Winchester Bay Vacation Rentals from $180: Search Short-Term Rentals

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Our top choices for Winchester Bay vacation rentals

A house with a green exterior, a wooden front porch with a red chair, and a small garden area with a pond.

1. Soothing Crab themed 3-bedroom home with WiFi and a hot tub in Winchester Bay.

Winchester Bay

Caleb

$352 nightly

Nov 8 - Nov 9

Total with taxes and fees

A living room with a fireplace, a television, a sofa, a coffee table, and a dining area with a table and chairs.

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

Winchester Bay

JAY B.

$627 nightly

Nov 9 - Nov 10

Total with taxes and fees

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

Winchester Bay

Johnny H.

$749 nightly

Nov 8 - Nov 9

Total with taxes and fees

A wooden dock with two chairs facing a calm lake, surrounded by forested hills.

4. 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

Taylor I.

$281 nightly

Dec 1 - Dec 2

Total with taxes and fees

A room with a large window overlooking a lake and forest.

5. 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

PDX S.

$209 nightly

Nov 17 - Nov 18

Total with taxes and fees

A modern kitchen with stainless steel appliances, white cabinets, and a blue-tiled backsplash.

6. The Salty Duplex (Left Side)

Reedsport

Judy B.

$186 nightly

Nov 9 - Nov 10

Total with taxes and fees

A modern kitchen with white cabinets, a granite countertop, a wooden island with bar stools, a microwave, a refrigerator, and a large window.

7. The Salty Duplex (Right Side)

Reedsport

Di L.

$192 nightly

Nov 9 - Nov 10

Total with taxes and fees

A wooden dock extending into a lake, surrounded by lush greenery and trees.

8. #StayinMyDistrict Majestic Shores Lake Bear Cabin

North Bend

Travis and Tabitha N.

$162 nightly

Nov 8 - Nov 9

Total with taxes and fees

A compact living space with a kitchenette, a sofa, and a dining area.

9. #StayinMyDistrict Lakeside Cottage

Lakeside

Shaun W.

$187 nightly

Nov 9 - Nov 10

Total with taxes and fees

A cozy living room with a sectional sofa, a small table, a lamp, and a TV mounted on the wall.

10. So much to enjoy at this 2-bedroom cottage in Charming Lakeside.

Lakeside

Candy H.

$220 nightly

Dec 4 - Dec 5

Total with taxes and fees

A house with a sloped roof, large windows, and a deck.

11. Cozy A-Frame w/Spa+14 acres+EV+Trails+Lake Access

Lakeside

Luba K.

$381 nightly

Nov 10 - Nov 11

Total with taxes and fees

A two-story house with a front porch, a garage, and a well-maintained garden.

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

Lakeside

David

$324 nightly

Dec 1 - Dec 2

Total with taxes and fees

A house with a large front window, a wooden deck, and a black trash bin.

13. Cozy Cabin near Everything!

North Bend

Todd W.

$162 nightly

Nov 9 - Nov 10

Total with taxes and fees

A hot tub in a forested area with wooden steps leading up to it.

14. Barnhaus-Spa+11 Acres+EV+Gym+Lake Access

Lakeside

Julie S.

$367 nightly

Nov 8 - Nov 9

Total with taxes and fees

A serene outdoor setting with a pond, surrounded by dense trees and a fire pit.

15. Ultimate Guesthouse•Curated Luxury with Lake+Kayak

North Bend

CHARLES W.

$324 nightly

Nov 8 - Nov 9

Total with taxes and fees

A modern living room with a flat-screen TV, a coffee table with board games, a dining area with a table and chairs, and a kitchen with white cabinets and a microwave.

16. #StayInMyDistrict NorthBend Duplex Dog Friendly

North Bend

$204 nightly

Nov 8 - Nov 9

Total with taxes and fees

A modern, two-story cabin with a sloped roof, surrounded by lush greenery and a flowering bush.

17. 2 Homes-14 Acres+2 Spas +Lake Access+Kayaks

Lakeside

$770 nightly

Nov 10 - Nov 11

Total with taxes and fees

A modern living room with a sofa, coffee table, and a kitchen area with a countertop and stools.

18. #StayInMyDistrict NorthBend Retreat Dog Friendly

North Bend

$205 nightly

Nov 9 - Nov 10

Total with taxes and fees

A room with wooden flooring, a flat-screen TV mounted on the wall, a grey armchair, a brown leather chair, and a green sofa.

19. #StayinMyDistrict Brussells Bungalow

North Bend

Gary W.

$180 nightly

Nov 8 - Nov 9

Total with taxes and fees

A house with a wooden deck and a flagpole with flags.

20. Siltcoos Station Retreats

Westlake

Andrew

$311 nightly

Nov 8 - Nov 9

Total with taxes and fees

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Find vacation rentals that suit your style

Top Winchester Bay Hotel Reviews

A hotel with a covered outdoor area, a parking lot, and a sign indicating it is a Best Western Inn & Suites.

Best Western Salbasgeon Inn & Suites Of Reedsport

Reedsport

10/10 Excellent

Olga

A spacious room with a large bed, a sofa, and a chair, all facing a scenic lake view.

The Florentine Waterfront Hotel

Westlake

10/10 Excellent

Shawn at check-in was so pleasantly nice and very helpful and even messed up our room so that he can make sure we understood the code to get in and some of the amenities! Very cute Lee decorated and the bed was super super comfy!!! Next time one night is not enough it will definitely be at least two! Very nice lake that is calm with kayaks and are boat dock that you can fish off of and no 🙂‍↔️ wind whatsoever just a beautiful experience in a beautiful place!

Amy

A building with a covered parking area, a view of the water, and a sign indicating a business.

Best Western Pier Point Inn

Florence

10/10 Excellent

Sudakshina

A motel with a neon sign, outdoor seating, and a gravel parking area.

The Star Trek - USS Enterprise Room at the Itty Bitty Inn

North Bend

10/10 Excellent

Cooper

A nighttime view of a hotel with a parking lot, outdoor seating area, and a small garden.

Ocean Breeze Motel

Florence

10/10 Excellent

Reminds me of watching Schitt’s Creek…in the best ways possible! This place has been a delight to stay in. The manager treats this place as if it were her own! She’s gone all out with the Halloween decor and creates a feeling of “family” here. Our room was immaculate and welcoming, spacious and comfy. ADA accessible and pet-friendly. Safe fire-pit to warm around some evenings. I would absolutely come back.

Sherilyn

A hotel room with two beds, a TV mounted on the wall, a window with curtains, a bedside table with a lamp, and a view of the outside.

Economy Inn Reedsport

Reedsport

10/10 Excellent

Katherine

Siltcoos Station Retreats

Westlake

10/10 Excellent

Out of all of the places we stayed on our trip driving up the coast, this was by far our favorite stop. We stayed at fancy resorts and swanky hotels, but the Siltcoos retreat was just magical! The amount of detail everywhere you look was amazing. The time and effort put into our conductors cabin, had us in awe. You guys are legendary for what you’ve accomplished there. Y’all we had deer walk up to us in the back yard! They didn’t even care we were there! The next time we are in Oregon, we will...

Danielle

A small, A-frame cabin with a balcony and a porch area.

Park Motel and Cabins

Florence

10/10 Excellent

Richard

A hotel room with two beds, a small table, and a chair. There is a window with a view of a body of water and trees.

Bay Bridge Motel

North Bend

10/10 Excellent

Anonymous traveler

Find out more about Winchester Bay

Everything you need to know about Winchester Bay vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester Bay vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester Bay vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winchester Bay vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchester Bay. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winchester Bay in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $180 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winchester Bay rentals

At Expedia, we put the best Winchester Bay vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winchester Bay rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester Bay vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester Bay. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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 with 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 balcony, 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. You can relax into your vacation with a selection of games and a hot tub. Another good choice for your trip to Winchester Bay is Soothing Crab themed 3-bedroom home with WiFi and a hot tub in Winchester Bay..

How many vacation rentals will I find in Winchester Bay?

Choose from 15 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.

Explore a world of travel with Expedia

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Winchester Bay Vacation Rentals

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Check prices for these dates

Our top choices for Winchester Bay vacation rentals

1. Soothing Crab themed 3-bedroom home with WiFi and a hot tub in Winchester Bay.

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

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

4. 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.

5. 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.

6. The Salty Duplex (Left Side)

7. The Salty Duplex (Right Side)

8. #StayinMyDistrict Majestic Shores Lake Bear Cabin

9. #StayinMyDistrict Lakeside Cottage

10. So much to enjoy at this 2-bedroom cottage in Charming Lakeside.

11. Cozy A-Frame w/Spa+14 acres+EV+Trails+Lake Access

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

13. Cozy Cabin near Everything!

14. Barnhaus-Spa+11 Acres+EV+Gym+Lake Access

15. Ultimate Guesthouse•Curated Luxury with Lake+Kayak

16. #StayInMyDistrict NorthBend Duplex Dog Friendly

17. 2 Homes-14 Acres+2 Spas +Lake Access+Kayaks

18. #StayInMyDistrict NorthBend Retreat Dog Friendly

19. #StayinMyDistrict Brussells Bungalow

20. Siltcoos Station Retreats

Find vacation rentals that suit your style

Top Winchester Bay Hotel Reviews

Best Western Salbasgeon Inn & Suites Of Reedsport

10/10 Excellent

Find out more about Winchester Bay

Everything you need to know about Winchester Bay vacation rentals

Winchester Bay vacation rentals: An excellent choice for every season

How to find incredible deals on Winchester Bay rentals

Frequently Asked Questions

Can I find vacation rentals in Winchester Bay?

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

How many vacation rentals will I find in Winchester Bay?

What’s there to see and do in Winchester Bay?

What’s a vacation rental in Winchester Bay like?

Explore a world of travel with Expedia