Winchester Ski Chalets
Ski Chalet
10.0(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
912 ft²
Hot Tub
Fireplace/Heating
Balcony/Terrace
Kitchen
R10,457/Night
7 Nights - R73,207
Ski Chalet
4 Bedrooms
3 Baths
8 Guests
3799.66 ft²
View
Pet Friendly
Parking
Air Conditioner
R8,474/Night
7 Nights - R59,326
Ski Chalet
10.0(80 Reviews)
4 Bedrooms
3 Baths
10 Guests
2800 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R115,854/Night
7 Nights - R810,988
Ski Chalet
10.0(62 Reviews)
3 Bedrooms
3 Baths
6 Guests
3300 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R5,818/Night
7 Nights - R40,727
Ski Chalet
10.0(55 Reviews)
4 Bedrooms
3 Baths
10 Guests
3000 ft²
- Hot Tub
- Fireplace/Heating
Pool
Ocean View
R10,177/Night
7 Nights - R71,231
Ski Chalet
10.0(5 Reviews)
4 Bedrooms
2 Baths
11 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R8,259/Night
7 Nights - R57,808
Ski Chalet
9.6(20 Reviews)
3 Bedrooms
4 Baths
6 Guests
2000 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R5,371/Night
7 Nights - R37,591
House
10.0(111 Reviews)
2 Bedrooms
2 Baths
6 Guests
1800 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R9,415/Night
7 Nights - R65,907
House
10.0(2 Reviews)
4 Bedrooms
4 Baths
6 Guests
4380.91 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
Internet
R6,363/Night
7 Nights - R44,548
Hotel
9.6(581 Reviews)
1 Bath
- Pool
- Balcony/Terrace
Breakfast- Kitchen
R2,320/Night
7 Nights - R16,248
Cabin
10.0(45 Reviews)
1 Bedroom
1 Bath
2 Guests
1250 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R3,632/Night
7 Nights - R25,426
House
10.0(1 Review)
3 Bedrooms
2 Baths
7 Guests
2497.23 ft²
Oceanfront- Fireplace/Heating
- Ocean View
- View
R6,543/Night
7 Nights - R45,805
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Why Choose Rent By Owner for your Winchester Ski Chalets?
What makes our Ski Chalets special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Winchester
How to Book Your Winchester Ski Chalets
What's our booking process?
Our platform allows you to browse a curated selection of ski chalets. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Winchester
Common Ski Chalets Amenities
What amenities can you expect?
Our Ski Chalets are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Other Places to Stay in Winchester, VA
Warren County
Front Royal
Happy Creek
Frederick County
Old Town Winchester
Strasburg
Clarke County
Berryville
Bluemont
Russell
Stephens City
Frequently Asked Questions About Winchester Rental Ski Chalets
1. What are the top Ski Chalets in Winchester?
There are a lot of options in Winchester. If you plan on staying in the Winchester area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Ski Chalets in Winchester:
- Dog Friendly Skyline Drive Retreat: 3 King Suites, Views & Firepit! 1pm checkout
- Spectacular Cottage with Shenandoah River Views
- Fantasy Cottage: Private Pond, Waterfall, Hot Tub
- Rolling River Farm: Exquisite Riverfront Paradise
- Spacious Cabin on Cedar Creek, Shenandoah Forest Immersion!
- Whiskey Hill Cabin a mountain escape in Virginia wine country
- Riverfront - Happy Peach on the Shenandoah
- The Nest at Chester Gap
- Country Elegance overlooking the Shenandoah River
- Beautiful Historic Home Overlooking Shenandoah River and Blue Ridge Mountains
2. How many Ski Chalets are available in Winchester?
Currently, the total number of properties listed by RBO in 2026 is over 7 in the Winchester area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Ski Chalets in Winchester.
More Rentals You May Like Near Winchester
Cabin
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
750 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R2,987/Night
7 Nights - R20,902
Villa
10.0(1 Review)
3 Bedrooms
2 Baths
8 Guests
1323.96 ft²
- Hot Tub
- Balcony/Terrace
- View
- Pet Friendly
R14,920/Night
7 Nights - R104,446
Cabin
9.2(9 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R2,491/Night
7 Nights - R17,440
House
9.7(3 Reviews)
2 Bedrooms
2 Baths
10 Guests
2002.09 ft²
- Fireplace/Heating
- Parking
- Air Conditioner
Child Friendly
R3,176/Night
7 Nights - R22,225
House
8.0(4 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Internet
R2,869/Night
7 Nights - R20,086
Bed & Breakfast
9.5(209 Reviews)
3 Bedrooms
3 Baths
11 Guests
290.63 ft²
Skiing- Fireplace/Heating
- Balcony/Terrace
- View
R2,466/Night
7 Nights - R17,261
Apartment
7.4(9 Reviews)
1 Bedroom
1 Bath
4 Guests
- Pet Friendly
- Air Conditioner
- Internet
- Child Friendly
R3,247/Night
7 Nights - R22,731
House
9.5(8 Reviews)
6 Bedrooms
4 Baths
14 Guests
3304.52 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R6,246/Night
7 Nights - R43,731
Apartment
7.2(10 Reviews)
1 Bedroom
1 Bath
2 Guests
- Pet Friendly
- Kitchen
- Air Conditioner
- Internet
R3,452/Night
7 Nights - R24,168
House
6.8(3 Reviews)
1 Bedroom
1 Bath
4 Guests
- Kitchen
- Internet
- Child Friendly
Bedding/Linens
R3,362/Night
7 Nights - R23,531
Cottage
6.0(1 Review)
2 Bedrooms
2 Baths
5 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
R3,782/Night
7 Nights - R26,471
Apartment
1 Bedroom
1 Bath
2 Guests
700 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R4,286/Night
7 Nights - R29,998
