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Winchester Bay Vacation Rentals

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Winchester Bay vacation 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 ￥14,008
￥35,231 total
includes taxes & fees
Sep 1 - Sep 2
Dog-friendly ADU with a full kitchen & shared washer&dryer - near the water
Apartment (2 Bedrooms) | 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)
"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
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 ￥35,764
￥73,246 total
includes taxes & fees
Aug 25 - Aug 26
Soothing Crab themed 3-bedroom home with WiFi and a hot tub in Winchester Bay.
Exterior

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)
"Great and comfortable place to rest after a nice ride on the dunes! Location was perfect"
United States
Johnny H.
The price is ￥71,528
￥129,068 total
includes taxes & fees
Aug 24 - Aug 25
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, (237 reviews)
"Our stay was great!"
United States
Amy C.
The price is ￥56,507
￥101,882 total
includes taxes & fees
Aug 24 - Aug 25
Cozy Hilltop Home with Private Hot Tub, Direct Dune Access & Breathtaking Views
Marina

6. Winchester Bay Apt Near Dunes & State Parks!

Winchester Bay Apt Near Dunes & State Parks!
Winchester Bay
9.8 out of 10, Exceptional, (39 reviews)
"It was the perfect place for our trip will definitely come again "
United States
Chris P.
Winchester Bay Apt Near Dunes & State Parks!
Coffee/tea maker, fridge, microwave, oven

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 ￥14,735
￥34,884 total
includes taxes & fees
Aug 26 - Aug 27
The Salty Duplex (Left Side)
Coffee/tea maker, fridge, microwave, oven

8. The Salty Duplex (Right Side)

The Salty Duplex (Right Side)
Reedsport
10.0 out of 10, Exceptional, (85 reviews)
"Perfect place to stay and has everything you need for a nice long stay. Will definitely be back again!"
United States
Adam M.
The price is ￥20,664
￥41,286 total
includes taxes & fees
Sep 7 - Sep 8
The Salty Duplex (Right Side)
Interior

9. 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 ￥20,107
￥42,392 total
includes taxes & fees
Sep 23 - Sep 24
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

10. #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 ￥16,372
￥41,499 total
includes taxes & fees
Aug 24 - Aug 25
#StayinMyDistrict Lakeside Cottage
Smart TV, video games, books

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 ￥27,816
￥39,677 total
includes taxes & fees
Sep 13 - Sep 14
So much to enjoy at this 2-bedroom cottage in Charming Lakeside.
Property grounds

12. Welcome to the Dahlia house, a charming coastal retreat

Welcome to the Dahlia house, a charming coastal retreat
Reedsport
10.0 out of 10, Exceptional, (6 reviews)
Welcome to the Dahlia house, a charming coastal retreat
Property grounds

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 ￥17,326
￥43,817 total
includes taxes & fees
Sep 1 - Sep 2
#StayinMyDistrict Majestic Shores Lake Bear Cabin
Exterior

14. Cozy Cabin near Everything!

Cozy Cabin near Everything!
North Bend
8.8 out of 10, Excellent, (46 reviews)
"We truly enjoyed our stay, thanks for the great location."
United States
Phyllis H.
The price is ￥11,826
￥29,185 total
includes taxes & fees
Aug 26 - Aug 27
Cozy Cabin near Everything!
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 ￥25,750
￥55,327 total
includes taxes & fees
Aug 25 - Aug 26
Relaxing Getaway Lake Cabin with Pristine Views
Front of property

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 ￥38,036
￥42,410 total
includes taxes & fees
Aug 27 - Aug 28
Siltcoos Station Retreats
Property grounds

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 ￥33,046
￥58,384 total
includes taxes & fees
Aug 27 - Aug 28
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.
Exterior

18. 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, (35 reviews)
"Was a great place to stay especially with trailer "
United States
David
The price is ￥28,468
￥67,242 total
includes taxes & fees
Aug 27 - Aug 28
Lakeside house with access to dunes, lakes, and the ocean!
Living area

19. 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 ￥26,068
￥52,083 total
includes taxes & fees
Aug 30 - Aug 31
Hot Tub, Siltcoose Private Dock w/ ocean access, Cottage, w/ canoes!
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 ￥44,228
￥81,983 total
includes taxes & fees
Aug 25 - Aug 26
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

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

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

10/10 Excellent
"Cute property that meet our needs. Smooth check in and close to the docks and restaurants. Was perfect for my family and our dog."
Gillian W. 2-night trip
Posted 2 days ago
Cozy family beach cottage with hot tub, deck, WiFi, surfboard-walk to bay, Dogs ok

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

Frequently asked questions

Can I find vacation rentals in Winchester Bay?

Yes, we give you a choice of vacation rentals near popular points of interest in Winchester Bay, or you can choose a secluded option if you're looking for relaxation. Winchester Bay is known for its parks.

What are some of the best vacation home rentals in Winchester Bay?

Cozy family beach cottage with hot tub, deck, WiFi, surfboard-walk to bay, Dogs ok: Visitors like this Winchester Bay vacation home rental. It is located in the city center and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You can relax into your vacation with a selection of games and a 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 vacation rentals will I find in Winchester Bay?

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

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 larger area, you’ll find Umpqua Lighthouse and Oregon Dunes National Recreation Area.

What’s a vacation rental in Winchester Bay like?

Vacation rentals are privately owned properties you can book for a couple of days or more in Winchester Bay. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll have all the comforts of home. If you're concerned about a clean environment, vacation rentals can offer a sense of privacy away from shared hotel elevators and busy concierge desks while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for a family trip or a small group gathering.