Cherry Plain Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Browse Select Cherry Plain Vacation Homes

Our top choices for Cherry Plain vacation homes

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

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

Comfortable Berkshires retreat on mtn resort, SISO

8.8 out of 10, Excellent, (6)
"Kind and responsive host."
The price is CA $223
CA $672 total
includes taxes & fees
Aug 26 - Aug 27
Comfortable Berkshires retreat on mtn resort, SISO

Mountain Sanctuary Dome Rustic Solitude 5BR

9.8 out of 10, Exceptional, (6)
"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

Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

9.8 out of 10, Exceptional, (93)
"We had another wonderful stay despite the weather, thank you for letting us enjoy your beautiful home"
The price is CA $225
CA $508 total
includes taxes & fees
Aug 26 - Aug 27
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

Home away from home

8.0 out of 10, Very good, (18)
"Very cozy and comfy place!"
Home away from home

Idyllic Berkshires Farmhouse

Idyllic Berkshires Farmhouse

Country Living just minutes from Everything!

10.0 out of 10, Exceptional, (28)
"Jandie's was the absolute best rental house we have ever stayed at. The house was clean and well kept, everything felt brand new. The set up was great, open kitchen, dining room and living room and made entertaining very easy. The kids had their own room and enjoyed spending time together in their own space. Julie was a pleasure to work with and accommodated us in anyway she could, from beginning to end. She even made us homemade delicious treats. We would highly recommend Jandie's and we...
Country Living just minutes from Everything!

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 Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

8.6 out of 10, Excellent, (32)
"Rustic but not too rustic, great location, excellent hot tub, plenty of blankets, well-appointed kitchen. Would definitely stay again. "
The price is CA $176
CA $420 total
includes taxes & fees
Aug 24 - Aug 25
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

2200sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox

9.8 out of 10, Exceptional, (68)
"Beautiful location, very spacious, comfortable and clean."
2200sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox

3 Bedroom Lakefront Home with Hot Tub & Fireplace

10.0 out of 10, Exceptional, (114)
"Our family of eight adults stayed in the home to celebrate a college graduation. It has a nice open floor plan that accommodated in-door time together as the weather was chilly for our stay. The nice balcony overlooks the lake. Only drawbacks are that there’s just one shower and futon sofa mattress was hard, not comfortable. Overall, very nice house and happy with our stay. "
3 Bedroom Lakefront Home with Hot Tub & Fireplace

Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

10.0 out of 10, Exceptional, (9)
"Nice spacious house with everything you could need for a short or long stay. We especially loved hanging out in the beautiful sunroom overlooking private backyard. Host was communicative and accommodating. Would highly recommend and consider staying again!"
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location

9.6 out of 10, Exceptional, (71)
"Our second stay at this lovely lakeside cottage-- great location, quiet and relaxing retreat."
Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location

Charming Berkshires Retreat – Minutes to Williamstown

8.0 out of 10, Very good, (4)
"Beautiful home, fully equipped, and fantastic location! We loved our stay. Also, the beds are so comfortable!"
Charming Berkshires Retreat – Minutes to Williamstown

Near Tanglewood: Historic Summer Retreat

9.6 out of 10, Exceptional, (22)
"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"
The price is CA $340
CA $710 total
includes taxes & fees
Aug 24 - Aug 25
Near Tanglewood: Historic Summer Retreat

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

9.4 out of 10, Exceptional, (45)
"The home is very nice and cozy. It really felt like a comfy home."
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

Spacious 7 bedroom house, Near jiminy Peak in Hancock ma , In the Berkshires

2.0 star property
10.0 out of 10, Exceptional, (6)
"A very good place to stay. Best of all, each bedroom has its own bathroom. There's plenty of hot water, even if multiple people are showering at the same time. The only downside to me is that the washer is broken when we checked in. We want to come again!"
Spacious 7 bedroom house, Near jiminy Peak in Hancock ma , In the Berkshires

19th c. Barn in the Berkshires

9.6 out of 10, Exceptional, (91)
"We planned to stay at this property in order to ski at Jiminy peak, and it was perfect, not a long drive at all. The barn stays very warm with the individual heaters as well as the wood stove in the middle of the main room. The kitchen was equipped with everything you need, they even had coffee and sugar! .. Communication with the hosts was seamless. We lost power due to a winter storm, the entire area did, and that wood stove worked its magic. The property owners made sure we were alright...
19th c. Barn in the Berkshires

Art House! Spacious Getaway By Mass Moca

10.0 out of 10, Exceptional, (11)
"We had a great girls weekend e joying local trails, MassMOCA, local restaurants and this very clean, spacious house! Location is walkable to the museum and down town and we enjoyed a soak in the tub after a day of hiking in local conservation areas! "
Art House! Spacious Getaway By Mass Moca
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Cherry Plain Hotel Reviews