Cherry Plain Vacation Rentals from ￥13,162: Search Short-Term Rentals

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

19th c. Barn in the Berkshires : Located near Cherry Plain, this vacation home rental is located in the mountains and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a library.

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Vacation Rentals in Cherry Plain

Enjoy cooking in this well-equipped kitchen with a central island, sink, and ample seating for two.

"One of the best properties i've ever stayed at "

￥42,797 total

includes taxes & fees

Jul 31 - Aug 1

Enjoy cooking in this well-equipped kitchen with a central island, stainless steel appliances, and a window with a view.

"Very clean and spacious! We enjoyed our stay with our small pup!"

￥96,867 total

includes taxes & fees

Aug 1 - Aug 2

Cozy retreat with a large bed, dresser, desk, and TV.

￥51,522 total

includes taxes & fees

Jul 14 - Jul 15

Cozy retreat with a neatly made bed, bedside table, and elegant mirror.

￥57,702 total

includes taxes & fees

Jul 14 - Jul 15

Step outside to a serene outdoor space with a deck, Adirondack chairs, and a charming playhouse.

￥60,504 total

includes taxes & fees

Jul 14 - Jul 15

Relax in a serene bedroom with a tufted headboard, desk, and dresser, perfect for work and rest.

￥70,273 total

includes taxes & fees

Jul 21 - Jul 22

Relax in this stylish living room with a large coffee table, two sofas, and a fireplace.

￥79,290 total

includes taxes & fees

Jul 21 - Jul 22

Cozy retreat with a large bed, dresser, and table, set amidst classic floral wallpaper and a decorative ceiling.

￥61,485 total

includes taxes & fees

Jul 31 - Aug 1

Stunning two-story house with a central entrance and lush green surroundings.

"Claudia is such a considerate and thoughtful host! We felt so welcome and at ease."

￥65,585 total

includes taxes & fees

Jul 14 - Jul 15

Relax in this inviting living room with a sofa, coffee table, and large window offering a view of the deck and surrounding trees.

"Great place to stay. House is brand new with plenty of room. Has 3 bedrooms plus a finished room in basement which is equivalent of a 4th room. Hiking and restaurants are close to the property. Plenty of parking. Highly recommend. Absolutely no complaints."

￥183,606 total

includes taxes & fees

Jul 16 - Jul 17

Relax by the large pool in our outdoor space.

"We had a wonderful stay, thank you! "

￥80,368 total

includes taxes & fees

Jul 14 - Jul 15

Relax by the pool surrounded by lush views and shaded lounge areas.

"Hosts were very responsiveHouse was clean and well maintainedExcellent locationOverall great stay"

￥70,715 total

includes taxes & fees

Jul 11 - Jul 12

Charming two-story house with a historic facade, featuring a prominent address and star symbol, set amidst a serene winter landscape.

"Very kinda hosts, and wonderful house."

￥160,837 total

includes taxes & fees

Jul 21 - Jul 22

Cozy space with a high ceiling, stone fireplace, and comfortable seating area.

"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!"

￥74,046 total

includes taxes & fees

Aug 2 - Aug 3

Enjoy cooking in this well-equipped kitchen with a stove, oven, refrigerator, coffee maker, and knife block.

"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"

￥59,227 total

includes taxes & fees

Jul 15 - Jul 16

Relax in a spacious outdoor living area with a comfortable sofa set and sheltered seating options.

￥69,862 total

includes taxes & fees

Jul 13 - Jul 14

Relax in our serene garden surrounded by lush greenery and a stone pathway.

"This VRBO was stocked to the brim with everything you would need. It was on the boarder of three different states , nestled on five acres of private property. It was the perfect private weekend getaway . Highly recommend for any family looking for a ski trip. The host responded to anything we needed immediately. We will definitely be back, 5 out of 5."

￥58,615 total

includes taxes & fees

Jul 13 - Jul 14

"Glass lake cottage was the perfect relaxing retreat while I was visiting for a wedding at the Old Daley Inn! The place was clean, had a well stocked kitchen and everything I needed. We were lucky to catch a fantastic sunset and enjoyed the view from the large deck. Will definitely be back! "

￥116,470 total

includes taxes & fees

Jul 14 - Jul 15

Escape to a serene cabin surrounded by a lush garden, featuring a spacious entrance and comfortable outdoor seating.

"Most AMAZING!!!!Going back sooooon!!!"

￥55,127 total

includes taxes & fees

Aug 5 - Aug 6

Relax in a secluded cabin surrounded by lush forest and plants, featuring a spacious entrance and a wooden deck with seating for two.

"June Farms is a hidden gem. We stayed there on an overnight trip. The grounds are beautiful and well maintained. We took an ATV tour w Michelle who gave us the grand tour and showed us all the properties and animals. The Pony Barn was open for pizzas, drinks top notch! It was dog park night and drew a fun crowd. Would def visit again!!!"

￥62,431 total

includes taxes & fees

Aug 3 - Aug 4

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

Sign in

Sign up, it's free

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!

Recent reviews of Cherry Plain properties

5/5 Excellent

"Property is decorated beautifully. The outdoor space is excellent. Overall a great find. Ill stay again if i go to Tanglewood "

A verified traveler stayed at Berkshires Untold

Posted 19 hours ago

Best Western Plus Franklin Square Inn Troy/Albany

5/5 Excellent

Loved this place!

"Very clean which is most important to me, great variety of breakfast foods and nice amount of hours that it was available, plus great little town, I will stay longer next time!! "

A verified traveler stayed at Best Western Plus Franklin Square Inn Troy/Albany

Posted 3 days ago

5/5 Excellent

"Did not use any amenities to speak of. But it was the perfect place to spend the night. No issues. Lovely bedrooms and living area. If we had more time I would have read my book on the peaceful deck. Well stocked with toiletries and extra blankets/pillows. "

A verified traveler stayed at Jiminy Peak Mountain Resort

Posted 5 days ago

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?

19th c. Barn in the Berkshires: Located near Cherry Plain, this vacation home rental is located in the mountains and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a library.

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. Cherry Plain State Park and Williamstown Theatre Festival 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.

Members save 10% or more on over 100,000 hotels worldwide when you’re signed in

Cherry Plain Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Vacation Rentals in Cherry Plain

Berkshire Village Carriage House - Super Private!!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Experience Timeless Elegance in The Edith Wharton Room!

Cozy Carriage House room with a double bed and private balcony

Historic Susan B. Anthony Room - Cozy & Charming Stay

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

Elegant suite with a king bed, fireplace, and kitchenette.

Elegant Carriage House room with a queen bed and private patio.

North Getaway Cottage

New Home - Heart of Williamstown 183

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Comfortable Berkshires retreat on mtn resort, SISO

Hancock Village Inn at Jiminy Peak

Mountain Sanctuary Dome Rustic Solitude 5BR

Near Tanglewood: Historic Summer Retreat

NEW RENO Historic Creamery in Berkshires w/hot tub

Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

Glass Lake Cottage

Treat yourself at the stunning June Farms Wellness Huts!

Treat yourself at the stunning June Farms Wellness Huts!

Find out more about Cherry Plain

Recent reviews of Cherry Plain properties

Berkshires Untold

The Yankee, Trademark Collection by Wyndham

Vacation Village in the Berkshires

Best Western Plus Franklin Square Inn Troy/Albany

Berkshire Mountain Lodge

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Jiminy Peak Mountain Resort

The Williams Inn

Hotel Downstreet, Ascend Hotel Collection

Frequently asked questions