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Winchester Bay Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Winchester Bay vacation rentals

A house with a green exterior, a wooden front porch with a red chair, and a small garden area with a pond.

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
$370 nightly
The price is $375
Nov 1 - Nov 2
Total with taxes and fees
Soothing Crab themed 3-bedroom home with WiFi and a hot tub in Winchester Bay.
A living room with a fireplace, a television, a sofa, a coffee table, and a dining area with a table and chairs.

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.
$607 nightly
The price is $616
Oct 27 - Oct 28
Total with taxes and fees
Cozy Hilltop Home with Private Hot Tub, Direct Dune Access & Breathtaking Views
Terrace/patio

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.
$785 nightly
The price is $796
Oct 27 - Oct 28
Total with taxes and fees
Luxurious Hilltop Home w/ Private Hot Tub and Direct Dune Access
A modern kitchen with white cabinets, a granite countertop, a wooden island with bar stools, a microwave, a refrigerator, and a large window.

4. 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.
$199 nightly
The price is $221
Nov 9 - Nov 10
Total with taxes and fees
The Salty Duplex (Right Side)
A room with a large window overlooking a lake and forest.

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.
$218 nightly
The price is $219
Oct 27 - Oct 28
Total with taxes and fees
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.
A modern kitchen with stainless steel appliances, white cabinets, and a blue-tiled backsplash.

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.
$194 nightly
The price is $215
Nov 9 - Nov 10
Total with taxes and fees
The Salty Duplex (Left Side)
A compact living space with a kitchenette, a sofa, and a dining area.

7. #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.
$198 nightly
The price is $215
Oct 27 - Oct 28
Total with taxes and fees
#StayinMyDistrict Lakeside Cottage
An outdoor seating area with a table and chairs, a grill, and a large tree in a forested setting.

8. #StayinMyDistrict Majestic Shores Lake Bear Cabin

#StayinMyDistrict Majestic Shores Lake Bear Cabin
North Bend
9.6 out of 10, Exceptional, (5 reviews)
$166 nightly
The price is $185
Nov 1 - Nov 2
Total with taxes and fees
#StayinMyDistrict Majestic Shores Lake Bear Cabin
A wooden dock with two chairs facing a calm lake, surrounded by forested hills.

9. 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.
$301 nightly
The price is $301
Oct 28 - Oct 29
Total with taxes and fees
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.
A house with a large front window, a wooden deck, and a black trash bin.

10. Cozy Cabin near Everything!

Cozy Cabin near Everything!
North Bend
8.8 out of 10, Excellent, (49 reviews)
"We truly enjoyed our stay, thanks for the great location."
United States
Phyllis H.
$159 nightly
The price is $177
Oct 27 - Oct 28
Total with taxes and fees
Cozy Cabin near Everything!
A cozy living room with a sectional sofa, a small table, a lamp, and a TV mounted on the wall.

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, (51 reviews)
"Wonderful secure property with easy access to the beach and town. Owner is very responsive and helpful."
United States
Candy H.
$206 nightly
The price is $224
Oct 27 - Oct 28
Total with taxes and fees
So much to enjoy at this 2-bedroom cottage in Charming Lakeside.
A two-story house with a front porch, a garage, and a well-maintained garden.

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
$324 nightly
The price is $353
Oct 28 - Oct 29
Total with taxes and fees
Lakeside house with access to dunes, lakes, and the ocean!
A house with a sloped roof, large windows, and a deck.

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, (117 reviews)
"Amazing Cabin experience. Fully stocked, clean and very roomy"
United States
Luba K.
$399 nightly
The price is $423
Oct 27 - Oct 28
Total with taxes and fees
Cozy A-Frame w/Spa+14 acres+EV+Trails+Lake Access
A modern living room with a sofa, coffee table, and a kitchen area with a countertop and stools.

14. #StayInMyDistrict NorthBend Retreat Dog Friendly

#StayInMyDistrict NorthBend Retreat Dog Friendly
North Bend
$219 nightly
The price is $243
Oct 27 - Oct 28
Total with taxes and fees
#StayInMyDistrict NorthBend Retreat Dog Friendly
A serene outdoor setting with a pond, surrounded by dense trees and a fire pit.

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.
$340 nightly
The price is $341
Oct 27 - Oct 28
Total with taxes and fees
Ultimate Guesthouse•Curated Luxury with Lake+Kayak
A row of wooden cabins with a stone wall and a green fence in front.

16. Brakeman's Bay - Charming Lakefront Studio - Wheelchair Accessible

Brakeman's Bay - Charming Lakefront Studio - Wheelchair Accessible
Westlake
9.4 out of 10, Exceptional, (10 reviews)
"Nice and quiet, great view of the lake. It was fun staying in a place with modern appliances from way back when. We had a good time."
United States
Andrew j.
$236 nightly
The price is $257
Oct 27 - Oct 28
Total with taxes and fees
Brakeman's Bay - Charming Lakefront Studio - Wheelchair Accessible
A hot tub in a forested area with wooden steps leading up to it.

17. 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.
$399 nightly
The price is $424
Oct 27 - Oct 28
Total with taxes and fees
Barnhaus-Spa+11 Acres+EV+Gym+Lake Access
A house with a wooden deck and a flagpole with flags.

18. 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
$218 nightly
The price is $243
Oct 31 - Nov 1
Total with taxes and fees
Siltcoos Station Retreats
A room with wooden flooring, a flat-screen TV mounted on the wall, a grey armchair, a brown leather chair, and a green sofa.

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.
$199 nightly
The price is $220
Oct 28 - Oct 29
Total with taxes and fees
#StayinMyDistrict Brussells Bungalow
Exterior

20. Paradise Cabin on Tenmile Lake

Paradise Cabin on Tenmile Lake
Lakeside
9.0 out of 10, Wonderful, (28 reviews)
"We loved our stay at this beautiful cottage! Tasteful, charming, and everything from mattress comfort to linens were top quality. Highly recommend!"
United States
Anonymous traveler
$571 nightly
The price is $580
Oct 27 - Oct 28
Total with taxes and fees
Paradise Cabin on Tenmile Lake
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

Bay Bridge Motel

Bay Bridge Motel

10/10 Excellent
"This place is amazing! Very clean, staff was friendly and helpful, there's numbered parking spots for each room so you foresure have parking in front of your room. Not to mention the fantastic views for the price!! We will absolutely be coming back here for our stays 🙏❤"
LeAnn 1-night trip
Posted 9 hours ago
Bay Bridge Motel

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Winchester Bay in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $219 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

Explore a world of travel with Expedia

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.