Cherry Plain Vacation Rentals

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Dec 12 - Dec 14

Vacation Rentals in Cherry Plain

Lobby
Vacation Village in the Berkshires

Condo in Williamstown

3.0 star property
8.8 out of 10, Excellent, (2158)
"Great stay and beautiful scenery close to Jiminy’s Peak Ski slopes. They have a heated pool for winter weather and extra outdoor for the summer plus other family oriented amenities"
United States
Karla
$101 nightly
The price is $113
Dec 3 - Dec 4
Total with taxes and fees
Vacation Village in the Berkshires
Exterior
Huttopia Berkshires

Camping in Williamstown

1.0 star property
10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
$151 nightly
The price is $169
Dec 14 - Dec 15
Total with taxes and fees
Huttopia Berkshires
Exterior
Jiminy Peak Mountain Resort

Condo resort in Hancock

3.0 star property
8.2 out of 10, Very Good, (986)
"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."
United States
Amy
$176 nightly
The price is $197
Dec 3 - Dec 4
Total with taxes and fees
Jiminy Peak Mountain Resort
Exterior detail
Taborton Harvest Boulder Pines Cabin in the woods

Cabin in Sand Lake

10.0 out of 10, Exceptional, (13)
"Loved the earthiness and serenity of the cabin and great room. Everything built and made and maintained by the Adamos- truly a haven "
United States
Joanna R.
$166 nightly
The price is $184
Dec 3 - Dec 4
Total with taxes and fees
Taborton Harvest Boulder Pines Cabin in the woods
Exterior
Club Wyndham Bentley Brook Resort - 2 Bedroom

Condo in Hancock

8.0 out of 10, Very Good, (4)
"Great spot for family ski trip. Location was great. Condo and amenities were great. Overall super happy and would stay again. "
United States
Ellamae G.
Club Wyndham Bentley Brook Resort - 2 Bedroom
A heated pool
Comfortable Berkshires retreat on mtn resort, SISO

Vacation Home in Hancock

9.0 out of 10, Wonderful, (7)
"Kind and responsive host."
United States
Javier
$722 nightly
The price is $733
Dec 3 - Dec 4
Total with taxes and fees
Comfortable Berkshires retreat on mtn resort, SISO
Smart TV, fireplace, DVD player, music library
FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!

Apartment in Pownal

9.4 out of 10, Exceptional, (85)
"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! "
United States
Elizabeth R.
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

Vacation Home in Pittsfield

9.8 out of 10, Exceptional, (150)
"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."
United States
Sarah A.
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Fridge, microwave, oven, stovetop
Taborton Harvest Timber Trails Unique cabin experience

Cabin in Sand Lake

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."
United States
Georgia M.
$165 nightly
The price is $183
Dec 3 - Dec 4
Total with taxes and fees
Taborton Harvest Timber Trails Unique cabin experience
Exterior
Hancock Village Inn Near Jiminy Peak

Vacation Home in Hancock

10.0 out of 10, Exceptional, (16)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
$1,015 nightly
The price is $1,099
Dec 3 - Dec 4
Total with taxes and fees
Hancock Village Inn Near Jiminy Peak
Interior
Charming 3-bedroom Cabin for nature lovers

Cabin in Stephentown

7.0 out of 10, Good, (2)
"It’s a duplex, half of an old farm house. The bedrooms are all up a steep staircase to the second floor. The only bathroom is on the main floor with the kitchen and LR. It was clean but had a mild old house smell. It’s out in the country with a great view from the enclosed porch and the open deck. The kitchen was well stocked with appliances and everything worked. It needs more seating and lights in the LR. "
United States
Bill B.
$258 nightly
The price is $286
Dec 3 - Dec 4
Total with taxes and fees
Charming 3-bedroom Cabin for nature lovers
Terrace/patio
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!

Vacation Home in Lanesborough

10.0 out of 10, Exceptional, (6)
"Everything was just as advertised and we really enjoyed the view and the hot tub. Perfect spot for a quick getaway! "
United States
Cindy B.
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!
Interior
Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location

Vacation Home in Lanesborough

9.6 out of 10, Exceptional, (74)
"Beautiful house and location that was perfect for a family weekend. Would 100% recommend!"
United States
Shaun L.
Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location
Interior
UNIQUE - 1BR Country Condo @ Jiminy Peak

Condo in Hancock

10.0 out of 10, Exceptional, (14)
"Clean, comfortable place with nice amenities. "
United States
Mike H.
$504 nightly
The price is $563
Dec 3 - Dec 4
Total with taxes and fees
UNIQUE - 1BR Country Condo @ Jiminy Peak
Exterior
Cozy cabin in tranquil Canaan NY with WiFi, AC

Cabin in Canaan

Cozy cabin in tranquil Canaan NY with WiFi, AC
Property grounds
2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox

Vacation Home in Hancock

9.8 out of 10, Exceptional, (70)
"Great stay at a comfortable house with three generations of our family. Debbie was very responsive to several questions we had. The house was perfectly situated for day trips in the area. Thanks much!"
United States
Wayne G.
2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox
Fridge, microwave, oven, stovetop
The Greylock Cabin

Vacation Home in Florida

10.0 out of 10, Exceptional, (4)
"Wonderful view, peaceful quiet area, cosy cabin."
United States
Anonymous traveler
$405 nightly
The price is $437
Dec 8 - Dec 9
Total with taxes and fees
The Greylock Cabin
Exterior
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

Apartment in Hancock

9.6 out of 10, Exceptional, (30)
"Great and clean property! Very easy to access and good parking too."
United States
Todd A.
$303 nightly
The price is $338
Dec 8 - Dec 9
Total with taxes and fees
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Exterior
Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4

Apartment in Hancock

10.0 out of 10, Exceptional, (1)
$246 nightly
The price is $275
Dec 3 - Dec 4
Total with taxes and fees
Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4
Fridge, microwave, oven, stovetop
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

Apartment in Dalton

2.0 star property
10.0 out of 10, Exceptional, (14)
"Easy check in, extremely well stocked kitchen, good wifi, and close to all the fun things to do in Western Mass! Extremely cute! Plenty of parking. We’d happily return. "
United States
Jacob S.
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
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

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Perfect "
Peter 2-night trip
Posted 14 hours ago
Hotel Downstreet, an Ascend Collection Hotel

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 $113 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

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?

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!: 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 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub.

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.