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Cherry Plain Vacation Rentals

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Check prices for these dates

In two weeks
11 Sep - 13 Sep
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Cherry Plain vacation rentals

Interior

1. Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center

Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center
Lenox
The price is AED 879
AED 1,228 total
includes taxes & fees
15 Sep - 16 Sep
Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center
Family Bungalow

2. Huttopia Berkshires

Huttopia Berkshires
2.5 star property
Williamstown
9.4 out of 10, Exceptional, (16 reviews)
"Healthy food too!"
United States
GEORGINA
The price is AED 357
AED 399 total
includes taxes & fees
8 Sep - 9 Sep
Huttopia Berkshires
Lobby

3. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,559 reviews)
"Place was clean and well equipped, pool and amenities were great too !"
United States
Nyra
The price is AED 319
AED 397 total
includes taxes & fees
31 Aug - 1 Sep
Vacation Village in the Berkshires
Gift shop

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

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Hancock
10.0 out of 10, Exceptional, (5 reviews)
"We had a great stay! The kids absolutely loved the room. Great location and lots to do. Thanks again!!"
United States
Jen B.
The price is AED 417
AED 904 total
includes taxes & fees
26 Aug - 27 Aug
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Lobby

5. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,089 reviews)
"A nice place to stay in the Berkshires."
United States
Robert
The price is AED 347
AED 470 total
includes taxes & fees
31 Aug - 1 Sep
Berkshire Mountain Lodge
Pool

6. Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (4 reviews)
"Quiet location"
United States
Alicia S.
The price is AED 407
AED 889 total
includes taxes & fees
26 Aug - 27 Aug
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
Coffee/tea maker, fridge, microwave, oven

7. Taborton Harvest Timber Trails Unique cabin experience

Taborton Harvest Timber Trails Unique cabin experience
Sand Lake
10.0 out of 10, Exceptional, (3 reviews)
"It was a great getaway "
United States
Chandra F.
The price is AED 459
AED 677 total
includes taxes & fees
26 Aug - 27 Aug
Taborton Harvest Timber Trails Unique cabin experience
Gift shop

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

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Hancock
10.0 out of 10, Exceptional, (13 reviews)
"Staying right in the mountain was ideal. The condo was perfect. "
United States
patricia f.
The price is AED 407
AED 889 total
includes taxes & fees
26 Aug - 27 Aug
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Indoor pool

9. Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Hancock
9.8 out of 10, Exceptional, (22 reviews)
"Great skiing and proximity to mountain. Great for families"
United States
John F.
The price is AED 407
AED 889 total
includes taxes & fees
26 Aug - 27 Aug
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Indoor pool, a heated pool

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

1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
Hancock
9.4 out of 10, Exceptional, (6 reviews)
"Convenience to slopes and restaurants really great….,had a nice stay"
United States
Thomas S.
The price is AED 420
AED 908 total
includes taxes & fees
26 Aug - 27 Aug
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
Pool

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

Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Hancock
9.4 out of 10, Exceptional, (18 reviews)
"Nice Place"
United States
Tom C.
The price is AED 397
AED 878 total
includes taxes & fees
26 Aug - 27 Aug
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Outdoor dining

12. New Studio In Town, By the Water

New Studio In Town, By the Water
Williamstown
10.0 out of 10, Exceptional, (18 reviews)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
New Studio In Town, By the Water
Outdoor dining

13. Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
9.6 out of 10, Exceptional, (10 reviews)
"Perfect setup for anyone visiting Williamstown."
United States
Michael P.
The price is AED 533
AED 1,137 total
includes taxes & fees
15 Sep - 16 Sep
Downtown | Waterfront | Walk to Shops
Outdoor dining

14. 2-Bdr Apt In Town, By the Water

2-Bdr Apt In Town, By the Water
Williamstown
9.2 out of 10, Wonderful, (16 reviews)
"Location was very good-close to campus. Host was responsive. Accommodations were just right"
United States
Dan R.
The price is AED 477
AED 1,083 total
includes taxes & fees
10 Sep - 11 Sep
2-Bdr Apt In Town, By the Water
TV, DVD player, books

15. WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn

WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Hancock
9.0 out of 10, Wonderful, (17 reviews)
"Great stay! Perfect location by the pool and nicely renovated as advertised!"
United States
Matthew B.
The price is AED 407
AED 889 total
includes taxes & fees
26 Aug - 27 Aug
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Exterior

16. Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods
Sand Lake
10.0 out of 10, Exceptional, (17 reviews)
"This was a dash away and perfect! "
United States
Linda R.
The price is AED 459
AED 677 total
includes taxes & fees
26 Aug - 27 Aug
Taborton Harvest Boulder Pines Cabin in the woods
1 bedroom, WiFi (free), bed sheets

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

Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway
Sand Lake
The price is AED 514
AED 746 total
includes taxes & fees
5 Sep - 6 Sep
Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway
Dining

18. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (6 reviews)
"This home is super cozy and had all the amenities I needed after a long drive. I will be staying here again."
United States
Jess M.
The price is AED 426
AED 757 total
includes taxes & fees
30 Aug - 31 Aug
Cozy Home in Pownal VT
Coffee/tea maker, fridge, microwave, oven

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

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
United States
Joanna P.
The price is AED 257
AED 743 total
includes taxes & fees
26 Aug - 27 Aug
NEW RENO - Chalet-style farm loft near Tanglewood
Exterior

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

Getaway Near Mass MoCA, Great Hiking, Scenic Views
Stamford
10.0 out of 10, Exceptional, (34 reviews)
"Perfect for our weekend getaway. Close to the activities we wanted in North Adams, Mass, but just across the state line in a lovely rural setting. A very nice apartment... just as described. So happy to have chosen this for our stay!"
United States
Bill
The price is AED 281
AED 562 total
includes taxes & fees
26 Aug - 27 Aug
Getaway Near Mass MoCA, Great Hiking, Scenic Views
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 On North

Hotel On North

10/10 Excellent
"Such a comfortable hotel and the art and decor made for a unique stay!"
Gregory 1-night trip
Posted 5 hours ago
Hotel On North

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?

NEW RENO Historic Creamery in Berkshires w/hot tub: 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. 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.