A white lighthouse with a black top, surrounded by trees and a cloudy sky.

Winchester Bay Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Winchester Bay holiday rentals

Interior

1. Dog-friendly ADU with a full kitchen & shared washer&dryer - near the water

Dog-friendly ADU with a full kitchen & shared washer&dryer - near the water
Reedsport
10.0 out of 10, Exceptional, (2 reviews)
"Bookings are orbits was extremely difficult especially since the property was through verbo I had to constantly call verbo to get my information since I wasn't a member of orbits the whole situation was extremely difficult That being said I will deal directly with the people who are the property management from here on out The place was lovely It was beautiful and it was for my anniversary so that was special but the in between stage finally getting all of the information was extremely difficult"
United States
Guy
The price is HK$657
HK$1,696 total
includes taxes & fees
16 Aug - 17 Aug
Dog-friendly ADU with a full kitchen & shared washer&dryer - near the water
Interior

2. Winchester Bay Apt Near Dunes & State Parks!

Winchester Bay Apt Near Dunes & State Parks!
3.0 star property
Reedsport
10.0 out of 10, Exceptional, (4 reviews)
The price is HK$1,169
HK$2,160 total
includes taxes & fees
23 Aug - 24 Aug
Winchester Bay Apt Near Dunes & State Parks!
Exterior

3. 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, (32 reviews)
"Very nice stay!"
United States
Jennifer
The price is HK$1,765
HK$3,639 total
includes taxes & fees
13 Aug - 14 Aug
Soothing Crab themed 3-bedroom home with WiFi and a hot tub in Winchester Bay.
Coffee/tea maker, fridge, microwave, oven

4. 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)
"We absolutely loved staying at this beautiful home overlooking the bay, the beach and the dunes in the distance. Absolutely stunning views from all angles of the house; the pelicans dive-bombing nightly was a new site for all of us and we spent hours gazing at the horizon. The rooms were perfect for our group and everything was spotless! We were very lucky to have snagged this gem at the last minute, I see it is already booked for next year Memorial Day, or we would have booked...
United States
Austene
The price is HK$3,530
HK$6,370 total
includes taxes & fees
17 Aug - 18 Aug
Luxurious Hilltop Home w/ Private Hot Tub and Direct Dune Access
Outdoor dining

5. 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, (236 reviews)
"My family and I love are stayed at this beautiful property with amazing views, we’re already planning to come back in the summer are host was great thank you for having us.Love the in and out dune access."
United States
Ruben G.
The price is HK$2,789
HK$5,052 total
includes taxes & fees
9 Sept - 10 Sept
Cozy Hilltop Home with Private Hot Tub, Direct Dune Access & Breathtaking Views
Coffee/tea maker, fridge, microwave, oven

6. The Salty Duplex (Left Side)

The Salty Duplex (Left Side)
Reedsport
10.0 out of 10, Exceptional, (60 reviews)
"This place is perfect..... period."
United States
Mike G.
The price is HK$805
HK$1,816 total
includes taxes & fees
24 Aug - 25 Aug
The Salty Duplex (Left Side)
Coffee/tea maker, fridge, microwave, oven

7. The Salty Duplex (Right Side)

The Salty Duplex (Right Side)
Reedsport
10.0 out of 10, Exceptional, (84 reviews)
"Great little place, has everything you need."
United States
Aaron A.
The price is HK$996
HK$2,037 total
includes taxes & fees
13 Aug - 14 Aug
The Salty Duplex (Right Side)
Interior

8. 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
10.0 out of 10, Exceptional, (18 reviews)
"Host was welcoming and the amenities where good"
United States
Shain O.
The price is HK$1,036
HK$2,159 total
includes taxes & fees
1 Sept - 2 Sept
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.
Interior

9. #StayinMyDistrict Lakeside Cottage

#StayinMyDistrict Lakeside Cottage
Lakeside
9.4 out of 10, Exceptional, (22 reviews)
"We loved our stay. Our cottage/cabin had everything we needed and more to make our stay great!"
United States
Shari
The price is HK$902
HK$2,178 total
includes taxes & fees
16 Aug - 17 Aug
#StayinMyDistrict Lakeside Cottage
Exterior

10. Cozy Cabin near Everything!

Cozy Cabin near Everything!
North Bend
8.8 out of 10, Excellent, (42 reviews)
"The cozy cabin is a perfect description of this vacation rental. As a solo traveler on this trip, I felt safe. It was comfortable and was sufficiently stocked. Also, the fee was very reasonable. "
United States
Tammy M.
The price is HK$584
HK$1,440 total
includes taxes & fees
9 Sept - 10 Sept
Cozy Cabin near Everything!
Exterior

11. Scenic and relaxing Lake Cottage with Views

Scenic and relaxing Lake Cottage with Views
Coos County
The price is HK$1,326
HK$2,797 total
includes taxes & fees
27 Aug - 28 Aug
Scenic and relaxing Lake Cottage with Views
Smart TV, video games, books

12. 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, (45 reviews)
"It was very clean and private with everything that you would need. Will book again the next time we are down."
United States
Charlene K.
The price is HK$1,491
HK$2,104 total
includes taxes & fees
6 Sept - 7 Sept
So much to enjoy at this 2-bedroom cottage in Charming Lakeside.
Front of property

13. Siltcoos Station Retreats

Siltcoos Station Retreats
4.0 star property
Westlake
9.2 out of 10, Wonderful, (10 reviews)
"Great lake access for kayaking"
United States
Andrew
The price is HK$2,040
HK$2,275 total
includes taxes & fees
16 Aug - 17 Aug
Siltcoos Station Retreats
Property grounds

14. #StayinMyDistrict Majestic Shores Lake Bear Cabin

#StayinMyDistrict Majestic Shores Lake Bear Cabin
North Bend
9.6 out of 10, Exceptional, (4 reviews)
"Nice cozy cabin and great access to the lake for kayaking."
United States
Travis and Tabitha N.
The price is HK$973
HK$2,333 total
includes taxes & fees
7 Sept - 8 Sept
#StayinMyDistrict Majestic Shores Lake Bear Cabin
Exterior

15. Relaxing Getaway Lake Cabin with Pristine Views

Relaxing Getaway Lake Cabin with Pristine Views
Coos County
9.6 out of 10, Exceptional, (25 reviews)
"Everything from booking to checkout was perfect. The directions were clear and made finding the cabin easy. The view from the deck is beautiful and the cabin is as described. Highly recommend! "
United States
Shaunie M.
The price is HK$1,357
HK$2,834 total
includes taxes & fees
31 Aug - 1 Sept
Relaxing Getaway Lake Cabin with Pristine Views
Living area

16. Hot Tub, Siltcoose Private Dock w/ ocean access, Cottage, w/ canoes!

Hot Tub, Siltcoose Private Dock w/ ocean access, Cottage, w/ canoes!
Dunes City
9.4 out of 10, Exceptional, (28 reviews)
"Nice little place with hidden amenities! "
United States
Lolita H.
The price is HK$1,287
HK$2,571 total
includes taxes & fees
19 Aug - 20 Aug
Hot Tub, Siltcoose Private Dock w/ ocean access, Cottage, w/ canoes!
Exterior

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

Lakeside house with access to dunes, lakes, and the ocean!
Lakeside
9.8 out of 10, Exceptional, (34 reviews)
"Was a great place to stay especially with trailer "
United States
David
The price is HK$1,476
HK$3,404 total
includes taxes & fees
17 Aug - 18 Aug
Lakeside house with access to dunes, lakes, and the ocean!
Property grounds

18. 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, (33 reviews)
"An absolute wonderful getaway cabin. Everything was extremely convenient, clean and comfortable. Definitely the best short-term rental I have experienced. The drive to the cabin was long, but the instructions were very clear. Water is HOT!"
United States
Noel S.
The price is HK$1,709
HK$2,967 total
includes taxes & fees
10 Sept - 11 Sept
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.
TV, offices

19. #StayinMyDistrict Brussells Bungalow

#StayinMyDistrict Brussells Bungalow
North Bend
8.4 out of 10, Very good, (9 reviews)
"It was great! Would definitely stay again."
United States
Gary W.
The price is HK$965
HK$2,310 total
includes taxes & fees
23 Aug - 24 Aug
#StayinMyDistrict Brussells Bungalow
Terrace/patio

20. 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, (115 reviews)
"Great space, great hosts. Wonderful and relaxing cabin. "
United States
Carmel K.
The price is HK$2,208
HK$4,042 total
includes taxes & fees
3 Sept - 4 Sept
Cozy A-Frame w/Spa+14 acres+EV+Trails+Lake Access
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Bay Hotel Reviews

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.

10/10 Excellent
"Very good house"
Herrera's Germán Shepherds m. 2-night trip
Posted 10 hours ago
Soothing Crab themed 3-bedroom home with WiFi and a hot tub in Winchester Bay.

Find out more about Winchester Bay

Search for holiday rentals in Winchester Bay on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester Bay using one of the methods below:

  • View our selection of featured holiday rentals in Winchester Bay
  • Use the map to find apartments and other holiday homes in the Winchester Bay neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winchester Bay while they last

Look no further and take a look at our great range of rental properties in Winchester Bay!

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. Some other homes for rent in Winchester Bay include Soothing Crab themed 3-bedroom home with WiFi and a hot tub in Winchester Bay. and Dog-friendly coastal-themed home with a full kitchen & washer&dryer.

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.