
Holiday houses in Winchester Bay
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Top-rated holiday rentals in Winchester Bay
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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.

"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.

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.

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.

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!

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.

Tenmile Lakeview Hideaway
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.

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.

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.

☆Sully's Sanctuary☆ Centrally located/North Bend
** Discount applied when you stay 2 nights or more! Also, ask about National Education Association or Oregon Education Association membership discounts.** Enjoy a stay on the Oregon coast in this spacious guest suite (508 sq. ft.), complete w/ private entrance, comfy queen-size bed, large private bathroom & eating area. A mini-fridge/freezer, microwave, wi-fi, smart TV/DVDs & dedicated parking are provided.

Simply Spectacular. Read our reviews.
❄️ December at The North Bend Tower ❄️ Four stories. Infinite calm. The hot tub steams into crisp winter air while the cold plunge awakens every sense. Morning fog blankets the bay; afternoons glow soft and silvery. Evenings bring that rare, quiet magic only December can offer. This isn’t a vacation — it’s a reset. A return to clarity. Winter rates are now live. Book now before your boss does

(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
Other great holiday rentals in Winchester Bay

Coastal 2BR Dog Friendly | Deck | Firepit

Stay In Lakeside - Lake Front Oasis

3BR close to the ocean and adventure

Private Riverfront stay on the Siuslaw

Luxurious Hilltop Home w/ Direct Dune Access

Beautiful 1BR Riverfront | Patio | W/D

Little Cabin on the River - A Waterfall Wonderland

Maud Lake Lodge - Dune Access Lakefront Home
When is the best time to visit Winchester Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $535 AUD | $535 AUD | $601 AUD | $639 AUD | $639 AUD | $466 AUD | $556 AUD | $556 AUD | $639 AUD | $601 AUD | $535 AUD | $535 AUD |
| Avg. temp | 7°C | 7°C | 8°C | 9°C | 11°C | 13°C | 14°C | 14°C | 14°C | 11°C | 9°C | 7°C |
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 $75 AUD 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 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
20 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!
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