Holiday rentals in Winchester Bay

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Top-rated holiday rentals in Winchester Bay

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Guest favourite
The spacious living area features floor-to-ceiling windows that afford sweeping ocean views. A comfortable sectional sofa and several accent chairs are arranged around a central coffee table on a patterned rug. The warm wooden ceiling adds an inviting touch to the room.
Home in Coos Bay
4.87 out of 5 average rating, 373 reviews

#StayinMyDistrict Cape Arago Sanctuary at the Sea

#StayInMyDistrict Cape Arago Sanctuary on the Sea! Oceanfront home features sweeping views of the ocean & direct access to Lighthouse Beach. Located on a pointe overlooking the sea, w/ floor to ceiling windows & views for miles. This mid century beauty was designed for both style & comfort. Outdoor space with large grassed yard w/ gas fire pit, & comfortable seating. Enjoy local hiking, convenient to Charleston & Coos Bay. 2 bed/2 bath, cozy fireplace, W/D,Sleeps up to 8, BBQ Grill, Oceanfront.

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, 139 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
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, 116 reviews

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!

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, 121 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, 201 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
4.97 out of 5 average rating, 128 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.

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
4.93 out of 5 average rating, 107 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, 127 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, 487 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 spacious bedroom is depicted, featuring a large bed dressed in white and navy linens. A dresser and mirror are positioned near windows that allow natural light to fill the room. A cozy chair and decorative plants add a touch of warmth.
Guest suite in Florence
4.96 out of 5 average rating, 523 reviews

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.

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, 141 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
A cabin surrounded by lush green forest is set amidst a spacious yard. Sunlight filters through the trees, casting a soft glow on the gravel driveway leading to the entrance. Nearby foliage and colorful blooms add natural beauty to the serene environment.
Cabin in Coos Bay
4.89 out of 5 average rating, 645 reviews

Glenn Creek Cabin

Glenn Creek Cabin is set on Glenn Creek in a beautiful Pacific Northwest forest. Only 3 miles from Golden & Silver Falls, you will find it's a great place to unwind from the pressures of life. The cabin offers modern accommodations for up to 4 guests with a fully-equipped kitcen, and everything you need to relax.

Popular amenities for Winchester Bay holiday rentals

  1. Airbnb
  2. United States
  3. Oregon
  4. Douglas County
  5. Winchester Bay