Cherry Plain Vacation Rentals

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Vacation Rentals in Cherry Plain

Our top choices for Cherry Plain vacation rentals

Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1983)
"Beautiful location!"
$130 nightly
The price is $145
Sep 14 - Sep 15
Total with taxes and fees
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (970)
"Quiet, clean, accessible. "
$159 nightly
The price is $178
Sep 2 - Sep 3
Total with taxes and fees
Jiminy Peak Mountain Resort
Huttopia Berkshires
Restaurant

Huttopia Berkshires

1.0 star property
10.0 out of 10, Exceptional, (4)
"Perfect place for a relaxing getaway! We loved everything! "
$90 nightly
The price is $101
Sep 10 - Sep 11
Total with taxes and fees
Huttopia Berkshires
Taborton Harvest Boulder Pines Cabin in the woods
Exterior detail

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."
$172 nightly
The price is $191
Sep 2 - Sep 3
Total with taxes and fees
Taborton Harvest Boulder Pines Cabin in the woods
Hancock Village Inn at Jiminy Peak
Exterior

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (13)
"Very kinda hosts, and wonderful house."
$969 nightly
The price is $1,047
Sep 2 - Sep 3
Total with taxes and fees
Hancock Village Inn at Jiminy Peak
FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!
Smart TV, fireplace, DVD player, music library

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

9.4 out of 10, Exceptional, (82)
"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!
Taborton Harvest Timber Trails Unique cabin experience
Fridge, microwave, oven, stovetop

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
Sep 2 - Sep 3
Total with taxes and fees
Taborton Harvest Timber Trails Unique cabin experience
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Outdoor dining

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

9.8 out of 10, Exceptional, (146)
"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
Comfortable Berkshires retreat on mtn resort, SISO
A heated pool

Comfortable Berkshires retreat on mtn resort, SISO

8.8 out of 10, Excellent, (6)
"Kind and responsive host."
$469 nightly
The price is $475
Sep 2 - Sep 3
Total with taxes and fees
Comfortable Berkshires retreat on mtn resort, SISO
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Pool

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"
$293 nightly
The price is $327
Oct 1 - Oct 2
Total with taxes and fees
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Fridge, microwave, oven, stovetop

Cozy Rustic Apt in 18th c Berkshire Farmhouse

9.6 out of 10, Exceptional, (62)
"Great value, so much better than all the touristy motels in the area!"
$189 nightly
The price is $208
Sep 2 - Sep 3
Total with taxes and fees
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Florida Mountain Log Cabin!
TV

Florida Mountain Log Cabin!

2.0 star property
10.0 out of 10, Exceptional, (3)
"Place was super clean. Beds were comfortable. Location was great."
$371 nightly
The price is $392
Sep 3 - Sep 4
Total with taxes and fees
Florida Mountain Log Cabin!
Contemporary Berkshire Home with Views of Taconic Golf Course
Smart TV, fireplace, DVD player, books

Contemporary Berkshire Home with Views of Taconic Golf Course

10.0 out of 10, Exceptional, (5)
Contemporary Berkshire Home with Views of Taconic Golf Course
Private Indoor Heated Pool + Hot Tub + Fire Pit + Pond, on 35 Acres - sleeps 20
Exterior

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
Cozy cabin in tranquil Canaan NY with WiFi, AC
Exterior

Cozy cabin in tranquil Canaan NY with WiFi, AC

Cozy cabin in tranquil Canaan NY with WiFi, AC
A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything
Exterior

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

10.0 out of 10, Exceptional, (125)
"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
2200sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox
Property grounds

2200sf 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."
2200sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox
Park Street Penthouse Apartment
Game room

Park Street Penthouse Apartment

9.4 out of 10, Exceptional, (10)
"The penthouse was beautiful and spacious. The Host Lea was very congenial and offered great suggestions for the location. I will definitely be coming back "
$199 nightly
The price is $222
Sep 2 - Sep 3
Total with taxes and fees
Park Street Penthouse Apartment
UNIQUE - 1BR Country Condo @ Jiminy Peak
Interior

UNIQUE - 1BR Country Condo @ Jiminy Peak

10.0 out of 10, Exceptional, (12)
"Clean and quiet, nicely decorated! "
$279 nightly
The price is $312
Sep 11 - Sep 12
Total with taxes and fees
UNIQUE - 1BR Country Condo @ Jiminy Peak
Mountain Sanctuary Dome Rustic Solitude 5BR
Interior

Mountain Sanctuary Dome Rustic Solitude 5BR

9.6 out of 10, Exceptional, (8)
"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
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

Find out more about Cherry Plain

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 $101 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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?

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table: This vacation home rental near Cherry Plain is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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.