Cherry Plain Hotels

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Check Cherry Plain hotel prices

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

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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 P11,521
P12,869 total
includes taxes & fees
Nov 3 - Nov 4
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 P9,750
P11,274 total
includes taxes & fees
Oct 20 - Oct 21
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 P8,263
P9,229 total
includes taxes & fees
Oct 27 - Oct 28
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 P7,177
P8,017 total
includes taxes & fees
Oct 31 - Nov 1
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 P5,436
P6,072 total
includes taxes & fees
Nov 15 - Nov 16
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 P9,534
P11,805 total
includes taxes & fees
Oct 27 - Oct 28
Berkshire Mountain Lodge
Jiminy Peak Mountain Resort
Exterior
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (906)
"It was amazing! Great place, clean and very nice. The location was perfect"
The price is P8,187
P8,981 total
includes taxes & fees
Oct 20 - Oct 21
Jiminy Peak Mountain Resort
Hotel Downstreet
Hypo-allergenic bedding, laptop workspace, blackout drapes
Hotel Downstreet
3.0 star property
8.6 out of 10, Excellent, (1006)
"I would recommend, clean comfortable room, good location "
The price is P6,714
P7,500 total
includes taxes & fees
Nov 3 - Nov 4
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 P7,113
P7,945 total
includes taxes & fees
Nov 14 - Nov 15
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 P4,565
P5,099 total
includes taxes & fees
Oct 20 - Oct 21
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 P4,969
P5,550 total
includes taxes & fees
Nov 12 - Nov 13
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 P9,253
P10,335 total
includes taxes & fees
Oct 20 - Oct 21
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 P6,827
P7,625 total
includes taxes & fees
Nov 3 - Nov 4
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 P4,565
P5,099 total
includes taxes & fees
Oct 27 - Oct 28
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 P7,338
P8,197 total
includes taxes & fees
Nov 4 - Nov 5
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 P5,782
P6,459 total
includes taxes & fees
Nov 3 - Nov 4
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 P9,290
P11,346 total
includes taxes & fees
Nov 17 - Nov 18
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 P3,987
P4,453 total
includes taxes & fees
Oct 20 - Oct 21
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 P5,638
P6,298 total
includes taxes & fees
Nov 3 - Nov 4
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 P4,800
P5,361 total
includes taxes & fees
Nov 3 - Nov 4
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 traveler data. Two other choices for your visit to 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! 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 579 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, 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. 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.