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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
9.6 out of 10, Exceptional, (34 reviews)
"Clean house friendly host the little house is right in the middle of town easy to find and walking distance for food and fishing"
United States
Anonymous traveller
The price is CA $283
CA $613 total
includes taxes & fees
Oct 1 - Oct 2
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)
"Our stay was great!"
United States
Amy C.
The price is CA $497
CA $888 total
includes taxes & fees
Sep 22 - Sep 23
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 $629
CA $1,117 total
includes taxes & fees
Sep 22 - Sep 23
Luxurious Hilltop Home w/ Private Hot Tub and Direct Dune Access

4. The Salty Duplex (Left Side)

The Salty Duplex (Left Side)
Reedsport
10.0 out of 10, Exceptional, (64 reviews)
"The house was very clean and well presented with lots of extra/thoughtful touches to make it a pleasant stay."
United Kingdom
Philippa
The price is CA $133
CA $310 total
includes taxes & fees
Oct 4 - Oct 5
The Salty Duplex (Left Side)

5. The Salty Duplex (Right Side)

The Salty Duplex (Right Side)
Reedsport
10.0 out of 10, Exceptional, (87 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 CA $164
CA $345 total
includes taxes & fees
Oct 12 - Oct 13
The Salty Duplex (Right Side)

6. 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, (19 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 $146
CA $341 total
includes taxes & fees
Sep 30 - Oct 1
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.

7. #StayinMyDistrict Lakeside Cottage

#StayinMyDistrict Lakeside Cottage
Lakeside
9.4 out of 10, Exceptional, (23 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 CA $129
CA $342 total
includes taxes & fees
Sep 22 - Sep 23
#StayinMyDistrict Lakeside Cottage

8. #StayinMyDistrict Majestic Shores Lake Bear Cabin

#StayinMyDistrict Majestic Shores Lake Bear Cabin
North Bend
9.6 out of 10, Exceptional, (5 reviews)
The price is CA $134
CA $360 total
includes taxes & fees
Sep 22 - Sep 23
#StayinMyDistrict Majestic Shores Lake Bear Cabin

9. 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, (49 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 $231
CA $328 total
includes taxes & fees
Oct 19 - Oct 20
So much to enjoy at this 2-bedroom cottage in Charming Lakeside.

10. Scenic and relaxing Lake Cottage with Views

Scenic and relaxing Lake Cottage with Views
Coos County
The price is CA $168
CA $419 total
includes taxes & fees
Sep 22 - Sep 23
Scenic and relaxing Lake Cottage with Views

11. 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)
"The entire environment was amazing. The place was very welcoming and felt very at home. We definitely plan to come back and stay again."
United States
Sarah O.
The price is CA $246
CA $459 total
includes taxes & fees
Sep 30 - Oct 1
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.

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)
"A perfect cabin for our bro-in-law getaway. Not too fancy, but everything we needed. We'll stocked with all the essentials and you can't beat the views. Good dock for boat tie up too!"
United States
Curt H.
The price is CA $221
CA $473 total
includes taxes & fees
Oct 20 - Oct 21
Relaxing Getaway Lake Cabin with Pristine Views

13. 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, (116 reviews)
"Great space, great hosts. Wonderful and relaxing cabin. "
United States
Carmel K.
The price is CA $292
CA $600 total
includes taxes & fees
Oct 1 - Oct 2
Cozy A-Frame w/Spa+14 acres+EV+Trails+Lake Access

14. Cozy Cabin near Everything!

Cozy Cabin near Everything!
North Bend
8.8 out of 10, Excellent, (48 reviews)
"We truly enjoyed our stay, thanks for the great location."
United States
Phyllis H.
The price is CA $104
CA $255 total
includes taxes & fees
Sep 22 - Sep 23
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
9.6 out of 10, Exceptional, (40 reviews)
"Was a great place to stay especially with trailer "
United States
David
The price is CA $205
CA $530 total
includes taxes & fees
Sep 22 - Sep 23
Lakeside house with access to dunes, lakes, and the ocean!

16. 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 $257
CA $286 total
includes taxes & fees
Oct 4 - Oct 5
Siltcoos Station Retreats

17. 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 $229
CA $490 total
includes taxes & fees
Sep 29 - Sep 30
Ultimate Guesthouse•Curated Luxury with Lake+Kayak

18. Ticketmaster Chamber - Historic Lakefront Studio Cabin with Kayaking

Ticketmaster Chamber - Historic Lakefront Studio Cabin with Kayaking
oregon
10.0 out of 10, Exceptional, (7 reviews)
"Perfect little get away spot, wish we had stayed longer! Loved the decor, amenities, friendly vibe, lake access, etc!"
United States
Mariah M.
The price is CA $262
CA $422 total
includes taxes & fees
Sep 29 - Sep 30
Ticketmaster Chamber - Historic Lakefront Studio Cabin with Kayaking

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, (33 reviews)
"Cute little cottage, everything was wonderful! We will be returning for another stay in the future!"
United States
Carissa B.
The price is CA $229
CA $458 total
includes taxes & fees
Sep 24 - Sep 25
Hot Tub, Siltcoose Private Dock w/ ocean access, Cottage, w/ canoes!

20. Barnhaus-Spa+11 Acres+EV+Gym+Lake Access

Barnhaus-Spa+11 Acres+EV+Gym+Lake Access
Lakeside
10.0 out of 10, Exceptional, (4 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 $601 total
includes taxes & fees
Sep 27 - Sep 28
Barnhaus-Spa+11 Acres+EV+Gym+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 vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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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.