Photo by Vicki Chandler

Vacation rentals in Winchester Bay

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Top vacation rentals in Winchester Bay

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.

0.29 mi from city center
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This vacation home featured laundry facilities and barbecue grills.
Kitchen
Washer
Cozy family beach cottage w/ hot tub, deck, WiFi, surfboard-walk to bay, Dogs ok

Cozy family beach cottage w/ hot tub, deck, WiFi, surfboard-walk to bay, Dogs ok

0.05 mi from city center
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A hot tub is featured at this vacation home, along with a garden and barbecue grills.
Hot Tub
Kitchen
Dog-friendly coastal-themed home with a full kitchen & washer/dryer

Dog-friendly coastal-themed home with a full kitchen & washer/dryer

0.07 mi from city center
$252 nightly
The price is $255 total per night
$255 total
Oct 5 - Oct 6
Total with taxes and fees
This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Hilltop Home with Dune Access and Breathtaking Views

Hilltop Home with Dune Access and Breathtaking Views

1.25 mi from city center
$632 nightly
The price is $641 total per night
$641 total
Oct 6 - Oct 7
Total with taxes and fees
A hot tub is featured at this vacation home, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Hot Tub
Kitchen
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

0.07 mi from city center
$183 nightly
The price is $186 total per night
$186 total
Oct 5 - Oct 6
Total with taxes and fees
This apartment featured laundry facilities and barbecue grills.
Kitchen
Washer
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.

0.08 mi from city center
$314 nightly
The price is $319 total per night
$319 total
Oct 19 - Oct 20
Total with taxes and fees
A hot tub is featured at this vacation home, along with laundry facilities and barbecue grills.
Hot Tub
Washer
Winchester Bay Apt Near Dunes & State Parks!

Winchester Bay Apt Near Dunes & State Parks!

3 out of 5
0.04 mi from city center
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This apartment doesn't skimp on freebies - guests receive free WiFi and free self parking. Barbecue grills are provided for your convenience.
Kitchen
Pet friendly
Winchester Bay Vacation Rental Near Dunes & Atv!

Winchester Bay Vacation Rental Near Dunes & Atv!

3 out of 5
0.03 mi from city center
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This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. Barbecue grills are provided for your convenience.
Kitchen
Washer
Direct Dune Access Sleeps 10 In House, 6 In BunkHouses - Bath Houses.

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

10.62 mi from city center
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This vacation home featured laundry facilities and barbecue grills.
Kitchen
Washer
Overlooking Old Town yet In a Secluded Forest Setting

Overlooking Old Town yet In a Secluded Forest Setting

19.87 mi from city center
$302 nightly
The price is $337 total per night
$337 total
Oct 6 - Oct 7
Total with taxes and fees
This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Mcdragonfly Cabin-wow! This Is Some Cabin.

Mcdragonfly Cabin-wow! This Is Some Cabin.

6.51 mi from city center
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This vacation home featured laundry facilities and barbecue grills.
Kitchen
Washer
Southern Oregon Mid -Century Coastal Charmer Summer Discount- Aug & Sept 2025

Southern Oregon Mid -Century Coastal Charmer Summer Discount- Aug & Sept 2025

15.74 mi from city center
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This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Dog-Friendly Home with Expansive Deck with Hot Tub and Dock on Woahink Lake

Dog-Friendly Home with Expansive Deck with Hot Tub and Dock on Woahink Lake

16.89 mi from city center
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A hot tub is featured at this vacation home, along with laundry facilities and barbecue grills.
Hot Tub
Kitchen
New Listing! Luxury 6 bedroom, 5 bath lake home with hot tub, sauna. dock and lake access

New Listing! Luxury 6 bedroom, 5 bath lake home with hot tub, sauna. dock and lake access

16.3 mi from city center
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A hot tub is featured at this vacation home, along with laundry facilities and barbecue grills.
Hot Tub
Kitchen
Great Vintage 2500sq ft. country cabin amazing river front setting!

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

16.41 mi from city center
$359 nightly
The price is $364 total per night
$364 total
Oct 8 - Oct 9
Total with taxes and fees
This cabin features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
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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 Best Way to Find your Vacation Rentals in Winchester Bay

How cheap can a vacation rental in Winchester Bay be?

You can find vacation rentals in Winchester Bay for as low as $186 per night.

How do you look for the best vacation rental deals in Winchester Bay with Travelocity?

Travelocity provides the best vacation rental deals in various locations throughout Winchester Bay so you can create the perfect plan for you. You can search and filter by type of property, amenities, neighborhood, price range, number of bedrooms, and more.

Are cancellations free on vacation rentals with Travelocity?

Each vacation rental has its own cancellation policy. It’s essential to understand the terms of your agreement before booking. Most rentals in Winchester Bay can be canceled for free when notifying the property before the cancellation deadline.

What types of vacation rentals are available in Winchester Bay?

Short term rentals come in all shapes and sizes. Choose from properties for a wide range of budgets and types of holidays. Families, couples, outdoor adventurers, and leisure travelers alike will find the perfect place for them. Check out our Winchester Bay vacation apartments to get started building your trip.

What are the benefits of booking a short-term rental in Winchester Bay?

Whether it’s for a summer getaway, a winter excursion, or a routine business trip, Winchester Bay vacation homes are often an excellent choice. You can enjoy group vacations with short term rentals to fit your party size. You might take a romantic weekend for two or plan a family reunion, and all stay under one roof. The options are endless, and you can find them on Travelocity.

Why is Travelocity the best site to find your vacation rental in Winchester Bay?

With Travelocity, all your travel needs are taken care of in one convenient platform. We offer fantastic deals on our large selection of vacation rentals to get you the most savings and rewards back on every booking. Save more when you bundle bookings together, including car rentals, flights, and activities. Here, you can build custom Winchester Bay vacations.

How to cancel your vacation rental with Travelocity?

To cancel your vacation rental, contact the property manager. You can find their contact information in the ‘Itinerary’ section of your Travelocity account. Most properties receive a full refund when you cancel before the cancellation deadline. Policies vary by property, so it’s important to understand the terms before booking. For more information, visit our customer service portal.