
Holiday rentals in Winchester Bay
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Top-rated holiday rentals in Winchester Bay
Guests agree: these stays are highly rated for location, cleanliness and more.

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.

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.

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!

Coastal Charm & Views - Near Oregon Dunes & Golf
Bayview House is located in a quiet historic neighborhood with amazing views . A place to relax and unwind. Enjoy beautiful sunrises, storm watch, barbecues on the deck or hang out by the fire with friends and family. Enjoy all the coast has to offer: fishing, crabbing, clamming, beach combing, hiking, kayaking, ATV-ing and golf. Bayview House has easy access to Bandon Dunes golf resort and several state parks including Shore Acres and Oregon Dunes National Recreational Area!

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.

Stunning Views • Hot Tub • Cold Plunge
A few precious summer nights remain available at the Tower. Morning coffee above the bay. Hot tub under the stars. Cold plunge if you’re brave enough. Four stories of views, deep sleep, records, tons of curated books & magazines, games, and quiet that resets your whole nervous system. Not a basic Airbnb. Not a touristy beige hotel room with tiny lotion bottles. The kind of place you leave already planning to come back to. There’s a reason we have such RAVE 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.

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 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.

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.
Popular amenities for Winchester Bay holiday rentals
Other great holiday rentals in Winchester Bay

Lakeside Retreat

Cozy Cattail Cottage Coastal Woodland Retreat

Your Coastal Adventure

Coastal 2BR Dog Friendly | Deck | Firepit

Creekside Bungalow-Lake and Dune Access

Lost in Lakeside

Winchester Bay Vacation Rental Near Dunes & ATV!

Harbor view Cozy Cottage
Frequently Asked Questions
Are there family-friendly vacation rentals in Winchester Bay?
Winchester Bay has more than 10 family-friendly stays. 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 $90 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 €69 per night before taxes and fees

Verified guest reviews
Over 740 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

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

4.9 Average rating
Winchester Bay stays are highly rated by guests – averaging 4.9 out of 5!
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