
Vacation Village in the Berkshires
Life House Berkshires
Lobby
Life House Berkshires
3.5 star property
9.0 out of 10, Wonderful, (419)
"Pros: Loved the decor. It was nice, modern and well looked after. The location was convenient. You check yourself in at a iPad which was odd but quick. I needed extra towels and wasn’t sure who worked there but the person behind the bar helped. Feels like a hands off property. Cons: The Apple TV was hard to use accessing cable. Rooms open to the outside like a motel. My room was on the first floor so luckily I didn’t need to carry luggage upstairs but that might bother some. "
The price is S$210
includes taxes & fees
27 Oct - 28 Oct
Life House Berkshires
The Yankee, Trademark Collection by Wyndham
Exterior
The Yankee, Trademark Collection by Wyndham
2.5 star property
9.0 out of 10, Wonderful, (1002)
"Clean room"
The price is S$182
includes taxes & fees
31 Oct - 1 Nov
The Yankee, Trademark Collection by Wyndham
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Indoor pool
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
3.0 star property
7.8 out of 10, Good, (657)
"Nice staff. Clean room. Good complimentary breakfast."
The price is S$138
includes taxes & fees
15 Nov - 16 Nov
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Berkshire Mountain Lodge
Fridge, microwave, stovetop, coffee/tea maker
Berkshire Mountain Lodge
3.0 star property
8.8 out of 10, Excellent, (393)
"Old world mountain lodge, kept clean and comfortable. All around great stay."
The price is S$268
includes taxes & fees
27 Oct - 28 Oct
Berkshire Mountain Lodge
Jiminy Peak Mountain Resort
Exterior
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (906)
"Friendly, well-stocked, well-thought-out, comfotable."
The price is S$215
includes taxes & fees
20 Oct - 21 Oct
Jiminy Peak Mountain Resort
Hotel Downstreet
Hypo-allergenic bedding, laptop workspace, blackout curtains
Hotel Downstreet
3.0 star property
8.6 out of 10, Excellent, (1007)
"I would recommend, clean comfortable room, good location "
The price is S$170
includes taxes & fees
3 Nov - 4 Nov
Hotel Downstreet
Hotel On North
Front of property – evening/night
Hotel On North
3.5 star property
9.6 out of 10, Exceptional, (638)
"Really great staff and comfy bed!"
The price is S$181
includes taxes & fees
13 Nov - 14 Nov
Hotel On North
FairBridge Inn Express
Desk, iron/ironing board, free WiFi, bed sheets
FairBridge Inn Express
2.5 star property
5.4 out of 10, (667)
"The room was clean. The heat was very loud And the refrigerator was very loud at night."
The price is S$116
includes taxes & fees
27 Oct - 28 Oct
FairBridge Inn Express
Berkshire Inn
Desk, iron/ironing board, free WiFi, bed sheets
Berkshire Inn
2.0 star property
7.6 out of 10, Good, (727)
"Could be somewhat updated but we didn’t care that much. Coffee should be updated. Maybe a better coffee."
The price is S$126
includes taxes & fees
29 Oct - 30 Oct
Berkshire Inn
Stay Berkshires
Lake view
Stay Berkshires
2.0 star property
8.4 out of 10, Very good, (349)
"We arrived late, but Joe was there to greet us and get us settled. Room was decent, nice little stream running behind parking lot with fire pit and gazebo. Saw the pool but no time to go in. Breakfast was very good! Waffles and fresh strawberries and blueberries. Management was there taking care of dishes and wishing everyone a good morning. Highly recommend!"
The price is S$235
includes taxes & fees
29 Oct - 30 Oct
Stay Berkshires
Hampton Inn & Suites Berkshires-Lenox
Exterior
Hampton Inn & Suites Berkshires-Lenox
2.5 star property
9.2 out of 10, Wonderful, (1001)
"The property is located very conveniently on Route 7 and you can walk to some dining establishments as well as shops. Our room was clean and the staff very courteous."
The price is S$173
includes taxes & fees
6 Nov - 7 Nov
Hampton Inn & Suites Berkshires-Lenox
Howard Johnson by Wyndham Lenox
Exterior
Howard Johnson by Wyndham Lenox
2.0 star property
7.6 out of 10, Good, (692)
"Our room was on the upper floor and was quiet, clean and spacious with 2 double beds, desk and chair, armchair, and round table with 2 chairs. No lingering smell of smoke or disinfectant and beds were comfortable. Did not try the breakfast but would easily stay here again."
The price is S$116
includes taxes & fees
27 Oct - 28 Oct
Howard Johnson by Wyndham Lenox
Courtyard by Marriott Lenox Berkshires
Indoor pool
Courtyard by Marriott Lenox Berkshires
3.0 star property
9.2 out of 10, Wonderful, (530)
"Very comfortable beds, spacious room, loved the firepit outside, friendly staff, easy check in"
The price is S$186
includes taxes & fees
4 Nov - 5 Nov
Courtyard by Marriott Lenox Berkshires
Howard Johnson by Wyndham Williamstown
Pool
Howard Johnson by Wyndham Williamstown
2.0 star property
6.4 out of 10, (819)
"Check in staff was friendly. Room was clean and comfy bed."
The price is S$147
includes taxes & fees
7 Nov - 8 Nov
Howard Johnson by Wyndham Williamstown
The Porches Inn at Mass MoCA
Exterior
The Porches Inn at Mass MoCA
3.5 star property
9.4 out of 10, Exceptional, (363)
"rooms done with rustic touches yet keeping updated amenities"
The price is S$258
includes taxes & fees
17 Nov - 18 Nov
The Porches Inn at Mass MoCA
Wagon Wheel Inn
Property grounds
Wagon Wheel Inn
2.0 star property
7.2 out of 10, Good, (591)
"Great location. Pleasant staff."
The price is S$101
includes taxes & fees
30 Oct - 31 Oct
Wagon Wheel Inn
Best Western Plus Berkshire Hills Inn & Suites
Lobby sitting area
Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
8.4 out of 10, Very good, (1002)
"Nice Property "
The price is S$143
includes taxes & fees
3 Nov - 4 Nov
Best Western Plus Berkshire Hills Inn & Suites
Willows Motel Williamstown
Exterior
Willows Motel Williamstown
2.0 star property
8.8 out of 10, Excellent, (861)
"Breakfast was excellent with delicious fresh fruit and healthy options and the staff were very helpful."
The price is S$122
includes taxes & fees
3 Nov - 4 Nov
Willows Motel Williamstown
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Frequently asked questions

Where is the best place to stay in Cherry Plain?

Hotel Downstreet, located 13.3 mi (21.5 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 Life House Berkshires and The Yankee, Trademark Collection by Wyndham. 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 579 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, Jiminy Peak Mountain Resort and Mount Greylock State Reservation. You'll also find Mount Greylock State Reservation Visitor Center and Sterling and Francine Clark Art Institute 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.