Winchester Bay Vacation Rentals

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Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for Winchester Bay vacation rentals

Apartment (2 Bedrooms) | Interior

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, (3 reviews)
"The apartment was cozy and clean. The owner was responsive and even accommodated an early check-in. "
United States
Katie
$208 nightly
The price is $211
May 28 - May 29
Total with taxes and fees
Winchester Bay Apt Near Dunes & State Parks!
Exterior

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, (27 reviews)
"Very nice stay!"
United States
Jennifer
$457 nightly
The price is $464
May 16 - May 17
Total with taxes and fees
Soothing Crab themed 3-bedroom home with WiFi and a hot tub in Winchester Bay.
Terrace/patio

Luxurious Hilltop Home with Direct Dune Access

Luxurious Hilltop Home with Direct Dune Access
Winchester Bay
9.0 out of 10, Wonderful, (2 reviews)
"Our family stay for 4 days was exceptional in this lovely home with views of the river, beach and dunes. Interior amenities were very clean, comfortable and accommodating for 4 adults and 3 children. We all appreciated the attention to details, well stocked kitchen, modern bathrooms, very comfortable beds and linens. Having the STARLINK WiFi and televisions was so useful. Just a few items were of concern 1) no barbecue 2) the broken railing at front stairs was a challenge and 3) lower next door...
United States
Gary P.
$818 nightly
The price is $830
May 18 - May 19
Total with taxes and fees
Luxurious Hilltop Home with Direct Dune Access
Smart TV, fireplace, video games, DVD player

Hilltop Home with Dune Access and Breathtaking Views

Hilltop Home with Dune Access and Breathtaking Views
Winchester Bay
9.8 out of 10, Exceptional, (229 reviews)
"Our stay was great!"
United States
Amy C.
$642 nightly
The price is $652
May 17 - May 18
Total with taxes and fees
Hilltop Home with Dune Access and Breathtaking Views
Interior

#StayinMyDistrict Lakeside Cottage

#StayinMyDistrict Lakeside Cottage
Lakeside
9.4 out of 10, Exceptional, (19 reviews)
"We loved our stay. Our cottage/cabin had everything we needed and more to make our stay great!"
United States
Shari
$197 nightly
The price is $214
May 17 - May 18
Total with taxes and fees
#StayinMyDistrict Lakeside Cottage
Fridge, microwave, oven, dishwasher

The Salty Duplex (Right Side)

The Salty Duplex (Right Side)
Reedsport
10.0 out of 10, Exceptional, (79 reviews)
"Great little place, has everything you need."
United States
Aaron A.
$195 nightly
The price is $216
May 18 - May 19
Total with taxes and fees
The Salty Duplex (Right Side)
Exterior

Cozy Cabin near Everything!

Cozy Cabin near Everything!
North Bend
8.8 out of 10, Excellent, (36 reviews)
"The cozy cabin is a perfect description of this vacation rental. As a solo traveler on this trip, I felt safe. It was comfortable and was sufficiently stocked. Also, the fee was very reasonable. "
United States
Tammy M.
$183 nightly
The price is $203
May 18 - May 19
Total with taxes and fees
Cozy Cabin near Everything!
Fridge, microwave, oven, stovetop

The Salty Duplex (Left Side)

The Salty Duplex (Left Side)
Reedsport
10.0 out of 10, Exceptional, (56 reviews)
"Enjoyed the stay"
United States
amy c.
$192 nightly
The price is $213
May 18 - May 19
Total with taxes and fees
The Salty Duplex (Left Side)
Panoramic House | Living area

Siltcoos Station Retreats

Siltcoos Station Retreats
4.0 star property
Westlake
8.8 out of 10, Excellent, (6 reviews)
"It was easy to locate, I received great communication from the property, definitely dog friendly, unique and interesting furnishings throughout the property. It’s such a peaceful and quiet place. We had a great time there—truly getting away from city life. "
United States
Kelly
$201 nightly
The price is $224
May 17 - May 18
Total with taxes and fees
Siltcoos Station Retreats
Interior

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, (16 reviews)
"So peaceful & the host was so informative. Would recommend to anyone trying to get away for a weekend 💛"
United States
Natasha L.
$266 nightly
The price is $267
Jun 2 - Jun 3
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.
Living area

Hot Tub, Siltcoose Private Dock w/ ocean access, Cottage, w/ canoes!

Hot Tub, Siltcoose Private Dock w/ ocean access, Cottage, w/ canoes!
Dunes City
9.2 out of 10, Wonderful, (20 reviews)
"Enjoyed our stay, great location. Would stay again."
United States
terri
$281 nightly
The price is $305
May 17 - May 18
Total with taxes and fees
Hot Tub, Siltcoose Private Dock w/ ocean access, Cottage, w/ canoes!
Exterior

Relaxing Getaway Lake Cabin with Pristine Views

Relaxing Getaway Lake Cabin with Pristine Views
Coos County
9.6 out of 10, Exceptional, (24 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.
$326 nightly
The price is $329
May 17 - May 18
Total with taxes and fees
Relaxing Getaway Lake Cabin with Pristine Views
Interior

Charming 2-bedroom house with AC, WiFi in North Bend, pets ok, crabbing tools

Charming 2-bedroom house with AC, WiFi in North Bend, pets ok, crabbing tools
North Bend
8.2 out of 10, Very Good, (15 reviews)
"Great option to stay at while I did my captain's course at Columbia Pacific Maritime. Convenient location with surrounding restaurants and grocery stores. Nice stay for 2-3 people."
United States
Pierre d.
$216 nightly
The price is $240
May 20 - May 21
Total with taxes and fees
Charming 2-bedroom house with AC, WiFi in North Bend, pets ok, crabbing tools
Property grounds

Overlooking Old Town yet In a Secluded Forest Setting

Overlooking Old Town yet In a Secluded Forest Setting
Florence
8.2 out of 10, Very Good, (153 reviews)
"We enjoyed our stay, and would like to revisit when the weather is warmer to enjoy the outdoor features."
United States
Linda H.
$267 nightly
The price is $298
May 18 - May 19
Total with taxes and fees
Overlooking Old Town yet In a Secluded Forest Setting
Property grounds

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, (29 reviews)
"Great little place on the lake"
United States
Karen C.
$350 nightly
The price is $350
May 19 - May 20
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.
Terrace/patio

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, (111 reviews)
"It’s was perfect little get away, very clean and we all had so much fun! "
United States
Brooke M.
$340 nightly
The price is $360
May 28 - May 29
Total with taxes and fees
Cozy A-Frame w/Spa+14 acres+EV+Trails+Lake Access
Smart TV, video games, books

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, (41 reviews)
"We had a nice stay at the little red house. "
United States
Brandy T.
$225 nightly
The price is $245
May 25 - May 26
Total with taxes and fees
So much to enjoy at this 2-bedroom cottage in Charming Lakeside.
Exterior

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.
$295 nightly
The price is $319
May 17 - May 18
Total with taxes and fees
Brakeman's Bay - Charming Lakefront Studio - Wheelchair Accessible
Exterior

Lakeside house with access to dunes, lakes, and the ocean!

Lakeside house with access to dunes, lakes, and the ocean!
Lakeside
10.0 out of 10, Exceptional, (31 reviews)
"Was a great place to stay especially with trailer "
United States
David
$379 nightly
The price is $414
May 21 - May 22
Total with taxes and fees
Lakeside house with access to dunes, lakes, and the ocean!
Property grounds

Engineer’s Suite - Historic Lakefront 2-Bedroom Cabin with Kayaking

Engineer’s Suite - Historic Lakefront 2-Bedroom Cabin with Kayaking
Westlake
9.8 out of 10, Exceptional, (8 reviews)
"We had a terrific experience for two nights at this unique property. The view is unbeatable and my husband, who loves trains and antiques, was able to fully relax in a space that felt built just for him. "
United States
Carolyn W.
$442 nightly
The price is $478
May 17 - May 18
Total with taxes and fees
Engineer’s Suite - Historic Lakefront 2-Bedroom Cabin with Kayaking
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

Winchester Bay Apt Near Dunes & State Parks!

Winchester Bay Apt Near Dunes & State Parks!

10/10 Excellent
"We were greeted by our contact person, Gail, who is friendly and personable. And a terrific artist as you will see when you are on the property. This is a very cute, fun and artsy apartment. We used the bedroom at the front of the house and found it roomy and the bed is very comfortable. The water pressure is outstanding and the hot water arrives almost instantly. The kitchen is fully stocked. Just bring your own food. We will definitely book a room here when we are near Winchester Bay again."
Karen 2-night trip
Posted 8 hours ago
Winchester Bay Apt Near Dunes & State Parks!

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 $211 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.

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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?

Soothing Crab themed 3-bedroom home with WiFi and a hot tub in Winchester Bay.: This Winchester Bay vacation home rental offers a fireplace, a hot tub, and a barbecue grill to help you feel perfectly comfortable in your new surroundings.

How many vacation rentals will I find in Winchester Bay?

Choose from 16 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.