Cherry Plain Vacation Rentals from $123: Search Short-Term Rentals

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Our top choices for Cherry Plain vacation rentals

A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

1. Vacation Village in the Berkshires

Williamstown

Adrianne

$126 nightly

Nov 18 - Nov 19

Total with taxes and fees

A bedroom with a wooden bed, a window with a view of trees, and a red chair.

2. Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway

Sand Lake

Trena

$166 nightly

Oct 19 - Oct 20

Total with taxes and fees

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

3. Berkshire Mountain Lodge

Pittsfield

Joel

$110 nightly

Nov 18 - Nov 19

Total with taxes and fees

A snow-covered outdoor area with a fire pit, tables, and chairs.

4. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Hancock

Maura D.

$205 nightly

Oct 20 - Oct 21

Total with taxes and fees

A wooden cabin with a porch, a door, and a window.

5. Taborton Harvest Boulder Pines Cabin in the woods

Sand Lake

Nathan

$153 nightly

Oct 19 - Oct 20

Total with taxes and fees

A modern living room with a grey sofa, a bed with grey bedding, and a wooden wall with a mounted TV.

6. Berkshires Apartment at the Stephentown Hotel

Stephentown

Nicole O.

$233 nightly

Oct 19 - Oct 20

Total with taxes and fees

A rustic wooden interior with various stalls selling items like books, snacks, and wine.

7. Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Hancock

Ann

$205 nightly

Oct 20 - Oct 21

Total with taxes and fees

A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

8. Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Hancock

Tom C.

$205 nightly

Oct 20 - Oct 21

Total with taxes and fees

Four people seated at a table with food and drinks, wearing winter sports helmets.

9. Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

Hancock

Wendy D.

$208 nightly

Oct 19 - Oct 20

Total with taxes and fees

A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

10. 1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

Hancock

Thomas S.

$214 nightly

Oct 19 - Oct 20

Total with taxes and fees

"The best part of this place is the backyard. Sitting next to the river, watching the fire was real FUN! It felt like camping without the inconvenience of real camping.." ...Lina (no fee for firewood)

11. New Studio In Town, By the Water

Williamstown

Lydia J.

$240 nightly

Oct 19 - Oct 20

Total with taxes and fees

A spacious kitchen with wooden cabinets, a large island, and a dining area with benches.

12. Taborton Harvest Timber Trails Unique cabin experience

Sand Lake

Chandra F.

$153 nightly

Oct 19 - Oct 20

Total with taxes and fees

A wooden kitchen with a central island, bar stools, and a dining table with chairs.

13. Cozy Home in Pownal VT

Pownal

Jeri R.

$183 nightly

Oct 20 - Oct 21

Total with taxes and fees

14. Downtown | Waterfront | Walk to Shops

Williamstown

Tricia

$249 nightly

Nov 4 - Nov 5

Total with taxes and fees

A wicker sofa with a floral cushion, a wicker table with magazines, and a standing fan in a room with large windows and wooden floors.

15. Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

North Adams

Ruthie K.

$163 nightly

Oct 21 - Oct 22

Total with taxes and fees

A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

16. NEW RENO - Chalet-style farm loft near Tanglewood

New Lebanon

Joanna P.

$205 nightly

Oct 19 - Oct 20

Total with taxes and fees

A two-story blue house with a porch, surrounded by a garden with orange flowers.

17. Getaway Near Mass MoCA, Great Hiking, Scenic Views

Stamford

Bill

$128 nightly

Oct 19 - Oct 20

Total with taxes and fees

18. Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

Hancock

Shmaya G.

$279 nightly

Oct 19 - Oct 20

Total with taxes and fees

A wooden deck with outdoor furniture, a glass door leading to a view of a grassy area with trees.

19. Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views

Hancock

"I chose this place at the very last minute. It was all that I expected and wanted and more: two bedrooms with three beds, a comfortable living space, two full bathrooms, kitchen with all the basic necessities, TV in each bedroom and in the living room, a dining table and chairs, an outside porch with table, a big open space, and grill, easy parking and access, quiet, .and access to two pools. The place was well tended: clean, with towels and extras blankets ready. Howard, the owner, checked on...

Cecilia S.

$273 nightly

Oct 20 - Oct 21

Total with taxes and fees

A bedroom with a large bed, a nightstand, an air conditioning unit, and a view through the window.

20. 2 Bed Berkshire Apt minutes to Jiminy Peak Ski

Stephentown

Christine P.

$269 nightly

Oct 19 - Oct 20

Total with taxes and fees

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Top Cherry Plain Hotel Reviews

Courtyard by Marriott Lenox Berkshires

10/10 Excellent

"The room was clean and property was well maintained."

The Yankee Inn

8/10 Good

"Lovely, super clean unit with nice furnishings, however, the dining chair cushions need a good cleaning as the dirt could be seen. There also was candy/gum stuck to one of the cushions and another cushion was completely loose from the chair. There was mention of a "two-burner hotplate" in the description, but the photos showed a two-burner electric stove top. What actually is there is a two-burner infared hotplate. Instructions on how to use it is posted on the wall above the sink, not on the wall above the hotplate. Unfortunately, we were assigned an end unit in Building #13, which is currently being renovated. There was a family occupying the unit above us. The children ran up and down the stair and allowed the outside door to slam each and every time until late in the evening. No noise during quiet hours though. :o)"

Berkshire Mountain Lodge

8/10 Good

"This really is a great place and I will give it five stars, except the Wi-Fi is really crappy. We were on the fifth floor, but five MB/s is unacceptable in this day and age. The room was beautiful, and the kitchen was fabulous. One more nit is that they didn't make up the sofa bed. Most places make the sofa bed and fold it with the sheets and blanket inside. I found that sound late at night, and was not happy, but I understand. Still except for the WiFi this is 5 stars."

Jiminy Peak Mountain Resort

8/10 Good

"Everything was great here except our keys did not work so I had to go back to front desk for new keys on check in. Then on our 2nd morning we went to breakfast and came back to keys not working again. Front desk was helpful and reprogrammed them right away so not a huge deal. The hotel also has pretty thin walls so noise travels. Luckily our neighbors for the weekend were mostly quiet. I wish we knew John Harvards was closed till Thanksgiving but the other pub was great with an excellent beer selection on tap, great service & live entertainment every night. I wish there was free breakfast but thats not a big deal. I would recommend this place especially if you like to ski. We will consider this location for future Berkshire trips as its a fairly good central county location. Just keep in mind most shopping and restaurants are about 15-20+ minutes away."

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 $123 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.

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?

Lake Front Home in Heart of the Berkshires Near Jiminy Peak: Located near Cherry Plain, this vacation home rental 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 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 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.

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Check prices for these dates

Our top choices for Cherry Plain vacation rentals

1. Vacation Village in the Berkshires

2. Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway

3. Berkshire Mountain Lodge

4. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

5. Taborton Harvest Boulder Pines Cabin in the woods

6. Berkshires Apartment at the Stephentown Hotel

7. Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

8. Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

9. Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

10. 1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

11. New Studio In Town, By the Water

12. Taborton Harvest Timber Trails Unique cabin experience

13. Cozy Home in Pownal VT

14. Downtown | Waterfront | Walk to Shops

15. Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

16. NEW RENO - Chalet-style farm loft near Tanglewood

17. Getaway Near Mass MoCA, Great Hiking, Scenic Views

18. Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

19. Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views

20. 2 Bed Berkshire Apt minutes to Jiminy Peak Ski

Find vacation rentals that suit your style

Top Cherry Plain Hotel Reviews

Courtyard by Marriott Lenox Berkshires

The Yankee Inn

Comfort Inn & Suites East Greenbush - Albany

Berkshire Mountain Lodge

Hotel Downstreet, an Ascend Collection Hotel

Berkshires Untold

Jiminy Peak Mountain Resort

FairBridge Inn Express

Find out more about Cherry Plain

Frequently asked questions

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