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Winchester Bay vacation rentals

We found 75 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:Feb 27 - Mar 6

Image gallery for Cozy Boathouse On The Lake W/ Spacious Dock. Boat access only

Boathouse View
9.4 out of 10, Exceptional, (9 reviews)
Exceptional
(9 reviews)

Cozy Boathouse On The Lake W/ Spacious Dock. Boat access only

Lakeside, OR

5% off
Price is $203
$1,419 for 7 nights
All fees included
Cozy Boathouse On The Lake W/ Spacious Dock. Boat access only

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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 when booking a vacation rental?
When planning a vacation rental in Winchester Bay, Oregon, a great area to consider is the waterfront district. This charming neighborhood offers stunning views of the bay and easy access to beautiful sandy beaches. Staying here puts you in close proximity to popular attractions such as the Umpqua River Lighthouse, which is not only a historical landmark but also provides opportunities for photography and exploration. Additionally, the nearby Winchester Bay Marina is superb for those who enjoy boating, fishing, or simply taking in the scenic beauty of the coastline.

Another appealing area is the Dunes area, known for its proximity to the expansive Oregon Dunes National Recreation Area. This region is ideal for adventure enthusiasts who want to experience activities like sandboarding and off-road vehicle riding. The Dunes area also offers a variety of vacation rental properties, allowing visitors to choose from cozy cabins to larger homes, suiting different group sizes and preferences.

Overall, both the waterfront district and the Dunes area boast a variety of rental options, making them excellent choices for a memorable stay in Winchester Bay.
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 best time to visit Winchester Bay for a vacation rental is during the peak summer season from June to August, with July being the most popular month. This vibrant period is superb for travelers seeking outdoor adventures and family-friendly activities along the beautiful Oregon coast. With warm temperatures typically ranging from the mid-50s to low 80s Fahrenheit, visitors can enjoy an array of recreational pursuits, including fishing, crabbing, and beachcombing, all while soaking in the picturesque coastal views.

In addition to the stunning beaches, July offers a variety of events and festivals that bring the community together, creating a lively atmosphere. The local marina buzzes with activity, and visitors can take advantage of opportunities for kayaking and paddleboarding in the calm waters of Winchester Bay.

For those looking for a more budget-conscious option, consider visiting in December. While this is the low season, it provides a unique charm with fewer crowds and the chance to enjoy the tranquil beauty of the coastline during the winter months.
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?
In Winchester Bay, visitors can explore a variety of attractions that highlight the area's natural beauty and maritime heritage. The picturesque Winchester Bay Lighthouse offers stunning views of the coastline and is a popular spot for photography. Nearby, the Umpqua River Lighthouse Museum provides insight into the region's history and maritime navigation.

For outdoor enthusiasts, the expansive Oregon Dunes National Recreation Area is just a short drive away, where activities like dune hiking, ATV riding, and beachcombing are readily available. The local marina is a hub for fishing and crabbing, allowing visitors to experience the area's rich marine life.

Additionally, the scenic beaches along the Pacific Coast are ideal for relaxing or enjoying water sports.
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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