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, 830 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.

Guest favorite
A serene outdoor space features a lush green lawn bordered by ferns. A rustic red bench sits in the foreground, overlooking the Siuslaw River and surrounded by tall trees providing shade. The peaceful setting showcases the natural beauty of the property.
Guesthouse in Mapleton
4.89 out of 5 average rating, 401 reviews

Cozy River Cabin

Sitting on nearly two acres of river front land, this tiny cabin is packed with charm. Enjoy the view of the beautiful Siuslaw River out of the large picture windows. This property is the perfect place to unplug from technology and plug into the great outdoors. Relax in the jacuzzi nestled in a grove of mature firs. Wander the orchard and taste the sun ripened seasonal fruits. Bring your fishing pole and catch a fresh salmon for supper. Leave your worries behind and come unwind at the cabin.

Top guest favorite
An open floor plan showcases a kitchenette equipped with wooden cabinetry, a black refrigerator, and a microwave. The living area includes a comfortable couch with decorative pillows. A bright blue door leads to the outside, providing natural light and access to a private deck.
Loft in Florence
4.94 out of 5 average rating, 230 reviews

Sylvia's Sanctuary

Upscale recently renovated private loft in quiet wooded neighborhood. High ceilings, deep carpet, glass and ceramic tile, roomy shower. Luxury linens & comfortable Cal King bed Free WiFi, new 50" smart TV. Kitchenette with dishes, utensils, cookware. New 1800 watt cooktop Pantry has snacks and goodies. Private entrance and deck up stairs. Country feeling right in town. Minutes from shopping, Old Town, beach, dunes, trails. Respectful owners onsite. Raised Aerobed available for 3rd guest.

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
4.97 out of 5 average rating, 121 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, 261 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, 101 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.

Superhost
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, 632 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.

Superhost
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
4.8 out of 5 average rating, 144 reviews

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

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, 515 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 welcoming entrance is framed by lush greenery and well-maintained landscaping. A stone pathway leads to a charming porch, where light blue double doors create a focal point. Mature trees and vibrant plants enhance the peaceful outdoor setting.
Home in Florence
4.95 out of 5 average rating, 217 reviews

Cozy Coastal Cottage

Keep it simple at this peaceful and centrally-located place. Easy walk to Bay Street and all the charm, great eats and fun that Old Town Florence offers! Stroll to the Exploding Whale Memorial Park in moments, walk along the sandy river "beach" and through its magical forest, as you look across at the Oregon dunes that inspired the book and movie series, "Dune". A large grocery store is close by, too. Breathe the air and relax!

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, 135 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.

Superhost
A spacious bed is dressed in crisp white linens, complemented by neatly rolled towels. A decorative plant adds a touch of greenery, while a floral painting provides a soft visual accent above the bed. A cozy sitting area is positioned nearby with cushions.
Apartment in Florence
4.73 out of 5 average rating, 312 reviews

(U2)Great studio apartment in Florence by Old Town

This small upstairs studio apartment is in a safe double entrance building walking distance to downtown Old Town! Enjoy this 1950 era charming building that has been completely renovated. Enjoy the breeze from the skylight and welcoming ambience of the building. This simple clean unit is great for someone looking for a relaxing quiet place to stay after enjoying the beach or nearby shopping.

Popular amenities for Winchester Bay vacation rentals

When is the best time to visit Winchester Bay?

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Avg. priceG$74,479 GYDG$74,479 GYDG$83,684 GYDG$88,915 GYDG$88,915 GYDG$64,855 GYDG$83,266 GYDG$83,266 GYDG$83,684 GYDG$83,684 GYDG$74,479 GYDG$74,479 GYD
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Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Winchester Bay?

    Yes! Work meets play with ease at over 10 vacation rentals in Winchester Bay featuring dedicated workspaces. Stay connected and productive in your home away from home.

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

    Four-legged friends are welcome in Winchester Bay. Choose from more than 10 vacation rentals for guests traveling with pets.

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

    Winchester Bay has more than 20 family-friendly house rentals. 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 $100 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 G$10,461 GYD per night before taxes and fees

  • Verified guest reviews

    Over 830 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • 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

  • 4.8 Average rating

    Winchester Bay stays are highly rated by guests—averaging 4.8 out of 5!

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