Winslow Vacations

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    Better together
    Save up to ￥45,448 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Find the Best Winslow Vacation Packages

Winslow Hotel Deals

Maine Evergreen Hotel, Ascend Hotel Collection
Maine Evergreen Hotel, Ascend Hotel Collection
2.5 out of 5
65 Whitten Rd, Augusta, ME
Fully refundableReserve now, pay when you stay
The price is ￥24,446 per night from Jul 6 to Jul 7
￥24,446
￥26,646 total
Jul 6 - Jul 7
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
"Very cool hotel with a great wine bar. Wish we could have stayed longer to hang by the pool"

Reviewed on Jun 26, 2025

Maine Evergreen Hotel, Ascend Hotel Collection
Fireside Inn & Suites Waterville
Fireside Inn & Suites Waterville
2 out of 5
376 Main Street, Waterville, ME
Fully refundableReserve now, pay when you stay
The price is ￥22,633 per night from Jul 1 to Jul 2
￥22,633
￥24,670 total
Jul 1 - Jul 2
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"The staff are very friendly, and they support one another. The breakfast is nicely laid out, and you had an option of preparing a bag to take with you. On a couple of days we prepared a lunch of bagel and cream cheese to take with us. This is an older hotel, but will maintained, and reminiscent of ..."

Reviewed on Jun 22, 2025

Fireside Inn & Suites Waterville
The Elmwood
The Elmwood
2.5 out of 5
455 Kennedy Memorial Dr, Waterville, ME
Fully refundableReserve now, pay when you stay
The price is ￥21,553 per night from Jul 1 to Jul 2
￥21,553
￥23,493 total
Jul 1 - Jul 2
includes taxes & fees
8.6/10 Excellent! (410 reviews)
"Continental breakfast was good. Location was convenient. Value could have been better …"

Reviewed on Jun 27, 2025

The Elmwood
See all 454 properties in Winslow
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?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a vacation to Winslow costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Winslow?
If you're hoping to book a cheap Winslow vacation package, consider visiting in January, February and March. You'll usually find better rates on flights and hotels during these months --- perfect for a budget-friendly break.
How many days is enough for Winslow?
Generally, a handful of days is enough to go to the major sights during your Winslow vacation. But if you want to have time to kick back or take day trips, think about extending your trip.
How to find the best Winslow package deals?
Bagging a cheap Winslow package deal is a cinch with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your budget range, add some filters and see what's available. You can customize your search by "Amenities," "Property type," "Popular locations" and more. Sort the results by "Price: low to high" to discover the most affordable Winslow package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are generally lower.
Is it cheaper to book a Winslow vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging accommodations and flights individually. Better still, you can customize your Winslow getaway to match your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Winslow?
Score incredible bargains by reserving your flights early with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for a spur-of-the-moment Winslow adventure.
How to plan a trip to Winslow?

  1. Choose when to get away: Check your diary and pack your bags. Your favorite season and the available activities will also help you decide when to visit Winslow.
  2. Set your budget: Factor in costs like flights, food and transportation when calculating how much to put aside for your trip to Winslow. Then, choose a hotel that matches your budget, whether that's an economical option or a deluxe getaway.
  3. Determine how many days away: Start by making a list of all the attractions you want to get to in Winslow. Then, estimate how long you'll need at each, including any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a personalized Winslow vacation package.

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