Winchester Bay Vacations from $690

Book a Hotel + Flight or Car together to unlock savings

Photo by Kim Larson

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Your Winchester Bay Vacation

From its coastal scenery to its spectacular views and beyond, there's a lot to love about Winchester Bay. Discover the delights of this interesting city with a Winchester Bay vacation package that's made for you. Love to start exploring your surroundings? Oregon Dunes National Recreation Area, Umpqua Lighthouse and Umpqua Lighthouse State Park are a few of the top places to visit during your trip to Winchester Bay. Your perfect Winchester Bay vacation is a few clicks away. Browse hotels, flights and more on Expedia for an adventure that's tailored to suit your style.

The Latest Winchester Bay vacation packages

Price found within the past 48 hours. Click for updated prices.
Jot's Resort

Jot's Resort

2.5 out of 5
per person
Oct 13 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) to North Bend (OTH)
8.8/10 Excellent! (1,866 reviews)
Enjoyed our stay at Jot's on our way up the Oregon Coast. Limited dining options in the area, especially later in the evening, but a beautiful view from the room

Reviewed on Jul 29, 2025

Beachfront Inn

Beachfront Inn

2.5 out of 5
per person
Oct 13 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) to North Bend (OTH)
9/10 Wonderful! (1,005 reviews)
The room was clean and the bed comfortable. The staff was kind and helpful. The property itself needs more upkeep to the structure itself. All said, it was a good option for a last-minute stay.

Reviewed on Jul 27, 2025

Bay Point Landing

Bay Point Landing

3.5 out of 5
per person
Aug 28 - Aug 31
found 6 hours ago
Roundtrip non-stop flight included
San Antonio (SAT) to North Bend (OTH)
9.2/10 Wonderful! (226 reviews)
Beautiful location along the water. Quiet and safe.

Reviewed on Jul 26, 2025

Bandon Marina Inn

Bandon Marina Inn

2 out of 5
per person
Oct 19 - Oct 24
found 9 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to North Bend (OTH)
8.8/10 Excellent! (181 reviews)
We had an awsome time: able to walk around and were able to walk to all dining and this is an awsome location to be able to stay able to go out for a cocktail and not have to drive. Very clean an tidy place

Reviewed on Jul 28, 2025

Bandon Inn

Bandon Inn

3 out of 5
per person
Oct 19 - Oct 24
found 9 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to North Bend (OTH)
9.4/10 Exceptional! (1,204 reviews)
Staff was very helpful and nice. Room service has to be requested. Good location and view of harbor

Reviewed on Jul 27, 2025

Don't see what you're looking for?
See all available trips from Columbus to Winchester Bay
View all trips

Discover the most popular places to visit in Winchester Bay

#OnTheRoad another beautiful #lighthouse on the Oregon Coast

Umpqua Lighthouse

Learn about the local history of Winchester Bay with a stop at Umpqua Lighthouse. Wander the riverfront and beaches while you're in the area.

Umpqua Lighthouse

Dean Creek Elk Viewing Area

Learn about the local history of Reedsport with a stop at Dean Creek Elk Viewing Area. While you're in the area, stroll along the riverfront.

Dean Creek Elk Viewing Area

Overlook Beach Trail

You can take time to visit Overlook Beach Trail during your travels to Westlake. While you're in the area, stroll along the riverfront.

Overlook Beach Trail

What to do in Winchester Bay

Oregon Coast: Audio Driving Tour

Self-Guided Audio Driving Tour in Oregon Coast

$20
per traveler
Self-Guided Audio Driving Tour in Oregon Coast
See all activities in Winchester Bay

Winchester Bay Hotel Deals

Winchester Bay Inn

Winchester Bay Inn

2.5 out of 5
390 Broadway Ave, Reedsport, OR
Fully refundableReserve now, pay when you stay
$96 nightly
The price is $107 total per night from Jul 30 to Jul 31
$107 total
Jul 30 - Jul 31
Total includes taxes and fees
7.2/10 Good! (767 reviews)
"Close to the Ocean"

Reviewed on Jul 20, 2025

Winchester Bay Inn
Cozy family beach cottage w/ hot tub, deck, WiFi, surfboard-walk to bay, Dogs ok

Cozy family beach cottage w/ hot tub, deck, WiFi, surfboard-walk to bay, Dogs ok

Reedsport
9.6/10 Exceptional! (16 reviews)
The sleepy little beach town that goes “BRAAAP”
"Wonderful two bedroom house perfect for our family including our dog. We spent four nights and had plenty to keep us busy with great restaurants within walking distance will likely return and definitely recommend."

Reviewed on Jun 30, 2025

Get rates
Cozy family beach cottage w/ hot tub, deck, WiFi, surfboard-walk to bay, Dogs ok
Paradise in Winchester Bay - with Dune Access

Paradise in Winchester Bay - with Dune Access

Reedsport
$644 nightly
The price is $653 total per night from Aug 11 to Aug 12
$653 total
Aug 11 - Aug 12
Total includes taxes and fees
9.8/10 Exceptional! (219 reviews)
"Excellent experience overall!"

Reviewed on Jul 20, 2025

Paradise in Winchester Bay - with Dune Access
See all 188 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.

Find the Best Winchester Bay Vacation Packages

Winchester Bay Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Southwest Oregon Regional Airport (OTH)
Population
380
Max Temp Winter
50ºF
Max Temp Summer
65ºF
Top Sights
Umpqua Lighthouse State Park, Dean Creek Elk Viewing Area and Umpqua Lighthouse

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Winchester Bay vacation package cost?
You'll find cheap prices from $690 on Expedia for your Winchester Bay escape. However, a range of factors like the hotel choice, length of stay and season will influence how much your vacation to Winchester Bay costs.
What are the cheapest months to go to Winchester Bay?
November, December and January are the best times to look for cheap Winchester Bay vacation packages. Traveling in less busy periods means you'll typically find better prices on hotels and flights.
How many days is enough for Winchester Bay?
The ideal length of your Winchester Bay vacation depends on what you'd like to see and do. Usually, a handful of days to a week will give you enough time to go to all the main sights and explore some hidden gems along the way.
How to find the best Winchester Bay package deals?
Begin your search for a Winchester Bay package deal by entering your destination and preferred trip dates under our "Packages" tab. Then select a few filters, like "Property type" and "Guest rating," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Winchester Bay package deal straight away, simply play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Winchester Bay adventure off to a flying start.
Is it cheaper to book a Winchester Bay vacation as a package?
You can enjoy significant savings on your next Winchester Bay escape by booking a personalized vacation package. Click on the "Package" heading, then select your travel dates and destination to browse some great flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Winchester Bay?
If you're considering a spur-of-the-moment Winchester Bay vacation, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can land amazing deals on your flights and hotels by booking well in advance.
How to plan a trip to Winchester Bay?

  1. Pick your travel dates: The things you plan to do in Winchester Bay and your favorite season will help you decide when to travel.
  2. Plan your budget wisely: On top of the price of your hotel, you should factor in other expenses too. These include food, flights and transportation. Also, put aside a little extra for unexpected expenses that could arise during your trip to Winchester Bay.
  3. Use our trip planning tool to explore Winchester Bay: Research every aspect of your trip to Winchester Bay with this comprehensive planner. Invite friends or family to collaborate on a group getaway, search for stays or things to do and make bookings.
  4. Decide how long to go for: Now that you're more familiar with Winchester Bay, you can work out the perfect length of your break. Put together a rough itinerary and give yourself enough time to cover everything you want to do.
  5. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to find a Winchester Bay vacation package that brings all your bookings together.
  6. Book any excursions or activities: Now to the fun part — locking in everything you want to see and do. Browse some of the exciting things to do in Winchester Bay and reserve your tickets in advance to save time (and maybe some cash too!).

Does Expedia offer Book Now, Pay Later Winchester Bay vacation packages?
Jet off on your dream escape to Winchester Bay with help from Expedia's Book Now, Pay Later vacations. No need to scrimp and save or wait for the next payday — we've teamed up with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans let you spread the total cost over 3, 6 or 12 months. With no hidden charges or late payment fees, it's easy to stick to your budget and snap up cheap deals while they last.

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.