Family-friendly holiday rentals in Winchester Bay

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Winchester Bay

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite
An insulated dome interior showcases a cozy space with a plush brown blanket draped over a spacious bed. A stone hearth is centrally positioned, with wood-fired heating. Two tall tables with chairs and a sectional sofa are located near expansive windows that provide views of the outdoors.
Dome in Scottsburg
4.96 out of 5 average rating, 167 reviews

Tide's Reach of the Umpqua

All it's own type thing, in it's own type place, a RIVERSIDE LUXERY GLAMP! Nooked in Oregon Coastal Mountains at edge of inland tidal waters. Set to the background of a small historic rural township, tucked just out of sight of the beaten route to/from the Pacific Ocean and Oregon Dunes a short 16mi away at Reedsport.  Year round floating dock and river access all to yourself, different experience with each tide change, and kayaks provided. Otter, eagle, seal, fish, etc : a nature theme park!

Top guest favourite
A spacious deck features several light wooden chairs arranged for outdoor seating. Potted flowers add color, while the river and distant landscape are visible in the background, illuminated by warm sunset hues.
Home in Florence
4.99 out of 5 average rating, 117 reviews

GEM ON THE OREGON COAST

Looking over the river, sand dunes and the ocean, this 2 story - 3 bd Cape Cod home captures views from every room!! The open floor plan and interior decor makes it easy to entertain with a chef’s kitchen. The patio is exposed to the elements of the Oregon Coast and captivates it’s wildlife and natural beauty. This home is equipped for entering inside and out with a jacuzzi situated off the master bedroom. Don’t forget to enjoy the river rock fireplace for those cooler evenings. We welcome you!

Guest favourite
An older mobile home is shown, surrounded by gravel parking. The structure features a wooden ramp leading to the entrance, with large windows allowing natural light. Tall trees provide shade, creating a serene outdoor environment.
Home in North Bend
4.83 out of 5 average rating, 141 reviews

Saunders Lakefront Retreat 600ft from Dunes

Lakefront home on Saunder’s Lake. Located 600ft from the dune entrance and a five minute ATV ride to the beach. Purchased property to build new home in a few years. We enjoy staying there so much that we decided to rent out the current older mobile as an opportunity to stay lakefront 600ft from the sand until construction begins for a fraction of what the price will be after we build. Please keep in mind that this is an older mobile as the price reflects so don’t expect a newly remodeled home.

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, 122 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
An aerial view showcases a two-story home surrounded by lush greenery and a well-maintained lawn leading to the water. Two wooden docks extend into the lake, with a sandy area to the left and a kayak resting nearby. Outdoor seating is visible on the spacious deck.
Home in Florence
4.92 out of 5 average rating, 202 reviews

Lakeside Landing

Enjoy Stunning 180 degree Lake Views from the upstairs (separate unit) of a 2 story home on one of Oregon's Most Beautiful Lakes! You'll have your own Private 40' Deck & Private entrance, Full Kitchen, Full Bath, Dining Room, Living Room & Laundry Room. Wake up to magnificent sunrises out your bedroom window, lovely grass Lawn down to the lake, 2 docks, Jet Ski ramp, Sandy Beach & BBQ. After a fun day on the Lake or Exploring ALL the Oregon Coast has to offer, Come Home to Paradise!

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.
Flat in Reedsport
4.96 out of 5 average rating, 132 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, 277 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
4.94 out of 5 average rating, 110 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.

Guest favourite
Cabin in Lakeside
4.94 out of 5 average rating, 129 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, 491 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, 142 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.

Top guest favourite
The exterior of a charming A-frame house is showcased, featuring a green wood facade and a large front deck. Several wooden chairs are arranged on the deck, while tall grass surrounds the entrance. A tall tree can be seen to the left, contributing to the coastal ambiance.
Cabin in Bandon
4.95 out of 5 average rating, 932 reviews

Bandon Beach Shack - modern, clean & cozy A-frame

Charming, modernly styled A-frame cabin across from the beach, walkable to local shops and restaurants. This is a no-shoe home. If this isn't your jam, please book a different listing. There are so many! We are right across the street from the beach, but beach access is at either end of our street, about a 2-minute walk. Directly across from our house are protected dunes that cannot be traversed.

Popular amenities for Winchester Bay family-friendly rentals

Quick stats about holiday rentals that are family-friendly in Winchester Bay

  • Total holiday rentals

    Explore 10 holiday rentals in Winchester Bay

  • Nightly prices starting at

    Winchester Bay holiday rentals start at $102 SGD per night before taxes and fees

  • Verified guest reviews

    Over 510 verified reviews to help you choose

  • Wifi availability

    10 of Winchester Bay holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Winchester Bay rentals

  • 4.9 Average rating

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