Cherry Plain Vacation Rentals

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In two weeks
Oct 31 - Nov 2
In one month
Nov 14 - Nov 16
In two months
Dec 12 - Dec 14
In three months
Jan 9 - Jan 11

Vacation Rentals in Cherry Plain

Lobby
Vacation Village in the Berkshires
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (2070)
"Nice room clean and friendly staff"
$112 nightly
The price is $125
Oct 30 - Oct 31
Total with taxes and fees
Vacation Village in the Berkshires
Exterior
Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (981)
"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."
$146 nightly
The price is $164
Oct 19 - Oct 20
Total with taxes and fees
Jiminy Peak Mountain Resort
Restaurant
Huttopia Berkshires
Huttopia Berkshires
1.0 star property
10.0 out of 10, Exceptional, (5)
"Perfect place for a relaxing getaway! We loved everything! "
$98 nightly
The price is $109
Oct 16 - Oct 17
Total with taxes and fees
Huttopia Berkshires
Exterior detail
Taborton Harvest Boulder Pines Cabin in the woods
Taborton Harvest Boulder Pines Cabin in the woods
10.0 out of 10, Exceptional, (12)
"Such a sweet spot in the woods! Can’t wait to come back."
$165 nightly
The price is $183
Oct 16 - Oct 17
Total with taxes and fees
Taborton Harvest Boulder Pines Cabin in the woods
Exterior
Hancock Village Inn at Jiminy Peak
Hancock Village Inn at Jiminy Peak
10.0 out of 10, Exceptional, (14)
"Amazing Inn. Cozy and everything we needed. "
$969 nightly
The price is $1,047
Oct 21 - Oct 22
Total with taxes and fees
Hancock Village Inn at Jiminy Peak
A heated pool
Comfortable Berkshires retreat on mtn resort, SISO
Comfortable Berkshires retreat on mtn resort, SISO
8.8 out of 10, Excellent, (6)
"Kind and responsive host."
$478 nightly
The price is $485
Oct 16 - Oct 17
Total with taxes and fees
Comfortable Berkshires retreat on mtn resort, SISO
Fridge, microwave, oven, stovetop
Taborton Harvest Timber Trails Unique cabin experience
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."
$165 nightly
The price is $183
Oct 16 - Oct 17
Total with taxes and fees
Taborton Harvest Timber Trails Unique cabin experience
Interior
Charming 3-bedroom Cabin for nature lovers
Charming 3-bedroom Cabin for nature lovers
8.0 out of 10, Very Good, (1)
"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...
$264 nightly
The price is $293
Oct 16 - Oct 17
Total with taxes and fees
Charming 3-bedroom Cabin for nature lovers
Smart TV, fireplace, DVD player, music library
FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!
FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!
9.4 out of 10, Exceptional, (84)
"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! "
FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!
Outdoor dining
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
9.8 out of 10, Exceptional, (149)
"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."
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Fridge, microwave, oven, stovetop
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
2.0 star property
10.0 out of 10, Exceptional, (12)
"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! "
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Property grounds
2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox
2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox
9.8 out of 10, Exceptional, (69)
"Beautiful location, very spacious, comfortable and clean."
2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox
Smart TV, fireplace, DVD player, books
Contemporary Berkshire Home with Views of Taconic Golf Course
Contemporary Berkshire Home with Views of Taconic Golf Course
10.0 out of 10, Exceptional, (8)
"Lovely property. Well kept house, nicely decorated. Very much enjoyed our stay."
Contemporary Berkshire Home with Views of Taconic Golf Course
Exterior
Private Indoor Heated Pool + Hot Tub + Fire Pit + Pond, on 35 Acres - sleeps 20
Private Indoor Heated Pool + Hot Tub + Fire Pit + Pond, on 35 Acres - sleeps 20
9.2 out of 10, Wonderful, (5)
"Amazing stay in Hoosick! The kids loved the pool and the the views from the property were stunning"
Private Indoor Heated Pool + Hot Tub + Fire Pit + Pond, on 35 Acres - sleeps 20
Exterior
Cozy cabin in tranquil Canaan NY with WiFi, AC
Cozy cabin in tranquil Canaan NY with WiFi, AC
Cozy cabin in tranquil Canaan NY with WiFi, AC
Pool
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
8.0 out of 10, Very Good, (8)
"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"
$307 nightly
The price is $343
Oct 20 - Oct 21
Total with taxes and fees
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Interior
Mountain Sanctuary Dome Rustic Solitude 5BR
Mountain Sanctuary Dome Rustic Solitude 5BR
9.6 out of 10, Exceptional, (9)
"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
Exterior
Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4
Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4
$241 nightly
The price is $269
Oct 20 - Oct 21
Total with taxes and fees
Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4
Outdoor dining
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
8.0 out of 10, Very Good, (1)
"very nice and roomy! really enjoyed."
$269 nightly
The price is $300
Oct 20 - Oct 21
Total with taxes and fees
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Fridge, microwave, oven, stovetop
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
8.6 out of 10, Excellent, (34)
"Beautiful location. House isn't perfect and cleaning could be more detailed. But its a camp in the woods in vermont so its to be expected. "
$290 nightly
The price is $310
Oct 16 - Oct 17
Total with taxes and fees
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
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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Top Cherry Plain Hotel Reviews

Courtyard by Marriott Albany Troy/Waterfront

Courtyard by Marriott Albany Troy/Waterfront

10/10 Excellent
"Parking was easy and safe."
Anthony 2-night trip
Posted 2 days ago
Courtyard by Marriott Albany Troy/Waterfront

Find out more about Cherry Plain

Everything you need to know about Cherry Plain vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cherry Plain vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cherry Plain vacation 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 low season months. For more hustle and bustle, you may prefer to visit Cherry Plain in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $109 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Cherry Plain rentals

At Expedia, we put the best Cherry Plain vacation 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 vacation.

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.

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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.