Cherry Plain holiday homes

We found 186 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:1 Jan - 8 Jan

Private kitchen
Terrace/patio
Living area
Dining
Exceptional
(20 reviews)

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

Williamstown

12% off
NZ$5,349
for 7 nights, 1 cottage
NZ$764 per night
includes taxes & fees
Family-friendly, private three bedroom cottage in the beautiful Berkshires
Gourmet kitchen has everything you need to prepare delicious meals
Beautiful period woodwork and Victorian details
Huge wraparound porch is perfect for visiting with family and friends
Build a cozy fire in our wood fireplace, watch the game or play pool!
Exceptional
(157 reviews)

Huge Luxe Williamstown Updated Victorian, All Ensuite Baths, Walk to Spring St!

Williamstown

7% off
NZ$10,579
for 7 nights, 1 home
NZ$1,511 per night
includes taxes & fees
Huge Luxe Williamstown Updated Victorian, All Ensuite Baths, Walk to Spring St!
Exterior
Interior
Room
Interior
Exceptional
(44 reviews)

A MAGIC SPOT: Booking all year. A perfect, private, quiet mountaintop location.

Stephentown

8% off
NZ$3,029
for 7 nights, 1 home
NZ$433 per night
includes taxes & fees
A MAGIC SPOT: Booking all year. A perfect, private, quiet mountaintop location.
Private kitchen
Outdoor dining
Room
Exterior
Exceptional
(12 reviews)

Glass Lake Cottage

Averill Park

8% off
NZ$5,874
for 7 nights, 1 home
NZ$839 per night
includes taxes & fees
Glass Lake Cottage
Renovated kitchen
Outdoor dining
Dining
Property grounds
Exceptional
(39 reviews)

Large, family-friendly farmhouse located in the beautiful Berkshires

Williamstown

20% off
NZ$7,102
for 7 nights, 1 home
NZ$1,015 per night
includes taxes & fees
Large, family-friendly farmhouse located in the beautiful Berkshires
Beaver Pond Pool/clubhouse
new backyard table
another view of same bedroom as well as makeup table
another view of kitchen
Exceptional
(17 reviews)

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

Lanesborough

22% off
NZ$6,487
for 7 nights, 1 apartment
NZ$927 per night
includes taxes & fees
3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY
Bathroom
Interior
Property grounds
Interior
Exceptional
(6 reviews)

Historic Stone Church in The Berkshires

Lanesborough

8% off
NZ$4,963
for 7 nights, 1 home
NZ$709 per night
includes taxes & fees
Historic Stone Church in The Berkshires
Interior
Interior
Pool
Exterior
Exceptional
(18 reviews)

UNIQUE - 1BR Country Condo @ Jiminy Peak

Hancock

8% off
NZ$5,190
for 7 nights, 1 apartment
NZ$741 per night
includes taxes & fees
UNIQUE - 1BR Country Condo @ Jiminy Peak
  • 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)
  • Zema's Nursery (7.3 mi / 11.8 km)
  • Williams College Taconic Golf Course (9.2 mi / 14.9 km)
  • Pineridge Cross Country Ski Center (6.9 mi / 11.1 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)
  • Burden Lake (10.6 mi / 17.1 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.

More holiday ideas