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Check prices for these dates

Our top choices for Winchester Bay holiday rentals

1. Soothing Crab themed 3-bedroom home with WiFi and a hot tub in Winchester Bay.

Soothing Crab themed 3-bedroom home with WiFi and a hot tub in Winchester Bay.
Winchester Bay
9.8 out of 10, Exceptional, (36 reviews)
"Highly recommend. The host is the absolute best host I’ve ever experienced renting a house. Will certainly be back."
United States
Caleb
The price is £259
includes taxes & fees
8 Nov - 9 Nov
Soothing Crab themed 3-bedroom home with WiFi and a hot tub in Winchester Bay.

2. Cozy Hilltop Home with Private Hot Tub, Direct Dune Access & Breathtaking Views

Cozy Hilltop Home with Private Hot Tub, Direct Dune Access & Breathtaking Views
Winchester Bay
9.8 out of 10, Exceptional, (237 reviews)
"Great location, easy dune access, beautiful view. The host was very nice and accommodating."
United States
JAY B.
The price is £486
includes taxes & fees
9 Nov - 10 Nov
Cozy Hilltop Home with Private Hot Tub, Direct Dune Access & Breathtaking Views

3. Luxurious Hilltop Home w/ Private Hot Tub and Direct Dune Access

Luxurious Hilltop Home w/ Private Hot Tub and Direct Dune Access
Winchester Bay
9.6 out of 10, Exceptional, (7 reviews)
"Great and comfortable place to rest after a nice ride on the dunes! Location was perfect"
United States
Johnny H.
The price is £565
includes taxes & fees
8 Nov - 9 Nov
Luxurious Hilltop Home w/ Private Hot Tub and Direct Dune Access

4. Secluded 1-bedroom lakefront cabin in Lakeside, OR. Ideal for writers or couples seeking solitude. Features a King bed, wood stove, kayak for 2, and stargazing from your private dock.

Secluded 1-bedroom lakefront cabin in Lakeside, OR. Ideal for writers or couples seeking solitude. Features a King bed, wood stove, kayak for 2, and stargazing from your private dock.
Lakeside
9.4 out of 10, Exceptional, (34 reviews)
"Very secluded. Perfect for a couples weekend away from it all"
United States
Taylor I.
The price is £209
includes taxes & fees
12 Nov - 13 Nov
Secluded 1-bedroom lakefront cabin in Lakeside, OR. Ideal for writers or couples seeking solitude. Features a King bed, wood stove, kayak for 2, and stargazing from your private dock.

5. Remote 1 BR Lakefront Cabin. Features a King loft bed with lake views, private dock, and provided paddleboards/kayaks. Perfect for fishing, stargazing, and quiet nature escapes.

Remote 1 BR Lakefront Cabin. Features a King loft bed with lake views, private dock, and provided paddleboards/kayaks. Perfect for fishing, stargazing, and quiet nature escapes.
Lakeside
9.8 out of 10, Exceptional, (21 reviews)
"The place was great. Clean and in good shape. Im planning to make it an annual trip."
United States
PDX S.
The price is £159
includes taxes & fees
17 Nov - 18 Nov
Remote 1 BR Lakefront Cabin. Features a King loft bed with lake views, private dock, and provided paddleboards/kayaks. Perfect for fishing, stargazing, and quiet nature escapes.

6. The Salty Duplex (Left Side)

The Salty Duplex (Left Side)
Reedsport
10.0 out of 10, Exceptional, (69 reviews)
"Excellent quite location."
United States
Judy B.
The price is £156
includes taxes & fees
9 Nov - 10 Nov
The Salty Duplex (Left Side)

7. The Salty Duplex (Right Side)

The Salty Duplex (Right Side)
Reedsport
10.0 out of 10, Exceptional, (88 reviews)
"Great stay!"
United States
Di L.
The price is £163
includes taxes & fees
9 Nov - 10 Nov
The Salty Duplex (Right Side)

8. #StayinMyDistrict Majestic Shores Lake Bear Cabin

#StayinMyDistrict Majestic Shores Lake Bear Cabin
North Bend
9.6 out of 10, Exceptional, (5 reviews)
"Nice cozy cabin and great access to the lake for kayaking."
United States
Travis and Tabitha N.
The price is £136
includes taxes & fees
8 Nov - 9 Nov
#StayinMyDistrict Majestic Shores Lake Bear Cabin

9. #StayinMyDistrict Lakeside Cottage

#StayinMyDistrict Lakeside Cottage
Lakeside
9.6 out of 10, Exceptional, (25 reviews)
"The house was very clean and comfortable. Would stay here again."
United States
Shaun W.
The price is £154
includes taxes & fees
9 Nov - 10 Nov
#StayinMyDistrict Lakeside Cottage

10. So much to enjoy at this 2-bedroom cottage in Charming Lakeside.

So much to enjoy at this 2-bedroom cottage in Charming Lakeside.
Lakeside
9.6 out of 10, Exceptional, (51 reviews)
"Wonderful secure property with easy access to the beach and town. Owner is very responsive and helpful."
United States
Candy H.
The price is £180
includes taxes & fees
4 Dec - 5 Dec
So much to enjoy at this 2-bedroom cottage in Charming Lakeside.

11. Cozy A-Frame w/Spa+14 acres+EV+Trails+Lake Access

Cozy A-Frame w/Spa+14 acres+EV+Trails+Lake Access
Lakeside
10.0 out of 10, Exceptional, (117 reviews)
"Amazing Cabin experience. Fully stocked, clean and very roomy"
United States
Luba K.
The price is £308
includes taxes & fees
10 Nov - 11 Nov
Cozy A-Frame w/Spa+14 acres+EV+Trails+Lake Access

12. Lakeside house with access to dunes, lakes, and the ocean!

Lakeside house with access to dunes, lakes, and the ocean!
Lakeside
9.6 out of 10, Exceptional, (42 reviews)
"Was a great place to stay especially with trailer "
United States
David
The price is £269
includes taxes & fees
16 Nov - 17 Nov
Lakeside house with access to dunes, lakes, and the ocean!

13. Cozy Cabin near Everything!

Cozy Cabin near Everything!
North Bend
8.8 out of 10, Excellent, (49 reviews)
"Great location near the riverfront."
United States
Todd W.
The price is £136
includes taxes & fees
10 Nov - 11 Nov
Cozy Cabin near Everything!

14. Barnhaus-Spa+11 Acres+EV+Gym+Lake Access

Barnhaus-Spa+11 Acres+EV+Gym+Lake Access
Lakeside
10.0 out of 10, Exceptional, (6 reviews)
"We just checked out and left the beautiful property. We had a great stay! Just had a couple minor tips for the owners. Thank You!!!"
United States
Julie S.
The price is £292
includes taxes & fees
8 Nov - 9 Nov
Barnhaus-Spa+11 Acres+EV+Gym+Lake Access

15. Ultimate Guesthouse•Curated Luxury with Lake+Kayak

Ultimate Guesthouse•Curated Luxury with Lake+Kayak
North Bend
10.0 out of 10, Exceptional, (3 reviews)
"Great little spot for just a couple or the kids too! Cool guesthouse with a King, an extra bedroom with bunks and two more singles up in a loft over the main room. Loved our stay there and would certainly return again! Beautiful kitchen, nice walk in shower bath, cool electric fireplace and a deck overlooking the lake."
United States
CHARLES W.
The price is £247
includes taxes & fees
8 Nov - 9 Nov
Ultimate Guesthouse•Curated Luxury with Lake+Kayak

16. #StayInMyDistrict NorthBend Duplex Dog Friendly

#StayInMyDistrict NorthBend Duplex Dog Friendly
North Bend
The price is £171
includes taxes & fees
8 Nov - 9 Nov
#StayInMyDistrict NorthBend Duplex Dog Friendly

17. 2 Homes-14 Acres+2 Spas +Lake Access+Kayaks

2 Homes-14 Acres+2 Spas +Lake Access+Kayaks
Lakeside
The price is £570
includes taxes & fees
10 Nov - 11 Nov
2 Homes-14 Acres+2 Spas +Lake Access+Kayaks

18. #StayInMyDistrict NorthBend Retreat Dog Friendly

#StayInMyDistrict NorthBend Retreat Dog Friendly
North Bend
The price is £172
includes taxes & fees
9 Nov - 10 Nov
#StayInMyDistrict NorthBend Retreat Dog Friendly

19. #StayinMyDistrict Brussells Bungalow

#StayinMyDistrict Brussells Bungalow
North Bend
8.2 out of 10, Very good, (10 reviews)
"It was great! Would definitely stay again."
United States
Gary W.
The price is £151
includes taxes & fees
8 Nov - 9 Nov
#StayinMyDistrict Brussells Bungalow

20. Siltcoos Station Retreats

Siltcoos Station Retreats
4.0 star property
Westlake
9.4 out of 10, Exceptional, (12 reviews)
"Great lake access for kayaking"
United States
Andrew
The price is £228
includes taxes & fees
6 Nov - 7 Nov
Siltcoos Station Retreats
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find holiday rentals that suit your style

Top Winchester Bay Hotel Reviews

Find out more about Winchester Bay

Everything you need to know about Winchester Bay holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester Bay holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester Bay holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winchester Bay holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchester Bay. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester Bay holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester Bay holiday rentals we have selected for you start as low as £136 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winchester Bay rentals

At Expedia, we put the best Winchester Bay holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winchester Bay rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester Bay holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester Bay. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find holiday rentals in Winchester Bay?

Yes, there are holiday rentals close to the most popular sights in Winchester Bay, or you can select a more secluded option if you're looking for a relaxing stay. Winchester Bay is known for its parks.

What are some of the best holiday rentals that Winchester Bay has to offer?

Cozy family beach cottage with hot tub, deck, WiFi, surfboard-walk to bay, Dogs ok: This highly rated holiday home rental in Winchester Bay is located in the city centre, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a selection of games and 1 hot tub. Another good choice for your trip to Winchester Bay is Soothing Crab themed 3-bedroom home with WiFi and a hot tub in Winchester Bay..

How many holiday rentals will I find in Winchester Bay?

Choose from 15 Expedia holiday rentals in Winchester Bay for a memorable holiday.

What’s there to see and do in Winchester Bay?

Umpqua River and Umpqua Lighthouse State Park are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find Umpqua Lighthouse and Oregon Dunes National Recreation Area.

What’s a holiday rental in Winchester Bay like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchester Bay. Holiday rentals feature amenities such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive option for family trips.