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Winchester Bay Vacation Rentals

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Our top choices for Winchester Bay vacation 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 CA $208
CA $499 total
includes taxes & fees
Nov 15 - Nov 16
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 CA $498
CA $902 total
includes taxes & fees
Nov 9 - Nov 10
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 CA $624
CA $1,074 total
includes taxes & fees
Nov 8 - Nov 9
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 CA $202
CA $388 total
includes taxes & fees
Nov 12 - Nov 13
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 CA $120
CA $295 total
includes taxes & fees
Nov 17 - Nov 18
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 CA $129
CA $287 total
includes taxes & fees
Nov 9 - Nov 10
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 CA $137
CA $299 total
includes taxes & fees
Nov 9 - Nov 10
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 CA $67
CA $254 total
includes taxes & fees
Nov 8 - Nov 9
#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 CA $97
CA $283 total
includes taxes & fees
Nov 9 - Nov 10
#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 CA $250
CA $338 total
includes taxes & fees
Dec 4 - Dec 5
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 CA $292
CA $565 total
includes taxes & fees
Nov 17 - Nov 18
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 CA $197
CA $494 total
includes taxes & fees
Dec 1 - Dec 2
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 CA $105
CA $252 total
includes taxes & fees
Nov 11 - Nov 12
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 CA $292
CA $566 total
includes taxes & fees
Nov 19 - Nov 20
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 CA $219
CA $454 total
includes taxes & fees
Nov 15 - Nov 16
Ultimate Guesthouse•Curated Luxury with Lake+Kayak

16. #StayInMyDistrict NorthBend Duplex Dog Friendly

#StayInMyDistrict NorthBend Duplex Dog Friendly
North Bend
The price is CA $108
CA $317 total
includes taxes & fees
Nov 8 - Nov 9
#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 CA $585
CA $1,077 total
includes taxes & fees
Nov 19 - Nov 20
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 CA $109
CA $319 total
includes taxes & fees
Nov 9 - Nov 10
#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 CA $89
CA $279 total
includes taxes & fees
Nov 8 - Nov 9
#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 CA $386
CA $430 total
includes taxes & fees
Nov 13 - Nov 14
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 vacation rentals that suit your style

Top Winchester Bay Hotel Reviews

Find out more about Winchester Bay

Everything you need to know about Winchester Bay vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester Bay vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winchester Bay vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester Bay vacation rentals we have selected for you start as low as CA $67 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 vacation 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 vacation.

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 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. 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 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.

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