Cherry Plain holiday homes

We found 180 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Cherry Plain that are perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday homes have the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a hot tub. No matter what you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Cherry Plain

Showing deals for:13 Nov - 20 Nov

Dining
Outdoor dining
Property grounds
Renovated kitchen
Exceptional
(39 reviews)

Large, family-friendly farmhouse located in the beautiful Berkshires

Williamstown

20% off
NZ$6,670
for 7 nights, 1 home
NZ$953 per night
includes taxes & fees
Large, family-friendly farmhouse located in the beautiful Berkshires
Dining
Private kitchen
Interior
Private kitchen
Exceptional
(5 reviews)

Dog Friendly Country Farmhouse, 2 bed / 2 bath; 1.5 miles from Jiminy Peak

Williamstown

20% off
NZ$3,559
for 7 nights, 1 room
NZ$508 per night
includes taxes & fees
Dog Friendly Country Farmhouse, 2 bed / 2 bath; 1.5 miles from Jiminy Peak
Room
Terrace/patio
Living area
Private kitchen
Exceptional
(20 reviews)

Family-friendly, private three bedroom cottage in the beautiful Berkshires

Williamstown

12% off
NZ$5,070
for 7 nights, 1 cottage
NZ$724 per night
includes taxes & fees
Family-friendly, private three bedroom cottage in the beautiful Berkshires
View from ski room to trail thru woods to Grouse Run - fantastic location!!
Spring at Jiminy Peak 2019
Interior
Night skiing view from living room
Exceptional
(46 reviews)

Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.

Hancock

12% off
NZ$9,625
for 7 nights, 1 home
NZ$1,375 per night
includes taxes & fees
Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.
Interior
Interior
Room
Exterior
Exceptional
(40 reviews)

A MAGIC SPOT: Booking all year. The perfect spring/summer mountaintop location.

Stephentown

7% off
NZ$2,961
for 7 nights, 1 home
NZ$423 per night
includes taxes & fees
A MAGIC SPOT: Booking all year. The perfect spring/summer mountaintop location.
Outdoor Pool near The Country Store
The Deck at Christiansen's Tavern
Outdoor dining
The Country Store
Exceptional
(24 reviews)

Five-Star Family Friendly Townhouse in the Heart of Jiminy Peak

Hancock

8% off
NZ$8,939
for 7 nights, 1 home
NZ$1,277 per night
includes taxes & fees
Five-Star Family Friendly Townhouse in the Heart of Jiminy Peak
another view of same bedroom as well as makeup table
new backyard table
Beaver Pond Pool/clubhouse
kitchen and laundry room area
Exceptional
(17 reviews)

3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY

Lanesborough

22% off
NZ$6,261
for 7 nights, 1 apartment
NZ$894 per night
includes taxes & fees
3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY
Large Smart HDTV with electric fireplace in living room, showing dining room
View from 2nd floor balcony (after leaves have fallen)
Entrance into house with wood burning stove to right and staircase
Smart TV in Downstairs room with view of entrance to house and doors to room
Exceptional
(72 reviews)

2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox

Williamstown

12% off
NZ$4,163
for 7 nights, 1 home
NZ$595 per night
includes taxes & fees
2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Book a holiday rental for your Cherry Plain getaway

Learn about the unique charm of Cherry Plain with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in Cherry Plain

Do you want to find top things to see and do in the city? Venture out of your holiday home and check out everything that makes Cherry Plain a one-of-a-kind holiday spot. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Jiminy Peak Mountain Resort (6.2 mi / 10 km)
  • Waubeeka Golf Links (6.3 mi / 10.1 km)
  • Bousquet Ski Area (15.4 mi / 24.9 km)
  • Pineridge Cross Country Ski Center (6.9 mi / 11.1 km)
  • Zema's Nursery (7.3 mi / 11.8 km)
  • Williams College Taconic Golf Course (9.2 mi / 14.9 km)

Exploring the natural features in Cherry Plain

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Cherry Plain is a great spot to appreciate mother nature. These are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Brodie Mountain (5.8 mi / 9.4 km)
  • Taconic Lake (7.7 mi / 12.4 km)
  • Mount Greylock State Reservation (9 mi / 14.5 km)
  • Mount Greylock State Reservation Visitor Center (9.1 mi / 14.6 km)
  • Mount Greylock (9.8 mi / 15.7 km)
  • Pontoosuc Lake (10.9 mi / 17.5 km)

Transport to and around Cherry Plain

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 14.6 mi (23.5 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into Albany, NY (ALB-Albany Intl.), which is 24.2 mi (39 km) away.

Frequently asked questions

How much does it cost to rent a holiday home in Cherry Plain?
The average price for a holiday home in Cherry Plain can vary depending on factors such as property type, length of stay and season. Whether you're in search of a sprawling house with room for friends and family or a cosy cabin just for the two of you, just enter your travel dates to discover stays with terrific value.
How much does it cost to rent a beach house in Cherry Plain?
When you travel and the size and style of the property will help determine the cost of your beachside holiday home. Type in your Cherry Plain travel dates to see your options on Bookabach. Looking for a backyard so the kids can run around, or a pool to keep them busy? Use our filters to pick the features and amenities you want.
How old do you have to be to rent a holiday home in Cherry Plain?
You'll need to check with the Cherry Plain holiday property you're looking at on Bookabach as the age limit differs. However, typically it's 16, 18 or 21.
How long can I rent a holiday home in Cherry Plain for?
It all depends on the Cherry Plain property. To view a list of options offering extended stays, simply enter your dates and number of guests into the Bookabach search page. You can enjoy having the whole property to yourself, as well as comforts such as a kitchen, air conditioning and an outdoor space where the kids can play. Keep your eyes open for long-term stays that offer discounted weekly or monthly prices.

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