Winchester Bay Vacation Rentals from AED 168: Search Short-Term Rentals

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Our top choices for Winchester Bay vacation rentals

A cozy living room with a sofa, armchair, and a coffee table.

1. Dog-friendly ADU with a full kitchen & shared washer&dryer - near the water

Reedsport

Annie B.

AED 768 total

includes taxes & fees

11 Nov - 12 Nov

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

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

Winchester Bay

Caleb

AED 1,310 total

includes taxes & fees

11 Nov - 12 Nov

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

Winchester Bay

Johnny H.

AED 2,790 total

includes taxes & fees

11 Nov - 12 Nov

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

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

Winchester Bay

Grant M.

AED 2,336 total

includes taxes & fees

11 Nov - 12 Nov

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

5. The Salty Duplex (Right Side)

Reedsport

Di L.

AED 794 total

includes taxes & fees

11 Nov - 12 Nov

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

6. 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.

AED 818 total

includes taxes & fees

2 Dec - 3 Dec

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

7. The Salty Duplex (Left Side)

Reedsport

Judy B.

AED 802 total

includes taxes & fees

16 Nov - 17 Nov

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

8. #StayinMyDistrict Lakeside Cottage

Lakeside

Shaun W.

AED 713 total

includes taxes & fees

12 Nov - 13 Nov

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

9. 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.

AED 1,051 total

includes taxes & fees

12 Nov - 13 Nov

An outdoor seating area with a table and chairs, a grill, and a large tree in a forested setting.

10. #StayinMyDistrict Majestic Shores Lake Bear Cabin

North Bend

Travis and Tabitha N.

AED 654 total

includes taxes & fees

11 Nov - 12 Nov

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

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

Lakeside

Angela

AED 809 total

includes taxes & fees

11 Nov - 12 Nov

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

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

Lakeside

Luba K.

AED 1,444 total

includes taxes & fees

11 Nov - 12 Nov

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

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

Lakeside

David

AED 1,262 total

includes taxes & fees

15 Nov - 16 Nov

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

14. Cozy Cabin near Everything!

North Bend

Todd W.

AED 658 total

includes taxes & fees

11 Nov - 12 Nov

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

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

Lakeside

Julie S.

AED 1,437 total

includes taxes & fees

14 Nov - 15 Nov

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

16. Ultimate Guesthouse•Curated Luxury with Lake+Kayak

North Bend

CHARLES W.

AED 1,193 total

includes taxes & fees

15 Nov - 16 Nov

A spacious room with large windows, a leather sofa, and two leather armchairs.

17. Private Lakefront *180° Lake View & Dock

North Bend

Rick M.

AED 1,634 total

includes taxes & fees

15 Nov - 16 Nov

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

18. 2 Homes-14 Acres+2 Spas +Lake Access+Kayaks

Lakeside

AED 2,831 total

includes taxes & fees

17 Nov - 18 Nov

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

19. Siltcoos Station Retreats

Westlake

Andrew

AED 1,159 total

includes taxes & fees

13 Nov - 14 Nov

20. Lakeside Cabin with custom artwork near Florence

Westlake

AED 635 total

includes taxes & fees

12 Nov - 13 Nov

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Find vacation rentals that suit your style

Top Winchester Bay Hotel Reviews

A room with a round wooden table and four chairs, a window with curtains, and a view of a blue building and a bridge.

Winchester Bay Inn

Reedsport

10/10 Excellent

art

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

Amanda

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 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

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

An Econom Inn with a signboard advertising clean rooms, fridge, microwave, TV, and weekly rates.

Economy Inn Reedsport

Reedsport

10/10 Excellent

Katherine

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 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

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.

Winchester Bay Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winchester Bay vacation rentals

1. Dog-friendly ADU with a full kitchen & shared washer&dryer - near the water

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

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

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

5. The Salty Duplex (Right Side)

6. 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.

7. The Salty Duplex (Left Side)

8. #StayinMyDistrict Lakeside Cottage

9. 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.

10. #StayinMyDistrict Majestic Shores Lake Bear Cabin

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

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

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

14. Cozy Cabin near Everything!

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

16. Ultimate Guesthouse•Curated Luxury with Lake+Kayak

17. Private Lakefront *180° Lake View & Dock

18. 2 Homes-14 Acres+2 Spas +Lake Access+Kayaks

19. Siltcoos Station Retreats

20. Lakeside Cabin with custom artwork near Florence

Find vacation rentals that suit your style

Top Winchester Bay Hotel Reviews

Winchester Bay Inn

10/10 Excellent

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?