Photo by Erin Frank

Winchester Bay vacation rentals

We found 74 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.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

Find out more about Winchester Bay

Why visit Winchester Bay

  • Outdoor Adventures: Winchester Bay is perfect for outdoor enthusiasts, offering activities like hiking, fishing, and exploring nearby state parks.
  • Stunning Natural Scenery: Enjoy breathtaking ocean views and the picturesque Oregon coast, ideal for relaxation and scenic walks.
  • Sand Dunes Exploration: Discover the unique sand dunes in the area, providing opportunities for fun and adventure.
  • Welcoming Community: Experience the friendly atmosphere where locals embrace visitors, enhancing your vacation experience.
  • Diverse Accommodations: Choose from charming vacation homes, cozy condos, and delightful cottages to suit your preferences.

Popular types of accommodation in Winchester Bay

If you’re wondering what type of accommodation awaits you in Winchester Bay, look no further. Our most popular vacation rentals include charming houses, cozy condos, and delightful cottages. Whether you’re seeking beachfront rentals or a serene vacation home, we have the perfect options to suit your needs. Enjoy the beauty of Winchester Bay with the reassurance of transparent information and great savings.

  • Houses: The top choice for vacation rentals in Winchester Bay, offering spacious and comfortable accommodations for families or groups.
  • Condos: A popular option for those seeking modern amenities and convenience, ideal for short or extended stays.
  • Cottages: Charming and quaint, these rentals provide a cozy atmosphere, perfect for a relaxing getaway.
  • Cabins: A favourite among nature lovers, these rustic retreats offer a unique experience surrounded by the outdoors.
  • Apartments: Convenient and practical, apartments are great for solo travellers or couples looking for a home-like feel.**

Top attractions near Winchester Bay

Winchester Bay, Oregon, is an ideal destination for outdoor enthusiasts seeking adventure and stunning scenery. Visitors can explore nearby state parks, lakes, and rivers while enjoying various outdoor activities. For those looking for accommodations, there are apartments for rent in the area. The local beach also offers a perfect spot for relaxation and recreation. Whether you're after thrilling adventures or serene natural beauty, Winchester Bay has something for everyone.

  • Oregon Dunes National Recreation Area: Located 4.8km from Winchester Bay, this stunning park features towering sand dunes, providing exciting adventures for off-roading and hiking, surrounded by breathtaking coastal scenery.
  • Umpqua River: Just 6.4km away, this scenic river offers tranquil views and a variety of outdoor activities, such as fishing and kayaking, in a picturesque setting.
  • Tenmile Lake: Situated 12.9km from Winchester Bay, this beautiful lake boasts sandy beaches and romantic vibes, perfect for picnics, swimming, and enjoying nature.

Things to do recommended for couples

Winchester Bay offers delightful experiences for couples, such as a scenic walk along the picturesque beach, a cozy dinner at a waterfront restaurant, or a sunset cruise on the Umpqua River. Don't miss exploring the charming lighthouse and enjoying local seafood together for a memorable getaway.

Things to do recommended for families

Families in Winchester Bay can enjoy a thrilling day at the Oregon Dunes National Recreation Area, where kids can explore the sandy landscapes. A visit to the nearby Umpqua River Lighthouse offers educational fun, and fishing along the river provides memorable family bonding time.

Things to do recommended for groups

Explore the stunning John Dellenback Dunes Trail, perfect for hiking enthusiasts, just 9.7km from Winchester Bay. For a fun shopping experience, visit the Pony Village Mall, located 30.6km away, or stop by Books by the Bay for a unique local find.

*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

When planning your trip, whether you're traveling with a group, family, pets, or seeking extended stays, it's important to prioritize your needs when filtering options. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Winchester Bay with a group: Think about how many bedrooms you'll require, as well as any additional features like a complete kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Winchester Bay with young kids: Traveling with young children can present its own set of challenges. It's important to prioritize their comfort and safety, which includes looking for age-appropriate amenities like a private swimming pool. Additionally, considering your closeness to family-friendly attractions can enhance your travel experience.
  • Taking your pets with you to Winchester Bay: For many, a family getaway isn't truly satisfying without their furry companions. If this resonates with you, explore Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer 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 offering special rates for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Winchester Bay

Winchester Bay, Oregon, offers a delightful escape for outdoor enthusiasts and families alike. With stunning ocean views and the breathtaking Oregon coast, you’ll find a perfect west coast getaway. Explore nearby sand dunes and enjoy a friendly atmosphere where locals welcome visitors with open arms. All these attractions are within walking distance, making it easy to soak in the scenic beauty and adventure that this charming village has to offer.

  • Reedsport: Nestled along the Umpqua River, Reedsport is a charming city where adventure meets scenic beauty. As the gateway to Winchester Bay, it offers an array of outdoor activities for nature lovers. Visitors can enjoy hiking trails that meander through lush landscapes, explore the nearby national and state parks, or unwind at local resorts. The city is known for its breathtaking scenery, with stunning beaches and picturesque river views that invite relaxation and exploration. Whether you're kayaking on the river or hiking in the hills, Reedsport is a perfect spot for those seeking a dose of adventure.
  • Lakeside: Located a short drive away from Winchester Bay, Lakeside is a serene city known for its tranquil atmosphere and stunning natural surroundings. Ideal for outdoor enthusiasts, Lakeside features beautiful lakes and recreational areas perfect for fishing and boating. The city also offers charming resorts and a well-maintained golf course for those looking to relax. With the backdrop of the national state park, Lakeside is a romantic destination for couples wanting to connect with nature and enjoy scenic views. Strolling along the lakefront or enjoying a picnic in the park makes for a delightful experience.
  • Gardiner: Just a short distance from Winchester Bay, the quaint village of Gardiner offers a unique blend of outdoor adventure and scenic beauty. Known for its access to hiking trails and recreational areas, it’s a haven for those who love exploring the great outdoors. Visitors can stroll along the beach, cast a line in the nearby river, or enjoy the stunning views of the lake. Gardiner’s close-knit community adds to its charm, making it an inviting spot for travelers seeking both adventure and a taste of local culture.

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

Looking to save on your next adventure? Consider being flexible with your travel dates, as prices can fluctuate. Furthermore, booking an extended stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, use our filters to refine your search by price, location, and type of vacation rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's unique Trip Board offers you a dedicated space to plan new adventures, pick up right where you left off, or manage your travel arrangements with ease. You can find properties you’ve saved or booked under Potential, Upcoming, or Current Trips. To start using Trip Boards, please visit: https://www.vrbo.com/en-ca/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)
  • Umpqua Lighthouse State Park (1.5 mi / 2.4 km)
  • Siltcoos Lake (14.4 mi / 23.2 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 considering a vacation rental in Winchester Bay, Oregon, a popular area to stay is near the waterfront. This neighbourhood offers stunning views of the Umpqua River and is conveniently located close to several attractions. The picturesque scenery makes it an ideal spot for those who appreciate nature and outdoor activities. There are a variety of vacation rentals available in this area, ranging from cosy cabins to larger homes, allowing you to find something that suits your needs.

Staying near the waterfront puts you within easy reach of top attractions such as the iconic Umpqua River Lighthouse, which is a lovely place to explore and offers breathtaking views of the coastline. Additionally, the nearby Oregon Dunes National Recreation Area is great for adventurous spirits, providing opportunities for dune hiking, ATV riding, or simply enjoying a leisurely stroll along the expansive sandy beaches.
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 travelling 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.
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. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
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 travellers 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.
What are popular rental amenities in Winchester Bay?
In Winchester Bay, the most popular rental amenities are not specifically detailed, but vacation rentals typically offer basic comforts for a pleasant stay. Visitors can expect properties to feature essentials such as kitchens for self-catering, comfortable living areas for relaxation, and outdoor spaces to enjoy the coastal scenery. Some rentals may also provide access to recreational equipment for beach activities, reflecting the area's maritime charm and natural beauty.
When is the best time to visit Winchester Bay for a vacation rental?
July is the most popular time to visit Winchester Bay, as it falls within the vibrant peak season from June to August. During these summer months, the coastal charm of Winchester Bay truly shines, offering visitors a great blend of warm weather and exciting outdoor activities. This is an ideal time for beach lovers, as the temperatures typically reach the low 20s Celsius, creating a comfortable environment for sunbathing, fishing, and exploring the stunning coastal scenery.

In July, the atmosphere is lively, with families and adventure seekers flocking to the beaches and local attractions. You can enjoy a variety of water sports, including kayaking and paddleboarding, while taking in the breathtaking views of the Pacific Ocean. The nearby Umpqua Lighthouse State Park also provides excellent opportunities for walking and sightseeing, great for those who appreciate natural beauty and history.

For those looking for a more budget-friendly experience, consider visiting in December. It's cooler, with temperatures hovering around 5 degrees Celsius, this month allows for a tranquil getaway with fewer crowds. Winter visits can be quite magical, with the opportunity to witness the rugged coastline and perhaps even enjoy a peaceful stroll along the beach, all whilst wrapped in a warm coat.
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.
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 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 travellers 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 cosy cabin or a beach house, 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.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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, 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 organising 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.

More Vacation Ideas