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Winchester Bay Holiday Rentals

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Check prices for these dates

Tonight
24 Dec - 25 Dec
Tomorrow
25 Dec - 26 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Winchester Bay holiday rentals

1 bedroom, iron/ironing board, Internet, bed sheets
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

Dog-friendly ADU with a full kitchen & shared washer/dryer - near the water
Reedsport
8.8 out of 10, Excellent, (40)
"What a quaint little place in the coast. 10/10 amazing stay!"
United States
Brigitte D.
The price is HK$490
HK$1,686 total
includes taxes & fees
27 Dec - 28 Dec
Dog-friendly ADU with a full kitchen & shared washer/dryer - near the water
Fridge, microwave, oven, stovetop
Dog-friendly coastal-themed home with a full kitchen & washer/dryer

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 HK$778
HK$2,383 total
includes taxes & fees
27 Dec - 28 Dec
Dog-friendly coastal-themed home with a full kitchen & washer/dryer
Outdoor dining
Hilltop Home with Dune Access and Breathtaking Views

Hilltop Home with Dune Access and Breathtaking Views

Hilltop Home with Dune Access and Breathtaking Views
Reedsport
10.0 out of 10, Exceptional, (227)
"Great communication, great house and lasting memories. "
United States
Theresa M.
The price is HK$3,072
HK$5,297 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hilltop Home with Dune Access and Breathtaking Views
Exterior
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.

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 HK$1,470
HK$3,189 total
includes taxes & fees
7 Jan - 8 Jan 2026
Soothing Crab themed 3-bedroom home with WiFi and a hot tub in Winchester Bay.
Fridge, microwave, oven, stovetop
Luxurious Hilltop Home with Direct Dune Access

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 HK$3,889
HK$6,678 total
includes taxes & fees
7 Jan - 8 Jan 2026
Luxurious Hilltop Home with Direct Dune Access
Terrace/patio
#StayinMyDistrict Lakeside Cottage

#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 HK$498
HK$1,442 total
includes taxes & fees
29 Dec - 30 Dec
#StayinMyDistrict Lakeside Cottage
Fridge, microwave, oven, stovetop
Cozy Cabin near Everything!

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 HK$677
HK$1,528 total
includes taxes & fees
7 Jan - 8 Jan 2026
Cozy Cabin near Everything!
Fridge, microwave, oven, stovetop
The Salty Duplex (Left Side)

The Salty Duplex (Left Side)

The Salty Duplex (Left Side)
Reedsport
10.0 out of 10, Exceptional, (50)
"Super clean and comfortable property, love that everything is pet friendly"
United States
Carolyn
The price is HK$700
HK$1,658 total
includes taxes & fees
7 Jan - 8 Jan 2026
The Salty Duplex (Left Side)
Fridge, microwave, oven, stovetop
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

Charming 2-bedroom house with AC, WiFi in North Bend, pets ok, crabbing tools
2.0 star property
North Bend
8.6 out of 10, Excellent, (12)
"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 HK$747
HK$1,761 total
includes taxes & fees
1 Jan - 2 Jan 2026
Charming 2-bedroom house with AC, WiFi in North Bend, pets ok, crabbing tools
Fridge, microwave, oven, dishwasher
The Salty Duplex (Right Side)

The Salty Duplex (Right Side)

The Salty Duplex (Right Side)
Reedsport
10.0 out of 10, Exceptional, (72)
"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 HK$700
HK$1,650 total
includes taxes & fees
5 Jan - 6 Jan 2026
The Salty Duplex (Right Side)
Property grounds
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.

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 HK$708
HK$1,767 total
includes taxes & fees
20 Jan - 21 Jan 2026
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.
Fridge, oven, stovetop, coffee/tea maker
Hot Tub, Siltcoose Private Dock w/ ocean access, Cottage, w/ canoes!

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 HK$1,275
HK$2,388 total
includes taxes & fees
30 Dec - 31 Dec
Hot Tub, Siltcoose Private Dock w/ ocean access, Cottage, w/ canoes!
Exterior detail
So much to enjoy at this 2-bedroom cottage in Charming Lakeside.

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, (34)
"We were just passing through but found the accommodations to be fantastic. "
United States
Brian M.
The price is HK$1,043
HK$1,662 total
includes taxes & fees
29 Dec - 30 Dec
So much to enjoy at this 2-bedroom cottage in Charming Lakeside.
TV
Relaxing Getaway Lake Cabin with Pristine Views

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 HK$926
HK$2,290 total
includes taxes & fees
25 Dec - 26 Dec
Relaxing Getaway Lake Cabin with Pristine Views
Exterior detail
Lakefront Octagon • Hot Tub • Wine Bar • Game Room

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 HK$2,850
HK$4,694 total
includes taxes & fees
7 Jan - 8 Jan 2026
Lakefront Octagon • Hot Tub • Wine Bar • Game Room
Outdoor dining
Great Vintage 2500sq ft. country cabin amazing river front setting!

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 HK$1,237
HK$2,731 total
includes taxes & fees
4 Jan - 5 Jan 2026
Great Vintage 2500sq ft. country cabin amazing river front setting!
Outdoor dining
#StayinMyDistrict Brussells Bungalow

#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 HK$457
HK$1,505 total
includes taxes & fees
28 Dec - 29 Dec
#StayinMyDistrict Brussells Bungalow
Smart TV, stereo
Cozy A-Frame w/Spa+14 acres+EV+Trails+Lake Access

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 HK$1,625
HK$3,021 total
includes taxes & fees
6 Jan - 7 Jan 2026
Cozy A-Frame w/Spa+14 acres+EV+Trails+Lake Access
Exterior
Overlooking Old Town yet In a Secluded Forest Setting

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, (145)
"Sweet view, nice pellet heater. We really enjoyed this place. "
United States
Katelinde
The price is HK$1,043
HK$2,299 total
includes taxes & fees
7 Jan - 8 Jan 2026
Overlooking Old Town yet In a Secluded Forest Setting
Smart TV
Private Lakefront *180° Lake View & Dock

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 HK$2,042
HK$3,475 total
includes taxes & fees
4 Jan - 5 Jan 2026
Private Lakefront *180° Lake View & Dock
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

Best Western Salbasgeon Inn & Suites Of Reedsport

Best Western Salbasgeon Inn & Suites Of Reedsport

10/10 Excellent
"The room was lovely and clean, except for the carpet. It looked new and was a beautiful dark green, but it hadn't been vacuumed. Sitting on the bed, I glanced down and saw a raisin on the carpet. Then I noticed little blades of grass and small indicators of not vacuuming. The bottoms of my feet were clean, so it wasn't filthy, just not completely clean. "
Jerayne 1-night trip
Posted 4 days ago
Best Western Salbasgeon Inn & Suites Of Reedsport

Find out more about Winchester Bay

Search for holiday rentals in Winchester Bay on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester Bay using one of the methods below:

  • View our selection of featured holiday rentals in Winchester Bay
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Look no further and take a look at our great range of rental properties in Winchester Bay!

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. Another good choice for your trip to Winchester Bay is Cozy family beach cottage w/ hot tub, deck, WiFi, surfboard-walk to bay, Dogs ok.

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.