A white lighthouse with a black top, surrounded by trees and a cloudy sky.

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

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

Dog-friendly ADU with a full kitchen & shared washer&dryer - near the water
Reedsport
The price is NZ$416
includes taxes & fees
7 July - 8 July
Dog-friendly ADU with a full kitchen & shared washer&dryer - near the water

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
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, (29 reviews)
"Very nice stay!"
United States
Jennifer
The price is NZ$813
includes taxes & fees
6 July - 7 July
Soothing Crab themed 3-bedroom home with WiFi and a hot tub in Winchester Bay.

Luxurious Hilltop Home w/ Dune Access

Luxurious Hilltop Home w/ Dune Access
Winchester Bay
9.2 out of 10, Wonderful, (5 reviews)
"We absolutely loved staying at this beautiful home overlooking the bay, the beach and the dunes in the distance. Absolutely stunning views from all angles of the house; the pelicans dive-bombing nightly was a new site for all of us and we spent hours gazing at the horizon. The rooms were perfect for our group and everything was spotless! We were very lucky to have snagged this gem at the last minute, I see it is already booked for next year Memorial Day, or we would have booked...
United States
Austene
The price is NZ$1,463
includes taxes & fees
15 July - 16 July
Luxurious Hilltop Home w/ 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, (230 reviews)
"Our stay was great!"
United States
Amy C.
The price is NZ$1,198
includes taxes & fees
15 July - 16 July
Hilltop Home with Dune Access and Breathtaking Views

Winchester Bay Apt Near Dunes & State Parks!

Winchester Bay Apt Near Dunes & State Parks!
Winchester Bay
9.8 out of 10, Exceptional, (37 reviews)
"It was the perfect place for our trip will definitely come again "
United States
Chris P.
Winchester Bay Apt Near Dunes & State Parks!

Siltcoos Station Retreats

Siltcoos Station Retreats
4.0 star property
Westlake
9.2 out of 10, Wonderful, (10 reviews)
"Great lake access for kayaking"
United States
Andrew
The price is NZ$379
includes taxes & fees
6 July - 7 July
Siltcoos Station Retreats

Cozy Cabin near Everything!

Cozy Cabin near Everything!
North Bend
8.8 out of 10, Excellent, (42 reviews)
"The unit needs some attention. Heater is too loud. Location is great "
United States
Linda D.
The price is NZ$370
includes taxes & fees
14 July - 15 July
Cozy Cabin near Everything!

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

Hot Tub, Siltcoose Private Dock w/ ocean access, Cottage, w/ canoes!
Dunes City
9.4 out of 10, Exceptional, (23 reviews)
"I loved how clean and comfortable the home was. The kitchen had everything we needed and then some "
United States
Carmen M.
The price is NZ$562
includes taxes & fees
12 July - 13 July
Hot Tub, Siltcoose Private Dock w/ ocean access, Cottage, w/ canoes!

The Salty Duplex (Left Side)

The Salty Duplex (Left Side)
Reedsport
10.0 out of 10, Exceptional, (58 reviews)
"Enjoyed the stay"
United States
amy c.
The Salty Duplex (Left Side)

#StayinMyDistrict Brussells Bungalow

#StayinMyDistrict Brussells Bungalow
North Bend
9.0 out of 10, Wonderful, (8 reviews)
"It was great! Would definitely stay again."
United States
Gary W.
The price is NZ$453
includes taxes & fees
9 July - 10 July
#StayinMyDistrict Brussells Bungalow

The Salty Duplex (Right Side)

The Salty Duplex (Right Side)
Reedsport
10.0 out of 10, Exceptional, (82 reviews)
"Great little place, has everything you need."
United States
Aaron A.
The price is NZ$456
includes taxes & fees
8 July - 9 July
The Salty Duplex (Right Side)

#StayinMyDistrict Majestic Shores Lake Bear Cabin

#StayinMyDistrict Majestic Shores Lake Bear Cabin
North Bend
The price is NZ$476
includes taxes & fees
9 July - 10 July
#StayinMyDistrict Majestic Shores Lake Bear Cabin

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, (17 reviews)
"Host was welcoming and the amenities where good"
United States
Shain O.
The price is NZ$498
includes taxes & fees
9 July - 10 July
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.

#StayinMyDistrict Lakeside Cottage

#StayinMyDistrict Lakeside Cottage
Lakeside
9.4 out of 10, Exceptional, (20 reviews)
"We loved our stay. Our cottage/cabin had everything we needed and more to make our stay great!"
United States
Shari
The price is NZ$439
includes taxes & fees
5 July - 6 July
#StayinMyDistrict Lakeside Cottage

Ticketmaster Chamber - Historic Lakefront Studio Cabin with Kayaking

Ticketmaster Chamber - Historic Lakefront Studio Cabin with Kayaking
oregon
10.0 out of 10, Exceptional, (7 reviews)
"Perfect little get away spot, wish we had stayed longer! Loved the decor, amenities, friendly vibe, lake access, etc!"
United States
Mariah M.
The price is NZ$419
includes taxes & fees
6 July - 7 July
Ticketmaster Chamber - Historic Lakefront Studio Cabin with Kayaking

Comfortable Coast Stay North Bend, Coos bay & Dunes

Comfortable Coast Stay North Bend, Coos bay & Dunes
North Bend
9.6 out of 10, Exceptional, (25 reviews)
"Beautiful home and perfect location to beaches and activities!"
United States
Ronda B.
The price is NZ$618
includes taxes & fees
7 July - 8 July
Comfortable Coast Stay North Bend, Coos bay & Dunes

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, (159 reviews)
"Nice view & secluded for Florence OR."
United States
Ajenol
The price is NZ$563
includes taxes & fees
7 July - 8 July
Overlooking Old Town yet In a Secluded Forest Setting

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, (31 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 NZ$653
includes taxes & fees
3 Aug - 4 Aug
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.

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, (45 reviews)
"Place was smaller than we thought but other than that it was great. Beds were very comfortable, outdoor shower was cool, fire pit was perfect and had tons of wood already cut and good privacy. Overall, a fun and affordable place!"
United States
Jacob I.
The price is NZ$475
includes taxes & fees
8 July - 9 July
So much to enjoy at this 2-bedroom cottage in Charming Lakeside.
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 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$370 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. 

Explore a world of travel with Expedia

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 with 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 balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a selection of games and 1 hot tub. Some other homes for rent in Winchester Bay include Dog-friendly coastal-themed home with a full kitchen & washer&dryer and Soothing Crab themed 3-bedroom home with WiFi and a hot tub in Winchester Bay..

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.