Photo by Kim Larson

Winchester Bay holiday lettings

We found 77 holiday rentals — enter your dates for availability
Discover a selection of 15 homes and other holiday rentals in Winchester Bay that are perfect for your trip. Whether you're travelling with your children or with friends, holiday rentals have the best amenities for spending time at your holiday home, such as air conditioning and Wi-Fi. You'll be able to choose a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Winchester Bay

Showing deals for:27 Nov - 4 Dec

Private kitchen
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,...
Cozy Cattail Cabin on a sunny July day
Exceptional
(72 reviews)

CozyCattail Cabin on our secluded coastal estuary woodland retreat

Reedsport

8% off
£1,068
for 7 nights, 1 cabin
£153 per night
includes taxes & fees
CozyCattail Cabin on our secluded coastal estuary woodland retreat
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

8% off
£1,241
for 7 nights, 1 cottage
£177 per night
includes taxes & fees
Cozy Cattail Cottage a comfortable coastal estuary woodland home near Reedsport
Living area
Exterior
Living area
Interior
Exceptional
(191 reviews)

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

Lakeside

6% off
£966
for 7 nights, 1 home
£138 per night
includes taxes & fees
Don't Get a Room....Get a House! the Homey House
Aerial view of main house, guest house, courtyard, surrounding trees and shed.
Courtyard & firepit area. Main house with covered patio area (right).
Kitchen area, dining areas, and cozy living room with stone fireplace & artwork.
Stairs leading to the upper deck and guest house.
Exceptional
(28 reviews)

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

Lakeside

8% off
£1,587
for 7 nights, 1 home
£227 per night
includes taxes & fees
Whispering Pines ~ Home & Guesthouse ~ Dunes nearby & Gated ATV parking
What an AMAZING VIEW from inside the Studio. Enjoy morning coffee on the patio
Aframe left, Studio right. Amazing retreat! Beach is shared between homes
Homes are down drive. DUNES ARE 30 SECONDS STRAIGHT AND 57 SECONDS FROM STUDIO!!
Enjoy the peace and tranquility of lake life!
Exceptional
(48 reviews)

Dunehaven STUDIO DUNE ACCESS LAKE FRONT Retreat

North Bend

8% off
£1,712
for 7 nights, 1 apartment
£245 per night
includes taxes & fees
Dunehaven STUDIO DUNE ACCESS LAKE FRONT Retreat
Exterior
Property grounds
Private kitchen
Outdoor dining
Exceptional
(6 reviews)

Welcome to the Dahlia house, a charming coastal retreat

Reedsport

8% off
£1,131
for 7 nights, 1 home
£162 per night
includes taxes & fees
Welcome to the Dahlia house, a charming coastal retreat

  • 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, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Explore the natural setting in Winchester Bay

The parks and other outdoor surroundings create an inviting atmosphere in Winchester Bay. This city has something for everyone. If you're looking for accommodation options with space to entertain friends and family, HomeAway 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 an adventurous traveller or just want to take in the scenery, Winchester Bay is a great place to get outside. Here are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • 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)

Travelling 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 centre.

Frequently asked questions

How much does it cost to rent a holiday home in Winchester Bay?
Prices for holiday 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 holiday 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 holiday rentals in Winchester Bay?
A long-stay holiday 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 holiday rentals with parking?
Vrbo offers a wide selection of holiday 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.
When is the best time to visit Winchester Bay for a holiday rental?
The best time to visit Winchester Bay for a holiday rental is during the peak season from June to August, especially in July, when the weather is at its warmest and the outdoor activities are in full swing. This period draws families and adventure seekers looking to enjoy the stunning coastal scenery, with opportunities for fishing, crabbing, and beachcombing along the beautiful Oregon coast.In July, visitors can expect pleasant temperatures ranging from 15 to 25 degrees Celsius, making it ideal for sunbathing or exploring the nearby dunes and the picturesque Umpqua River. The lively option during this time means you'll find plenty of fellow travellers and opportunities for socialising at local events and festivities.For those considering a more budget-friendly option, December presents a quieter charm, superb for a peaceful getaway. While the weather can be cooler, this month allows for a great experience of coastal solitude and the chance to enjoy the beauty of winter along the shore.
How early should I book a Winchester Bay holiday rental?
Book your Winchester Bay holiday 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 holiday 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 enjoy a variety of attractions that highlight the area's natural beauty and maritime charm. The Winchester Bay Lighthouse, located near the entrance to the Umpqua River, is a picturesque spot and a popular photo opportunity. The surrounding area offers access to beautiful sandy beaches, great for relaxing or beachcombing.For those interested in outdoor activities, the nearby Umpqua National Forest provides numerous trails for hiking and opportunities for fishing and wildlife viewing. The picturesque dunes of the Oregon Dunes National Recreation Area are also a major draw, attracting those who want to explore the unique landscape or partake in activities like ATV riding and sandboarding.Additionally, the local marina offers boat rentals and fishing charters, making it easy for visitors to experience the abundant marine life off the coast.
Can I change or cancel my Winchester Bay home rental booking on Vrbo?
To find Winchester Bay holiday 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 holiday 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, 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.

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