Romantic Wine Tours - Vacation Rentals in Cherry Plain

Cozy Ski in out Cabin in Berkshire Resort From US $323
         

10.0 (4 Reviews)
House
  • Air Conditioner
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  • Pet Friendly
Huttopia Berkshires From US $190
         

10.0 (7 Reviews)
RV Rental
  • Parking
  • Pet Friendly
  • Pool
Ski In & Ski Out - Deluxe 1 Bedroom Condo Sleeps 5 From US $574
         

Luxury Places to Stay in Cherry Plain

Over 279+ Luxury Places to Stay in or Near Cherry Plain
*Your Own B&B* From US $1,951
         

New
House
  • Air Conditioner
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  • Pet Friendly
ONTARA. From US $1,117
         

New
Other
  • Parking
  • TV
  • Balcony/Terrace
The entire Stephentown Hotel! 28 person occupancy From US $1,110
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
The entire Stephentown Hotel. 28 person occupancy From US $841
         

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10.0 (1 Review)
House
  • Air Conditioner
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  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Cherry Plain

Over 204+ Top-Rated Vacation Rentals with a Pool in or Near Cherry Plain
Ski season is here! From US $539
         

10.0 (50 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Farm House in Mt. Meadow From US $225
         

10.0 (34 Reviews)
Other
  • Air Conditioner
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Wyndham Bentley Brook Jiminy Peak ski in/out unit From US $700
         

Pet-Friendly Vacation Rentals in Cherry Plain

Over 31+ Pet-Friendly Vacation Rentals in or Near Cherry Plain
5 Bed/3 bath Apt Near Jiminy Peak Berkshires From US $667
         

10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
5 Bed/3 bath Apt Near Jiminy Peak Berkshires From US $494
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous From US $302
         

9.0 (2 Reviews)
Condo
  • Air Conditioner
  • Pet Friendly
  • Pool
2 Bed Berkshire Apt minutes to Jiminy Peak Ski From US $183
         

8.4 (12 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Dadzpad Cabin in Stephentown From US $150
         

5.0 (2 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
Stylish Mountain Cabin Close To Jiminy Peak From US $453
         

Stylish Mountain Cabin Close To Jiminy Peak From US $448
         

New
Cabin
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  • Pet Friendly
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Large Vacation Homes & Villas in Cherry Plain

Over 9+ Large Vacation Homes & Villas in or Near Cherry Plain
Comfortable Berkshires retreat on mtn resort, SISO From US $733
         

Huttopia Berkshires From US $148
         

9.7 (3 Reviews)
Other
  • Parking
  • Pet Friendly
  • Pool

Wheelchair Accessible Vacation Homes in Cherry Plain

Over 75+ Wheelchair Accessible Vacation Homes in or Near Cherry Plain
Vacation Village in the Berkshires From US $225
         

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8.6 (1438 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Jiminy Peak Mountain Resort From US $237
         

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8.2 (988 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool

Cherry Plain Varoom and Airbnb Places to Stay Under $200

Over 62+ Cherry Plain Varoom and Airbnb Places to Stay Under $200
2 Bed Berkshire Getaway minutes to Jiminy Peak Ski From US $132
         

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9.8 (8 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Vacation Village in the Berkshires From US $140
         

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8.8 (2202 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Quiet All-Season Creekside Escape in Upstate! From US $185
         

New
House
  • Parking
  • Balcony/Terrace
  • Security/Safety

Instantly Bookable Vacation Homes in Cherry Plain

Over 108+ Instantly Bookable Vacation Homes in or Near Cherry Plain
Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4 From US $268
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous From US $392
         

9.8 (31 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool

About Cherry Plain Vacation Rentals

With more than 288 Cherry Plain vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Romanticwinetours and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Cherry Plain.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Romanticwinetours Cherry Plain, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Cherry Plain. Places to stay near Cherry Plain are 662.56 ft² on average, with prices averaging $377 a night.

Romanticwinetours makes it easy and safe to find and compare vacation rentals in Cherry Plain with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Cherry Plain

Type Count
Resorts 62
Holiday Apartments 53
Vacation Homes 38
Others 6
Hotels with Suites 5
Cabin Rentals 4
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Cherry Plain

Pro Tip: Romanticwinetours makes it easy to compare the best listings on Romanticwinetours homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Romanticwinetours homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Cherry Plain.

Weather in Cherry Plain

View the weather forecast for Cherry Plain before booking your Cherry Plain Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F