Winchester Bay Vacation Rentals

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Our top choices for Winchester Bay vacation rentals

Winchester Bay Apt Near Dunes & State Parks!

Winchester Bay Apt Near Dunes & State Parks!
3.0 star property
Reedsport
10.0 out of 10, Exceptional, (2 reviews)
"The apartment was cozy and clean. The owner was responsive and even accommodated an early check-in. "
United States
Katie
Winchester Bay Apt Near Dunes & State Parks!

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, (27 reviews)
"Very nice stay!"
United States
Jennifer
The price is CA $306
CA $629 total
includes taxes & fees
May 7 - May 8
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 $646
CA $1,144 total
includes taxes & fees
May 11 - May 12
Luxurious Hilltop Home with Direct Dune Access

Hilltop Home with Dune Access and Breathtaking Views

Hilltop Home with Dune Access and Breathtaking Views
Winchester Bay
9.8 out of 10, Exceptional, (229 reviews)
"Our stay was great!"
United States
Amy C.
The price is CA $511
CA $908 total
includes taxes & fees
May 8 - May 9
Hilltop Home with Dune Access and Breathtaking Views

#StayinMyDistrict Lakeside Cottage

#StayinMyDistrict Lakeside Cottage
Lakeside
9.4 out of 10, Exceptional, (19 reviews)
"We loved our stay. Our cottage/cabin had everything we needed and more to make our stay great!"
United States
Shari
The price is CA $94
CA $271 total
includes taxes & fees
May 7 - May 8
#StayinMyDistrict Lakeside Cottage

Cozy Cabin near Everything!

Cozy Cabin near Everything!
North Bend
8.8 out of 10, Excellent, (36 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 $127
CA $279 total
includes taxes & fees
May 7 - May 8
Cozy Cabin near Everything!

The Salty Duplex (Right Side)

The Salty Duplex (Right Side)
Reedsport
10.0 out of 10, Exceptional, (78 reviews)
"Great stay clean and pet friendly great for crabbing fishing or duck hunting or just a coast get away "
United States
isaac l.
The price is CA $132
CA $301 total
includes taxes & fees
May 19 - May 20
The Salty Duplex (Right Side)

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 $150
CA $338 total
includes taxes & fees
May 7 - May 8
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.

The Salty Duplex (Left Side)

The Salty Duplex (Left Side)
Reedsport
10.0 out of 10, Exceptional, (56 reviews)
"Enjoyed the stay"
United States
amy c.
The price is CA $125
CA $293 total
includes taxes & fees
May 18 - May 19
The Salty Duplex (Left Side)

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 $234
CA $434 total
includes taxes & fees
May 7 - May 8
Brakeman's Bay - Charming Lakefront Studio - Wheelchair Accessible

Siltcoos Station Retreats

Siltcoos Station Retreats
4.0 star property
Westlake
8.8 out of 10, Excellent, (6 reviews)
"It was easy to locate, I received great communication from the property, definitely dog friendly, unique and interesting furnishings throughout the property. It’s such a peaceful and quiet place. We had a great time there—truly getting away from city life. "
United States
Kelly
The price is CA $270
CA $301 total
includes taxes & fees
May 21 - May 22
Siltcoos Station Retreats

Lakeside house with access to dunes, lakes, and the ocean!

Lakeside house with access to dunes, lakes, and the ocean!
Lakeside
10.0 out of 10, Exceptional, (31 reviews)
"Was a great place to stay especially with trailer "
United States
David
The price is CA $205
CA $524 total
includes taxes & fees
May 7 - May 8
Lakeside house with access to dunes, lakes, and the ocean!

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

Hot Tub, Siltcoose Private Dock w/ ocean access, Cottage, w/ canoes!
Dunes City
9.2 out of 10, Wonderful, (20 reviews)
"Enjoyed our stay, great location. Would stay again."
United States
terri
The price is CA $223
CA $416 total
includes taxes & fees
May 7 - May 8
Hot Tub, Siltcoose Private Dock w/ ocean access, Cottage, w/ canoes!

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, (111 reviews)
"It’s was perfect little get away, very clean and we all had so much fun! "
United States
Brooke M.
The price is CA $213
CA $449 total
includes taxes & fees
May 18 - May 19
Cozy A-Frame w/Spa+14 acres+EV+Trails+Lake Access

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, (29 reviews)
"Great little place on the lake"
United States
Karen C.
The price is CA $211
CA $416 total
includes taxes & fees
May 13 - May 14
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.

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, (153 reviews)
"We enjoyed our stay, and would like to revisit when the weather is warmer to enjoy the outdoor features."
United States
Linda H.
The price is CA $183
CA $401 total
includes taxes & fees
May 7 - May 8
Overlooking Old Town yet In a Secluded Forest Setting

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
North Bend
8.2 out of 10, Very good, (15 reviews)
"Great option to stay at while I did my captain's course at Columbia Pacific Maritime. Convenient location with surrounding restaurants and grocery stores. Nice stay for 2-3 people."
United States
Pierre d.
The price is CA $129
CA $325 total
includes taxes & fees
May 19 - May 20
Charming 2-bedroom house with AC, WiFi in North Bend, pets ok, crabbing tools

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 $365
CA $657 total
includes taxes & fees
May 8 - May 9
Engineer’s Suite - Historic Lakefront 2-Bedroom Cabin with Kayaking

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 $204
CA $453 total
includes taxes & fees
May 9 - May 10
Relaxing Getaway Lake Cabin with Pristine Views

Ultimate Guesthouse•Curated Luxury with Lake+Kayak

Ultimate Guesthouse•Curated Luxury with Lake+Kayak
North Bend
10.0 out of 10, Exceptional, (1 review)
"This house is amazing. It’s perfect for traveling with your family and furry friends. You truly feel like you’re up in the trees. The heated floors in the bathroom and towel warmer were a nice luxury. There is a loft space and a small bedroom with bunks- perfect for kiddos. The kitchen has everything you could need. The view was amazing, especially the stars! The entrance is located up some pretty steep stairs so that is something to consider. The host was quick to respond and we would...
United States
Kortney P.
The price is CA $213
CA $396 total
includes taxes & fees
May 17 - May 18
Ultimate Guesthouse•Curated Luxury with Lake+Kayak
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

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.