Vacation rentals in Winchester Bay

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Top-rated vacation rentals in Winchester Bay

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A sweeping view of the Umpqua River surrounded by lush greenery and rolling hills under a clear blue sky. The vibrant landscape features a mix of water and grasslands, with wooded areas lining the riverbanks, creating a serene natural setting.
Guest suite in Reedsport
4.99 out of 5 average rating, 857 reviews

The Elk View Suite- 5 min to town, 15 min to Beach

The views of the Umpqua River and Elk Reserve are breathtaking from this spacious, cozy studio! The location is a perfect launching pad for adventures, but is also a relaxing place to stay & unwind. We provide quality amenities, a high level of cleanliness and personal touches to ensure a fabulous experience. Enjoy a cup of coffee or glass of wine on custom made furniture stationed right outside your door! Located 15 minutes from local beaches & only 30 min from either Coos Bay or Florence.

Top guest favorite
Two glasses of red wine sit on a wooden railing beside a bottle, overlooking a tranquil duck pond. Lush greenery surrounds the water, with ducks visible in the background, providing a serene setting for relaxation.
Home in Lakeside
4.98 out of 5 average rating, 128 reviews

The Casita on Duck Pond: Dune Access

Direct dune access!! Coastal adventure meets quiet retreat! This hidden gem of a home sleeps 4 and offers direct dune access, a short walk to Tenmile Lake, and quick drives to beaches and trails. Ride your ATVs, fish for bass, hike the coast, or simply relax by the pond with the ducks and a good book. Bring your ATVs, fishing boat, hiking boots, or stack of books and enjoy this peaceful spot to unwind after the day’s fun. Perfect for couples or small families seeking the best of both worlds.

Superhost
A covered porch extends from the home's exterior, featuring wooden railings and ample seating. A black grill is positioned on the side, with outdoor furniture nearby. The lawn is spacious and well-maintained, surrounded by trees in a peaceful setting.
Home in Winchester Bay
4.72 out of 5 average rating, 65 reviews

Little House w/ Creek in Backyard near Ocean

Two-story, two bedroom home, sleeps a maximum of five. Near Halfmoon Bay where the Umpqua meets the pacific. Close to the sand dunes, fishing charters and restaurants. Secure and safe neighborhood with plenty of parking. Trailer accessible + room for boats and other toys. Small kid-friendly creek in in the backyard for fishing. Plenty of room for having a BBQ and campfires. Full kitchen with dishes and appliances. Living room with TV for streaming movies on Netflix, etc. Internet access.

Top guest favorite
A bright and airy living room is furnished with a comfortable beige sofa and a recliner. A white coffee table is centered on a blue area rug. The space features two side tables with lamps and a television mounted above a modern electric fireplace.
Apartment in Reedsport
4.96 out of 5 average rating, 138 reviews

Ridgeway Hideaway

This stylish place to stay is in the middle of everything. You are a short walk away from the disc golf course, Reedsport golf course and the hospital. A short drive (2-miles) from Winchester Bay where crabbing, fishing, the beach, and dunes are located. Minutes from downtown restaurants, shopping and boat launches. If you're a fisherman or ATV'r there is room to park your trailer in the spacious driveway. You will be able to keep a watchful eye on your trailer just outside your door.

Guest favorite
The exterior of a two-story duplex is seen, featuring a light-colored siding and multiple large windows. A small garage is located to the right, and a fenced yard provides privacy. The sky displays soft hues during sunset, enhancing the calm ambiance.
Home in Reedsport
4.94 out of 5 average rating, 283 reviews

The Salty Duplex (Right Side)

We are located uptown, only 4 minutes from Winchester Bay! The neighborhood is very quiet and comfy. There is a fully stocked kitchen with lots of gadgets, a Keurig coffee pot with a random assortment of kcups, and gas BBQ, and a bar for good conversation. In the Livingroom we have Spectrum cable TV and high speed WiFi. There are 2 bedrooms with one king and one queen bed both upstairs. There is plenty of room for an air mattress in the Livingroom, which is in the closet downstairs!

Guest favorite
The exterior of a single-story home is featured, characterized by brown siding and a peaked roof. A wooden fence surrounds the front yard, and an American flag is displayed near the entrance. Soft evening light casts a warm glow over the inviting porch area.
Vacation home in Reedsport
4.94 out of 5 average rating, 118 reviews

Coastal Shenanigans!

This home is right in the middle of everything to do on the coast. Whether it's fishing the Umpqua river or the ocean, riding the dunes or shopping old town Florence. It's all 10- 30 minutes away. Go for a sunset walk on the beach! There is a nice little coffee shop close and some very good restaurants close by. There is free parking on the premises and on the street. Our driveway is 38' L x 20' W. If you are a boater, we have towels in the garage to wipe your boat off.

Top guest favorite
A two-level chalet is surrounded by vibrant greenery and blooming flowers. Large windows allow natural light to fill the interior. A patio area with outdoor seating and a fire pit is visible in the yard, enhancing the inviting outdoor space.
Cabin in Lakeside
4.95 out of 5 average rating, 683 reviews

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

Looking to create a “Lifetime Memory?” Welcome to Treetop Lodge—a renovated two-level A-frame on 14 private acres. Nestled in the hills of Lakeside, it feels secluded but is just minutes from town. Hike private forest trails that end at at the lake, soak in the Jacuzzi under the stars, toast marshmallows by the firepit, or curl up in the cozy loft for the ultimate movie night. Whether you're chasing adventure or seeking calm, the experience is yours to create.

Guest favorite
A wooden dock extends over a calm lake, featuring two folding chairs positioned for serene views of the water and surrounding trees. The bright sky enhances the peaceful atmosphere, inviting moments of solitude and relaxation.
Cabin in Lakeside
4.88 out of 5 average rating, 266 reviews

Nestled in the Pines Lakefront Retreat W/Kayak

Perfect for writers, creatives, or those seeking peaceful solitude to recharge. - Private Dock & Kayak for 2 - Fishing, boating, and kayaking right at your doorstep. - Cozy Indoor Amenities - King bed - Wood stove . - Hot shower - With High-speed WiFi - With Smart TV - Outdoor Cooking - Propane grill to cook your catch of the day or enjoy a meal under the stars. - Stargaze from the dock or enjoy the serene, quiet atmosphere. Ideal for Solo Retreats

Top guest favorite
A spacious bedroom is depicted, featuring a large bed dressed in white and navy linens. A dresser and mirror are positioned near windows that allow natural light to fill the room. A cozy chair and decorative plants add a touch of warmth.
Guest suite in Florence
4.96 out of 5 average rating, 547 reviews

Quiet, serene retreat near stream, lakes, & ocean

Relax and renew in our private coastal guest suite with its own entrance. Enjoy a large sunlit bedroom, spacious bathroom with double vanity, sitting room with desk, and outdoor patio. Watch deer nibble blackberries outside your picture windows. Just minutes from beaches, dunes, lakes, and the charming town of Florence— The stars don't get brighter or the days more peaceful than at this quiet, secluded spot. Your peaceful retreat awaits.

Top guest favorite
A serene harbor scene at dusk features docked boats reflecting in calm water. Soft lights illuminate the marina, creating a peaceful ambiance. Wooden pylons stand in the water, contributing to the tranquil setting surrounded by forested hills.
Home in Winchester Bay
4.99 out of 5 average rating, 152 reviews

Beautiful home with spectacular harbor view

Make some unforgettable beach memories at this unique and family-friendly place. Mid-century meets the 21st in this lovingly renovated home with spectacular harbor view. Within walking distance of the beach, dunes, lighthouse, harbor, and restaurants. Beautiful enclosed garden room provides sheltered space for dining and relaxing. Young children will love the one-of-a-kind alcove beds. Well-behaved dogs are welcome.

Guest favorite
A cabin-style home is surrounded by towering conifers, with a spacious deck overlooking a lush green lawn. The structure features a combination of wood siding and a pitched roof, reflecting a blend of natural elements and rustic charm. Clear blue skies enhance the serene atmosphere.
Home in North Bend
4.94 out of 5 average rating, 160 reviews

Forested Retreat Close to Dunes/Beach/Town

Enjoy unmatched privacy with over an acre of land all to yourself and close proximity to town, the dunes and beach! Located 5 minutes from Hwy 101, 10 minutes from downtown North Bend and 15 minutes from Horsefall Beach! Relax on the expansive deck by the fire-pit with your coffee/wine or BBQ a feast while soaking in the country like setting. If your lucky a momma deer with her fawns may make an appearance!

Guest favorite
A bright seating area features four modern white chairs arranged around a wooden accent table. Large panoramic windows offer expansive views of the bay and the surrounding landscape, allowing natural light to fill the space.
Tower in North Bend
4.92 out of 5 average rating, 178 reviews

Stay Above It All | Hot Tub + Cold Plunge

People don’t book the Tower because they need a place to sleep. They book it because they’re tired. Tired of noise. Tired of screens. Tired of being on. This is where you come when you need to hear yourself think again. Morning coffee above the bay. Cold ocean air. Hot tub after sunset. A rooftop that makes your problems look smaller. A handful of summer dates remain.

Popular amenities for Winchester Bay vacation rentals

Frequently Asked Questions

  • Are there family-friendly vacation rentals in Winchester Bay?

    Winchester Bay has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Winchester Bay?

    Experience the best of Winchester Bay with our house rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Quick stats about vacation rentals in Winchester Bay

  • Total vacation rentals

    Explore 20 vacation rentals in Winchester Bay

  • Nightly prices starting at

    Winchester Bay vacation rentals start at ﺩ.ﺇ 294 per night before taxes and fees

  • Verified guest reviews

    Over 740 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Wi-Fi availability

    20 of Winchester Bay vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace across Winchester Bay rentals

  • 4.9 Average rating

    Winchester Bay stays are highly rated by guests—averaging 4.9 out of 5!

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