Holiday Rentals in Cherry Plain

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Holiday Rentals in Cherry Plain

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1862)
"Very nice places "
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (947)
"Everything was convenient and the staff was friendly and helpful, even though we were there in the off season"
The price is €170
includes taxes & fees
13 Jul - 14 Jul
Jiminy Peak Mountain Resort

Taborton Harvest Boulder Pines Cabin in the woods

10.0 out of 10, Exceptional, (11)
"Such a sweet spot in the woods! Can’t wait to come back."
The price is €144
includes taxes & fees
12 Jul - 13 Jul
Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Timber Trails Unique cabin experience

10.0 out of 10, Exceptional, (1)
"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."
The price is €155
includes taxes & fees
11 Jul - 12 Jul
Taborton Harvest Timber Trails Unique cabin experience

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

9.8 out of 10, Exceptional, (144)
"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! "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Charming 3-bedroom Cabin for nature lovers

The price is €298
includes taxes & fees
15 Jul - 16 Jul
Charming 3-bedroom Cabin for nature lovers

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

10.0 out of 10, Exceptional, (7)
"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. "
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (12)
"Very kinda hosts, and wonderful house."
The price is €963
includes taxes & fees
5 Aug - 6 Aug
Hancock Village Inn at Jiminy Peak

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

10.0 out of 10, Exceptional, (58)
"We had a wonderful time and loved the house! We will definitely be back!"
Lake Front Home in Heart of the Berkshires Near Jiminy Peak

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

10.0 out of 10, Exceptional, (121)
"Had an amazing weekend in this beautiful cabin! Highly recommend staying here! Great host, amazing views, beautiful property!"
A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything

Huttopia Berkshires

1.0 star property
Huttopia Berkshires

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

9.4 out of 10, Exceptional, (81)
"Nice place, just what we were looking for to stay the weekend. "
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

9.8 out of 10, Exceptional, (68)
"Beautiful location, very spacious, comfortable and clean."
Secluded Beautiful House w/16 Acres-fits 8 - Low rates- 2 min to Jiminy Peak

Comfortable Berkshires retreat on mtn resort, SISO

9.6 out of 10, Exceptional, (4)
"Hosts were very responsiveHouse was clean and well maintainedExcellent locationOverall great stay"
The price is €423
includes taxes & fees
11 Jul - 12 Jul
Comfortable Berkshires retreat on mtn resort, SISO

Mountainside Condo Ski In Ski Out

9.0 out of 10, Wonderful, (28)
"Perfect stay."
Mountainside Condo Ski In Ski Out

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

9.0 out of 10, Wonderful, (29)
"Rustic but not too rustic, great location, excellent hot tub, plenty of blankets, well-appointed kitchen. Would definitely stay again. "
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

19th c. Barn in the Berkshires

9.6 out of 10, Exceptional, (89)
"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...
19th c. Barn in the Berkshires

Mountain Sanctuary Dome Rustic Solitude 5BR

9.8 out of 10, Exceptional, (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!"
Mountain Sanctuary Dome Rustic Solitude 5BR

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

10.0 out of 10, Exceptional, (2)
"Very comfortable! Very clean!"
The price is €171
includes taxes & fees
14 Jul - 15 Jul
Charming 1-bedroom apartment in cool Troy with WiFi, AC

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

10.0 out of 10, Exceptional, (2)
"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. "
Secluded w/ Deck Views, Hot Tub, & Ping Pong | Hudson in the Berks by AvantStay
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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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.