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Winchester Bay Holiday Rentals

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Our top choices for Winchester Bay holiday rentals

1. 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)
"First thing we noticed was how clean this place was. Very impressed. We loved the exterior artsmanship. Very creative. The place was quiet and very comfortable for a good nights rest. We would definitely stay here again if we get back to the area."
United States
Stephan P
The price is NZ$467
includes taxes & fees
23 Aug - 24 Aug
Winchester Bay Apt Near Dunes & State Parks!

2. 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 NZ$384
includes taxes & fees
19 Aug - 20 Aug
Dog-friendly ADU with a full kitchen & shared washer&dryer - near the water

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 NZ$770
includes taxes & fees
25 Aug - 26 Aug
Soothing Crab themed 3-bedroom home with WiFi and a hot tub in Winchester Bay.

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 NZ$1,338
includes taxes & fees
18 Aug - 19 Aug
Luxurious Hilltop Home w/ Private Hot Tub and Direct Dune Access

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, (237 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 NZ$1,071
includes taxes & fees
24 Aug - 25 Aug
Cozy Hilltop Home with Private Hot Tub, Direct Dune Access & Breathtaking Views

6. Winchester Bay Apt Near Dunes & State Parks!

Winchester Bay Apt Near Dunes & State Parks!
Winchester Bay
9.8 out of 10, Exceptional, (38 reviews)
"It was the perfect place for our trip will definitely come again "
United States
Chris P.
The price is NZ$475
includes taxes & fees
23 Aug - 24 Aug
Winchester Bay Apt Near Dunes & State Parks!

7. 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 NZ$377
includes taxes & fees
24 Aug - 25 Aug
The Salty Duplex (Left Side)

8. 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 NZ$445
includes taxes & fees
7 Sept - 8 Sept
The Salty Duplex (Right Side)

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 NZ$441
includes taxes & fees
18 Aug - 19 Aug
#StayinMyDistrict Lakeside Cottage

10. 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 NZ$450
includes taxes & fees
31 Aug - 1 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.

11. 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)
"We appreciated having enough beds for our family of 6! It was a private location, the stay was comfortable, and we had everything we needed for our night there."
United States
Jennifer W.
The price is NZ$411
includes taxes & fees
13 Sept - 14 Sept
So much to enjoy at this 2-bedroom cottage in Charming Lakeside.

12. 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 NZ$549
includes taxes & fees
31 Aug - 1 Sept
Relaxing Getaway Lake Cabin with Pristine Views

13. #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 NZ$493
includes taxes & fees
7 Sept - 8 Sept
#StayinMyDistrict Majestic Shores Lake Bear Cabin

14. Cozy Cabin near Everything!

Cozy Cabin near Everything!
North Bend
8.8 out of 10, Excellent, (45 reviews)
"Great place for us to spend the night and be able to relax a bit!"
United States
David L.
The price is NZ$320
includes taxes & fees
26 Aug - 27 Aug
Cozy Cabin near Everything!

15. 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 NZ$690
includes taxes & fees
18 Aug - 19 Aug
Lakeside house with access to dunes, lakes, and the ocean!

16. 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 NZ$468
includes taxes & fees
27 Aug - 28 Aug
Siltcoos Station Retreats

17. 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 NZ$626
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.

18. 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, (32 reviews)
"Cute little cottage, everything was wonderful! We will be returning for another stay in the future!"
United States
Carissa B.
The price is NZ$540
includes taxes & fees
19 Aug - 20 Aug
Hot Tub, Siltcoose Private Dock w/ ocean access, Cottage, w/ canoes!

19. 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 NZ$933
includes taxes & fees
16 Sept - 17 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.
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Top Winchester Bay Hotel Reviews

Find out more about Winchester Bay

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Winchester Bay holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Winchester Bay. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Winchester Bay. Seeing all the best attractions is bound to make you fall in love with Winchester Bay. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Winchester Bay short-term rentals, that won’t be hard to do.

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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 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 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.