Photo by Kim Larson

Winchester Bay vacation rentals

We found 76 vacation rentals — enter your dates for availability

Welcome to Winchester Bay, where stunning coastal landscapes meet the charm of a welcoming community. With picturesque beaches, thrilling outdoor adventures, and vibrant local culture, this destination offers something for everyone. Delight in activities from hiking in the Oregon Dunes to relaxing by the Umpqua River, all while enjoying diverse accommodations that cater to families and groups. Experience the comfort and convenience of a vacation rental, your home away from home, where cherished memories are just a stay away.

Holiday rentals with weekly discounts - Winchester Bay

Showing deals for:Nov 6 - Nov 13

Cozy Cattail Cabin on a sunny July day
A great place to sit outside on the porch/deck to enjoy you an afternoon snack.
Living Room with Blue Ray Dvd player, games, books, puzzles,...
Private kitchen
Exceptional
(71 reviews)

CozyCattail Cabin on our secluded coastal estuary woodland retreat

Reedsport

9% off
$202
$1,413 for 7 nights
All fees included
CozyCattail Cabin on our secluded coastal estuary woodland retreat
Exterior
Property grounds
Interior
Dining
Exceptional
(141 reviews)

Beautiful Road Access House with dock

Lakeside

8% off
$238
$1,665 for 7 nights
All fees included
Beautiful Road Access House with dock
Exterior detail
Front porch in the fall
Window view peeking thru the trees to the slough view
A rare snow day.
Exceptional
(68 reviews)

Cozy Cattail Cottage a comfortable coastal estuary woodland home near Reedsport

Reedsport

9% off
$236
$1,650 for 7 nights
All fees included
Cozy Cattail Cottage a comfortable coastal estuary woodland home near Reedsport
Interior
Exterior
Interior
Living area
Exceptional
(187 reviews)

Don't Get a Room....Get a House! the Homey House

Lakeside

6% off
$175
$1,224 for 7 nights
All fees included
Don't Get a Room....Get a House! the Homey House
Kitchen area, dining areas, and cozy living room with stone fireplace & artwork.
Courtyard & firepit area. Main house with covered patio area (right).
Living area and gallery of sea-inspired art and desk with view of front yard.
Stairs leading to the upper deck and guest house.
Exceptional
(28 reviews)

Whispering Pines ~ Home & Guesthouse ~ Dunes nearby & Gated ATV parking

Lakeside

8% off
$279
$1,956 for 7 nights
All fees included
Whispering Pines ~ Home & Guesthouse ~ Dunes nearby & Gated ATV parking
Living area
Cozy, comfy and 24/7 views! Large dining table w games in the blanket chest.
Exterior
Interior
Exceptional
(32 reviews)

DUNEHAVEN AFRAME CABIN LAKEFRONT DUNE ACCESS RETREAT

North Bend

8% off
$536
$3,751 for 7 nights
All fees included
DUNEHAVEN AFRAME CABIN LAKEFRONT DUNE ACCESS RETREAT
Homes are down drive. DUNES ARE 30 SECONDS STRAIGHT AND 57 SECONDS FROM STUDIO!!
Aframe left, Studio right. Amazing retreat! Beach is shared between homes
Enjoy the peace and tranquility of lake life!
The Studio has a front row seat to incredible views. Outside lights on timer
Exceptional
(47 reviews)

Dunehaven STUDIO DUNE ACCESS LAKE FRONT Retreat

North Bend

8% off
$323
$2,263 for 7 nights
All fees included
Dunehaven STUDIO DUNE ACCESS LAKE FRONT Retreat

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Find out more about Winchester Bay

Why visit Winchester Bay

  • Outdoor adventures: Winchester Bay is perfect for hiking, fishing, and water sports, surrounded by stunning landscapes.
  • Beautiful beaches: Enjoy easy access to picturesque beaches for relaxation and fun along the Oregon Coast.
  • Charming local culture: Experience the friendly vibe and coastal culture with welcoming locals and unique attractions.
  • Diverse accommodations: Choose from cozy cabins, modern condos, or hotels like the inviting Winchester Bay Inn.
  • Scenic parks: Explore nearby state parks and natural reserves for breathtaking views and outdoor exploration.

Popular types of accommodation in Winchester Bay

Discover the charm of Winchester Bay with our exceptional vacation rentals. Whether you're looking for houses, cozy cottages, or modern condos, we have the perfect accommodation to suit your needs. For a more traditional stay, explore our range of vacation cabins or hotels in Winchester Bay, including the inviting Winchester Bay Inn. Whatever your travel plans entail, we ensure you find the ideal spot for a memorable getaway.

  • Houses: The top choice for visitors in Winchester Bay, these homes offer ample space and amenities for families and groups.
  • Condos: A popular option for those seeking modern convenience and often stunning views, perfect for couples or small families.
  • Cottages: Charming and cozy, these quaint rentals provide a delightful, rustic experience close to nature.
  • Cabins: Ideal for adventurers, these rustic lodgings offer a getaway in the woods or by the water.
  • Apartments: A convenient choice for solo travelers or couples, offering a comfortable home base in the area.**

Top attractions near Winchester Bay

Winchester Bay, Oregon, is an ideal destination for outdoor enthusiasts seeking adventure and stunning scenery. With a variety of attractions such as state parks, lakes, and rivers, visitors can immerse themselves in nature and enjoy activities that cater to their adventurous spirit. Whether you're traveling solo, with family, or friends, Winchester Bay promises a memorable experience filled with beautiful landscapes and exciting outdoor pursuits.

  • Oregon Dunes National Recreation Area: Experience breathtaking scenery and thrilling outdoor adventures in this unique landscape of towering sand dunes. Ideal for hiking, ATV riding, and photography, it offers a diverse ecosystem and stunning coastal views just 2 miles from Winchester Bay.
  • Umpqua River: Enjoy the serene beauty of the Umpqua River, perfect for fishing, kayaking, and relaxing along its banks. Just 4 miles away, it provides picturesque views and an inviting atmosphere for outdoor enthusiasts.
  • Tenmile Lake: This idyllic lake, located 8 miles away, offers romantic beach spots, water activities, and scenic vistas, making it a perfect getaway for couples and families alike.

Things to do recommended for couples

Winchester Bay offers a charming escape for couples. Enjoy a scenic beach walk at sunset, explore the picturesque dunes, or indulge in a cozy dinner at a waterfront restaurant. Don’t miss a romantic boat tour for breathtaking views of the coastline and wildlife.

Things to do recommended for families

Families will have a fantastic time exploring the scenic dunes of the Oregon Dunes National Recreation Area, enjoying beachcombing at Winchester Bay's sandy shores, and visiting the nearby Umpqua Lighthouse for breathtaking views and fun history. There's plenty of outdoor adventure for everyone.

Things to do recommended for groups

Explore the beautiful dunes at the Oregon Dunes National Recreation Area, or enjoy a fun-filled day crabbing in Winchester Bay. Don't miss a scenic boat tour to take in the stunning coastal views and local wildlife, perfect for bonding with your group.

*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 planning a trip with a group, family, pets, or are interested in extended stays, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Winchester Bay with a group: Think about how many bedrooms you require and any additional features you might want, like a full kitchen or outdoor area for group gatherings. Luckily, Vrbo allows you to refine your search to include all of these options and more.
  • Traveling to Winchester Bay with young kids: Traveling with young kids can be tough. 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.
  • Taking your pets with you to Winchester Bay: For many families, a vacation wouldn’t be the same without their furry companions. If that resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Winchester Bay: If you’re in search of vacation rentals with discounts for stays of a month or more, you’ve come to the right spot. By using the right filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include preferences 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 an unforgettable getaway along the stunning Oregon Coast. With easy beach access and a family-friendly atmosphere, this charming village invites you to explore its beautiful scenery and outdoor adventures. Nearby attractions showcase the friendly locals and vibrant coastal culture, making it a perfect destination for relaxation and exploration. Embrace the spirit of the West Coast as you dive into the scenic beauty and welcoming experiences that Winchester Bay has to offer.

  • Reedsport: Nestled along the Umpqua River, Reedsport is the gateway to beautiful outdoor adventures. This charming city offers an abundance of recreational opportunities, from hiking in nearby national state parks to golfing at local courses. Travelers are drawn to the area's stunning scenery, which includes expansive beaches and tranquil lakes. Its close proximity to Winchester Bay ensures easy access to various attractions, including the picturesque Umpqua Lighthouse and the scenic Dunes National Recreation Area. Whether you’re seeking thrilling outdoor activities or a peaceful getaway, Reedsport has something for everyone.
  • Lakeside: Located a mere 7 miles from Winchester Bay, Lakeside is a hidden gem for those yearning for a scenic retreat. The city is surrounded by the natural beauty of lakes and lush forests, making it an ideal spot for outdoor enthusiasts and couples looking for a romantic escape. Popular activities include hiking along picturesque trails and relaxing at local resorts. You can explore the stunning Lakeside Beach and the expansive national state park nearby, making it a perfect destination for a day of exploration or a peaceful afternoon by the water.
  • Gardiner: Just 5 miles from Winchester Bay, Gardiner is a quaint village known for its breathtaking landscapes and outdoor adventures. Surrounded by scenic beaches and serene lakes, it offers a variety of recreational activities, including camping and golfing. The nearby national state park provides ample opportunities for exploration and nature appreciation. Gardiner’s welcoming atmosphere and proximity to natural attractions make it an excellent choice for those looking to immerse themselves in the beauty of Oregon’s coast while enjoying a range of outdoor pursuits.

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 on your upcoming journey? Being flexible with your travel dates can make a difference since prices often fluctuate. Additionally, consider booking an extended stay for even greater savings. To discover a Vrbo property that aligns with your budget, utilize our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect fit for your needs.

Vrbo Trips: Planning made easy

Vrbo's Trip Board offers a user-friendly platform where you can easily plan new trips, resume previous ones, or manage your travel arrangements. You'll find your saved or booked properties neatly organized under categories like Potential, Upcoming, or Current Trips. To begin exploring 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)
  • Tahkenitch Creek Loop Trail (9.5 mi / 15.2 km)
  • John Dellenback Dunes Trail (6.2 mi / 9.9 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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