Vacation rentals in Winchester Bay

4.96 out of 5 average rating, 156 reviews

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

Tide's Reach of the Umpqua

All it's own type thing, in it's own type place, a RIVERSIDE LUXERY GLAMP! Nooked in Oregon Coastal Mountains at edge of inland tidal waters. Set to the background of a small historic rural township, 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!

4.99 out of 5 average rating, 821 reviews

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

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.

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.

4.98 out of 5 average rating, 117 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.

4.96 out of 5 average rating, 112 reviews

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

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.

4.96 out of 5 average rating, 451 reviews

An inviting living area features a leather sofa and two armchairs, with large windows allowing natural light. A wooden dining table sits nearby, complemented by a light-colored tabletop. Artworks adorn the walls, and a subtle color palette enhances the spacious feel of the room.

Barn in Lakeside

ALL NEW!-Barnhaus-Spa+11 Acres+EV+Gym+Lake Access

The Barnhaus at Treetop Lodge—formerly The Studio—was completely and meticulously renovated for 2025. This handcrafted retreat sleeps 7 (2 kings, 1 bunkbed and a sofabed) with luxe TVs, a high-speed gaming PC, hot tub, firepit, EV Charging and gym. Set on 11 private acres with hiking trails through the forest that lead to a secluded lakefront. The private hot tub with string lighting is where rustic charm meets high-tech comfort—surrounded by nature and built for relaxation or play.

4.82 out of 5 average rating, 141 reviews

The exterior of the guest home features a sloped wooden ramp leading to a welcoming entrance. Large windows allow natural light to fill the interior, and a small yard is visible beside the structure, enhancing accessibility.

Tiny home in North Bend

Vacation by Dunes fenced yard,fireplace,cozy

Cozy newly furnished guest home. 1 bed/1 bath, gas stove, with cooking utensils, indoor fireplace provides cozy ambience. Home is close to beach, dunes, restaurants and shopping. Unit is not pet friendly due to pet allergies in one of our family members - if guest brings a pet a 200 deep cleaning fee will apply. Shared fenced yard (2 bed 1 bath unit is available for rent as well). Call us for special pricing on both. https://www.airbnb.com/h/northbendhome

4.94 out of 5 average rating, 121 reviews

Cabin in Lakeside

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.

4.95 out of 5 average rating, 505 reviews

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

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.

4.98 out of 5 average rating, 132 reviews

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

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.

4.94 out of 5 average rating, 143 reviews

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

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!

Cottage in North Tenmile Lake

The exterior of the Cocoon Cottage is showcased, featuring a unique, rounded design clad in wooden shingles. Large arched windows bring in natural light, framed by lush greenery and ferns. A wooden chair is positioned on the spacious deck, inviting relaxation in a serene environment.

4.87 out of 5 average rating, 126 reviews

The Cocoon Cottage 🐛

Are you ready to nestle down in the ultra cozy Cocoon Cottage? This unique getaway is enveloped in classic Pacific Northwest scenery. Surrounded by ferns and pine trees and just a few steps from Tenmile Lake, you’ll breathe easy while spending time disconnecting in the fresh air and lush vegetation. You'll arrive by boat to find yourself isolated on your own hillside paradise.

4.89 out of 5 average rating, 630 reviews

A cabin surrounded by lush green forest is set amidst a spacious yard. Sunlight filters through the trees, casting a soft glow on the gravel driveway leading to the entrance. Nearby foliage and colorful blooms add natural beauty to the serene environment.

Cabin in Eastside

Glenn Creek Cabin

Glenn Creek Cabin is set on Glenn Creek in a beautiful Pacific Northwest forest. Only 3 miles from Golden & Silver Falls, you will find it's a great place to unwind from the pressures of life. The cabin offers modern accommodations for up to 4 guests with a fully-equipped kitcen, and everything you need to relax.

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Popular amenities for Winchester Bay vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Winchester Bay

5 out of 5 average rating, 12 reviews

A wooden deck railing is featured in the foreground, providing a view of the surrounding outdoors. Tall trees are visible on either side, while a grassy landscape stretches into the distance, dotted with shrubs and plants under a cloudy sky.

Home in Florence

Florence Beach House

4.76 out of 5 average rating, 116 reviews

A rustic cabin is positioned on an expansive grassy area, featuring a wrap-around porch with wooden posts. A stack of firewood is neatly arranged beside the cabin. A scenic view of lush trees and distant hills is visible in the background under a cloudy sky.

Cabin in Coos Bay

Rustic Cabin Wrap-around View

A gravel driveway leads to a cozy house, with a covered entrance providing shelter. Surrounding greenery includes shrubs and trees, enhancing the natural setting. A shed is visible to the right, and a birdhouse is mounted on a wooden post near the driveway.

4.92 out of 5 average rating, 37 reviews

Lakeside Retreat

A spacious living area is centered around a large sectional sofa adorned with decorative cushions. Natural light enters through multiple windows, highlighting the wood-style flooring. An arc lamp provides additional light, and a small coffee table displays a few books and a decorative model.

4.96 out of 5 average rating, 78 reviews

Tenmile Retreat - on water, pet friendly, parking

A tranquil lakeside home is nestled among tall trees, showcasing a spacious driveway with manicured landscaping. The exterior features a contemporary design, accentuated by large windows that reflect the beautiful colors of the sunset in the background.

4.8 out of 5 average rating, 10 reviews

Stay In Lakeside - Lake Front Oasis

4.92 out of 5 average rating, 37 reviews

A charming red cabin with a sloped roof is set within a natural landscape. It features a spacious outdoor seating area with wooden furniture and a railing, providing a welcoming space to relax. Lush greenery frames the property, enhancing the serene environment.

Tiny home in Lakeside

Little Home in Lakeside+2 RV hookups

A living area features a comfortable teal sofa adorned with colorful cushions. Movie and art pieces hang above, showcasing surfboard designs. A white coffee table sits in front of the sofa, while a television and a decorative plant create a welcoming space. The entry door opens to the hallway.

Home in Reedsport

4.8 out of 5 average rating, 367 reviews

Tropical Paradise in Coastal Reedsport!