Winchester Bay Vacation 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 vacation rentals

Hilltop Home with Dune Access and Breathtaking Views

Hilltop Home with Dune Access and Breathtaking Views
Winchester Bay
10.0 out of 10, Exceptional, (227 reviews)
"Our stay was great!"
United States
Amy C.
The price is CA $539
CA $941 total
includes taxes & fees
Feb 19 - Feb 20
Hilltop Home with Dune Access and Breathtaking Views

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, (25 reviews)
"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 CA $243
CA $557 total
includes taxes & fees
Feb 22 - Feb 23
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
Winchester Bay
9.0 out of 10, Wonderful, (2 reviews)
"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 CA $648
CA $1,146 total
includes taxes & fees
Feb 19 - Feb 20
Luxurious Hilltop Home with Direct Dune Access

Siltcoos Station Retreats

Siltcoos Station Retreats
4.0 star property
Westlake
7.4 out of 10, Good, (3 reviews)
"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....
United States
Jesse
The price is CA $275
CA $348 total
includes taxes & fees
Mar 1 - Mar 2
Siltcoos Station Retreats

Romantic Cabin on the Lake with a Waterfront View - Stay at the Lavender Loft

Romantic Cabin on the Lake with a Waterfront View - Stay at the Lavender Loft
Dunes City
The price is CA $264
CA $302 total
includes taxes & fees
Feb 19 - Feb 20
Romantic Cabin on the Lake with a Waterfront View - Stay at the Lavender Loft

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, (227 reviews)
"It was a nice big house by the river!"
United States
Stephen S.
The price is CA $203
CA $464 total
includes taxes & fees
Feb 19 - Feb 20
Great Vintage 2500sq ft. country cabin amazing river front setting!

Cozy Cabin near Everything!

Cozy Cabin near Everything!
North Bend
8.8 out of 10, Excellent, (34 reviews)
"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 CA $119
CA $269 total
includes taxes & fees
Feb 23 - Feb 24
Cozy Cabin near Everything!

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, (108 reviews)
"Enjoyed our stay."
United States
Dana M.
The price is CA $285
CA $542 total
includes taxes & fees
Feb 19 - Feb 20
Cozy A-Frame w/Spa+14 acres+EV+Trails+Lake Access

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 reviews)
"Enjoyed our stay, great location. Would stay again."
United States
terri
The price is CA $224
CA $420 total
includes taxes & fees
Feb 19 - Feb 20
Hot Tub, Siltcoose Private Dock w/ ocean access, Cottage, w/ canoes!

The Salty Duplex (Right Side)

The Salty Duplex (Right Side)
Reedsport
10.0 out of 10, Exceptional, (75 reviews)
"We had a great time; would absolutely stay here again!"
United States
Hannah S.
The price is CA $123
CA $292 total
includes taxes & fees
Feb 19 - Feb 20
The Salty Duplex (Right Side)

Engineer’s Suite - Historic Lakefront 2-Bedroom Cabin with Kayaking

Engineer’s Suite - Historic Lakefront 2-Bedroom Cabin with Kayaking
Westlake
9.8 out of 10, Exceptional, (8 reviews)
"We had a terrific experience for two nights at this unique property. The view is unbeatable and my husband, who loves trains and antiques, was able to fully relax in a space that felt built just for him. "
United States
Carolyn W.
The price is CA $374
CA $669 total
includes taxes & fees
Feb 26 - Feb 27
Engineer’s Suite - Historic Lakefront 2-Bedroom Cabin with Kayaking

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, (36 reviews)
"We had a nice stay at the little red house. "
United States
Brandy T.
The price is CA $183
CA $268 total
includes taxes & fees
Feb 19 - Feb 20
So much to enjoy at this 2-bedroom cottage in Charming Lakeside.

Tenmile Lakeview Hideaway

Tenmile Lakeview Hideaway
Lakeside
9.6 out of 10, Exceptional, (49 reviews)
"Meticulously cared for. Great coffee options! Gorgeous bathrooms. Perfect place to stay for our family."
United States
MELISSA L.
The price is CA $143
CA $393 total
includes taxes & fees
Feb 19 - Feb 20
Tenmile Lakeview Hideaway

The Salty Duplex (Left Side)

The Salty Duplex (Left Side)
Reedsport
10.0 out of 10, Exceptional, (54 reviews)
"Enjoyed the stay"
United States
amy c.
The price is CA $123
CA $292 total
includes taxes & fees
Mar 1 - Mar 2
The Salty Duplex (Left Side)

Relaxing Getaway Lake Cabin with Pristine Views

Relaxing Getaway Lake Cabin with Pristine Views
Coos County
9.6 out of 10, Exceptional, (24 reviews)
"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 CA $205
CA $454 total
includes taxes & fees
Feb 19 - Feb 20
Relaxing Getaway Lake Cabin with Pristine Views

Coastal Elegance

Coastal Elegance
North Bend
9.8 out of 10, Exceptional, (18 reviews)
"Beautiful home and perfect location to beaches and activities!"
United States
Ronda B.
The price is CA $203
CA $404 total
includes taxes & fees
Feb 28 - Mar 1
Coastal Elegance

Brakeman's Bay - Charming Lakefront Studio - Wheelchair Accessible

Brakeman's Bay - Charming Lakefront Studio - Wheelchair Accessible
Westlake
9.4 out of 10, Exceptional, (10 reviews)
"Nice and quiet, great view of the lake. It was fun staying in a place with modern appliances from way back when. We had a good time."
United States
Andrew j.
The price is CA $194
CA $385 total
includes taxes & fees
Mar 2 - Mar 3
Brakeman's Bay - Charming Lakefront Studio - Wheelchair Accessible

Private Lakefront *180° Lake View & Dock

Private Lakefront *180° Lake View & Dock
North Bend
10.0 out of 10, Exceptional, (1 review)
"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 CA $355
CA $654 total
includes taxes & fees
Feb 24 - Feb 25
Private Lakefront *180° Lake View & Dock

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 reviews)
"Sweet view, nice pellet heater. We really enjoyed this place. "
United States
Katelinde
The price is CA $183
CA $403 total
includes taxes & fees
Feb 19 - Feb 20
Overlooking Old Town yet In a Secluded Forest Setting

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, (16 reviews)
"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 CA $125
CA $308 total
includes taxes & fees
Feb 19 - Feb 20
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.
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.

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Winchester Bay. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Soothing Crab themed 3-bedroom home with WiFi and a hot tub in Winchester Bay.: This Winchester Bay vacation home rental offers a fireplace, a hot tub, and a barbecue grill to help you feel perfectly comfortable in your new surroundings.

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.