A sailboat on calm waters with a mountainous backdrop and a cloudy sky.
Photo by Andrew Meade
Open Photo by Andrew Meade

Winslow Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

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

The Latest Winslow Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Jan 13 - Jan 18

    The Belltown Inn + Flight

    Downtown Seattle
    5 nights
    3.5 star property
    9.4/10 - Exceptional (5,215 reviews)
    Roundtrip • Toronto (YYZ) - Seattle (SEA)
    YYZ - SEA • 1 stop SEA - YYZ • 1 stop
    CA $1,208
    CA $920
    per traveller
    found 1 day ago
    The Belltown Inn
  • Dec 21 - Dec 27

    Homewood Suites by Hilton Seattle Downtown + Flight

    Downtown Seattle
    6 nights
    3.0 star property
    8.8/10 - Excellent (1,001 reviews)
    Roundtrip • Toronto (YYZ) - Seattle (SEA)
    YYZ - SEA • Nonstop SEA - YYZ • 1 stop
    CA $3,717
    CA $2,351
    per traveller
    found 1 day ago
    Homewood Suites by Hilton Seattle Downtown
  • Jan 13 - Jan 18

    Mediterranean Inn + Flight

    Downtown Seattle
    5 nights
    3.0 star property
    9.4/10 - Exceptional (6,276 reviews)
    "Fantastic place to stay. I highly recommend it!"
    Reviewed November 4, 2026
    Roundtrip • Toronto (YYZ) - Seattle (SEA)
    YYZ - SEA • 1 stop SEA - YYZ • 1 stop
    CA $1,391
    CA $1,009
    per traveller
    found 1 day ago
    Mediterranean Inn
  • Dec 24 - Dec 28

    @ Marbella Lane - Nature Escape at Shady Lake + Flight

    Renton
    4 nights
    3.0 star property
    Roundtrip • Calgary (YYC) - Seattle (SEA)
    YYC - SEA • Nonstop SEA - YYC • Nonstop
    CA $4,389
    CA $3,314
    per traveller
    found 1 day ago
    @ Marbella Lane - Nature Escape at Shady Lake
  • Jan 13 - Jan 18

    The State Hotel + Flight

    Downtown Seattle
    5 nights
    4.0 star property
    9.4/10 - Exceptional (1,369 reviews)
    "Excellent hotel right in the heart of Downtown"
    Reviewed November 4, 2026
    Roundtrip • Toronto (YYZ) - Seattle (SEA)
    YYZ - SEA • 1 stop SEA - YYZ • 1 stop
    CA $1,525
    CA $1,167
    per traveller
    found 1 day ago
    The State Hotel

Where to stay in Winslow

Find the best Winslow areas and neighborhoods for the activities you enjoy most.

Eagledale

Discover Eagledale Park, a 7-acre oasis on Bainbridge Island, featuring tennis courts, an off-leash dog park, picnic shelter, children's play area, sand volleyball court, and pottery studio. Enjoy stunning Mount Rainier views on clear days.

Port Madison

While visiting Port Madison, you might make a stop by sights like Bloedel Reserve and Treasure Island.

Port Blakely

If you're looking for some top things to see and do in Port Blakely and surrounding area, you can visit Bainbridge Island Japanese American Exclusion Memorial and Bainbridge Island Ferry Dock.

Crystal Springs

If you're looking for some top things to see and do in Crystal Springs and surrounding area, you can visit Illahee State Park and Islandwood.

Rolling Bay

While Rolling Bay might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Bainbridge Island Vineyards & Winery and Rolling Bay Winery.

Discover the most popular places to visit in Winslow

What to do near Winslow

Winslow Hotel Deals

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.

Frequently Asked Questions

How much does a Winslow vacation package cost?

Starting from an incredible CA $920, you can tailor make your Winslow package. Simply combine flights, hotels and car rentals and be rewarded with discounts.

How do I get a cheap travel package to Winslow?

One of the simplest ways to save money (and time) is to combine your bookings with Expedia. Flights, hotels, activities and rental cars — we've got them all. Select the combination that suits your style and see your savings pile up. Of course, a package deal is never a one-size-fits-all. That's why we offer over 550 airlines and 1,000,000 properties from all over the world, which lets you customize your Winslow vacation.

Where should I stay in Winslow?

You'll want to stay where the action is. Many people book hotels in the vicinity of popular sights, such as Bainbridge Island Historical Museum, Bainbridge Island Museum of Art and Bainbridge Island Japanese American Exclusion Memorial.

How far in advance should I book my Winslow vacation?

Reserving your flight early with Expedia means one less thing to worry about. Most carriers advertise tickets up to 12 months in advance. Typically, this is the cheapest time to book. If circumstances have left you booking late, last-minute deals to Winslow sometimes become available just a few weeks before departure.

What does an Expedia Winslow travel package include?

With Expedia, you can select a combination of flights, hotels and car rentals to build your ideal Winslow package. Once you've made your booking, you can add on all the fun stuff like sightseeing tours and activities. Remember — the more you bundle, the bigger the savings!

What should I know before booking a Winslow travel package?

Whether it's adventure or relaxation you're seeking, a Winslow vacation package lets you organize your escape your way. Plus, you'll score great discounts just for combining your hotel with your rental car and flights. The more you bundle, the bigger the savings!

Can I choose my airline with a Winslow Expedia vacation package?

Yes — that's the beauty of an Expedia package. You're in control. We have more than 550 airline partners worldwide, so you have lots of choice when creating your Winslow trip.

If I'm not able to travel, can I cancel my Winslow vacation package?

Certainly, and we're here to help. You may be able to amend or cancel your Winslow vacation package for free if you booked in the last 24 hours. But you may incur a fee from your hotel, airline or car rental company if you booked more than 24 hours ago. If your circumstances suddenly change, visit our Customer Service Portal for more information.

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