Cherry Plain Vacation Rentals from ￥16,450: Search Short-Term Rentals

Check prices for these dates

In two weeks

In two months

In three months

In four months

Vacation Rentals in Cherry Plain

"Extended stay since resort was so beautiful"

￥17,219 total

includes taxes & fees

Nov 2 - Nov 3

"This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the property has great sandwiches and things needed for your stay."

￥24,261 total

includes taxes & fees

Oct 19 - Oct 20

"Perfect place for a relaxing getaway! We loved everything! "

￥16,450 total

includes taxes & fees

Oct 9 - Oct 10

"Such a sweet spot in the woods! Can’t wait to come back."

￥27,524 total

includes taxes & fees

Oct 12 - Oct 13

"Amazing Inn. Cozy and everything we needed. "

￥159,005 total

includes taxes & fees

Nov 7 - Nov 8

"Kind and responsive host."

￥71,326 total

includes taxes & fees

Oct 9 - Oct 10

"The cabin was exactly what my daughter and I were looking for. Everything was clean, organized and family friendly. A bonus was the property connects to Bessie Woods and we were able to go for a hike on the trails without even having to leave the property. If you love quiet and the sounds of nature, this is the perfect place for you. We can’t wait to stay there again soon."

￥27,524 total

includes taxes & fees

Oct 15 - Oct 16

Smart TV, fireplace, DVD player, music library

"This unique hideaway was great for our family. The open layout might not work for everyone, but suited us just fine! We were only here a couple nights but enjoyed the location and using the hot tub! "

"Lovely property. Well kept house, nicely decorated. Very much enjoyed our stay."

"We had a fabulous stay at this lovely home in the Berkshires! The house was well equipped with everything needed to make our stay with our family so enjoyable. Great communication with the host in helping to resolve a small issue with loss of power on 2nd floor but was easily resolved."

"We came out to see James Taylor on the 4th. Kathy and Kit were terrific hosts. Friendly, accommodating and their home was very comfortable and clean. We would definitely rent from them again. Thank you! "

"Beautiful location, very spacious, comfortable and clean."

"Amazing stay in Hoosick! The kids loved the pool and the the views from the property were stunning"

"Cozy little condo, good for a group of four or five. We stayed there with my two kids 8 &10 and wife. It’s a nice place overall we had a great time. It is a short drive to the slopes, which is fine as long as you have a car but you still need to park at the inn"

￥52,058 total

includes taxes & fees

Nov 5 - Nov 6

"We had an awesome stay at Nate’s place! The stone architecture and wood oven fireplace gave a truly unique experience, and the house was very spacious. The fully equipped kitchen made for anxenjoyable cooking experience. Nate was also flexible and responsive. Definitely recommend this for your weekend getaway home!"

"Very nice place to stay for our 3 day hike on the AT. The view from the deck is amazing and the living room is huge with an old stone fireplace which we didn’t use because it was 90 degrees each day. The Mexican restaurant in town (Norte Azul) has an extensive menu and a good variety of beer on tap. Highly recommend visiting Mt Greylock in MA, about 30 mins away. It has an even better restaurant on top (you need reservations) and is right on the Appalachian Trail so you will meet all sorts on...

￥44,107 total

includes taxes & fees

Oct 9 - Oct 10

"Rustic but not too rustic, great location, excellent hot tub, plenty of blankets, well-appointed kitchen. Would definitely stay again. "

￥49,755 total

includes taxes & fees

Oct 19 - Oct 20

"Hindsale-perfect little hideaway, minutes from where we needed to be. Harrison’s little home was equipped with amenities/tasteful luxuries, and cozy nooks. We all loved the loft-could not believe how large the space was! Hot tub nights-perfect ending:) Thank you, Harrison."

"very nice and roomy! really enjoyed."

￥45,154 total

includes taxes & fees

Oct 28 - Oct 29

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Cherry Plain Hotel Reviews

Berkshire Mountain Lodge

10/10 Excellent

"Great stay, perfect "

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent

"We enjoyed our stay at Comfort Inn, East Greenbush, NY. The staff was friendly. Some areas in the bathroom like toilet and bathtub look outdated. Room was clean. Facilities were nicely kept. Buffet breakfast was a little limited in hot food options; just eggs, sausage, and waffles. It was more continental than anything. Gym equipment was a little rusty. There was excessive knocking like 2 hours before checkout time. They came to the room to ask if needed fresh towels and to take garbage out which is strange since it was so close to checkout time. There was a beeping sound on the 3rd floor and a complaint was made and the maintenance person came to fix it. Overall, it was a good place to stay overnight and get some rest. "

Jiminy Peak Mountain Resort

10/10 Excellent

"This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the property has great sandwiches and things needed for your stay."

Find out more about Cherry Plain

Search for holiday rentals in Cherry Plain on Expedia! You can easily find your home rentals, villas, holiday apartments in Cherry Plain using one of the methods below:

View our selection of featured holiday rentals in Cherry Plain
Use the map to find apartments and other holiday homes in the Cherry Plain neighbourhood you prefer
Enter your travel dates to view the best deals on holiday rentals in Cherry Plain while they last

Look no further and take a look at our great range of rental properties in Cherry Plain!

Frequently asked questions

Can I find a vacation rental in Cherry Plain?

Yes, you can find vacation rentals near well known local attractions in Cherry Plain, or you can choose a more remote option if you want a relaxing place to stay.

What's the top vacation rental that Cherry Plain has to offer?

Contemporary Berkshire Home with Views of Taconic Golf Course: This vacation home rental near 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.

What can I see and do in Cherry Plain?

Explore the area and family-friendly sights such as Berkshire Museum, or get out into nature at a spot like Brodie Mountain. Williamstown Theatre Festival and Jiminy Peak Mountain Resort are a couple of places you'll find in the larger area.

What are vacation rentals like in Cherry Plain?

Vacation rentals are private accommodations you can stay in for a few days or a quick weekend in Cherry Plain. Vacation rentals offer extras such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a sanitized environment, a vacation rental can provide a sense of safety away from shared hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for family trips or small group gatherings.

Unlock instant savings with Member Prices

Cherry Plain Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Vacation Rentals in Cherry Plain

Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

Huttopia Berkshires

Taborton Harvest Boulder Pines Cabin in the woods

Hancock Village Inn at Jiminy Peak

Comfortable Berkshires retreat on mtn resort, SISO

Taborton Harvest Timber Trails Unique cabin experience

FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!

Contemporary Berkshire Home with Views of Taconic Golf Course

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox

Private Indoor Heated Pool + Hot Tub + Fire Pit + Pond, on 35 Acres - sleeps 20

Cozy cabin in tranquil Canaan NY with WiFi, AC

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

Mountain Sanctuary Dome Rustic Solitude 5BR

Charming 3-bedroom Cabin for nature lovers

Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

Top Cherry Plain Hotel Reviews

Berkshire Mountain Lodge

Fairfield Inn & Suites Albany East Greenbush

Comfort Inn & Suites East Greenbush - Albany

Berkshires Untold

Courtyard by Marriott Albany Troy/Waterfront

The Williams Inn

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Jiminy Peak Mountain Resort

Find out more about Cherry Plain

Frequently asked questions

Go further with the Expedia app