Holiday rentals in Winchester Bay

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Top-rated holiday rentals in Winchester Bay

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Top guest favourite
Bright living area features large picture windows offering views of the bay. A comfortable seating area is complemented by a work desk positioned beside a round entryway. The wooden wall adds warmth to the space, while natural light enhances the inviting atmosphere.
Cottage in North Bend
4.95 out of 5 average rating, 513 reviews

Bayview Cottage - Charming Family Friendly Home With a View

Enjoy beautiful views of the bay and wildlife including deer and a variety of birds from the large picture windows that welcome you to Bayview Cottage. Gather around the waterfront fire pit after a day of adventures to enjoy s’mores and stunning sunsets. Everything you’ll need to prepare a gourmet meal or a quick snack is provided in the fully equipped kitchen including spices, bakeware, a variety of kitchen appliances, and other cooking essentials. All three beds feature memory foam and cozy bedding to provide a wonderful night’s sleep. The house is fully stocked with Smart televisions including cable, high speed wifi, a washer and dryer, toiletries, and plenty of books, puzzles, toys and games. Bayview Cottage is an ideal home for families or a group of friends enjoying the beautiful Southern Oregon Coast! Bayview Cottage may also be rented in conjunction with Bayview House, a larger home that sleeps 4 guests and is located right next door. Consider renting both homes together for larger parties or a gathering where families may want their own space. Together both homes can accommodate parties of 8 and each home has a full kitchen and a washer/dryer! This waterfront property is great for cozy evenings around the firepit. During low tide clam from the property or take a nature hike around the bay. Large picture windows provide views of the incredible sunsets while staying warm and cozy indoors. Along with the cottage, enjoy the deck with lawn chairs as well as the waterfront fire pit in the private backyard. I am available by phone, text or email at anytime during your stay. I live nearby if you need anything while you are at the cottage. The cottage is located just a few blocks from Downtown North Bend, a small coastal town with shops, restaurants, antique stores and pubs. Located at the end of a quiet road next to a nature park providing ample opportunity to observe wildlife including deer and many birds. A short drive to several beaches and sand dunes for a day full of outdoor adventures. Plenty of parking for your toys including boats and trailers is available. World famous Bandon Dunes Golf Course is less than a 30 minute drive away! Conveniently located just a few blocks off of the Scenic Coastal Highway and a quick 5 minute drive to the North Bend airport.

Top guest favourite
A cozy blue cottage is presented with a welcoming front porch and a light pathway leading to the entrance. Large windows allow natural light to brighten the interior. The lush green lawn contrasts with the vibrant exterior, while the water and trees create a serene backdrop.
Cottage in Coos Bay
4.98 out of 5 average rating, 567 reviews

"Uncle Joe's Place" Cozy Cottage with Water View

Uncle Joe's Place is a cozy cottage that sits close to the water with views of Charleston bridge and South Slough Estuary. Cottage is 490 square feet, perfect for singles or a couple visiting the area. Located just off Cape Arago Hwy and the town of Charleston. It's a short walk to convenience stores, restaurants and the Charleston Marina. Neighborhood is made up of small homes and mobile homes. Check yourself in with a lockbox. I'm very close by if you need any assistant or have questions.

Top guest favourite
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, 835 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 favourite
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.
Guest house in Mapleton
4.89 out of 5 average rating, 405 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 favourite
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.
Flat in Reedsport
4.97 out of 5 average rating, 122 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 favourite
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, 269 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!

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, 148 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

Guest favourite
Cabin in Lakeside
4.94 out of 5 average rating, 127 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 favourite
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, 518 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 favourite
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, 136 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 favourite
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, 147 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!

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.
Flat in Florence
4.74 out of 5 average rating, 319 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 holiday rentals

When is the best time to visit Winchester Bay?

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Avg. price$460 SGD$460 SGD$517 SGD$549 SGD$549 SGD$401 SGD$478 SGD$478 SGD$549 SGD$517 SGD$460 SGD$460 SGD
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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 $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Quick stats about holiday rentals in Winchester Bay

  • Total holiday rentals

    Explore 20 holiday rentals in Winchester Bay

  • Nightly prices starting at

    Winchester Bay holiday rentals start at $65 SGD per night before taxes and fees

  • Verified guest reviews

    Over 830 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Winchester Bay holiday rentals include wifi 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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