Winchester Bay vacation rentals

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Top-rated vacation rentals in Winchester Bay

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Lakeside

4.91 out of 5 average rating, 115 reviews

Lakeside Adventure Awaits

DIRECT DUNE ACCESS!! Nestled in the coastal town of Lakeside our beachy 2-bedroom, 2-bathroom home has been upgraded with all the amenities to make your stay comfortable and relaxing. The location is the perfect fising, hiking, or ATVers paradise. The home offers a great outdoor living space, full size washer and dryer, and much more. No shop access at this time. Park and ride your ATV out of the driveway to the dunes, walk to Tenmile Lake and a quick drive to beautiful beaches and State Parks.

Sep 25 – Oct 2

G$50,243 GYD per night

Guest favorite

Cottage in Coos Bay

4.98 out of 5 average rating, 397 reviews

"Uncle Joe's Place" Cozy Cottage with Water View

Uncle Joe's Place is a cozy cottage that sits close to the water with views of Charleston bridge and South Slough Estuary. Cottage is 490 square feet, perfect for singles or a couple visiting the area. Located just off Cape Arago Hwy and the town of Charleston. It's a short walk to convenience stores, restaurants and the Charleston Marina. Neighborhood is made up of small homes and mobile homes. Check yourself in with a lockbox. I'm very close by if you need any assistant or have questions.

Jun 15 – 22

G$34,223 GYD per night

Guest favorite

Home in North Bend

4.82 out of 5 average rating, 104 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.

Nov 16 – 23

G$33,522 GYD per night

Guest favorite

Guest suite in Reedsport

4.99 out of 5 average rating, 683 reviews

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.

Jan 16 – 21

G$25,641 GYD per night

Guest favorite

Home in Reedsport

4.95 out of 5 average rating, 187 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, Traeger 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!

Feb 18 – 25

G$21,876 GYD per night

Guest favorite

Cottage in Florence

4.86 out of 5 average rating, 162 reviews

The Love Shack by Heceta Beach

This adorable little 450 sq ft cottage is perfect for 1-2 guests and is just a short walk to spectacular Heceta Beach. Walk to Jerry's, a friendly local pub with a pool table, juke box, full bar, and darn good food! With the ocean, lakes, river, sand dunes and lush environment there's good reason that Florence is called "Oregon's Coastal Playground!" Need a separate workspace? We've got that too. We will considering allowing one pet, but it must be preapproved before booking. Thank you!

Jul 10 – 17

G$23,810 GYD per night

Guest favorite

Guest suite in Florence

4.95 out of 5 average rating, 393 reviews

Quiet, serene retreat near stream, lakes, & ocean

Come relax and renew on the coast in our private guest suite with its own entrance. The stars don't get brighter or the days more peaceful than at this quiet, secluded spot. This retreat with tons of natural light, includes a large bedroom, bathroom spacious shower and double vanity and a sitting room with desk/drawing table and outdoor patio. Enjoy the deer that meander past your large windows to eat blackberries. Just a few minutes away are the beach, dunes, lakes and Florence.

May 8 – 15

G$22,632 GYD per night

Superhost

Home in Florence

4.92 out of 5 average rating, 159 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!

Sep 30 – Oct 7

G$42,376 GYD per night

Guest favorite

Cottage in North Bend

4.97 out of 5 average rating, 131 reviews

Cottage on the Bay

Monthly rates available! Cottage style decor with shabby chic and slip-covered furniture. We are 3-1/2 miles from the North Bend (McCullough) Bridge and only about 5 miles from the nearest beach, Horsfall Beach, and the famous sand dunes. You will enjoy your privacy in this quiet little guest house with a very big and gorgeous view. The property is residential and there is also the main residence nearby, although you have plenty of privacy and a private deck to enjoy on your own.

Jan 4 – 11

G$31,581 GYD per night

Guest favorite

Home in North Bend

4.93 out of 5 average rating, 106 reviews

Private Forested Retreat Close to Town/Beach/Dunes

Private Forested Retreat hosted by Chloe & Jason, Sweeter Homes LLC! Enjoy unmatched privacy with over an acre of land all to yourself and close proximity to town, the dunes and beach! Located 5 minutes from Hwy 101, 10 minutes from downtown North Bend and 15 minutes from Horsefall Beach! Relax on the expansive deck by the fire-pit with your coffee/wine or BBQ a feast while soaking in the country like setting. If your lucky a momma deer with her fawns may make an appearance!

May 14 – 21

G$40,039 GYD per night

Guest favorite

Cabin in Lakeside

4.97 out of 5 average rating, 403 reviews

Exquisite Lake Views in Luxury Retreat!

Looking for the perfect place to enjoy all the Oregon Coast has to offer?? Then look no further than this stunning luxury cabin with breathtaking views over-looking Tenmile Lake. This modern, cozy space offers every amenity from a full deck for entertaining, fire pit in the backyard and brand new everything inside that comes with all modern amenities including Smart TV and high-speed WiFi for those needing to stay connected while being checked out :-)

May 13 – 20

G$99,114 GYD per night

Guest favorite

Guesthouse in North Bend

4.91 out of 5 average rating, 335 reviews

Glasgow Guest House

Our Glasgow Guest House is a 325 sq ft cottage behind our house on Coos Bay. Furnished with a queen bed, dresser, smart TV and a kitchenette. The kitchenette has an apartment-sized fridge, a hot plate, an electric skillet and a microwave. In a cupboard is a small convection/toaster oven. The space is warm, clean and quiet, with natural Douglas fir flooring and a tiled bath.

Nov 28 – Dec 5

G$17,227 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Winchester Bay vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Winchester Bay's top sights

Oregon Dunes National Recreation Area23 locals recommend

Double D's On The Rocks3 locals recommend

Griff's On the Bay Restaurant3 locals recommend

Fishpatrick's Crabby Cafe4 locals recommend

Ridin' Dirty ATV Rentals3 locals recommend

Ziolkouski Beach Park3 locals recommend

Other great vacation rentals in Winchester Bay

Guest favorite

Home in North Bend

4.98 out of 5 average rating, 401 reviews

Bayview House - Beautiful Family Friendly Home With a View

Dec 2 – 9

G$36,128 GYD per night

Guest favorite

Guesthouse in Florence

4.87 out of 5 average rating, 151 reviews

Seal Pup is a tiny home one blk from the beach.

Aug 16 – 23

G$23,815 GYD per night

Superhost

Home in Coos Bay

4.91 out of 5 average rating, 385 reviews

Below the Falls Lodge

Aug 2 – 9

G$88,908 GYD per night

Guest favorite

Camper/RV in Florence

4.89 out of 5 average rating, 105 reviews

Delightful Coastal Camper w/ Many Extras

Jul 17 – 24

G$24,379 GYD per night

Guest favorite

Cabin in Bandon

4.9 out of 5 average rating, 175 reviews

Bandon Cabin on Coquille River unobstructed views.

Dec 17 – 24

G$28,075 GYD per night

Guest favorite

Guest suite in North Bend

4.97 out of 5 average rating, 193 reviews

☆Sully's Sanctuary☆ Centrally located/North Bend

Nov 7 – 14

G$21,492 GYD per night

Guest favorite

Cottage in Mapleton

4.96 out of 5 average rating, 194 reviews

A River Cottage for Every Season

Jun 20 – 27

G$28,527 GYD per night

Superhost

Cottage in Dunes City

4.82 out of 5 average rating, 172 reviews

Hot tub ocean access river private dock cottage

Sep 7 – 14

G$40,904 GYD per night

Show all

Other great vacation rentals in Winchester Bay

Guest favorite

Home in Winchester Bay

4.97 out of 5 average rating, 75 reviews

Beautiful home with spectacular harbor view

Dec 31 – Jan 7

G$40,680 GYD per night

Superhost

Home in Reedsport

4.81 out of 5 average rating, 272 reviews

Tropical Paradise: Coastal Getaway!

Nov 17 – 24

G$16,667 GYD per night

Guest favorite

Guesthouse in Reedsport

4.9 out of 5 average rating, 52 reviews

Cabin with view of elk and coastal hills

Sep 27 – Oct 4

G$21,117 GYD per night

Guest favorite

Home in Lakeside

5.0 out of 5 average rating, 40 reviews

Home + Guesthouse ~ Dune Access, Gated ATV parking

Sep 17 – 24

G$55,971 GYD per night

Guest favorite

Home in Lakeside

4.92 out of 5 average rating, 49 reviews

Leashore Lodge near sand dunes, lakes and ocean.

Nov 23 – 30

G$38,117 GYD per night

Superhost

Home in Lakeside

4.84 out of 5 average rating, 122 reviews

#StayinMyDistrict Lakeside Near Oregon Dunes

Oct 8 – 15

G$32,672 GYD per night

Guest favorite

Home in Lakeside

4.98 out of 5 average rating, 84 reviews

The Casita on Duck Pond: Dune Access

May 22 – 29

G$39,475 GYD per night

Guest favorite

Cabin in Lakeside

4.97 out of 5 average rating, 34 reviews

Lakefront cabin getaway. Boat Access Only!

Aug 27 – Sep 3

G$32,098 GYD per night

Show all

Quick stats about vacation rentals in Winchester Bay

Total rentals
20 properties
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
450 reviews
Nightly prices starting at
G$12,533 GYD before taxes and fees

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Winchester Bay?
Yes! Work meets play with ease at over 10 vacation rentals in Winchester Bay featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Winchester Bay?
Four-legged friends are welcome in Winchester Bay. Choose from more than 10 vacation rentals for guests traveling with pets.
Are there family-friendly house rentals in Winchester Bay?
Winchester Bay has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Winchester Bay?
Experience the best of Winchester Bay with our house rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Winchester Bay vacation rentals

Top-rated vacation rentals in Winchester Bay

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Winchester Bay vacation rentals

Stay near Winchester Bay's top sights

Other great vacation rentals in Winchester Bay

Home in North Bend

Guesthouse in Florence

Home in Coos Bay

Camper/RV in Florence

Cabin in Bandon

Guest suite in North Bend

Cottage in Mapleton

Cottage in Dunes City

Other great vacation rentals in Winchester Bay

Home in Winchester Bay

Home in Reedsport

Guesthouse in Reedsport

Home in Lakeside

Home in Lakeside

Home in Lakeside

Home in Lakeside

Cabin in Lakeside

Quick stats about vacation rentals in Winchester Bay

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Winchester Bay?

Are there pet-friendly vacation rentals in Winchester Bay?

Are there family-friendly house rentals in Winchester Bay?

How much does it cost to stay in house rentals in Winchester Bay?

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