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Winchester Bay Holiday Rentals

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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
8.8 out of 10, Excellent, (40)
"Great value for the location and size of studio. We were here for one night and slept comfortably. We were really disappointed that there wasn't any coffee for the coffee machine and that the dishes weren't microwaveable. "
United States
Eden A.
The price is NZ$347
includes taxes & fees
4 Jan - 5 Jan
Dog-friendly ADU with a full kitchen & shared washer/dryer - near the water

Hilltop Home with Dune Access and Breathtaking Views

Hilltop Home with Dune Access and Breathtaking Views
Reedsport
10.0 out of 10, Exceptional, (227)
"Our stay was great!"
United States
Amy C.
The price is NZ$1,167
includes taxes & fees
4 Jan - 5 Jan
Hilltop Home with Dune Access and Breathtaking Views

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

Dog-friendly coastal-themed home with a full kitchen & washer/dryer
Reedsport
9.2 out of 10, Wonderful, (32)
"Nice quiet location, walkable to harbor"
United States
Jan M.
The price is NZ$476
includes taxes & fees
4 Jan - 5 Jan
Dog-friendly coastal-themed home with a full kitchen & washer/dryer

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, (24)
"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 NZ$571
includes taxes & fees
4 Jan - 5 Jan
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
Reedsport
9.0 out of 10, Wonderful, (2)
"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 NZ$1,470
includes taxes & fees
5 Jan - 6 Jan
Luxurious Hilltop Home with Direct Dune Access

#StayinMyDistrict Lakeside Cottage

#StayinMyDistrict Lakeside Cottage
2.0 star property
Lakeside
9.8 out of 10, Exceptional, (16)
"The place was clean, comfortable, and in a great location with easily walkable cafes and restaurants."
United States
Alexandra R.
The price is NZ$296
includes taxes & fees
4 Jan - 5 Jan
#StayinMyDistrict Lakeside Cottage

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

Hot Tub, Siltcoose Private Dock w/ ocean access, Cottage, w/ canoes!
Dunes City
9.0 out of 10, Wonderful, (18)
"Enjoyed our stay, great location. Would stay again."
United States
terri
The price is NZ$537
includes taxes & fees
12 Jan - 13 Jan
Hot Tub, Siltcoose Private Dock w/ ocean access, Cottage, w/ canoes!

Cozy Cabin near Everything!

Cozy Cabin near Everything!
North Bend
8.8 out of 10, Excellent, (33)
"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 NZ$341
includes taxes & fees
22 Jan - 23 Jan
Cozy Cabin near Everything!

Charming 2-bedroom house with AC, WiFi in North Bend, pets ok, crabbing tools

Charming 2-bedroom house with AC, WiFi in North Bend, pets ok, crabbing tools
2.0 star property
North Bend
8.8 out of 10, Excellent, (13)
"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 NZ$472
includes taxes & fees
1 Feb - 2 Feb
Charming 2-bedroom house with AC, WiFi in North Bend, pets ok, crabbing tools

The Salty Duplex (Left Side)

The Salty Duplex (Left Side)
Reedsport
10.0 out of 10, Exceptional, (51)
"Lovely stay in a very comfortable, clean, and roomy house. I would highly recommend and would stay there again."
United States
Andrew M.
The price is NZ$366
includes taxes & fees
6 Jan - 7 Jan
The Salty Duplex (Left Side)

Lakefront Octagon • Hot Tub • Wine Bar • Game Room

Lakefront Octagon • Hot Tub • Wine Bar • Game Room
2.0 star property
North Bend
10.0 out of 10, Exceptional, (1)
"Awesome house, great host! Will definitely stay again in the future!"
United States
Justen D.
The price is NZ$1,048
includes taxes & fees
5 Jan - 6 Jan
Lakefront Octagon • Hot Tub • Wine Bar • Game Room

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, (106)
"Beautiful home secluded in woods.Everything you need for your stay. "
United States
Mary D.
The price is NZ$458
includes taxes & fees
5 Jan - 6 Jan
Cozy A-Frame w/Spa+14 acres+EV+Trails+Lake Access

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, (15)
"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 NZ$380
includes taxes & fees
11 Jan - 12 Jan
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.

Private Lakefront *180° Lake View & Dock

Private Lakefront *180° Lake View & Dock
North Bend
10.0 out of 10, Exceptional, (1)
"We had a wonderful stay! The property is beautiful, secluded, and truly unique with amazing views. The home was very clean, fit our group comfortably, and was perfectly located close to the dunes. We had a great time celebrating a friend’s birthday here. Our dogs loved the area, and the cute pet-friendly vibe was a huge plus. Communication with the host was top notch. Highly recommend!"
United States
Alex N.
The price is NZ$732
includes taxes & fees
5 Jan - 6 Jan
Private Lakefront *180° Lake View & Dock

Relaxing Getaway Lake Cabin with Pristine Views

Relaxing Getaway Lake Cabin with Pristine Views
Coos County
9.6 out of 10, Exceptional, (24)
"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 NZ$520
includes taxes & fees
12 Jan - 13 Jan
Relaxing Getaway Lake Cabin with Pristine Views

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, (226)
"Nice cozy place to spend summer vacation. Swimming, kayaking, fishing, nice view."
United States
Martha H.
The price is NZ$585
includes taxes & fees
2 Feb - 3 Feb
Great Vintage 2500sq ft. country cabin amazing river front 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, (28)
"Great little place on the lake"
United States
Karen C.
The price is NZ$503
includes taxes & fees
11 Jan - 12 Jan
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.

Coastal Elegance

Coastal Elegance
North Bend
9.8 out of 10, Exceptional, (18)
"Beautiful home and perfect location to beaches and activities!"
United States
Ronda B.
The price is NZ$515
includes taxes & fees
10 Jan - 11 Jan
Coastal Elegance

#StayinMyDistrict Brussells Bungalow

#StayinMyDistrict Brussells Bungalow
North Bend
9.2 out of 10, Wonderful, (7)
"It was great! Would definitely stay again."
United States
Gary W.
The price is NZ$398
includes taxes & fees
29 Jan - 30 Jan
#StayinMyDistrict Brussells Bungalow

The Salty Duplex (Right Side)

The Salty Duplex (Right Side)
Reedsport
10.0 out of 10, Exceptional, (73)
"We always enjoy our stay there. The place is very nice and is affordable compared to hotels in the area."
United States
Ronny
The price is NZ$366
includes taxes & fees
5 Jan - 6 Jan
The Salty Duplex (Right 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

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$341 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 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 15 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.