Best Vacation Homes in Winchester
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $130/Night
For 7 Nights US $910
850.35 ft²
4 Guests
1 Bedroom
1 Bathroom
House
- Hot Tub
- Fireplace/Heating
- Parking
US $221/Night
For 7 Nights US $1,547
1 Bedroom
1 Bathroom
Family Friendly
Bed & Breakfast
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $193/Night
For 7 Nights US $1,352
950 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $125/Night
For 7 Nights US $877
172.22 ft²
2 Guests
1 Bedroom
1 Bathroom
Free Cancellation
Bed & Breakfast
- Skiing
- Fireplace/Heating
- Balcony/Terrace
US $295/Night
For 7 Nights US $2,065
2000 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
US $242/Night
For 7 Nights US $1,694
850 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $257/Night
For 7 Nights US $1,796
725 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
US $350/Night
For 7 Nights US $2,453
Winchester Luxury Rentals
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $586/Night
For 7 Nights US $4,101
1500 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $473/Night
For 7 Nights US $3,311
10 Guests
5 Bedrooms
2 Bathrooms
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $453/Night
For 7 Nights US $3,174
2314 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $432/Night
For 7 Nights US $3,027
2 Guests
1 Bedroom
1 Bathroom
Couples Retreat
Apartment
- Internet
- Child Friendly
- Laundry
US $411/Night
For 7 Nights US $2,878
854 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
US $382/Night
For 7 Nights US $2,675
8 Guests
4 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $380/Night
For 7 Nights US $2,663
1160 ft²
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $371/Night
For 7 Nights US $2,598
Winchester Pet Friendly Vacation Rentals
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $181/Night
For 7 Nights US $1,265
306.77 ft²
22 Guests
81 Bedrooms
1 Bathroom
Free Cancellation
Hotel
- Private Pool
- Hot Tub
- Fireplace/Heating
US $271/Night
For 7 Nights US $1,899
1000 ft²
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $232/Night
For 7 Nights US $1,625
1000 ft²
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $181/Night
For 7 Nights US $1,265
14 Guests
100 Bedrooms
1 Bathroom
Ocean View
Hotel
- Private Pool
- Oceanfront
- Hot Tub
US $161/Night
For 7 Nights US $1,128
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $181/Night
For 7 Nights US $1,265
4 Guests
1 Bedroom
1 Bathroom
Couples Retreat
Apartment
- Fireplace/Heating
- Pet Friendly
- Internet
US $121/Night
For 7 Nights US $847
10 Guests
4 Bedrooms
2 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Pool
US $327/Night
For 7 Nights US $2,286
Winchester Large Vacation Homes
2600 ft²
10 Guests
3 Bedrooms
1 Bathroom
Family Friendly
Bed & Breakfast
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $328/Night
For 7 Nights US $2,293
6200 ft²
8 Guests
4 Bedrooms
5 Bathrooms
Family Friendly
Villa
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
US $895/Night
For 7 Nights US $6,263
1799 ft²
10 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $200/Night
For 7 Nights US $1,402
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Air Conditioner
- Internet
US $325/Night
For 7 Nights US $2,274
Why Choose Rent By Owner for your Winchester Vacation Rental Homes?
What makes our Vacation Rentals 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.
Best Times to Visit Winchester
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here can greatly enhance your experience, as this destination offers different charms across the seasons, making it ideal to plan your stay when the weather and local events align with your preferences.
Peak Season Highlights
Summer (June to August)
During the warm summer months, you can enjoy longer daylight hours and pleasant weather, making it ideal for outdoor activities and exploring the region’s natural beauty.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
Fall (September to November)
As the region transitions into fall, vibrant foliage creates a picturesque setting that enhances your outdoor experiences and sightseeing adventures.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F
Off-Season Highlights
Winter (December to February)
The winter months bring cooler temperatures and quieter surroundings, offering a peaceful environment for those seeking solitude and cozy accommodations.
Average Temperature Daytime: 40°F to 50°F - Nighttime: 30°F to 40°F
Early Spring (March to May)
In early spring, fewer visitors and mild weather create a tranquil atmosphere perfect for enjoying the region’s scenic landscapes without the crowds.
Average Temperature Daytime: 50°F to 60°F - Nighttime: 35°F to 45°F
Weekly Weather Forecast for Winchester
How to Book Your Winchester Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. 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 Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals 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
Outdoor Amenities
- Enjoy outdoor dining with a spacious patio or picnic area to make the most of the region’s pleasant weather.
- Take advantage of private gardens or landscaped yards perfect for relaxing or outdoor activities.
- Make use of a barbecue grill for preparing meals while soaking in the scenic views of the surrounding area.
- Experience the convenience of nearby fire pits, ideal for cozy evenings under the stars.
- Benefit from access to outdoor furniture that allows you to unwind comfortably amidst nature.
- Explore well-maintained walking or hiking trails directly accessible from your rental here.
- Utilize designated parking areas suited for boats or recreational vehicles, ideal for adventure enthusiasts exploring the region.
Top Attractions Around Winchester
What attractions are nearby?
In this charming destination, you can explore scenic outdoor activities, historical sites, and local attractions that showcase the best of the area’s natural beauty and cultural heritage, all conveniently accessible from your vacation rental here in Winchester, Oregon.
Family Activities
- Winchester Bay State Park: Enjoy a family picnic and explore the scenic shoreline at this popular spot near the coast.
- South Jetty County Park: Perfect for fishing, birdwatching, and relaxing with your loved ones while taking in views of the Pacific Ocean.
- The Oregon Dunes National Recreation Area: Embark on an exciting dune exploration adventure, suitable for outdoor enthusiasts and families alike.
- Umpqua River Lighthouse & Museum: Discover the region's maritime history and enjoy breathtaking river views with your family during a visit to this historic lighthouse.
Adult Activities
- Winchester Bay Boat Tours: Explore the scenic waterways through guided boat tours that showcase the area's natural beauty and wildlife.
- Beachcombing at Bandon Beach: Stroll along the rugged coastline to discover unique shells, driftwood, and marine life in this popular Oregon destination.
- Hiking in Cape Arago State Park: Enjoy panoramic ocean views and diverse trails that wind through lush coastal landscapes in this nearby park.
- Seafood Dining Experiences: Savor fresh, locally caught seafood at renowned restaurants that highlight the region’s culinary delights.
Winchester Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Amenities: Take advantage of the area's amenities to enhance your stay, ensuring you have what you need within easy reach during your visit.
- Plan Outdoor Activities: Discover and plan outdoor activities that showcase the natural beauty of the region, making your trip memorable and engaging.
- Visit Nearby Attractions: Make time for local attractions that reflect the charm of the destination, providing a well-rounded experience of the area.
- Book in Advance: Secure your preferred vacation rentals early to guarantee availability and get the best rates during your stay here.
Transportation Options
- Winchester Bay Ferry Service: You can enjoy a scenic ferry ride across nearby waters, offering convenient access to surrounding attractions and outdoor activities.
- Local Taxi Services: Reliable taxi companies operate within the area, providing easy transportation for day trips or quick errands during your stay.
- Rental Car Agencies: Several rental car agencies are available nearby, giving you the flexibility to explore this region at your own pace.
- Bicycle Rentals: Biking is a popular way to experience the natural surroundings here, with local shops offering bicycle rentals suitable for all ages.
Local Customs Options
- Local Crafts and Artisans: You’ll find that supporting local artisans is a cherished custom, with handcrafted goods often showcased at markets and festivals here.
- Farmers' Market Traditions: Visiting the local farmers’ market is a common practice, reflecting a community that values fresh, locally sourced produce and handmade products.
- Community Celebrations: Participating in seasonal festivals and events is typical, fostering a strong sense of togetherness and cultural pride in this area.
- Respect for Nature: Respecting and preserving the natural environment is a significant custom, encouraging eco-friendly practices during your stay.
Frequently Asked Questions About Winchester?
1. What are the top vacation rentals 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 Vacation Rentals in Winchester:
- Sophisticated Bungalow, sparkling clean, walk to downtown, quiet neighborhood.
- Heavenly Bungalow, immaculately clean, close to downtown!
- Historical John Rast House
- Riverfront Log Cabin in Roseburg’s Wine Country
- Indigo Collective - Modern Comfort & Bold Design
- Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
- 4 BEDROOM House across from River in Best Roseburg area!
- Charming 4-bedroom Pearce Historic Farmhouse in Roseburg with AC and WIFI
- Singing Waters at N. Umpqua
- Stylish Escape - Chic & Cozy with relaxing backyard
2. How many vacation rentals have private pools in Winchester?
There are 3 vacation rentals with private pools near Winchester. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Winchester are best for families?
If you are looking for a family-friendly vacation home in Winchester, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Winchester:
4. How many Rentbyowner vacation rentals are available in Winchester?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 92 in the Winchester area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Winchester.
5. What is the cancellation policy for vacation rentals in Winchester, Oregon?
Cancellation policies vary by property. To understand the specific terms and any potential fees, please review the listing details carefully or contact the property owner directly before booking.
6. Are there any additional fees or charges I should be aware of when reserving a rental here?
Additional fees such as cleaning, service charges, or security deposits may apply and are detailed in each property’s listing. It's recommended to read the rental description thoroughly or reach out to the host for clarification.
7. How do I secure my reservation at a vacation rental in this region?
Reservations are confirmed once the required payment is processed and the booking is approved. For specific instructions or requirements, refer to the property listing or contact the owner directly.
8. Is there a minimum stay requirement for booking here?
Many properties have minimum night stay requirements that vary depending on the season or property owner preferences. Check the listing details or contact the owner for specific minimum stay policies.
9. What amenities are typically included in vacation rentals in Winchester, Oregon?
Amenities can differ between properties but often include essentials like Wi-Fi, parking, kitchen access, and outdoor spaces. For a complete list of amenities, review the individual property listing or ask the host directly.
Winchester Top Rated Vacation Rentals
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
Other
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $259/Night
For 7 Nights US $1,815
1 Bedroom
1 Bathroom
Family Friendly
Hotel
- Pool
- Balcony/Terrace
- Breakfast
US $178/Night
For 7 Nights US $1,244
US $139/Night
For 7 Nights US $971
US $95/Night
For 7 Nights US $663
US $104/Night
For 7 Nights US $731
1 Bedroom
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Breakfast
US $81/Night
For 7 Nights US $570
1 Bedroom
1 Bathroom
Family Friendly
Hotel
- Hot Tub
- Fireplace/Heating
- Pool
US $97/Night
For 7 Nights US $681
1 Bedroom
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Breakfast
US $75/Night
For 7 Nights US $528
