Photo by Vicki Chandler

Search Holiday Rentals in Winchester Bay

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Find properties with these dates

Tonight
May 3 - May 4
Tomorrow
May 4 - May 5
This weekend
May 3 - May 5

Top Holiday Rentals in Winchester Bay

Large home overlooking the harbor and some ocean views.
Property grounds
Large home overlooking the harbor and some ocean views.
10.0 out of 10, Exceptional, (16)
"Enjoyed our stay."
Large home overlooking the harbor and some ocean views.
Comfy dog-friendly bay home with kitchenette, gas grill, patio, yard, and W/D
Interior
Comfy dog-friendly bay home with kitchenette, gas grill, patio, yard, and W/D
10.0 out of 10, Exceptional, (1)
Comfy dog-friendly bay home with kitchenette, gas grill, patio, yard, and W/D
Coastal Elegance
Private kitchen
Coastal Elegance
10.0 out of 10, Exceptional, (1)
"This home is very spacious. Nice big living room, kitchen, and dining area. The dogs loved the fenced back yard! The back yard is huge. It's location is perfect. Easy to find and close to everything. A really nice quiet neighborhood. Large grocery store down the street. The casino is not far and lots of places to eat. I recommend the Wildflour restaurant, their food is excellent. Enjoyed this home and would stay there again!"
The price is £243
includes taxes & fees
5 May - 6 May
Coastal Elegance
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Renovated North Bend Cottage: Near Eateries!
Fridge, microwave, stovetop, dishwasher
Renovated North Bend Cottage: Near Eateries!
10.0 out of 10, Exceptional, (14)
"Fun location, near shopping and the bay! Nice backyard, although quite a bit of dog poo but that’s not the fault of the property owner. My awesome husband got it all picked up though. We had a wonderful time!!! Don’t miss out on this little gem of a home!"
Renovated North Bend Cottage: Near Eateries!
North Bend Home w/ Cornhole Court & Putting Green
Fridge, microwave, stovetop, dishwasher
North Bend Home w/ Cornhole Court & Putting Green
10.0 out of 10, Exceptional, (12)
"Location was great!"
North Bend Home w/ Cornhole Court & Putting Green
Gypsy by the Bay with Fireplace
Fridge, microwave, stovetop, coffee/tea maker
Gypsy by the Bay with Fireplace
10.0 out of 10, Exceptional, (4)
"Beautiful setting and lovely accommodations I wish we could have stayed longer"
The price is £256
includes taxes & fees
7 May - 8 May
Gypsy by the Bay with Fireplace
Luxurious Oregon Coast Townhouse with Mesmerizing Views!
Property grounds
Luxurious Oregon Coast Townhouse with Mesmerizing Views!
10.0 out of 10, Exceptional, (102)
"My family had a fantastic stay at this wonderful Coos Bay / North Bend townhouse. The 3-level design was great for the family to spread out and have their own space, while also sharing time together in the spacious kitchen/dining/livingroom area. Enjoyed spending time in the hot tub or relaxing on the deck while staring out over the bay. Surprised that there was absolutely zero noise from the adjoining townhouses - which made listening to the wind and seaguls that much better. Great Location as...
Luxurious Oregon Coast Townhouse with Mesmerizing Views!
Peaceful Setting on the Coast with Mountain Views and Partial Ocean View
Exterior
Peaceful Setting on the Coast with Mountain Views and Partial Ocean View
10.0 out of 10, Exceptional, (7)
"It was everything it said it was. It was in simple words perfect. For two adults and two senior 4-legged kids it was perfect. The decor is very nice. You are treated to what is in the photos. We loved every minute we spent on the coast and the hideout was central to everything. "
Peaceful Setting on the Coast with Mountain Views and Partial Ocean View
Winchester Bay Apt Near Dunes & State Parks!
Marina
Winchester Bay Apt Near Dunes & State Parks!
9.8 out of 10, Exceptional, (8)
"Enjoyed the stay. Apartment was very clean and suited us perfectly as we were visiting my brother who lives 4 blocks away"
Winchester Bay Apt Near Dunes & State Parks!
Spacious ranch with lots of parking, pet friendly, partial bay view.
Terrace/patio
Spacious ranch with lots of parking, pet friendly, partial bay view.
9.8 out of 10, Exceptional, (52)
"Nice easy to find location, lots of games and plenty of beds. Worked perfect for our family vacation."
Spacious ranch with lots of parking, pet friendly, partial bay view.
Below the Falls Lodge - Next to Golden & Silver Falls
Property grounds
Below the Falls Lodge - Next to Golden & Silver Falls
9.8 out of 10, Exceptional, (184)
"Couldn’t have been more impressed! Absolutely loved the house and everything it has to offer. Having everything thing we needed while being away from the public was a dream. My children and dog absolutely loved the creek and being able to enjoy the forest while us adults enjoyed the break from technology and being able to slow down a bit. Can’t wait to return!"
Below the Falls Lodge - Next to Golden & Silver Falls
The Old McCullough Home w/ Rooftop Deck, View
Exterior
The Old McCullough Home w/ Rooftop Deck, View
9.8 out of 10, Exceptional, (11)
"First thing to note is there is only 1 working shower. The pictures are incorrect. The upstairs shower head is capped off due to a leak causing damage to master bedroom below on main level. The bathtubs are fine, but use up all the hot water, so plan accordingly. Looking back at the reviews this has been an issue since Dec 14, 2023. Luckily, my family is flexible and goes with the flow. The other surprise was the oven not working. We were notified about this while driving with our cars full of...
The Old McCullough Home w/ Rooftop Deck, View
*NEW LISTING* Beautiful Lake Area Home, Pet Friendly, Close to Old town Florence & Dunes, Gas Grill
Beach
*NEW LISTING* Beautiful Lake Area Home, Pet Friendly, Close to Old town Florence & Dunes, Gas Grill
9.8 out of 10, Exceptional, (19)
"We had such a wonderful stay at this property! It was probably a bit bigger than we needed with our family of 5, but we absolutely enjoyed the extra space! It rained most of the time we were in Florence, so we spent a lot of time watching movies and playing games. The house had everything we needed and was very clean. Just a short drive into town and located in a very quiet neighborhood. We had access to the lake which was within walking distance. I would definitely recommend this property on...
*NEW LISTING* Beautiful Lake Area Home, Pet Friendly, Close to Old town Florence & Dunes, Gas Grill
Direct Dune Access Sleeps 10 In House, 6 In BunkHouses - Bath Houses.
Property grounds
Direct Dune Access Sleeps 10 In House, 6 In BunkHouses - Bath Houses.
9.8 out of 10, Exceptional, (122)
"Everything was perfect! We rented the the bunk house along with the property! Lots of parking for all the toys and vehicles! Totally fenced property great for the kids! We had a great time! W will definitely stay again!"
Direct Dune Access Sleeps 10 In House, 6 In BunkHouses - Bath Houses.
Lakeside house with access to dunes, lakes, and the ocean!
Property grounds
Lakeside house with access to dunes, lakes, and the ocean!
9.8 out of 10, Exceptional, (14)
"Spent Spring Break at this property with our family and teenagers friends. Perfect to hangout, enjoy games and great sleeping spaces. Close to dunes, our reason for this trip. Communication with host and check in/out process was great. Easy to recommend this property."
Lakeside house with access to dunes, lakes, and the ocean!
Relaxing Getaway Lake Cabin with Pristine Views
Relaxing Getaway Lake Cabin with Pristine Views
9.8 out of 10, Exceptional, (16)
"House is in a great location from the boat ramp and has a wonderful view of the lake. The owner had fast and friendly communication and the house was clean, we will rent again!"
The price is £240
includes taxes & fees
7 May - 8 May
Relaxing Getaway Lake Cabin with Pristine Views
Cozy family beach cottage with hot tub, deck, WiFi, surfboard - walk to bay
Fridge, microwave, oven, stovetop
Cozy family beach cottage with hot tub, deck, WiFi, surfboard - walk to bay
9.6 out of 10, Exceptional, (27)
"I may have misunderstood the description but while the adorable house is CLOSE to the beac it was not ON the beach. That being said, i would (already have) recommended to friends."
The price is £230
includes taxes & fees
6 May - 7 May
Cozy family beach cottage with hot tub, deck, WiFi, surfboard - walk to bay
*New Listing* Beautiful lake view home with shared lake access, gas grill and amazing views
Beach
*New Listing* Beautiful lake view home with shared lake access, gas grill and amazing views
9.6 out of 10, Exceptional, (17)
"We rented the house for our wedding week with family. Everyone had a great time. The house was clean and cute with everything we needed, minus groceries. Good times."
*New Listing* Beautiful lake view home with shared lake access, gas grill and amazing views
New Listing! Adorable lakefront cabin, private dock, hot tub, gas grill, amazing views
Beach
New Listing! Adorable lakefront cabin, private dock, hot tub, gas grill, amazing views
9.6 out of 10, Exceptional, (16)
"Very relaxing and great location"
New Listing! Adorable lakefront cabin, private dock, hot tub, gas grill, amazing views
#StayinMyDistrict Lakeside Near Oregon Dunes
Terrace/patio
#StayinMyDistrict Lakeside Near Oregon Dunes
9.6 out of 10, Exceptional, (5)
"The place was clean, comfortable, and in a great location with easily walkable cafes and restaurants."
The price is £166
includes taxes & fees
5 May - 6 May
#StayinMyDistrict Lakeside Near Oregon Dunes
Don't see what you're looking for?
See all available properties in Winchester Bay
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Winchester Bay you may be interested in

Winchester Bay Apt Near Dunes & State Parks!
Marina
Winchester Bay Apt Near Dunes & State Parks!
9.8 out of 10, Exceptional, (8)
"Enjoyed the stay. Apartment was very clean and suited us perfectly as we were visiting my brother who lives 4 blocks away"
Winchester Bay Apt Near Dunes & State Parks!
Cozy family beach cottage with hot tub, deck, WiFi, surfboard - walk to bay
Fridge, microwave, oven, stovetop
Cozy family beach cottage with hot tub, deck, WiFi, surfboard - walk to bay
9.6 out of 10, Exceptional, (27)
"I may have misunderstood the description but while the adorable house is CLOSE to the beac it was not ON the beach. That being said, i would (already have) recommended to friends."
The price is £230
includes taxes & fees
6 May - 7 May
Cozy family beach cottage with hot tub, deck, WiFi, surfboard - walk to bay
Coastal home with an enclosed yard, hot tub, grill, fireplace, and W/D - dogs ok
Fridge, microwave, oven, stovetop
Coastal home with an enclosed yard, hot tub, grill, fireplace, and W/D - dogs ok
8.0 out of 10, Very good, (7)
"It was a cute house with a convenient location to the Ocean! The only issue that we had was the power going out a few times because the circuit breakers were popping due to the plug in heater in the main room."
Coastal home with an enclosed yard, hot tub, grill, fireplace, and W/D - dogs ok
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Everything you need to know about Winchester Bay holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester Bay holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester Bay holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winchester Bay holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchester Bay. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester Bay holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester Bay holiday rentals we have selected for you start as low as £166 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winchester Bay rentals

At Expedia, we put the best Winchester Bay holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winchester Bay rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester Bay holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester Bay. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Winchester Bay?

Yes, there are holiday rentals close to the most popular sights in Winchester Bay, or you can select a more secluded option if you're looking for a relaxing stay. Winchester Bay is known for its parks.

What are some of the best holiday rentals that Winchester Bay has to offer?

Cozy family beach cottage with hot tub, deck, WiFi, surfboard - walk to bay: This highly rated holiday home rental in Winchester Bay is located in the city centre, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub. Another good choice for your trip to Winchester Bay is Coastal home with an enclosed yard, hot tub, grill, fireplace, and W/D - dogs ok.

How many holiday rentals will I find in Winchester Bay?

Choose from 14 Expedia holiday rentals in Winchester Bay for a memorable holiday.

What’s there to see and do in Winchester Bay?

Oregon Dunes National Recreation Area and Umpqua River are a couple of lovely local spots to get outside and enjoy nature. While here, Umpqua Lighthouse and Umpqua Lighthouse State Park are other places worth a visit.

What’s a holiday rental in Winchester Bay like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchester Bay. Holiday rentals feature amenities such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive option for family trips.

Recent reviews of Winchester Bay properties
Expedia verified reviews

Best Western Pier Point Inn

Best Western Pier Point Inn

5/5 Excellent
Great property
"A beautiful property in a convenient location. Only complaint, no elevator. Fortunately, didn’t need it this time! "
A verified traveller stayed at Best Western Pier Point Inn
Posted 3 days ago
Best Western Pier Point Inn