Holiday Rentals in Winchester Bay

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Our top choices for Winchester Bay holiday rentals

9.8 out of 10, Exceptional, (25 reviews)
"Nice cozy little spot that was perfect for us ro reset on our 16 day roadtrip from Michigan and back. "
United States
mike b.
The price is €340
includes taxes & fees
2 Mar - 3 Mar
Soothing Crab themed 3-bedroom home with WiFi and a hot tub in Winchester Bay.
10.0 out of 10, Exceptional, (227 reviews)
"Our stay was great!"
United States
Amy C.
The price is €579
includes taxes & fees
1 Mar - 2 Mar
Hilltop Home with Dune Access and Breathtaking Views
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.
The price is €708
includes taxes & fees
2 Mar - 3 Mar
Luxurious Hilltop Home with Direct Dune Access

Aparthotel in Westlake

Siltcoos Station Retreats
4.0 star property
7.4 out of 10, Good, (3 reviews)
"My partner and I had such a lovely time here. I don’t even know where to start. The room was very cute, comfortable, clean and had a soaking tub ( and some lovely bath salts) that was a real treat. We took a nice little swim in the lake which was the perfect temperature. The gentleman who owns this place is friendly and professional, i felt welcome and at ease while interacting with him. I met a dog and a cat. The cat was perfect in every way- mysterious yet friendly, unafraid and unconcerned....
United States
Jesse
The price is €186
includes taxes & fees
12 Mar - 13 Mar
Siltcoos Station Retreats

Cabin in North Bend

Cozy Cabin near Everything!
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.
The price is €170
includes taxes & fees
1 Mar - 2 Mar
Cozy Cabin near Everything!

Holiday Home in Reedsport

The Salty Duplex (Right Side)
10.0 out of 10, Exceptional, (75 reviews)
"We had a great time; would absolutely stay here again!"
United States
Hannah S.
The price is €183
includes taxes & fees
1 Mar - 2 Mar
The Salty Duplex (Right Side)

Holiday Home in Reedsport

The Salty Duplex (Left Side)
10.0 out of 10, Exceptional, (54 reviews)
"Enjoyed the stay"
United States
amy c.
The price is €183
includes taxes & fees
1 Mar - 2 Mar
The Salty Duplex (Left Side)
9.0 out of 10, Wonderful, (18 reviews)
"Enjoyed our stay, great location. Would stay again."
United States
terri
The price is €257
includes taxes & fees
4 Mar - 5 Mar
Hot Tub, Siltcoose Private Dock w/ ocean access, Cottage, w/ canoes!

Holiday Home in Lakeside

#StayinMyDistrict Lakeside Cottage
9.8 out of 10, Exceptional, (16 reviews)
"Property was clean and was good for what we needed"
United States
Nathan C.
The price is €131
includes taxes & fees
1 Mar - 2 Mar
#StayinMyDistrict Lakeside Cottage
The price is €199
includes taxes & fees
1 Mar - 2 Mar
Romantic Cabin on the Lake with a Waterfront View - Stay at the Lavender Loft
8.2 out of 10, Very good, (146 reviews)
"We enjoyed our stay, and would like to revisit when the weather is warmer to enjoy the outdoor features."
United States
Linda H.
The price is €248
includes taxes & fees
1 Mar - 2 Mar
Overlooking Old Town yet In a Secluded Forest Setting
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.
The price is €238
includes taxes & fees
13 Mar - 14 Mar
Brakeman's Bay - Charming Lakefront Studio - Wheelchair Accessible
9.6 out of 10, Exceptional, (37 reviews)
"We had a nice stay at the little red house. "
United States
Brandy T.
The price is €169
includes taxes & fees
2 Mar - 3 Mar
So much to enjoy at this 2-bedroom cottage in Charming Lakeside.
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.
The price is €347
includes taxes & fees
1 Mar - 2 Mar
Engineer’s Suite - Historic Lakefront 2-Bedroom Cabin with Kayaking
9.4 out of 10, Exceptional, (28 reviews)
"Great little place on the lake"
United States
Karen C.
The price is €250
includes taxes & fees
1 Mar - 2 Mar
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.
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.
The price is €277
includes taxes & fees
1 Mar - 2 Mar
Relaxing Getaway Lake Cabin with Pristine Views
10.0 out of 10, Exceptional, (16 reviews)
"great host! super clean. could not ask for more. beautiful "
United States
Sharada D.
The price is €186
includes taxes & fees
2 Mar - 3 Mar
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.
10.0 out of 10, Exceptional, (108 reviews)
"Very quick, helpful and friendly communication from the host! The house is set up so cute with everything we needed for the stay. Everything functioned well and it’s perfectly equipped for a family stay! "
United States
Ashley C.
The price is €331
includes taxes & fees
12 Mar - 13 Mar
Cozy A-Frame w/Spa+14 acres+EV+Trails+Lake Access
9.8 out of 10, Exceptional, (28 reviews)
"The place was great and the hosts were also wonderful and easy to communicate with. We would stay here again!"
United States
Candace G.
The price is €305
includes taxes & fees
1 Mar - 2 Mar
Lakeside house with access to dunes, lakes, and the ocean!
8.8 out of 10, Excellent, (13 reviews)
"Stayed here with our kiddo and dogs as prep for a 1/2 marathon, had a great time, it was so close to several great restaurants which was good after the race was over"
United States
Sam Q.
The price is €196
includes taxes & fees
29 Mar - 30 Mar
Charming 2-bedroom house with AC, WiFi in North Bend, pets ok, crabbing tools
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 €169 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.