Holiday Rentals in Winchester Bay

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Our top choices for Winchester Bay holiday rentals

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
The price is €236
includes taxes & fees
12 Jun - 13 Jun
Winchester Bay Apt Near Dunes & State Parks!

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
The price is €398
includes taxes & fees
1 Jun - 2 Jun
Soothing Crab themed 3-bedroom home with WiFi and a hot tub in Winchester Bay.

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.
The price is €570
includes taxes & fees
1 Jun - 2 Jun
Hilltop Home with Dune Access and Breathtaking Views

Luxurious Hilltop Home w/ Dune Access

Luxurious Hilltop Home w/ Dune Access
Winchester Bay
9.6 out of 10, Exceptional, (4 reviews)
"Great and comfortable place to rest after a nice ride on the dunes! Location was perfect"
United States
Johnny H.
The price is €718
includes taxes & fees
1 Jun - 2 Jun
Luxurious Hilltop Home w/ Dune Access

Siltcoos Station Retreats

Siltcoos Station Retreats
4.0 star property
Westlake
9.0 out of 10, Wonderful, (7 reviews)
"Great lake access for kayaking"
United States
Andrew
The price is €208
includes taxes & fees
2 Jun - 3 Jun
Siltcoos Station Retreats

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, (22 reviews)
"Enjoyed our stay, great location. Would stay again."
United States
terri
The price is €277
includes taxes & fees
1 Jun - 2 Jun
Hot Tub, Siltcoose Private Dock w/ ocean access, Cottage, w/ canoes!

The Salty Duplex (Right Side)

The Salty Duplex (Right Side)
Reedsport
10.0 out of 10, Exceptional, (80 reviews)
"Great little place, has everything you need."
United States
Aaron A.
The price is €200
includes taxes & fees
2 Jun - 3 Jun
The Salty Duplex (Right Side)

The Salty Duplex (Left Side)

The Salty Duplex (Left Side)
Reedsport
10.0 out of 10, Exceptional, (57 reviews)
"Enjoyed the stay"
United States
amy c.
The price is €198
includes taxes & fees
2 Jun - 3 Jun
The Salty Duplex (Left Side)

#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
#StayinMyDistrict Lakeside Cottage

Cozy Cabin near Everything!

Cozy Cabin near Everything!
North Bend
8.8 out of 10, Excellent, (37 reviews)
"The unit needs some attention. Heater is too loud. Location is great "
United States
Linda D.
The price is €187
includes taxes & fees
8 Jun - 9 Jun
Cozy Cabin near Everything!

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)
"Host was welcoming and the amenities where good"
United States
Shain O.
The price is €225
includes taxes & fees
1 Jun - 2 Jun
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.

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, (113 reviews)
"It’s was perfect little get away, very clean and we all had so much fun! "
United States
Brooke M.
Cozy A-Frame w/Spa+14 acres+EV+Trails+Lake Access

Conductor’s Quarters - Historic Lakefront 1-Bdrm with Kayaking near Florence

Conductor’s Quarters - Historic Lakefront 1-Bdrm with Kayaking near Florence
oregon
9.4 out of 10, Exceptional, (8 reviews)
"Conductor’s Quarters was really clean and had everything we needed including oat meal which was fantastic because we forgot our cereal! We love this place!"
United States
Susan M.
The price is €254
includes taxes & fees
1 Jun - 2 Jun
Conductor’s Quarters - Historic Lakefront 1-Bdrm with Kayaking near Florence

Anchors Away in North Bend, OR

Anchors Away in North Bend, OR
North Bend
9.4 out of 10, Exceptional, (3 reviews)
"Great place to stay!"
United States
Mark L.
The price is €289
includes taxes & fees
1 Jun - 2 Jun
Anchors Away in North Bend, OR

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, (43 reviews)
"Cute place. We enjoyed hanging out on the covered porch and out by the fire pit. The host was awesome and communication was on point. We'll be back to stay. "
United States
Chelsea S.
The price is €218
includes taxes & fees
7 Jun - 8 Jun
So much to enjoy at this 2-bedroom cottage in Charming Lakeside.

Big Caboose, Charming Lake Cottage w/ kayaking

Big Caboose, Charming Lake Cottage w/ kayaking
Westlake
The price is €311
includes taxes & fees
1 Jun - 2 Jun
Big Caboose, Charming Lake Cottage w/ kayaking

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

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.
Relaxing Getaway Lake Cabin with Pristine Views

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, (30 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 €305
includes taxes & fees
1 Jun - 2 Jun
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.

Comfortable Coast Stay North Bend, Coos bay & Dunes

Comfortable Coast Stay North Bend, Coos bay & Dunes
North Bend
9.6 out of 10, Exceptional, (22 reviews)
"Beautiful home and perfect location to beaches and activities!"
United States
Ronda B.
The price is €299
includes taxes & fees
7 Jun - 8 Jun
Comfortable Coast Stay North Bend, Coos bay & Dunes
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

Everything you need to know about Winchester Bay holiday rentals

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

Winchester Bay holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester Bay holiday rentals we have selected for you start as low as €208 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 holiday 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 holiday.

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 holiday rentals in Winchester Bay?

Yes, there are holiday rentals close to the most popular sights in Winchester Bay, or you can select a more secluded option if you're looking for a relaxing stay. Winchester Bay is known for its parks.

What are some of the best holiday rentals that Winchester Bay has to offer?

Soothing Crab themed 3-bedroom home with WiFi and a hot tub in Winchester Bay.: This highly rated holiday home rental in Winchester Bay offers a fireplace, 1 hot tub and a BBQ to help you feel perfectly comfortable in your new surroundings.

How many holiday rentals will I find in Winchester Bay?

Choose from 16 Expedia holiday rentals in Winchester Bay for a memorable holiday.

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 wider area, you’ll find Umpqua Lighthouse and Oregon Dunes National Recreation Area.

What’s a holiday rental in Winchester Bay like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchester Bay. Holiday rentals feature amenities such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive option for family trips.