Photo by Vicki Chandler

Winchester Bay Holiday Rentals

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Holiday Rentals in Winchester Bay

Cozy family beach cottage w/ hot tub, deck, WiFi, surfboard-walk to bay, Dogs ok

9.4 out of 10, Exceptional, (38)
"Nice cozy house, prefect for some much-needed quite time "
The price is AU$428
includes taxes & fees
1 Dec - 2 Dec
Cozy family beach cottage w/ hot tub, deck, WiFi, surfboard-walk to bay, Dogs ok

Dog-friendly coastal-themed home with a full kitchen & washer/dryer

9.2 out of 10, Wonderful, (24)
"Great quiet clean place with a well stocked kitchen and all the comforts. "
The price is AU$372
includes taxes & fees
1 Dec - 2 Dec
Dog-friendly coastal-themed home with a full kitchen & washer/dryer

Winchester Bay Apt Near Dunes & State Parks!

9.8 out of 10, Exceptional, (15)
"We needed a quiet place close to North Bend while visiting family and after a long drive it was nice to stay here instead of a hotel. The beds were comfortable and we had a kitchen to fix mesls. It was just right The beds wewre"
Winchester Bay Apt Near Dunes & State Parks!

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

9.2 out of 10, Wonderful, (29)
"It was nice and clean, comfortable and accommodating. Parking is on street and neighbors are not happy when you park in front of their house, the spot in front of the rental was occupied by a car all week with out moving so it's essentially impossible not to park in front of a neighboring home. After the neighbor told me to move my car, I used the driveway, since there was no one I in the front house most of the week. "
The price is AU$273
includes taxes & fees
1 Dec - 2 Dec
Dog-friendly ADU with a full kitchen & shared washer/dryer - near the water

Coastal home with an enclosed yard, hot tub, grill, fireplace, and W/D - dogs ok

8.2 out of 10, Very good, (12)
"Loved the unique Crab Shack. Great coffee bar set up. Stairs are a little steep for those older or toddlers. But we managed fine. Not sure how sleeping on the top bunks might be if you are tall. We didn't need to use them. Location is great. Nice private back yard with a hot tub. Would come back again for sure. "
Coastal home with an enclosed yard, hot tub, grill, fireplace, and W/D - dogs ok

Blue Heron Getaway. Come enjoy the spring and summer in our great cozy house.

10.0 out of 10, Exceptional, (25)
"One of the best house we have stayed "
Blue Heron Getaway. Come enjoy the spring and summer in our great cozy house.

Overlook the Winchester Bay Harbor from the spacious 3rd Level!

10.0 out of 10, Exceptional, (22)
"Great location and amazing views. Be ready for some stairs - that hidden dumbwaiter would be a blessing."
Overlook the Winchester Bay Harbor from the spacious 3rd Level!

Comfy dog-friendly bay home with kitchenette, gas grill, patio, yard, and W/D

8.6 out of 10, Excellent, (4)
"The only issue was the downstairs bath pocket door was in serious need of repair. This was not a serious issue for our group, but could be for others."
Comfy dog-friendly bay home with kitchenette, gas grill, patio, yard, and W/D

Winchester Bay Apt Near Dunes & State Parks!

3.0 star property
10.0 out of 10, Exceptional, (1)
Winchester Bay Apt Near Dunes & State Parks!

Winchester Bay Vacation Rental Near Dunes & ATV!

10.0 out of 10, Exceptional, (5)
"Great house for a family to stay. Close to the dunes which we enjoyed. The only recommendation is a bigger coffee pot. Which is a small thing for sure. We just love coffee! We would totally stay there again."
Winchester Bay Vacation Rental Near Dunes & ATV!

Cozy Cabin near Everything!

9.2 out of 10, Wonderful, (28)
"It was a nice stay while I am in town for work. Everything was very tidy and clean. The only issue I had was there was only about 7-8 mins of warm water in the shower; I had to hustle once it dropped in temperature. Otherwise, I was comfortable. Thank you. "
The price is AU$315
includes taxes & fees
2 Dec - 3 Dec
Cozy Cabin near Everything!

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

10.0 out of 10, Exceptional, (21)
"So much thought and effort has gone into making this a comfortable stay for 3 generations and pet. Old game stations and hand shuffle board had kids and oldsters playing together. Blankets made TV watching comfortable. Fenced yard was good for pet. Kitchen was well appointed and beds were comfortable. Big Foot design is fun too. We drove to Bastendorf Beach, North Bend, for dog run."
Lakeside house with access to dunes, lakes, and the ocean!

Overlooking Old Town yet In a Secluded Forest Setting

8.0 out of 10, Very good, (114)
"Hunted mushrooms on the property and had a ton of fun! Will for sure stay here again!"
Overlooking Old Town yet In a Secluded Forest Setting

Cozy Boathouse On The Lake W/ Spacious Dock. Boat access only

9.2 out of 10, Wonderful, (5)
"Great little property my wife and I had a great time relaxing and taking in the views of the lake and the Oregon coast."
Cozy Boathouse On The Lake W/ Spacious Dock. Boat access only

Renovated North Bend Cottage: Near Eateries!

10.0 out of 10, Exceptional, (27)
"The home is comfortable and nicely designed. The beds were super comfortable. We mostly cooked and ate in, and the kitchen had everything needed! We only wish the weather had been better for enjoying the lovely outdoor area and fire pit!"
Renovated North Bend Cottage: Near Eateries!

The Salty Duplex (Right Side)

10.0 out of 10, Exceptional, (64)
"Better than a 5 star rated hotel"
The price is AU$353
includes taxes & fees
2 Dec - 3 Dec
The Salty Duplex (Right Side)

Coastal Elegance

9.8 out of 10, Exceptional, (13)
"Three 60+ guys with a guide for fishing two days. Perfect fit for us, will use again"
Coastal Elegance

Direct Dune Access Sleeps 10 In House, 6 In BunkHouses - Bath Houses.

9.8 out of 10, Exceptional, (136)
"Awesome location! Lots of room and plenty of privacy! We will be back!"
Direct Dune Access Sleeps 10 In House, 6 In BunkHouses - Bath Houses.

New Listing! Adorable lakefront cabin, private dock, hot tub, gas grill, amazing views

9.4 out of 10, Exceptional, (20)
"Comfy spot! "
New Listing! Adorable lakefront cabin, private dock, hot tub, gas grill, amazing views

2-Bedroom Park Model Trailer 5 Minutes to Oregon Dunes National Recreation Area

10.0 out of 10, Exceptional, (16)
"Amazing location beautiful spacious lot comfortable setting! Cant wait to cone back."
2-Bedroom Park Model Trailer 5 Minutes to Oregon Dunes National Recreation Area
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.
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Other types of properties in Winchester Bay you may be interested in

Winchester Bay Inn

2.5 star property
7.2 out of 10, Good, (721)
"I find it quiet, clean and friendly. The woman at the desk is helpful and willing to assist."
The price is AU$147
includes taxes & fees
1 Dec - 2 Dec
Winchester Bay Inn

Cozy family beach cottage w/ hot tub, deck, WiFi, surfboard-walk to bay, Dogs ok

9.4 out of 10, Exceptional, (38)
"Nice cozy house, prefect for some much-needed quite time "
The price is AU$428
includes taxes & fees
1 Dec - 2 Dec
Cozy family beach cottage w/ hot tub, deck, WiFi, surfboard-walk to bay, Dogs ok

Coastal home with an enclosed yard, hot tub, grill, fireplace, and W/D - dogs ok

8.2 out of 10, Very good, (12)
"Loved the unique Crab Shack. Great coffee bar set up. Stairs are a little steep for those older or toddlers. But we managed fine. Not sure how sleeping on the top bunks might be if you are tall. We didn't need to use them. Location is great. Nice private back yard with a hot tub. Would come back again for sure. "
Coastal home with an enclosed yard, hot tub, grill, fireplace, and W/D - dogs ok
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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 w/ 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 patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub. Some other homes for rent in Winchester Bay include Coastal home with an enclosed yard, hot tub, grill, fireplace, and W/D - dogs ok and Blue Heron Getaway. Come enjoy the spring and summer in our great cozy house. .

How many holiday rentals will I find in Winchester Bay?

Choose from 13 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.