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Vacation rentals in Winchester Bay

Find and book unique accommodations on Airbnb

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!

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 cozy open-concept living area features two blue armchairs complemented by a small round table. An adjacent dining space includes a white table and wooden chairs. The modern kitchen, equipped with stainless steel appliances and light countertops, is visible in the background.
Apartment in Reedsport
4.96 out of 5 average rating, 26 reviews

Tidewater Haven

After a day spent flyfishing on the Umpqua River for steelhead, surf-fishing for perch, ocean fishing for salmon, crabbing, hiking, or long lazy walks on the beach getting your Vitamin Sea, you deserve a comfortable and quiet refuge. Tidewater Haven is located close to everything you like to do on the central Oregon Coast- it's all only 5-30 minutes away! Reedsport is also a culinary hot spot with several new and old restaurants spanning from farm-to-table dining experiences to fine dining.

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, 863 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, 129 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.

Guest favorite
An insulated dome interior showcases a cozy space with a plush brown blanket draped over a spacious bed. A stone hearth is centrally positioned, with wood-fired heating. Two tall tables with chairs and a sectional sofa are located near expansive windows that provide views of the outdoors.
Dome in Scottsburg
4.97 out of 5 average rating, 178 reviews

Tide's Reach of the Umpqua

All it's own type thing, in it's own type place, a unique RIVERSIDE GLAMP! Nooked in Oregon Coastal Mountains at edge of inland tidal waters. Set to the background of a small historic rural town, tucked just out of sight of the beaten route to/from the Pacific Ocean and Oregon Dunes a short 16mi away at Reedsport.  Year-round floating dock and river access all to yourself, different experience with each tide change, and kayaks provided. Otter, eagle, seal, fish, etc : a nature theme park!

Guest favorite
The exterior of a charming green cottage is illuminated at dusk, showcasing a crab emblem above the front door. Warm lighting enhances the welcoming atmosphere, while vibrant blue windows contrast with the wooden accents. A pathway is lined with decorative features, creating an inviting entrance.
Home in Winchester Bay
4.87 out of 5 average rating, 54 reviews

The Cozy Crab Cottage

Make some memories at this unique and family-friendly place. It’s located just 1 block off of Interstate 101 and 1 block from Salmon Harbor in Winchester Bay. The Oregon dunes park is 1/4 mile away and world class fishing, crabbing and eating are in walking distance. The Umpqua lighthouse is right around the corner and your less than an hour from Bandon Oregon golfing and Florence Oregon. This home is a 1940’s home in a quiet neighbor hood with a gated yard for your pets and secure parking.

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, 140 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 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
4.93 out of 5 average rating, 127 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, 684 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
Cabin in Lakeside
4.94 out of 5 average rating, 137 reviews

Secluded Lakefront Mini-Cabin W/ Paddleboards

Remote lakefront retreat—boat access only. We provide all arrival details after booking. Tucked away on North Tenmile Lake, this peaceful mini-cabin is perfect for a romantic escape or quiet writer’s retreat. Features a full kitchen, full bathroom with shower/tub combo, loft with king bed and lake views. Enjoy a private dock, paddleboards, high-speed WiFi, fishing, stargazing, and morning coffee by the water. The perfect mix of peace, privacy, and nature.

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, 155 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 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, 183 reviews

Hot Tub | Cold Plunge | Views | Stay Above It All

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.

Top guest favorite
A floating cabin exterior is shown, featuring a deep red wooden façade with large windows. Solar panels are mounted on the slanted roof. The cabin rests on a wooden deck overlooking the calm waters of Siltcoos Lake, surrounded by greenery and distant trees.
Houseboat in Dunes City
4.9 out of 5 average rating, 261 reviews

Siltcoos Floating Cabin

Floating Cabin on Siltcoos Lake. This intimate 9' x 12' space is perfect for a romantic getaway or a solo retreat into nature. Picture waking up to the gentle lapping of waves and panoramic lake views. Arrive before sunset to witness the lake's breathtaking beauty unfold and embark on your unforgettable lakeside adventure.

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.

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  5. Winchester Bay