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Winchester Bay Vacation Rentals

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Check prices for these dates

In two weeks
Oct 17 - Oct 19
In two months
Nov 28 - Nov 30
In three months
Dec 26 - Dec 28
In four months
Jan 23 - Jan 25

Vacation Rentals in Winchester Bay

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

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
TV

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
Fridge, microwave, oven, stovetop

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 ￥11,888
￥37,954 total
includes taxes & fees
Oct 5 - Oct 6
Dog-friendly coastal-themed home with a full kitchen & washer/dryer
Hilltop Home with Dune Access and Breathtaking Views
Outdoor dining

Hilltop Home with Dune Access and Breathtaking Views

10.0 out of 10, Exceptional, (225)
"Enjoyed our stay."
The price is ￥54,361
￥94,813 total
includes taxes & fees
Oct 6 - Oct 7
Hilltop Home with Dune Access and Breathtaking Views
Dog-friendly ADU with a full kitchen & shared washer/dryer - near the water
1 bedroom, iron/ironing board, internet, bed sheets

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!"
The price is ￥7,840
￥27,389 total
includes taxes & fees
Oct 2 - Oct 3
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.
Exterior

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 ￥16,792
￥49,020 total
includes taxes & fees
Oct 19 - Oct 20
Soothing Crab themed 3-bedroom home with WiFi and a hot tub in Winchester Bay.
Winchester Bay Apt Near Dunes & State Parks!
Apartment (2 Bedrooms) | Interior

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!
House (3 Bedrooms) | Interior

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.
Beach

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

9.8 out of 10, Exceptional, (151)
"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
Exterior

Overlooking Old Town yet In a Secluded Forest Setting

8.2 out of 10, Very Good, (139)
"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 ￥24,407
￥49,150 total
includes taxes & fees
Oct 2 - Oct 3
Overlooking Old Town yet In a Secluded Forest Setting
Mcdragonfly Cabin-wow! This Is Some Cabin.
Outdoor dining

Mcdragonfly Cabin-wow! This Is Some Cabin.

9.8 out of 10, Exceptional, (177)
"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
Fridge, microwave, oven, stovetop

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
Outdoor spa tub

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
Fridge, microwave, oven, stovetop

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!
Outdoor dining

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

9.6 out of 10, Exceptional, (223)
"We had a wonderful get together. The house was perfect for us and the location is fantastic. Right by the river. "
The price is ￥24,998
￥53,900 total
includes taxes & fees
Oct 25 - Oct 26
Great Vintage 2500sq ft. country cabin amazing river front setting!
So much to enjoy at this 2-bedroom cottage in Charming Lakeside.
Exterior detail

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 ￥22,499
￥31,942 total
includes taxes & fees
Oct 2 - Oct 3
So much to enjoy at this 2-bedroom cottage in Charming Lakeside.
Siltcoos Station Retreats
Exterior

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....
The price is ￥20,801
￥27,651 total
includes taxes & fees
Oct 15 - Oct 16
Siltcoos Station Retreats
Below the Falls Lodge - Next to Golden & Silver Falls
Property grounds

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!
Fridge, microwave, oven, stovetop

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 ￥11,390
￥26,599 total
includes taxes & fees
Oct 7 - Oct 8
Cozy Cabin near Everything!
The Salty Duplex (Left Side)
Fridge, microwave, oven, stovetop

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 ￥15,781
￥34,341 total
includes taxes & fees
Oct 2 - Oct 3
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

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

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

10/10 Excellent
"Laura was so nice and we really enjoyed staying here!"
Linda B. 2-night trip
Posted 2 days ago
Blue Heron Getaway. Come enjoy the spring and summer in our great cozy house.

Find out more about Winchester Bay

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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  • Enter your travel dates to view the best deals on holiday rentals in Winchester Bay while they last

Look no further and take a look at our great range of rental properties in Winchester Bay!

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Winchester Bay?

Yes, we give you a choice of vacation rentals near popular points of interest in Winchester Bay, or you can choose a secluded option if you're looking for relaxation. Winchester Bay is known for its parks.

What are some of the best vacation home rentals in Winchester Bay?

Cozy family beach cottage w/ hot tub, deck, WiFi, surfboard-walk to bay, Dogs ok: Visitors like this Winchester Bay vacation home rental. It is located in the city center and has a patio, a garden, and a barbecue grill 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 a hot tub. Another good choice for your trip to Winchester Bay is Hilltop Home with Dune Access and Breathtaking Views.

How many vacation rentals will I find in Winchester Bay?

Choose from 16 Expedia vacation rentals in Winchester Bay for a memorable vacation.

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 larger area, you’ll find Umpqua Lighthouse and Oregon Dunes National Recreation Area.

What’s a vacation rental in Winchester Bay like?

Vacation rentals are privately owned properties you can book for a couple of days or more in Winchester Bay. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll have all the comforts of home. If you're concerned about a clean environment, vacation rentals can offer a sense of privacy away from shared hotel elevators and busy concierge desks while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for a family trip or a small group gathering.