Holiday houses in Winchester Bay

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Quick stats about holiday rentals in Winchester Bay

  • Total holiday rentals

    Explore 30 holiday rentals in Winchester Bay

  • Nightly prices starting at

    Winchester Bay holiday rentals start at $138 NZD per night before taxes and fees

  • Verified guest reviews

    Over 960 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Winchester Bay holiday 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!

Top-rated holiday rentals in Winchester Bay

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

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Top Guest favourite
Home in Reedsport
4.56 out of 5 average rating, 9 reviews

Coastal Forest Rendezvous Suite for Two!

Coastal Forest Rendezvous is a cozy nest for two with a bird’s-eye view of natural green space. Some have likened the view to that of a view from a treehouse. Enjoy the relaxing sounds of wild birds during the day and drift off to sleep listening to frogs at night. My place is located in a nice rural residential neighborhood where homes are built on half an acre with lovely mature landscapes. The home’s dual purpose is as a nest to relax and a launching pad for a variety of coastal adventures!

Guest favourite
A single-story home is enclosed by a white picket fence, with manicured greenery and shrubs visible in the front yard. Two tall conifer trees stand prominently on either side of the house, complemented by a clear blue sky overhead.
Home in Reedsport
4.87 out of 5 average rating, 53 reviews

Wish You have a pleasant stay & wonderful trip.

Dear Our Good Guests: Airbnb just updated has two system pricing listing right now. The old one is not included all fees and new one is included all fees. Our price on calendar and listing is included all fees. Don't hesitate to ask if you have any questions. Our price without fee are $130-$150(depend on the dates) for 1 Guest and 2 Guests. If You have an extra Guest, You will have to pay $25 for per extra Guest, kid under 5 years old no charge. We thank You very much for Your understanding.

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, 872 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 favourite
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, 132 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 favourite
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
4.88 out of 5 average rating, 56 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 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.
Apartment in Reedsport
4.96 out of 5 average rating, 143 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 large two-story home is positioned amid lush greenery, showcasing a navy blue façade and multiple windows. A spacious driveway leads to the entrance, with surrounding gardens featuring shrubs and trees, creating a sense of privacy and tranquility.
Home in Reedsport
5.0 out of 5 average rating, 17 reviews

Ranch Road Retreat 3 bd 2.5 bath Sleeps 6

Located in town, but the feel of remote privacy in the country. Close proximity to grocery stores and restaurants. This home offers 3000 sq ft of space to spread out and enjoy family and friends. Downstairs enjoy the Theater room, Pool table, Dual Basket ball hoop, Air Hockey and Skeet-ball. Electric fire place. Open living space concept All bedrooms are located upstairs for privacy & furnished with smart TVs. Giant Master shower ensuite. Spectacular views off the private deck.

Guest favourite
A sweeping aerial view captures the serene shoreline bordered by lush greenery. The water reflects a blend of soft colors, while gentle hills rise in the background. Crisp lines of the road and the beach create a harmonious connection between land and water.
Home in Winchester Bay
5.0 out of 5 average rating, 6 reviews

1614 | Oregon Dunes Getaway on the Coast

Direct Dune access with Bay view. This spacious condo is a duner's dream, with the driveway connecting to the Oregon Dunes. Two car oversized garage with lots of room to store toys Crabbing, fishing and walking the beach is less than a 1/2 mile from home, Enjoy it all. Slab Granite countertops, Tile, stone, and carpet flooring. Jetted tub in Master suite. With the ocean to the west and the lighthouse to the east beautiful views can be found on all three balconies.

Top Guest favourite
A well-appointed living area is featured, showcasing a dark blue couch and a matching armchair. A wooden entertainment unit holds a flat-screen TV, while a decorative clock adorns the wall. Natural light enters through a window with closed blinds, and a small tree adds a touch of decor.
Home in Winchester Bay
4.94 out of 5 average rating, 49 reviews

Winchester bay Dungeness & dunes

Your family will be close to everything when you stay at this centrally-located place. Located in an amazing spot with fishing, dungeness crabbing, beaches, great food and entertainment, plus the dunes right out the front door. The home is within walking distance to several restaurants, tackle shops, and even a rock shop. Plenty of room to park a toy hauler, or other outdoor recreation vehicles like a boat. Experience amazing sunsets and sand between your toes.

Guest favourite
Cabin in Lakeside
4.94 out of 5 average rating, 138 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 covered outdoor seating area is presented with bright orange chairs and a white table, offering views of Tenmile Lake and the surrounding greenery. The clear blue sky enhances the serene atmosphere. Lush trees frame the picturesque backdrop while sunlight creates a warm ambiance.
Home in Lakeside
4.96 out of 5 average rating, 511 reviews

Tenmile Lakeview Retreat

Escape to the Oregon Coast and soak up stunning views of Tenmile Lake from this modern, cozy getaway. Sip your morning coffee on the full deck, gather around the backyard fire pit, or relax indoors while enjoying the lake view and streaming your favorite shows on the Smart TV with high-speed WiFi. Here, you’ll find the perfect balance of relaxation and convenience. Come unwind, recharge, and create unforgettable memories at this lakeside retreat.

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, 157 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.

Popular amenities for Winchester Bay holiday rentals

Frequently Asked Questions

  • 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 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 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.