Winchester Resorts
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
AU $179/Night
For 7 Nights AU $1,256
850.35 ft²
4 Guests
1 Bedroom
1 Bathroom
House
- Hot Tub
- Fireplace/Heating
- Parking
AU $305/Night
For 7 Nights AU $2,136
1 Bedroom
1 Bathroom
Family Friendly
Bed & Breakfast
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
AU $267/Night
For 7 Nights AU $1,867
950 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
AU $178/Night
For 7 Nights AU $1,245
172.22 ft²
2 Guests
1 Bedroom
1 Bathroom
Free Cancellation
Bed & Breakfast
- Skiing
- Fireplace/Heating
- Balcony/Terrace
AU $407/Night
For 7 Nights AU $2,851
2000 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
AU $328/Night
For 7 Nights AU $2,296
276.27 ft²
5 Guests
3 Bedrooms
6 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- View
AU $176/Night
For 7 Nights AU $1,236
850 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
AU $354/Night
For 7 Nights AU $2,480
882.64 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Parking
- Internet
- Child Friendly
AU $153/Night
For 7 Nights AU $1,073
725 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
AU $497/Night
For 7 Nights AU $3,482
226.04 ft²
5 Guests
2 Bedrooms
1 Bathroom
Free Cancellation
House
- Spa
- Fireplace/Heating
- Balcony/Terrace
AU $325/Night
For 7 Nights AU $2,274
2 Guests
1 Bedroom
1 Bathroom
Couples Retreat
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Air Conditioner
AU $264/Night
For 7 Nights AU $1,851
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:
- Riverfront Log Cabin in Roseburg’s Wine Country
- Indigo Collective - Modern Comfort & Bold Design
- 4 BEDROOM House across from River in Best Roseburg area!
- Holiday Inn Express And Suites Roseburg North By Ihg
- Singing Waters at N. Umpqua
- Stylish Escape - Chic & Cozy with relaxing backyard
- Fantastic 3-bedroom house with AC in Roseburg
- Modern Mid-Century Retreat with Stylish Amenities & Family-Friendly Comfort
- Relax & Rejuvenate in 4Br home with Hot Tub & Deck, in heart of Roseburg
- Amazing Mid-Century Modern Home-Incredible Views!
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.
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AU $245/Night
For 7 Nights AU $1,712
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
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5 Guests
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Family Friendly
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- Fireplace/Heating
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4 Guests
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- Fireplace/Heating
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- Kitchen
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For 7 Nights AU $1,905
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- Balcony/Terrace
- Kitchen
- Parking
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6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
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- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
AU $493/Night
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3 Guests
1 Bedroom
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Family Friendly
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- Fireplace/Heating
- Pet Friendly
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AU $249/Night
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4 Guests
2 Bedrooms
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- Fireplace/Heating
- Kitchen
- Parking
AU $345/Night
For 7 Nights AU $2,416
854 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
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- Fireplace/Heating
- Kitchen
- Air Conditioner
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