Winchester Bay Vacation Packages 2026 from $1,050

Winchester Bay flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Bandon Inn

$1,050

per person

Dec 24 - Dec 27

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to North Bend (OTH)

This motel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. Staff at the 24-hour front desk can provide around-the-clock assistance.

The Florentine Waterfront Hotel

$1,438

per person

Dec 24 - Dec 27

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to North Bend (OTH)

This hotel features a lazy river and a hot tub. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a garden, and a picnic area are also on offer.

Beachfront Inn

$1,414

per person

Nov 30 - Dec 7

just found

Roundtrip flight included

Colorado Springs (COS) to North Bend (OTH)

This hotel features an outdoor pool, a hot tub, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.

Rogue River Landing Resort

$1,156

per person

Dec 24 - Dec 27

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to North Bend (OTH)

Bay Point Landing

$1,096

per person

Dec 24 - Dec 27

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to North Bend (OTH)

A private beach and an indoor pool are featured at this aparthotel. Enjoy the 24-hour gym and perks like free self parking and free WiFi. A business center, a grocery/convenience store, and a picnic area are also on offer.

Top Winchester Bay hotels deals

Winchester Bay Inn

390 Broadway Ave Reedsport OR

Free Cancellation

Reserve now, pay when you stay

$87 nightly

$96 total

Nov 1 - Nov 2

Total with taxes and fees

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a picnic area are also on offer.

Parking included

Free WiFi

Soothing Crab themed 3-bedroom home with WiFi and a hot tub in Winchester Bay.

Winchester Bay OR

Free Cancellation

$352 nightly

$357 total

Nov 1 - Nov 2

Total with taxes and fees

A hot tub is featured at this vacation home, along with laundry facilities and barbecue grills.

Hot Tub

Kitchen

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

Reedsport OR

Get rates

A hot tub is featured at this vacation home, along with a garden and barbecue grills.

Hot Tub

Kitchen

Blue Heron Getaway. Come enjoy the spring and summer in our great cozy house.

Winchester Bay OR

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This vacation home featured laundry facilities and barbecue grills.

Kitchen

Washer

Luxurious Hilltop Home w/ Private Hot Tub and Direct Dune Access

Winchester Bay OR

$785 nightly

$796 total

Nov 1 - Nov 2

Total with taxes and fees

A hot tub is featured at this vacation home, along with a garden and barbecue grills.

Hot Tub

Kitchen

Winchester Bay Apt Near Dunes & State Parks!

Reedsport OR

Get rates

This apartment doesn't skimp on freebies - guests receive free WiFi and free self parking. Barbecue grills are provided for your convenience.

Kitchen

Pet friendly

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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.

Stay near popular Winchester Bay attractions

Umpqua Lighthouse

9.0/10 (168 reviews)

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.

See properties

Frequently asked questions

How much are vacation packages to Winchester Bay?

With offers starting from as little as $1,050, hotel and flight packages are a great way to stretch your vacation budget. Winchester Bay, here you come!

How long should my Winchester Bay vacation be?

Your Winchester Bay getaway can be as short or as long as you want it to be, but the majority of travelers stay roughly 2 nights. In the mood to venture out and discover some lesser-known sights? Lock in a few extra nights and experience another side of this place.

Where can I get the best vacation package deals for Winchester Bay?

You'll come across a terrific selection of Winchester Bay package deals on Travelocity. With 400 air carriers and 1,000,000 properties worldwide, organizing the perfect vacation will be a breeze.

Why should I book my Winchester Bay vacation package with Travelocity?

We take the stress out of travel planning. Whether you're seeking an amazing new place to roam around or want to make sure you get the best deal around, we're here to assist. Our 24/7 customer care, top-quality service and Price Match Guarantee mean you can book with confidence with Travelocity.

Will I save money on my Winchester Bay car rental if I combine it with a hotel or flight?

You sure can. And our Winchester Bay vacation packages will help you do it. In only a few clicks you can save cash as well as time by booking everything in one place. Collect the keys to your rental car and feel the freedom of the open road. Searching for things to do? Add some tours or experiences to your package and make savings on those too.

Which airport is best for Winchester Bay?

You'll find Southwest Oregon Regional Airport (OTH) 19 mi south of central Winchester Bay.

Where should I stay when visiting Winchester Bay?

If you're after someplace comfortable to base yourself, take a look at the Winchester Bay Inn. It's the top choice for many travelers.