Cherry Plain Cottages
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Cottages in Cherry Plain
Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires
Canaan NY
Located in Canaan, this cottage is on the waterfront, a 3-minute drive from Queechy Lake and 7 minutes from Furnace Brook Winery at Hilltop Orchards.
Kitchen
Pet friendly
Charming historic cottage on scenic road to Mt. Greylock
Lanesboro MA
With a stay at this cottage in Lanesborough, you'll be in the mountains, within a 10-minute drive of Jiminy Peak Mountain Resort and Mount Greylock State Reservation.
Kitchen
Free WiFi
Massachusetts Vacation Rental w/ Deck & Grill
Windsor MA
With a stay at this cottage in Windsor, you'll be 8.1 mi (13 km) from Susan B. Anthony Birthplace Museum and 8.2 mi (13.2 km) from Tannery Falls.
Kitchen
Washer
Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace
Nassau NY
Located in Nassau, this cottage is on the waterfront, within a 15-minute drive of Berkshire Retreat Center and Kinderhook Lake.
Kitchen
Free WiFi
Berkshires farm, 30+ guests, 50 acres
New Lebanon NY
$2,106 nightly
The price is $2,135 total per night
$2,135 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
With a stay at Berkshires farm, 30+ guests, 50 acres in New Lebanon, you'll be within a 5-minute drive of New Lebanon Library and Shatford Memorial Park.
Hot Tub
Kitchen
Luxury Vacation Rental in the Berkshires!
Williamstown MA
Located in Williamstown, this cottage is within a 5-minute drive of Mount Greylock State Reservation and Lower Linear Park.
Kitchen
Washer
Cozy cottage with pool, walking distance to lake
Averill Park NY
Located in Averill Park, this cottage is on a lake, within a 15-minute drive of Berkshire Retreat Center and Pineridge Cross Country Ski Center.
Pool
Kitchen
Chic Troy Home Near Downtown, 9 Mi to Albany!
336 Congress St Troy NY
With a stay at this cottage in Troy, you'll be within a 15-minute drive of MVP Arena and Rensselaer Polytechnic Institute.
Kitchen
Washer
Cozy Berkshire cottage with fireplace.
Pittsfield MA
With a stay at this cottage in Pittsfield, you'll be in the mountains, within a 15-minute drive of Tanglewood Music Center and Colonial Theater.
Kitchen
Washer
Entire cottage in Berkshire Villiage
Lanesborough MA
Located in Lanesborough, this cottage is on a lake, within a 10-minute drive of St Mary's of the Assumption Church and Crane Museum of Papermaking.
Kitchen
Washer
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.
Cherry Plain Cottages essential information
Accommodation | 46 Cottages |
|---|---|
Lowest Price | $2,135 |
Highest Price | $2,135 |
Popular accommodation | Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires, Charming historic cottage on scenic road to Mt. Greylock, Massachusetts Vacation Rental w/ Deck & Grill, Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace, Berkshires farm, 30+ guests, 50 acres, Luxury Vacation Rental in the Berkshires!, Cozy cottage with pool, walking distance to lake, Chic Troy Home Near Downtown, 9 Mi to Albany!, Cozy Berkshire cottage with fireplace., Entire cottage in Berkshire Villiage, Peaceful Seasonal lake front cottage with view of Burden Lake, Expansive Upstate Home w/ Home Theater! |