Winchester Ski Chalets
House
10.0(25 Reviews)
1 Bedroom
1 Bath
2 Guests
2000 ft²
Fireplace/Heating
Balcony/Terrace
Breakfast
Kitchen
US $310/Night
7 Nights - US $2,169
House
10.0(2 Reviews)
1 Bedroom
1 Bath
4 Guests
850.35 ft²
Hot Tub- Fireplace/Heating
Parking
Internet
US $221/Night
7 Nights - US $1,547
Bed & Breakfast
9.8(50 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $193/Night
7 Nights - US $1,352
Cottage
10.0(7 Reviews)
1 Bedroom
1 Bath
4 Guests
850 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $310/Night
7 Nights - US $2,173
Bed & Breakfast
9.8(67 Reviews)
1 Bedroom
1 Bath
2 Guests
172.22 ft²
Skiing- Fireplace/Heating
- Balcony/Terrace
View
US $295/Night
7 Nights - US $2,065
Apartment
10.0(3 Reviews)
1 Bedroom
1 Bath
2 Guests
725 ft²
- Fireplace/Heating
- Kitchen
Air Conditioner- Internet
US $360/Night
7 Nights - US $2,522
House
9.5(98 Reviews)
3 Bedrooms
6 Baths
5 Guests
276.27 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Breakfast
US $128/Night
7 Nights - US $895
Cottage
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Air Conditioner
- Internet
US $185/Night
7 Nights - US $1,297
House
9.5(11 Reviews)
1 Bedroom
1 Bath
2 Guests
882.64 ft²
- Balcony/Terrace
- Parking
- Internet
Child Friendly
US $111/Night
7 Nights - US $777
House
9.8(24 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
Pet Friendly- Kitchen
- Parking
US $113/Night
7 Nights - US $792
House
8.9(21 Reviews)
2 Bedrooms
1 Bath
5 Guests
226.04 ft²
Spa- Fireplace/Heating
- Balcony/Terrace
- View
US $235/Night
7 Nights - US $1,647
House
9.8(22 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $397/Night
7 Nights - US $2,780
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
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:
- Singing Waters at N. Umpqua
- Fantastic 3-bedroom house with AC in Roseburg
- Modern Bliss: Chic Retreat w/Stylish Amenities, Ideal for Vacation & Family Fun
- Relax & Rejuvenate in 4Br home with Hot Tub & Deck, in heart of Roseburg
- Holiday Inn Express And Suites Roseburg North By Ihg
- Comfy home in nice neighborhood. Short walk to shops, wine, breweries and food
- Hampton Inn & Suites Roseburg
- Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool
- Holiday Inn Express & Suites Roseburg North by IHG
- The Lodge at Roseburg
2. How many Ski Chalets are available in Winchester?
Currently, the total number of properties listed by RBO in 2026 is over 93 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.
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9.0(258 Reviews)
1 Bath
306.77 ft²
Private Pool- Hot Tub
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House
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House
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2 Bedrooms
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4 Guests
- Fireplace/Heating
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House
9.4(20 Reviews)
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
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- Kitchen
- Parking
US $181/Night
7 Nights - US $1,265
Apartment
9.4(3 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $296/Night
7 Nights - US $2,071
Apartment
1 Bedroom
1 Bath
2 Guests
854 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $387/Night
7 Nights - US $2,706
House
9.6(20 Reviews)
1 Bedroom
1 Bath
2 Guests
880 ft²
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
US $140/Night
7 Nights - US $977
Cabin
10.0(30 Reviews)
5 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $532/Night
7 Nights - US $3,725
House
10.0(24 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $356/Night
7 Nights - US $2,492
Bed & Breakfast
10.0(21 Reviews)
3 Bedrooms
1 Bath
10 Guests
2600 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $283/Night
7 Nights - US $1,979
House
10.0(15 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $280/Night
7 Nights - US $1,957
