Cherry Plain Holiday Rentals from €90: Search Short-Term Rentals

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Cherry Plain holiday 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

Luke

includes taxes & fees

1 Nov - 2 Nov

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

includes taxes & fees

24 Oct - 25 Oct

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

3. Berkshire Mountain Lodge

Pittsfield

Joel

includes taxes & fees

22 Nov - 23 Nov

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

4. Taborton Harvest Boulder Pines Cabin in the woods

Sand Lake

Nathan

includes taxes & fees

24 Oct - 25 Oct

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

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

Hancock

Maura D.

includes taxes & fees

26 Oct - 27 Oct

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.

includes taxes & fees

25 Oct - 26 Oct

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

7. Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Hancock

patricia f.

includes taxes & fees

27 Oct - 28 Oct

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

Hancock

Ann

includes taxes & fees

26 Oct - 27 Oct

9. Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat

Hancock

shannon m.

includes taxes & fees

26 Oct - 27 Oct

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

10. Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

Hancock

Kristina L.

includes taxes & fees

28 Oct - 29 Oct

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

11. Taborton Harvest Timber Trails Unique cabin experience

Sand Lake

Chandra F.

includes taxes & fees

24 Oct - 25 Oct

12. 1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

Hancock

Thomas S.

includes taxes & fees

28 Oct - 29 Oct

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

13. Cozy Home in Pownal VT

Pownal

Jeri R.

includes taxes & fees

26 Oct - 27 Oct

"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)

14. New Studio In Town, By the Water

Williamstown

Lydia J.

includes taxes & fees

25 Oct - 26 Oct

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

15. 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.

includes taxes & fees

25 Oct - 26 Oct

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.

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

North Adams

Ruthie K.

includes taxes & fees

28 Oct - 29 Oct

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

Hancock

Shmaya G.

includes taxes & fees

26 Oct - 27 Oct

18. Downtown | Waterfront | Walk to Shops

Williamstown

Douglas

includes taxes & fees

25 Oct - 26 Oct

A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

19. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

Stephentown

includes taxes & fees

5 Nov - 6 Nov

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

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

Hancock

Tom C.

includes taxes & fees

28 Oct - 29 Oct

View all properties

Find holiday rentals that suit your style

Aparthotels

Apartments

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Cherry Plain Hotel Reviews

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent

"Wonderful staff , great location ! Fresh brownies offered at check in , specialty cocktails in the evening , lovely breakfast in the morning:)"

The Yankee Inn

10/10 Excellent

"I would prefer more flexibility making reservations. Online and by phone, I wanted two rooms for two people. I was forced to request two rooms for THREE people to work around the algorithm that allowed only one room for two people. Also I was forced to accept two rooms in the same price range, when I wanted one premium king, not two. I left another hotel due to their inflexibility, and I will choose one with a personal approach next time."

Berkshires Untold

10/10 Excellent

"The lobby was absolutely beautiful, aesthetically and structurally! From all the greenery from the plants to the high ceilings, cute seating areas, and nice bar. The outdoor furniture was a plus, especially with the fire pits and the surrounded by the nice view of the berkshires. After an evening out, we came back and played a board game in the lobby and even did a little painting of our own while enjoying some good cocktails…you can definitely create a vibe. The room was clean, and overall it was a great stay if you’re just looking to relax, unwind, and get away for a bit!"

Berkshire Mountain Lodge

10/10 Excellent

"We've stayed at Berkshire Mountain Lodge in October a number of times now, and we really enjoy the property. The rooms are well-appointed, very clean, and quite comfortable. We appreciate the free washers and dryers as well as the many other amenities, and you cannot beat the location. There's a supermarket down the driveway and across the street and an excellent specialty grocer--Guido's Market--just down the road. We highly recommend this property. The District Restaurant in Pittsfield is excellent. We've also seen several great plays at Barrington Theatre Company. The area is loaded with historical and cultural activities. We like the proximity to Lenox and the Edith Wharton mansion as well as The Clark art museum in Williamstown, both of which have lovely grounds/gardens typically exhibiting sculptures. There are also abundant outdoor activities and opportunities for hiking and lovely scenic drives. This was a good year for fall color, and the red maples were glorious! It's a short ride to Vermont where we checked out Mt. Equinox for the first time. Highly recommend the drive to the top on a sunny, clear day."

Find out more about Cherry Plain

Everything you need to know about Cherry Plain holiday rentals

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

Cherry Plain holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cherry Plain holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cherry Plain holiday rentals we have selected for you start as low as €90 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Cherry Plain rentals

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

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 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?

Lake Front Home in Heart of the Berkshires Near Jiminy Peak: This holiday home rental outside of Cherry Plain is located on a lake, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. You can relax into your holiday 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 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.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Cherry Plain holiday 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. Taborton Harvest Boulder Pines Cabin in the woods

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

6. Berkshires Apartment at the Stephentown Hotel

7. Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

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

9. Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat

10. Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

11. Taborton Harvest Timber Trails Unique cabin experience

12. 1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

13. Cozy Home in Pownal VT

14. New Studio In Town, By the Water

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

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

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

18. Downtown | Waterfront | Walk to Shops

19. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

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

Find holiday rentals that suit your style

Top Cherry Plain Hotel Reviews

The Cornell Inn, Lenox & The Berkshires

Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

The Yankee Inn

Hotel Downstreet, an Ascend Collection Hotel

Hampton Inn & Suites Berkshires-Lenox

Berkshires Untold

Berkshire Mountain Lodge

The Williams Inn

Find out more about Cherry Plain

Frequently asked questions

Go further with the Expedia app

Holiday Rentals in Cherry Plain

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Cherry Plain holiday 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. Taborton Harvest Boulder Pines Cabin in the woods

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

6. Berkshires Apartment at the Stephentown Hotel

7. Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

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

9. Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat

10. Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

11. Taborton Harvest Timber Trails Unique cabin experience

12. 1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

13. Cozy Home in Pownal VT

14. New Studio In Town, By the Water

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

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

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

18. Downtown | Waterfront | Walk to Shops

19. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

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

Find holiday rentals that suit your style

Top Cherry Plain Hotel Reviews

The Cornell Inn, Lenox & The Berkshires

Find out more about Cherry Plain

Frequently asked questions

Go further with the Expedia app