Family-friendly holiday rentals in Winchester Bay

#StayinMyDistrict Cape Arago Studio Suite

#StayinMyDistrict Cape Arago Ocean View Suite! Oceanfront Private guest house features sweeping views of the ocean & direct access to Lighthouse Beach. Located on a Pointe overlooking the sea, with large windows & views for miles. Guest house was designed w/ guests comfort in mind. Enjoy local hiking, Close to Charleston & Coos Bay. 1 KING bed/1 bath, w/ pullout sofa, Sleeps up to 4, Stocked Kitchenette, Grill Outdoor space w/Ocean views, beach access, grassy yard, fire pit, & comfortable seatin

Indoor spaces · Family · Getting around

Hidden Dome Retreat in the Trees

Hidden in the trees at the end of a long private driveway, our Geodesic Dome House offers a unique adventure. Nestled on just over an acre provides the ultimate getaway for those seeking a one-of-a-kind vacation experience. Fully renovated, beautifully blends industrial modern design with natural surroundings, creating a tranquil escape you’ll cherish forever. Enjoy the outdoor kitchen and dining area, gather by the fire pit, soak in the peaceful surroundings for an unforgettable coastal retreat

Kitchen · Family · Outdoor spaces

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.

Family · Indoor spaces · Amenities

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.

Kitchen · Indoor spaces · Hospitality

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.

Kitchen · Family · Getting around

Tower Escape • Hot Tub • Cold Plunge • Views

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.

Indoor spaces · Kitchen · View

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.

Kitchen · Family · Check-in

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.

Family · Indoor spaces · Nearby

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.

Indoor spaces · Kitchen · Amenities

A River Cottage for Every Season

The Riverview Cottage is a little slice of heaven. Unbelievable views from every window; even on a rainy day, you'll catch yourself frittering away the time staring up river, or at the surrounding coast range mountains. Truly heaven on earth. This is the place to get away from technology and reconnect with nature. The Cottage is one of three houses on the property - only grassy areas and river bank are shared.

Kitchen · Indoor spaces · Quiet

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!

Kitchen · Family · Hospitality

Siltcoos Floating Cabin

Floating Cabin on Siltcoos Lake. This intimate 9' x 12' space is perfect for a romantic getaway or a solo retreat into nature. Picture waking up to the gentle lapping of waves and panoramic lake views. Arrive before sunset to witness the lake's breathtaking beauty unfold and embark on your unforgettable lakeside adventure.

Family · Indoor spaces · Parks