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Winchester Bay vacation rentals

We found 73 vacation rentals — enter your dates for availability

Discover a selection of 16 homes and other vacation rentals in Winchester Bay that are perfect for your trip. Whether you're traveling with a group or just with your pet, vacation rentals have the best amenities for spending time at your vacation home, which might include WiFi and a fireplace. You're sure to find a rental for everyone's needs, including options that are accessible or non-smoking.

Vacation rentals with weekly discounts - Winchester Bay

Showing deals for:May 22 - May 29

Image gallery for Cozy Cattail Cottage a comfortable coastal estuary woodland home near Reedsport

The Cozy Cattail Cottage
9.8 out of 10, Exceptional, (67 reviews)
Exceptional
(67 reviews)

Cozy Cattail Cottage a comfortable coastal estuary woodland home near Reedsport

Reedsport

9% off
Price is $226
$1,583 for 7 nights
All fees included
Cozy Cattail Cottage a comfortable coastal estuary woodland home near Reedsport

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Find out more about Winchester Bay

Why visit Winchester Bay

  • Stunning natural beauty: Experience breathtaking scenery and unforgettable sunsets along the Oregon coast.
  • Outdoor adventures: Enjoy a variety of outdoor activities, including hiking, fishing, and exploring nearby sand dunes.
  • Cozy accommodations: Choose from charming lakefront cabins, inviting condos, or the comfortable Winchester Bay Inn for your stay.
  • Welcoming atmosphere: Explore the friendly neighborhoods and create lasting memories with family and friends.
  • Easy access to parks: Discover national parks and picturesque lakes and rivers for a true nature immersion.

Popular types of accommodation in Winchester Bay

Planning a getaway to Winchester Bay? You're in for a treat. Discover the charm of this coastal destination with a range of vacation rentals to suit your needs. From cozy houses and inviting condos to charming cottages, there's something for everyone. Don't forget to explore options like the Winchester Bay RV Resort and the inviting Winchester Bay Inn for an overnight stay that promises comfort and relaxation. Your perfect vacation awaits.

  • Houses: These spacious accommodations offer a home-like atmosphere, perfect for families or groups looking to enjoy Winchester Bay together.
  • Condos: Ideal for those seeking a blend of convenience and comfort, condos provide modern amenities in a community setting near the beach.
  • Cottages: Charming and cozy, cottages are perfect for a romantic getaway or a peaceful retreat amidst nature.
  • Cabins: Rustic and inviting, cabins are great for those wanting to immerse themselves in the natural beauty of the area.
  • Apartments: Offering flexibility and convenience, apartments are a great choice for solo travelers or couples exploring Winchester Bay.**

Top attractions in and around Winchester Bay

Winchester Bay, Oregon, is a perfect destination for outdoor enthusiasts seeking adventure and stunning scenery. With its array of attractions, including national parks, lakes, and rivers, visitors can immerse themselves in nature and enjoy various outdoor activities. Whether you're traveling solo, with family, or friends, Winchester Bay offers unforgettable experiences that highlight its natural beauty and adventurous spirit.

  • Oregon Dunes National Recreation Area: A stunning expanse of towering sand dunes located 3 miles from Winchester Bay, offering thrilling outdoor adventures like dune boarding and hiking amidst mesmerizing landscapes.
  • Umpqua Lighthouse: A historic lighthouse located within Winchester Bay, rich in cultural significance, providing visitors with picturesque views and insights into maritime history.
  • Umpqua River: Flowing 4 miles from Winchester Bay, this scenic river is perfect for outdoor activities such as fishing, kayaking, and enjoying nature's beauty.

Things to do recommended for couples

Winchester Bay offers a romantic getaway with scenic beach walks and sunset views over the ocean. Explore the charming local shops or enjoy a cozy dinner at a waterfront restaurant. Don't miss a peaceful kayak ride in the bay, perfect for creating unforgettable memories together.

Things to do recommended for families

Families visiting Winchester Bay can explore the stunning Oregon Dunes National Recreation Area, enjoy a thrilling ride on a dune buggy, and spend quality time at the beautiful beaches. Don't miss the local seafood at nearby restaurants for a delicious family meal.

Things to do recommended for groups

Experience the beauty of the John Dellenback Dunes Trail for an adventurous hike just 6 miles from Winchester Bay. For some shopping and entertainment, visit Pony Village Mall, located 19 miles away, and don't miss out on browsing Books by the Bay, also 19 miles from your base.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Winchester Bay

If you're traveling with a group, family, or pets, or if you're planning an extended stay, be sure to set your filters according to your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Winchester Bay with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Winchester Bay with young kids: Traveling with little ones can be quite a task. It's important to prioritize their comfort and safety, along with finding suitable amenities like a private swimming pool. Additionally, think about how close you are to family-friendly attractions to make your trip even more enjoyable.
  • Taking your pets with you to Winchester Bay: For many families, a vacation wouldn’t feel complete without their furry companions. If you can relate to this, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Winchester Bay: If you're in search of vacation rentals that offer discounts for month-long stays, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Winchester Bay

Winchester Bay, Oregon, is a hidden gem for outdoor enthusiasts and adventure seekers. Nestled along the stunning Oregon coast, this charming village offers breathtaking scenery, unforgettable sunsets, and access to beautiful sand dunes. Whether you’re staying in a cozy lakefront cabin or exploring the friendly atmosphere of nearby neighborhoods, you're sure to create lasting memories with family and friends in this picturesque coastal paradise.

  • Reedsport: Nestled along the beautiful Oregon coast, Reedsport serves as the gateway to Winchester Bay and offers a blend of outdoor adventure and stunning scenery. Travelers flock to this city for its recreational areas and hiking trails, making it a perfect destination for those who love nature. Popular attractions include the nearby national state park, pristine beaches, and breathtaking views at the local resorts. With its inviting charm and access to various outdoor activities, Reedsport is a must-visit for anyone seeking an adventurous getaway.
  • Lakeside: Located just 7 miles from Winchester Bay, Lakeside is a picturesque city known for its romantic ambiance and natural beauty. Visitors can enjoy a variety of outdoor activities, including golfing and relaxing at local resorts. The nearby lake and national state park provide exceptional opportunities for exploration and leisure. With its serene landscapes and recreational areas, Lakeside is an ideal spot for couples and families looking to unwind and enjoy quality time together amidst nature.
  • Gardiner: A quaint village located 5 miles from Winchester Bay, Gardiner is a hidden gem for outdoor enthusiasts and adventure seekers. Surrounded by stunning landscapes, visitors can access a variety of hiking trails and recreational areas that showcase the beauty of the Oregon coast. Key attractions include the scenic beach, winding river, and tranquil lake, making it a perfect destination for those looking to immerse themselves in nature. Gardiner's charm and accessibility to outdoor adventures make it a great stop on your vacation itinerary.

Best time to go to Winchester Bay

If you're planning a trip to Winchester Bay, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs from June to August, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January45.9°F (7.7°C)Light RainMostly CloudyAverageSlightly Low
February45.1°F (7.3°C)Light RainMostly CloudyAverageSlightly Low
March46.2°F (7.9°C)Light RainMostly CloudyAverageAverage
April48.9°F (9.4°C)Light RainMostly CloudyAverageSlightly Low
May53.1°F (11.7°C)Light RainMostly SunnyAverageAverage
June57.0°F (13.9°C)No Rain (Dry)Mostly SunnyModerately HighSlightly High
July60.3°F (15.7°C)No Rain (Dry)Mostly SunnyModerately HighSlightly High
August61.2°F (16.2°C)No Rain (Dry)Mostly SunnyModerately HighSlightly High
September59.4°F (15.2°C)No Rain (Dry)Mostly SunnyAverageAverage
October54.7°F (12.6°C)Light RainMostly SunnyModerately LowAverage
November49.1°F (9.5°C)Light RainMostly CloudyModerately LowAverage
December45.0°F (7.2°C)Moderate RainMostly CloudyModerately LowAverage

Booking with Vrbo is a breeze

Are you hoping to save some cash on your next getaway? Being flexible with your travel dates can really help, as prices tend to vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Unlock savings with One Key

When you reserve an eligible Vrbo for your group getaway, you’ll earn OneKeyCash on the full booking amount. It's truly beneficial to be the organizer. By joining our OneKey rewards program, you can unlock exclusive savings for members and accumulate OneKeyCash on qualifying stays. Sign up today and begin reaping the rewards.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board is a fantastic tool that allows you to plan and manage your travel effortlessly. You can easily create new trips, pick up right where you left off, or organize your existing plans. All of your previously saved and booked properties are conveniently categorized under Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Explore the natural setting in Winchester Bay

The parks and other outdoor surroundings create an inviting atmosphere in Winchester Bay. There's no shortage of things to see and do in the area.If you're looking for accommodations with space to entertain friends and family, Vrbo has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Exploring the natural features in Winchester Bay

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Winchester Bay is a great spot to appreciate mother nature. Here are some of the area’s noteworthy features, all within 30 miles (48.2 km) of the city center:

  • Umpqua River (4.4 mi / 7.1 km)
  • Tenmile Lake (7.9 mi / 12.6 km)
  • Siltcoos Lake (14.4 mi / 23.2 km)
  • Umpqua Lighthouse State Park (1.5 mi / 2.4 km)
  • John Dellenback Dunes Trail (6.2 mi / 9.9 km)
  • Tahkenitch Creek Loop Trail (9.5 mi / 15.2 km)

Traveling to and around Winchester Bay

Fly into North Bend, OR (OTH-Southwest Oregon Regional), the closest airport, located 18.5 mi (29.8 km) from the city center.

Frequently asked questions

What is the best area to stay in Winchester Bay, Oregon, United States of America when booking a vacation rental?
When looking for the best area to stay in Winchester Bay, Oregon, you'll want to consider the charming neighborhood near the marina. This area offers a delightful blend of scenic views and convenient access to local attractions. You can enjoy the stunning vistas of the Umpqua River and the Pacific Ocean, making it a great spot for nature lovers and outdoor enthusiasts.

One of the top attractions nearby is the Winchester Bay Lighthouse, which provides a beautiful backdrop for photography and a glimpse into the area's maritime history. Additionally, the vicinity is known for its recreational opportunities, including fishing, crabbing, and beachcombing along the picturesque coastline.

For those who enjoy a bit of adventure, the nearby Oregon Dunes National Recreation Area offers miles of stunning sand dunes great for hiking, ATV riding, and exploring.
How much does it cost to rent a vacation home in Winchester Bay?
Prices for vacation rentals in Winchester Bay vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Winchester Bay to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Winchester Bay vacation house rentals?
You can find great discounts on house rentals in Winchester Bay on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I find long-stay vacation rentals in Winchester Bay?
A long-stay vacation rental in Winchester Bay is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there any Winchester Bay vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Winchester Bay with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
When is the best time to visit Winchester Bay for a vacation rental?
The peak travel season in Winchester Bay runs from June to August, with July being the most popular month for visitors. This vibrant period attracts families and outdoor enthusiasts eager to soak up the sun and enjoy activities like beachcombing, crabbing, and exploring the stunning coastal scenery. With average temperatures ranging from the mid-50s to the high 70s Fahrenheit, the warm weather is superb for water sports and leisurely strolls along the picturesque shore.

During these summer months, you can experience the lively option of local events and festivals, making it a wonderful time to connect with fellow travelers and enjoy the community spirit. The scenic dunes and breathtaking views of the Pacific Ocean add to the charm of the area, inviting you to partake in everything from hiking to relaxing beach days.

For those seeking a more budget-friendly experience, consider planning your visit in December. While this month falls outside the peak tourist season, it offers a unique opportunity to enjoy the peaceful winter landscape. You can take advantage of quieter beaches and explore the area's natural beauty without the summer crowds.
How early should I book a Winchester Bay vacation rental?
Book your Winchester Bay vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Winchester Bay, Oregon, United States of America?
In Winchester Bay, visitors can enjoy a variety of attractions that highlight the area's natural beauty and maritime charm. The stunning Umpqua Lighthouse, located within the Umpqua Lighthouse State Park, is a must-see, offering picturesque views of the coastline and the surrounding dunes. Nearby, the expansive Oregon Dunes National Recreation Area provides opportunities for outdoor activities such as hiking, off-roading, and sandboarding.

The harbor area is great for those interested in fishing, crabbing, or simply enjoying a scenic stroll along the waterfront. Visitors can also explore the local shops and restaurants that offer fresh seafood and coastal cuisine. For a more laid-back experience, the beaches in and around Winchester Bay, including the sandy stretches at the mouth of the Umpqua River, are ideal for beachcombing and relaxing by the ocean. The nearby Winchester Bay Marina is a hub for boating and water sports, making it a great destination for those looking to enjoy the water.
Can I change or cancel my Winchester Bay home rental booking on Vrbo?
To find Winchester Bay vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Winchester Bay vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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