Winchester Bay Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Winchester Bay holiday rentals

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 AU$513
includes taxes & fees
27 Apr - 28 Apr
Soothing Crab themed 3-bedroom home with WiFi and a hot tub in Winchester Bay.

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.
The price is AU$1,151
includes taxes & fees
27 Apr - 28 Apr
Luxurious Hilltop Home with Direct Dune Access

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 AU$917
includes taxes & fees
25 Apr - 26 Apr
Hilltop Home with Dune Access and Breathtaking Views

Siltcoos Station Retreats

Siltcoos Station Retreats
4.0 star property
Westlake
8.4 out of 10, Very good, (5 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
The price is AU$309
includes taxes & fees
29 Apr - 30 Apr
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, (19 reviews)
"Enjoyed our stay, great location. Would stay again."
United States
terri
The price is AU$427
includes taxes & fees
1 May - 2 May
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, (78 reviews)
"Great stay clean and pet friendly great for crabbing fishing or duck hunting or just a coast get away "
United States
isaac l.
The price is AU$301
includes taxes & fees
27 Apr - 28 Apr
The Salty Duplex (Right Side)

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.
The price is AU$309
includes taxes & fees
25 Apr - 26 Apr
The Salty Duplex (Left Side)

#StayinMyDistrict Lakeside Cottage

#StayinMyDistrict Lakeside Cottage
Lakeside
9.6 out of 10, Exceptional, (17 reviews)
"The place was clean, comfortable, and in a great location with easily walkable cafes and restaurants."
United States
Alexandra R.
The price is AU$245
includes taxes & fees
26 Apr - 27 Apr
#StayinMyDistrict Lakeside Cottage

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.
The price is AU$455
includes taxes & fees
12 May - 13 May
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, (29 reviews)
"Great little place on the lake"
United States
Karen C.
The price is AU$447
includes taxes & fees
11 May - 12 May
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.

Paradise Cabin on Tenmile Lake

Paradise Cabin on Tenmile Lake
Lakeside
8.8 out of 10, Excellent, (26 reviews)
"a great location overides all other issues."
United States
Hunter C.
The price is AU$710
includes taxes & fees
25 Apr - 26 Apr
Paradise Cabin on Tenmile Lake

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.
The price is AU$445
includes taxes & fees
25 Apr - 26 Apr
Brakeman's Bay - Charming Lakefront Studio - Wheelchair Accessible

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
The price is AU$509
includes taxes & fees
28 Apr - 29 Apr
Lakeside house with access to dunes, lakes, and the ocean!

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.
The price is AU$661
includes taxes & fees
25 Apr - 26 Apr
Engineer’s Suite - Historic Lakefront 2-Bedroom Cabin with Kayaking

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.
The price is AU$291
includes taxes & fees
30 Apr - 1 May
Cozy Cabin near Everything!

30% OFF Monthly Stay Convenient Location

30% OFF Monthly Stay Convenient Location
North Bend
9.0 out of 10, Wonderful, (23 reviews)
"This house is wonderful and we enjoyed our stay "
United States
Jacob J.
The price is AU$509
includes taxes & fees
25 Apr - 26 Apr
30% OFF Monthly Stay Convenient Location

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.
The price is AU$343
includes taxes & fees
11 May - 12 May
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.

Great Vintage 2500sq ft. country cabin amazing river front setting!

Great Vintage 2500sq ft. country cabin amazing river front setting!
Scottsburg
9.6 out of 10, Exceptional, (227 reviews)
"It was a nice big house by the river!"
United States
Stephen S.
The price is AU$567
includes taxes & fees
26 Apr - 27 Apr
Great Vintage 2500sq ft. country cabin amazing river front setting!

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.
The price is AU$462
includes taxes & fees
26 Apr - 27 Apr
Cozy A-Frame w/Spa+14 acres+EV+Trails+Lake Access

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, (152 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 AU$373
includes taxes & fees
28 Apr - 29 Apr
Overlooking Old Town yet In a Secluded Forest Setting
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.
Save an average of 15% on thousands of hotels when you're signed in

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, 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 favourite 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 depend 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 AU$291 per night. Entering your travel dates in the search wizard might find you 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.