Cherry Plain Holiday Rentals from €144: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Cherry Plain has to offer?

19th c. Barn in the Berkshires : This holiday home rental outside of Cherry Plain is located in the mountains, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a library.

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Holiday Rentals in Cherry Plain

Relax in a stylish living area with a large carpet, comfortable sofas, and a wooden coffee table.

"Very nice places "

Set amidst lush greenery, this hotel complex offers a serene escape with pathways connecting its various buildings.

"Everything was convenient and the staff was friendly and helpful, even though we were there in the off season"

includes taxes & fees

13 Jul - 14 Jul

Surrounded by trees, this cabin features a cozy porch and a white door.

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

includes taxes & fees

12 Jul - 13 Jul

Enjoy a cozy cabin stay with a front porch and deck area, perfect for taking in the surroundings.

"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."

includes taxes & fees

11 Jul - 12 Jul

Relax in the backyard patio area with a table, chairs, and cushioned benches under a pergola.

"Plenty of space to stay with friends but have your own space. Lots of outdoors activities in the area which was perfect. Clean, comfortable and pool table and hot tub were a plus! "

Cozy room with a stone fireplace, flat-screen TV, and patterned rug.

includes taxes & fees

15 Jul - 16 Jul

Relax in a serene outdoor space with Adirondack chairs and a shaded gazebo.

"Elise was an excellent host and super easy to work with. The property was even bigger, nicer, and cleaner than we expected. Plenty of room for a family getaway. "

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."

includes taxes & fees

5 Aug - 6 Aug

Stunning two-story home with a spacious balcony and beautifully manicured lawn.

"We had a wonderful time and loved the house! We will definitely be back!"

Relax on the spacious deck with a covered seating area, surrounded by lush greenery.

"Had an amazing weekend in this beautiful cabin! Highly recommend staying here! Great host, amazing views, beautiful property!"

Situated in a lush forest, this cabin offers a serene retreat with a picnic table for outdoor dining or relaxation.

Relax in this inviting living room with a comfortable sofa, a lamp, and a TV.

"Nice place, just what we were looking for to stay the weekend. "

Enjoy a serene view of the surrounding grassy field and forest from this outdoor deck.

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

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

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

includes taxes & fees

11 Jul - 12 Jul

Relax by the pool surrounded by lush hills and enjoy the scenic views.

"Perfect stay."

Features an oven, microwave, and refrigerator, along with a large window and ceiling lights.

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

Relax in this spacious living room with a high ceiling, leather sofa, and wooden coffee table.

"We planned to stay at this property in order to ski at Jiminy peak, and it was perfect, not a long drive at all. The barn stays very warm with the individual heaters as well as the wood stove in the middle of the main room. The kitchen was equipped with everything you need, they even had coffee and sugar! .. Communication with the hosts was seamless. We lost power due to a winter storm, the entire area did, and that wood stove worked its magic. The property owners made sure we were alright...

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!"

includes taxes & fees

2 Aug - 3 Aug

Cozy living space with a kitchenette, sofa, and coffee table.

"Very comfortable! Very clean!"

includes taxes & fees

15 Jul - 16 Jul

Cozy living area with a stone fireplace, dining table, and large windows offering views of the surrounding landscape.

"We had a large family group, 10 people, for graduation weekend. This property was an easy drive from Albany—we had plenty of space in a nice, secluded area. We will definitely keep this property in mind for future events. "

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Find out more about Cherry Plain

Everything you need to know about Cherry Plain holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cherry Plain holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cherry Plain holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cherry Plain holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cherry Plain. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cherry Plain holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cherry Plain holiday rentals we have selected for you start as low as €144 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Cherry Plain rentals

At Expedia, we put the best Cherry Plain holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Cherry Plain rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cherry Plain holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cherry Plain. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Recent reviews of Cherry Plain properties

Hotel Downstreet, Ascend Hotel Collection

5/5 Excellent

"Good"

A verified traveller stayed at Hotel Downstreet, Ascend Hotel Collection

Posted 2 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 traveller stayed at Jiminy Peak Mountain Resort

Posted 4 days ago

Frequently asked questions

Can I find a holiday rental in Cherry Plain?

Yes, there are holiday rentals close to the most popular sights in Cherry Plain, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Cherry Plain has to offer?

19th c. Barn in the Berkshires: This holiday home rental outside of Cherry Plain is located in the mountains, and has a fireplace, a patio and a BBQ 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 that 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 wider area.

What are holiday rentals like in Cherry Plain?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Cherry Plain. Holiday rentals provide amenities like kitchens and laundry facilities so you'll feel right at home. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from shared hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for a small group gathering.

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Holiday Rentals in Cherry Plain

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Holiday Rentals in Cherry Plain

Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Timber Trails Unique cabin experience

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

Charming 3-bedroom Cabin for nature lovers

Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

Hancock Village Inn at Jiminy Peak

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything

Huttopia Berkshires

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

Secluded Beautiful House w/16 Acres-fits 8 - Low rates- 2 min to Jiminy Peak

Comfortable Berkshires retreat on mtn resort, SISO

Mountainside Condo Ski In Ski Out

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

19th c. Barn in the Berkshires

Mountain Sanctuary Dome Rustic Solitude 5BR

Charming 1-bedroom apartment in cool Troy with WiFi, AC

Secluded w/ Deck Views, Hot Tub, & Ping Pong | Hudson in the Berks by AvantStay

Find out more about Cherry Plain

Recent reviews of Cherry Plain properties

Hotel Downstreet, Ascend Hotel Collection

The Yankee, Trademark Collection by Wyndham

The Williams Inn

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Best Western Plus Franklin Square Inn Troy/Albany

Berkshire Mountain Lodge

Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

Hotel On North

Frequently asked questions