Holiday rentals in Winchester Bay

4.86 out of 5 average rating, 28 reviews

Harbor view Cozy Cottage

Adorable, unique one bedroom plus Loft and Large sunroom. Queen main bedroom Queen foldout living room 2 air beds in loft Sleepable sofa Sunroom. Westward bay windows overlooking Salmon Harbor. Short walk to Pizza, Seafood Market, Bars, restaurants, gifts, ATV rentals. 1/2 mi. to Beach, Crab dock, Dunes. Close to Umpqua Lighthouse, Lakes, hiking trails and Elliott Forest. Fully fenced yard, sleeps 6. In the heart of Winchester Bay a Recreation Mecca PLEASE NOTE: PET FEE IS PER EACH PET

4.99 out of 5 average rating, 74 reviews

Home in Lakeside

Home + Guesthouse ~ Dune Access, Gated ATV parking

Whispering Pines is a main house PLUS guest house and game room! Blocks from town, yet privacy among trees. Ride to the dunes from this property on the PAVED ATV Route! Enjoy the lake. Gated parking for boats, ATVs. Chill by the fire. Cozy fireplace. Soak in the deep clawfoot bathtub. Book the tiny home next door (Tiny Pines, separate listing). Whether you are looking for getaway full of adventure, romantic weekend, or peaceful vacation, Whispering Pines is a special Oregon Coast Oasis getaway!

4.99 out of 5 average rating, 781 reviews

Guest suite in Reedsport

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.

4.98 out of 5 average rating, 103 reviews

Home in Lakeside

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.

4.96 out of 5 average rating, 609 reviews

Cabin in Lakeside

Exclusive Hideaway at Treetop Lodge

Looking for that "Lifetime Memory?" Come experience “Tree Top Lodge” a fully renovated 2 level chalet tucked away on 10 acres with lake views nestled in the hills of Lakeside. Located min away from downtown but hidden away on the hillside overlooking "Tenmile Lake" with access to your own private acres of beautiful Oregon Forest. Hike the woods, star-gaze in the Jacuzzi, build yourself a bonfire, or perhaps snuggle up in the cozy loft and simply Netflix and Chill. The choice is yours :-)

Superhost

4.71 out of 5 average rating, 58 reviews

Little House w/ Creek in Backyard near Ocean

Two-story, two bedroom home, sleeps a maximum of five. Near Halfmoon Bay where the Umpqua meets the pacific. Close to the sand dunes, fishing charters and restaurants. Secure and safe neighborhood with plenty of parking. Trailer accessible + room for boats and other toys. Small kid-friendly creek in in the backyard for fishing. Plenty of room for having a BBQ and campfires. Full kitchen with dishes and appliances. Living room with TV for streaming movies on Netflix, etc. Internet access.

4.96 out of 5 average rating, 89 reviews

Flat in Reedsport

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.

Superhost

Cabin in Lakeside

4.94 out of 5 average rating, 109 reviews

Secluded Lakefront Mini-Cabin W/ Paddleboards

Remote Lakefront Retreat – Boat Access Only (Boat Taxi Available) -Secluded Mini-Cabin -Private lakefront location, accessible only by boat -Cozy and charming with modern comforts - Private dock for easy water access - Paddle boards for two - Enjoy fishing, boating, and swimming - Stargazing opportunities -King-sized bed - With High-speed WiFi - Fully equipped kitchenette - Hot shower - Propane grill for outdoor cooking - Ideal for connecting over coffee, wine, or a game of cards

4.95 out of 5 average rating, 241 reviews

Home in Reedsport

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!

5 out of 5 average rating, 9 reviews

Home in Reedsport

Ranch Road Retreat 3 bd 2.5 bath Sleeps 6

Located in town, but the feel of remote privacy in the country. Close proximity to grocery stores and restaurants. This home offers 3000 sq ft of space to spread out and enjoy family and friends. Downstairs enjoy the Theater room, Pool table, Dual Basket ball hoop, Air Hockey and Skeet-ball. Electric fire place. Open living space concept All bedrooms are located upstairs for privacy & furnished with smart TVs. Giant Master shower ensuite. Spectacular views off the private deck.

4.91 out of 5 average rating, 91 reviews

Guest house in Reedsport

Cabin with view of elk and coastal hills

It’s a quiet, peaceful retreat, backed up to the Elliot state forest. Only 15 minutes from the beach. There are elk roaming the property, and many different birds. You can hear barred owls at night. In the fall you can see and hear elk bugling. You can explore the Elliot state forest which is only 5 minutes away, or you can explore the dunes! The Umpqua river is only a stones throw away. Reedsport and Winchester bay have many nice restaurants and activities.

Holiday home in Reedsport

4.94 out of 5 average rating, 72 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. If you are a boater, we have towels in the garage to wipe your boat off.

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Other great holiday rentals in Winchester Bay

4.67 out of 5 average rating, 6 reviews

3BR Dog Friendly | Deck | Firepit | W/D

TiAnnaRating, 5 stars8 months ago

Wonderful place to stay right in Winchester Bay, a couple blocks from the harbor restaurants and shops. The “mother-in-law” suite was perfect for our family vacation that we brought my in-laws along. They had their own space but were able to easily come down stairs to gather and spend time with the kids. We would definitely stay again!

4.72 out of 5 average rating, 43 reviews

Coastal 2BR Dog Friendly | Deck | Firepit

DaminiRating, 5 stars3 weeks ago

The instructions provided to locate the house, check in and check out was very clear. The house was very clean and had warm vibes. The hosts were responsive and answered all the questions. In all it was a comfortable stay.

Flat in Reedsport

4.83 out of 5 average rating, 6 reviews

Tidewater Haven

L.Rating, 5 stars1 week ago

We had a great time staying at Nicole’s place. We were impressed by the quality and comfort of the home. It’s in a great location with lovely local shops and cafes, and a short drive to the beach and places to walk and hike.

4.8 out of 5 average rating, 5 reviews

Home in Reedsport

Reedsport Coastal Adventure

JamieRating, 5 stars2 months ago

Valerie was great with communicating with me. The place was clean and inviting. I loved the wrap around patio. Next time I will stay in the summer. I appreciate the quick response to my emails. I would stay there again.

4.8 out of 5 average rating, 10 reviews

3BR close to the ocean and adventure

AlyssaRating, 5 stars3 weeks ago

The place was very nice, peaceful, and quiet. The place looked exactly as the pictures and the master bed was the best bed I’ve slept on while on vacation. It was close to the dunes and had several places to visit for good food and drinks. They were extremely responsive, friendly, and professional when we reached out to them.

Cabin in Dunes City

5 out of 5 average rating, 3 reviews

Romantic Cabin w/ Panoramic View

ChristinaRating, 5 stars1 month ago

Our little lake front cabana was as cute as button, clean and nicely decorated. We loved the area, location and especially the views. The dock and lake was simply stunning. The property was easy to find, peaceful and tranquil. Would love to come back in the summer for some lake activities.

Cabin in Reedsport

4.91 out of 5 average rating, 67 reviews

Cozy Cattail Cabin Coastal Retreat

LindsayRating, 5 stars1 month ago

This is one of my favorite places to stay ever. The cabin is the perfect size and has everything for a forest retreat. The setting is beautiful, there is access to the river and slough, and the cabin itself is cozy and comfortable. I have stayed here twice already and I will keep coming back.