Holiday houses in Winchester Bay

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Top-rated holiday rentals in Winchester Bay

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Top Guest favourite
Home in North Bend
4.98 out of 5 average rating, 507 reviews

Bayview House - Beautiful Family Friendly Home With a View

Enjoy beautiful views of the bay and stunning sunsets through the large picture windows that welcome you to Bayview House. Observe the local wildlife including deer and a variety of birds while you sip your morning coffee. The waterfront outdoor fire pit is a perfect place to roast s’mores and relax after a day of adventures to nearby beaches, lakes, dunes and endless hiking trails. Everything you’ll need to prepare a quick snack or gourmet meal is provided in the bright and fully equipped kitchen. Memory foam topped beds, 100% cotton linens, and fluffy towels help to ensure a comfortable stay. You will find everything you need to feel right at home including SMART televisions with cable, high speed wifi, a washer and dryer, toiletries, a game room with foosball table, and plenty of board games, puzzles, books and children’s toys. Bayview Home is an ideal place for a family or group of friends to enjoy the beautiful Southern Oregon Coast! Bayview House may also be rented in conjunction with Bayview Cottage, a smaller 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! Bayview home has a beautiful outdoor area that includes a fire-pit, bench, and table. During high-tide you can Stand Up Paddle or kayak right from the back yard. There are trails that head around the bay. Wildlife including egrets, deer, and geese often visit right out back! 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 house. The house 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. The house is fully handicap accessible with a ramp up to the front door and extra wide doors throughout the house. Please also note there is no barrier between the yard and the water (at high tide). Children will need to be supervised to ensure safety.

Top Guest favourite
A spacious bed with patterned bedding is placed against a bright yellow wall, accentuated by a metal artwork featuring trees. Two bedside lamps provide soft lighting, and a nightstand holds personal items, creating a cozy sleeping area.
Guesthouse in Florence
4.98 out of 5 average rating, 335 reviews

Petite Suite Near Bay Street

At this peaceful and centrally-located suite tucked behind a 1930’s home up a little hill, you will be close to everything important. Walk 1/5 of a mile to Old Town, where you may visit The Port of Siuslaw, many well known restaurants, art galleries and shops. Hwy 101 is a couple blocks away where our famous Pono Hukilau Restaurant is located. Walk a wee bit further to Exploding Whale Park and enjoy sitting on the river’s beach for a picnic or take a short drive to Heceta Beach for the day.

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, 121 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.

Top Guest favourite
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, 236 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 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
4.97 out of 5 average rating, 123 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.

Top 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, 273 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 favourite
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.
Holiday home in Reedsport
4.93 out of 5 average rating, 106 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 private porch area is visible, featuring two wooden rocking chairs and a small side table. Light streams in through large windows, enhancing the calm atmosphere. Decorative elements, including an anchor sign, add subtle charm to the space, which connects to a cozy interior.
Apartment in Coos Bay
4.79 out of 5 average rating, 307 reviews

#StayinMyDistrict Historic Heritage Walk to Bay

#StayinMyDistrict Downtown Coos Bay! Beautiful and quiet residential neighborhood close to downtown Coos Bay Shopping, Dining & Entertainment. (6-8 blocks walking distance). This 1 bedroom- 1 bath apartment sleeps up to (4). This private residence with updates and amenities throughout offers a comfortable place to stay in Coos Bay. Fully furnished, Cable & WIFI, full kitchen, WD and FREE parking. Comfortable outdoor space & great desk area to sit and work with a view.

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.

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, 480 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 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, 521 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, 139 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 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.

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