Winchester Resorts
House
10.0(83 Reviews)
2 Bedrooms
1 Bath
4 Guests
Fireplace/Heating
Balcony/Terrace
Kitchen
Parking
US $133/Night
7 Nights - US $933
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
House
10.0(55 Reviews)
2 Bedrooms
1 Bath
4 Guests
950 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $134/Night
7 Nights - US $941
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
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
9.5(108 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(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
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
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
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
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
Why Choose Rent By Owner for your Winchester Resorts?
What makes our Resorts 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 Resorts
What's our booking process?
Our platform allows you to browse a curated selection of resorts. 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 Resorts Amenities
What amenities can you expect?
Our Resorts 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 Resorts
1. What are the top Resorts 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 Resorts in Winchester:
- Indigo Collective - Modern Comfort & Bold Design
- Charming 4-bedroom Pearce Historic Farmhouse in Roseburg with AC and WIFI
- 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
- Amazing Mid-Century Modern Home-Incredible Views!
- Comfy home in nice neighborhood. Short walk to shops, wine, breweries and food
- Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool
- Holiday Inn Express & Suites Roseburg North by IHG
2. How many Resorts 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 Resorts in Winchester.
More Rentals You May Like Near Winchester
Hotel
9.0(258 Reviews)
1 Bath
306.77 ft²
Private Pool- Hot Tub
- Fireplace/Heating
Pool
US $271/Night
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House
9.8(97 Reviews)
2 Bedrooms
1 Bath
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- Fireplace/Heating
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- Parking
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House
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- Fireplace/Heating
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- Parking
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House
9.8(22 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
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House
9.8(8 Reviews)
1 Bedroom
1 Bath
3 Guests
360 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $110/Night
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House
9.6(39 Reviews)
2 Bedrooms
1 Bath
4 Guests
900 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $148/Night
7 Nights - US $1,035
House
9.6(30 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $131/Night
7 Nights - US $920
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
House
9.4(20 Reviews)
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Pet Friendly
- 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 $250/Night
7 Nights - US $1,750
Apartment
1 Bedroom
1 Bath
2 Guests
854 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $387/Night
7 Nights - US $2,706
Cabin
10.0(29 Reviews)
5 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $572/Night
7 Nights - US $4,007
