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

The Surf House w/ private beach access & hot tub!

The Surf House offers special access to one of the wildest and most beautiful stretches of the Oregon Coast. Perched on the bluffs between Heceta Head and Cape Perpetua, it offers a serene & spectacular oceanfront experience. Descend private stairs from the yard to the secluded beach below to access some of Oregon's best tide pools, agates & beachcombing. An oceanview outdoor shower, fully decked hot tub, fire pit, lush gardens, & stocked surf shack w/ arcade enrich the wild coast experience.

GEM ON THE OREGON COAST

Looking over the river, sand dunes and the ocean, this stunning 3 bd Cape Cod home captures views from every room!! The open floor plan and interior decor makes it easy to entertain with a chefs 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!

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.

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!

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.

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.

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.

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.

The Cocoon Cottage 🐛

The Cocoon Cottage is suspiciously good at making people forget their inboxes. Curved wood walls glow at night, windows frame forest and water, and urgency goes missing. Expect baths, books, long pauses, sauna sessions, lake views and ideas that show up when you stop trying so hard.