Photo by Erin Frank

Search Chalets in Winchester Bay from CA $86

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Find vacation rentals that suit your style

cabin image
Cabins
Cabins
Apartment image
Apartments
Apartments

Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3
No exact matches found, but these alternatives could be just right

Recommended hotels in Winchester Bay

A motel with a blue exterior, a sign indicating free WiFi, and a parking lot with red flowers in the foreground.

1. Winchester Bay Inn

Winchester Bay Inn
2.5 star property
Reedsport
7.4 out of 10, Good, (960 reviews)
"Was a fun stay right off the harbor."
United States
Greg
The price is CA $112
CA $135 total
includes taxes & fees
Nov 8 - Nov 9
Winchester Bay Inn
A house with a green exterior, a wooden front porch with a red chair, and a small garden area with a pond.

2. 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, (36 reviews)
"Highly recommend. The host is the absolute best host I’ve ever experienced renting a house. Will certainly be back."
United States
Caleb
The price is CA $208
CA $500 total
includes taxes & fees
Nov 8 - Nov 9
Soothing Crab themed 3-bedroom home with WiFi and a hot tub in Winchester Bay.
Terrace/patio

3. Luxurious Hilltop Home w/ Private Hot Tub and Direct Dune Access

Luxurious Hilltop Home w/ Private Hot Tub and Direct Dune Access
Winchester Bay
9.6 out of 10, Exceptional, (7 reviews)
"Great and comfortable place to rest after a nice ride on the dunes! Location was perfect"
United States
Johnny H.
The price is CA $624
CA $1,075 total
includes taxes & fees
Nov 8 - Nov 9
Luxurious Hilltop Home w/ Private Hot Tub and Direct Dune Access
A wooden deck with a glass table and chairs, overlooking a beach and water.

4. Cozy Hilltop Home with Private Hot Tub, Direct Dune Access & Breathtaking Views

Cozy Hilltop Home with Private Hot Tub, Direct Dune Access & Breathtaking Views
Winchester Bay
9.8 out of 10, Exceptional, (237 reviews)
"Great location, easy dune access, beautiful view. The host was very nice and accommodating."
United States
JAY B.
The price is CA $498
CA $903 total
includes taxes & fees
Nov 9 - Nov 10
Cozy Hilltop Home with Private Hot Tub, Direct Dune Access & Breathtaking Views
A hotel with a covered outdoor area, a parking lot, and a sign indicating it is a Best Western Inn & Suites.

5. Best Western Salbasgeon Inn & Suites Of Reedsport

Best Western Salbasgeon Inn & Suites Of Reedsport
2.5 star property
Reedsport
7.8 out of 10, Good, (1,000 reviews)
"Clean room and staff was super helpful. I enjoyed the hottub."
United States
Nathalie
The price is CA $131
CA $145 total
includes taxes & fees
Nov 15 - Nov 16
Best Western Salbasgeon Inn & Suites Of Reedsport
A hotel with a sign indicating vacancy, a landscaped garden, and a multi-story building with balconies.

6. Oregon Dunes Hotel

Oregon Dunes Hotel
2.0 star property
Reedsport
The price is CA $136
CA $149 total
includes taxes & fees
Nov 17 - Nov 18
Oregon Dunes Hotel
A two-story Economy Inn with a blue roof and a signboard advertising clean rooms, a fridge, microwave, TV, and weekly TV.

7. Economy Inn Reedsport

Economy Inn Reedsport
2.0 star property
Reedsport
8.0 out of 10, Very good, (402 reviews)
"Great one night stop. For how old the building is they have done a great job at maintaining the rooms! Bed was comfortable! It was exactly what we needed for our one night stop!"
United States
Katrina
The price is CA $121
CA $134 total
includes taxes & fees
Nov 8 - Nov 9
Economy Inn Reedsport
A wooden deck with two chairs and a small table, overlooking a lake with a forested shoreline.

8. The Florentine Waterfront Hotel

The Florentine Waterfront Hotel
2.0 star property
Westlake
9.6 out of 10, Exceptional, (102 reviews)
"This was our second year staying at this location and we decided to stay for longer this time and it did not disappoint! Breathtaking lake views and attentive hospitality. Everyone was so kind and the fire pits were a plus! The halloween decorations were amazing!!"
United States
Jessica
The price is CA $160
CA $179 total
includes taxes & fees
Nov 12 - Nov 13
The Florentine Waterfront Hotel
A lodge with a large parking area, a covered outdoor seating area, and a view of a lake.

9. Lakeshore Lodge

Lakeshore Lodge
2.0 star property
Lakeside
8.6 out of 10, Excellent, (165 reviews)
"Great location"
United States
John
The price is CA $223
CA $243 total
includes taxes & fees
Nov 8 - Nov 9
Lakeshore Lodge
A hotel with a sign reading 'Quality Inn & Suites by Choice Hotels,' featuring a modern design with stone accents and large windows.

10. Quality Inn & Suites at Coos Bay

Quality Inn & Suites at Coos Bay
2.5 star property
North Bend
7.8 out of 10, Good, (1,004 reviews)
"Very accessible and comfortable! Great included Breakfast! Reasonable room prices!"
United States
William
The price is CA $139
CA $154 total
includes taxes & fees
Nov 9 - Nov 10
Quality Inn & Suites at Coos Bay
A two-story house with a garage, a white fence, and two trash bins.

11. The Salty Duplex (Right Side)

The Salty Duplex (Right Side)
Reedsport
10.0 out of 10, Exceptional, (88 reviews)
"Great stay!"
United States
Di L.
The price is CA $135
CA $296 total
includes taxes & fees
Nov 9 - Nov 10
The Salty Duplex (Right Side)
A covered corridor with a row of single windows, a concrete floor, and a row of white plastic chairs.

12. Seadrift Motel & RV Park

Seadrift Motel & RV Park
2.5 star property
Lakeside
7.8 out of 10, Good, (83 reviews)
"We stay here often. Overall great place to stay, super helpful staff"
United States
robert
The price is CA $111
CA $130 total
includes taxes & fees
Nov 8 - Nov 9
Seadrift Motel & RV Park
A house with a covered patio, a fenced backyard, and a gravel path leading to the house.

13. The Salty Duplex (Left Side)

The Salty Duplex (Left Side)
Reedsport
10.0 out of 10, Exceptional, (69 reviews)
"Excellent quite location."
United States
Judy B.
The price is CA $129
CA $288 total
includes taxes & fees
Nov 9 - Nov 10
The Salty Duplex (Left Side)
A small, A-frame cabin with a balcony and a porch area.

14. Park Motel and Cabins

Park Motel and Cabins
2.0 star property
Florence
8.8 out of 10, Excellent, (871 reviews)
"Very quiet and well equipped. Host is a great communicator. Would definitely stay again."
United States
Nicholas
The price is CA $116
CA $130 total
includes taxes & fees
Dec 8 - Dec 9
Park Motel and Cabins
A building with a covered parking area, a view of the water, and a sign indicating a business.

15. Best Western Pier Point Inn

Best Western Pier Point Inn
2.5 star property
Florence
8.6 out of 10, Excellent, (1,001 reviews)
"Loved the breakfast , facility was clean and the beds are excellent"
Canada
Annie
The price is CA $196
CA $219 total
includes taxes & fees
Nov 8 - Nov 9
Best Western Pier Point Inn
A cabin with a deck overlooking a lake, surrounded by dense forest.

16. 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
9.8 out of 10, Exceptional, (21 reviews)
"The place was great. Clean and in good shape. Im planning to make it an annual trip."
United States
PDX S.
The price is CA $124
CA $296 total
includes taxes & fees
Nov 8 - Nov 9
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.
A wooden deck overlooking a lake with a dock and a decorative hanging ornament.

17. 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, (34 reviews)
"Very secluded. Perfect for a couples weekend away from it all"
United States
Taylor I.
The price is CA $215
CA $403 total
includes taxes & fees
Nov 12 - Nov 13
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.
A nighttime view of a hotel with a parking lot, outdoor seating area, and a small garden.

18. Ocean Breeze Motel

Ocean Breeze Motel
2.0 star property
Florence
8.8 out of 10, Excellent, (1,002 reviews)
"Great little hotel"
United States
Tamara
The price is CA $87
CA $100 total
includes taxes & fees
Nov 8 - Nov 9
Ocean Breeze Motel
A motel with a signboard, a two-story building, and a landscaped garden.

19. Anchor Bay Inn

Anchor Bay Inn
2.5 star property
Reedsport
6.8 out of 10, (814 reviews)
"Rooms are clean. Staff was good to work with and knowledgable."
United States
Tom
The price is CA $141
CA $169 total
includes taxes & fees
Dec 8 - Dec 9
Anchor Bay Inn
A small, single-story house with a green roof and a porch.

20. #StayinMyDistrict Lakeside Cottage

#StayinMyDistrict Lakeside Cottage
Lakeside
9.6 out of 10, Exceptional, (25 reviews)
"The house was very clean and comfortable. Would stay here again."
United States
Shaun W.
The price is CA $97
CA $283 total
includes taxes & fees
Nov 9 - Nov 10
#StayinMyDistrict Lakeside Cottage
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.
View all properties

Learn more about Winchester Bay

Crabbing from the docks and exploring the Umpqua River Lighthouse are must-do activities in this charming coastal village. Adventurers can ride ATVs on the Oregon Dunes or cast a line for salmon in nearby Reedsport's waters.

See all hotels in Winchester Bay
A desert landscape with sand dunes, a small body of water, and sparse vegetation.
Photo by Erin Frank
Open Photo by Erin Frank

Top reviews in Winchester Bay

A wooden deck with two chairs and a small table, overlooking a lake with a forested shoreline.
The Florentine Waterfront Hotel

The Florentine Waterfront Hotel

The Florentine Waterfront Hotel
Westlake

10/10 Excellent

Wow! What a pleasant experience. Rooms were stylish and smelled great, facing out on a beautiful lake. They decorated for the season and did a really good job. They also had 3 resident cats which were very cute, adding to the ambiance. Would stay again and recommend to anyone considering the area.
Canada
Jakob
Reviewed September 29, 2026
The Florentine Waterfront Hotel

Explore a world of travel with Expedia