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Winchester Bay Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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
9.6 out of 10, Exceptional, (35 reviews)
"Highly recommend. The host is the absolute best host I’ve ever experienced renting a house. Will certainly be back."
United States
Caleb
$389 nightly
The price is $395
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 wooden deck with a glass table and chairs, overlooking a beach and water.

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)
"Comfortable house with a fantastic view. It had everything our family needed for a fun and relaxing trip."
United States
Jill L.
$627 nightly
The price is $636
Oct 5 - Oct 6
Total with taxes and fees
Cozy Hilltop Home with Private Hot Tub, Direct Dune Access & Breathtaking Views
A house with a large deck, a hot tub, and a view of the ocean.

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.
$789 nightly
The price is $801
Oct 5 - Oct 6
Total with taxes and fees
Luxurious Hilltop Home w/ Private Hot Tub and Direct Dune Access
A marina with multiple boats docked, a clear sky, and a calm water surface reflecting the boats.

4. 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 perfect location! Walking distance to the bay and plenty of dining close by as well."
United States
Denise S.
Winchester Bay Apt Near Dunes & State Parks!
A modern kitchen with white cabinets, a granite countertop, a wooden island with bar stools, a microwave, a refrigerator, and a large window.

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.
$202 nightly
The price is $224
Oct 14 - Oct 15
Total with taxes and fees
The Salty Duplex (Right Side)
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, (65 reviews)
"The house was very clean and well presented with lots of extra/thoughtful touches to make it a pleasant stay."
United Kingdom
Philippa
$197 nightly
The price is $218
Oct 12 - Oct 13
Total with taxes and fees
The Salty Duplex (Left Side)
A cozy living room with a sectional sofa, a small table, a lamp, and a TV mounted on the wall.

7. 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, (50 reviews)
"Wonderful secure property with easy access to the beach and town. Owner is very responsive and helpful."
United States
Candy H.
$212 nightly
The price is $231
Oct 5 - Oct 6
Total with taxes and fees
So much to enjoy at this 2-bedroom cottage in Charming Lakeside.
A house with a sloped roof, large windows, and a deck.

8. 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)
"Great space, great hosts. Wonderful and relaxing cabin. "
United States
Carmel K.
$402 nightly
The price is $426
Oct 5 - Oct 6
Total with taxes and fees
Cozy A-Frame w/Spa+14 acres+EV+Trails+Lake Access
A house with a wooden deck and a flagpole with flags.

9. 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
$144 nightly
The price is $161
Nov 1 - Nov 2
Total with taxes and fees
Siltcoos Station Retreats
Exterior

10. 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 6 - Oct 7
Total with taxes and fees
Paradise Cabin on Tenmile Lake
A deck with a table and chairs overlooking a lake surrounded by trees.

11. Tenmile Lakeview Hideaway

Tenmile Lakeview Hideaway
Lakeside
9.6 out of 10, Exceptional, (53 reviews)
"Great place to stay. Quiet and tucked away while close enough to plenty of activities. Host was communicative and helpful and check in/out was a breeze."
United States
Calin M.
$327 nightly
The price is $330
Oct 5 - Oct 6
Total with taxes and fees
Tenmile Lakeview Hideaway
A wooden house with a deck, surrounded by trees.

12. Scenic and relaxing Lake Cottage with Views

Scenic and relaxing Lake Cottage with Views
Coos County
$291 nightly
The price is $291
Oct 6 - Oct 7
Total with taxes and fees
Scenic and relaxing Lake Cottage with Views
A compact living space with a kitchenette, a sofa, and a dining area.

13. #StayinMyDistrict Lakeside Cottage

#StayinMyDistrict Lakeside Cottage
Lakeside
9.6 out of 10, Exceptional, (24 reviews)
"The house was very clean and comfortable. Would stay here again."
United States
Shaun W.
$206 nightly
The price is $223
Oct 6 - Oct 7
Total with taxes and fees
#StayinMyDistrict Lakeside Cottage
A two-story house with a front porch, a garage, and a well-maintained garden.

14. 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, (41 reviews)
"Was a great place to stay especially with trailer "
United States
David
$319 nightly
The price is $347
Oct 5 - Oct 6
Total with taxes and fees
Lakeside house with access to dunes, lakes, and the ocean!
A spacious room with large windows, a leather sofa, and two leather armchairs.

15. Private Lakefront *180° Lake View & Dock

Private Lakefront *180° Lake View & Dock
North Bend
10.0 out of 10, Exceptional, (6 reviews)
"We had a wonderful stay! The property is beautiful, secluded, and truly unique with amazing views. The home was very clean, fit our group comfortably, and was perfectly located close to the dunes. We had a great time celebrating a friend’s birthday here. Our dogs loved the area, and the cute pet-friendly vibe was a huge plus. Communication with the host was top notch. Highly recommend!"
United States
Alex N.
$525 nightly
The price is $526
Oct 5 - Oct 6
Total with taxes and fees
Private Lakefront *180° Lake View & Dock
A coastal landscape with sand dunes and a beach.

16. Coos bay - Lake house - Direct Dune access - Saunders Lake - Oregon Dunes

Coos bay - Lake house - Direct Dune access - Saunders Lake - Oregon Dunes
North Bend
9.8 out of 10, Exceptional, (131 reviews)
"The property was great .everything as described "
United States
Bob B.
$531 nightly
The price is $539
Oct 10 - Oct 11
Total with taxes and fees
Coos bay - Lake house - Direct Dune access - Saunders Lake - Oregon Dunes
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, (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.
$402 nightly
The price is $427
Oct 5 - Oct 6
Total with taxes and fees
Barnhaus-Spa+11 Acres+EV+Gym+Lake Access
A bedroom with a bed, a blue wardrobe, a wall art piece, and a window with blinds.

18. 2 Homes-14 Acres+2 Spas +Lake Access+Kayaks

2 Homes-14 Acres+2 Spas +Lake Access+Kayaks
Lakeside
$770 nightly
The price is $771
Oct 5 - Oct 6
Total with taxes and fees
2 Homes-14 Acres+2 Spas +Lake Access+Kayaks
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

Best Western Pier Point Inn

Best Western Pier Point Inn

10/10 Excellent
"Room was clean. The breakfast was very good..The check in was very easy..great Staff '"
sharon 1-night trip
Posted 4 hours ago
Best Western Pier Point Inn

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 $161 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.