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Winchester Bay Holiday Rentals

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Holiday Rentals in Winchester Bay

Blue Heron Getaway. Come enjoy the spring and summer in our great cozy house.

10.0 out of 10, Exceptional, (39)
"Everything very clean and tidy."
Blue Heron Getaway. Come enjoy the spring and summer in our great cozy house.

Cozy family beach cottage w/ hot tub, deck, WiFi, surfboard-walk to bay, Dogs ok

9.4 out of 10, Exceptional, (47)
"The little beach house has had extensive remodeling . Very bright, clean and comfortable on the inside. Good location in a quiet neighborhood. "
Cozy family beach cottage w/ hot tub, deck, WiFi, surfboard-walk to bay, Dogs ok

Dog-friendly coastal-themed home with a full kitchen & washer/dryer

9.2 out of 10, Wonderful, (32)
"The weather, small town atmosphere"
The price is NZ$441
includes taxes & fees
5 Oct - 6 Oct
Dog-friendly coastal-themed home with a full kitchen & washer/dryer

Hilltop Home with Dune Access and Breathtaking Views

10.0 out of 10, Exceptional, (225)
"Enjoyed our stay."
The price is NZ$1,106
includes taxes & fees
6 Oct - 7 Oct
Hilltop Home with Dune Access and Breathtaking Views

Dog-friendly ADU with a full kitchen & shared washer/dryer - near the water

9.2 out of 10, Wonderful, (34)
"What a quaint little place in the coast. 10/10 amazing stay!"
Dog-friendly ADU with a full kitchen & shared washer/dryer - near the water

Soothing Crab themed 3-bedroom home with WiFi and a hot tub in Winchester Bay.

10.0 out of 10, Exceptional, (19)
"This was our favorite stay of our OR coast trip, quaint, quiet, spacious and authentic. Thank you for a great place to stay with our family :)"
The price is NZ$550
includes taxes & fees
19 Oct - 20 Oct
Soothing Crab themed 3-bedroom home with WiFi and a hot tub in Winchester Bay.

Winchester Bay Apt Near Dunes & State Parks!

3.0 star property
10.0 out of 10, Exceptional, (2)
"The apartment was cozy and clean. The owner was responsive and even accommodated an early check-in. "
Winchester Bay Apt Near Dunes & State Parks!

Winchester Bay Vacation Rental Near Dunes & Atv!

3.0 star property
10.0 out of 10, Exceptional, (1)
"It was a great stay for my family. The only disappointment was could not get the gas fireplace to work."
Winchester Bay Vacation Rental Near Dunes & Atv!

Direct Dune Access Sleeps 10 In House, 6 In BunkHouses - Bath Houses.

9.8 out of 10, Exceptional, (152)
"This is our 2nd year coming to this location, & we absolutely love it. Plenty of room for everyone & easy access to the dunes. Host's are great & easy to communicate with."
Direct Dune Access Sleeps 10 In House, 6 In BunkHouses - Bath Houses.

Overlooking Old Town yet In a Secluded Forest Setting

8.2 out of 10, Very good, (140)
"Loved this property! Tucked back in the woods was the perfect setting. Lots of room and very clean. By far one of our favorites!"
The price is NZ$579
includes taxes & fees
8 Oct - 9 Oct
Overlooking Old Town yet In a Secluded Forest Setting

Mcdragonfly Cabin-wow! This Is Some Cabin.

9.8 out of 10, Exceptional, (178)
"Beautiful cabin! Perfect for our family getaway. Loved the many amenities this cabin offered! Would definitely stay again! "
Mcdragonfly Cabin-wow! This Is Some Cabin.

Southern Oregon Mid -Century Coastal Charmer Summer Discount- Aug & Sept 2025

9.8 out of 10, Exceptional, (166)
"Great property, in a quiet neighborhood. Beautiful view. Very happy with our stay."
Southern Oregon Mid -Century Coastal Charmer Summer Discount- Aug & Sept 2025

Dog-Friendly Home with Expansive Deck with Hot Tub and Dock on Woahink Lake

7.8 out of 10, Good, (22)
"Close to town, serene setting, great for the price! We’ll be back!"
Dog-Friendly Home with Expansive Deck with Hot Tub and Dock on Woahink Lake

New Listing! Luxury 6 bedroom, 5 bath lake home with hot tub, sauna. dock and lake access

8.6 out of 10, Excellent, (4)
"It was a beautiful, spacious home and a great base to explore the area! Our family had a wonderful visit."
New Listing! Luxury 6 bedroom, 5 bath lake home with hot tub, sauna. dock and lake access

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

9.6 out of 10, Exceptional, (224)
"We had a wonderful get together. The house was perfect for us and the location is fantastic. Right by the river. "
The price is NZ$626
includes taxes & fees
8 Oct - 9 Oct
Great Vintage 2500sq ft. country cabin amazing river front setting!

So much to enjoy at this 2-bedroom cottage in Charming Lakeside.

9.6 out of 10, Exceptional, (28)
"We were just passing through but found the accommodations to be fantastic. "
The price is NZ$376
includes taxes & fees
3 Oct - 4 Oct
So much to enjoy at this 2-bedroom cottage in Charming Lakeside.

Siltcoos Station Retreats

4.0 star property
7.4 out of 10, Good, (3)
"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....
Siltcoos Station Retreats

Below the Falls Lodge - Next to Golden & Silver Falls

9.8 out of 10, Exceptional, (198)
"Such a beautiful place to stay with lots to do! We went in the creek multiple times, sauna, hammock, and hiked the falls. I can tell how much love they put into this place because there is artistry put into every detail. A true hidden gem in the woods."
Below the Falls Lodge - Next to Golden & Silver Falls

Cozy Cabin near Everything!

8.8 out of 10, Excellent, (33)
"The place was very clean and nice. Kitchen was well stocked. Located in a nice neighborhood and convenient to everything. Would definitely stay again. Thanks for a pleasant stay.Lynda & David"
The price is NZ$309
includes taxes & fees
8 Oct - 9 Oct
Cozy Cabin near Everything!

The Salty Duplex (Left Side)

10.0 out of 10, Exceptional, (47)
"Super clean and comfortable property, love that everything is pet friendly"
The price is NZ$396
includes taxes & fees
5 Oct - 6 Oct
The Salty Duplex (Left Side)
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

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 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 NZ$309 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?

Cozy family beach cottage w/ hot tub, deck, WiFi, surfboard-walk to bay, Dogs ok: This highly rated holiday home rental in Winchester Bay is located in the city centre, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub. Another good choice for your trip to Winchester Bay is Hilltop Home with Dune Access and Breathtaking Views.

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.