Vacation rentals in Winchester Bay

Home + Guesthouse ~Dunes Nearby, Gated ATV parking

Whispering Pines is a main house PLUS guesthouse 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 too (Tiny Pines is a separate listing). Whether you are looking for adventure getaway, romantic weekend, or peaceful vacation, Whispering Pines is a special Oregon Coast Oasis getaway!

Tidewater Haven

After a day spent flyfishing on the Umpqua River for steelhead, surf-fishing for perch, ocean fishing for salmon, crabbing, hiking, or long lazy walks on the beach getting your Vitamin Sea, you deserve a comfortable and quiet refuge. Tidewater Haven is located close to everything you like to do on the central Oregon Coast- it's all only 5-30 minutes away! Reedsport is also a culinary hot spot with several new and old restaurants spanning from farm-to-table dining experiences to fine dining.

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.

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.

Stunning Views • Hot Tub • Cold Plunge

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.

Winchester bay Dungeness & dunes

Your family will be close to everything when you stay at this centrally-located place. Located in an amazing spot with fishing, dungeness crabbing, beaches, great food and entertainment, plus the dunes right out the front door. The home is within walking distance to several restaurants, tackle shops, and even a rock shop. Plenty of room to park a toy hauler, or other outdoor recreation vehicles like a boat. Experience amazing sunsets and sand between your toes.

Nestled in the Pines Lakefront Retreat W/Kayak

Perfect for writers, creatives, or those seeking peaceful solitude to recharge. - Private Dock & Kayak for 2 - Fishing, boating, and kayaking right at your doorstep. - Cozy Indoor Amenities - King bed - Wood stove . - Hot shower - With High-speed WiFi - With Smart TV - Outdoor Cooking - Propane grill to cook your catch of the day or enjoy a meal under the stars. - Stargaze from the dock or enjoy the serene, quiet atmosphere. Ideal for Solo Retreats

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.

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.

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.