Winslow Vacations from $433
Book a Hotel + Flight or Car together to unlock savings
Your Winslow Vacation
Take the worry out of organizing your next grand adventure with a Winslow vacation package. Whether you're visiting for its cuisine, history, art or other highlights, you'll find countless exciting experiences to delve into. Every trip to Winslow needs a well-designed itinerary. Fill yours with leading attractions like Colby College, Waterville Opera House and Thomas College. Your dream Winslow vacation is just clicks away. Explore hotels, flights and more on Expedia for a trip that's tailored to suit your travel style.
The Latest Winslow vacation packages
Price found within the past 48 hours. Click for updated prices.
Evergreen Valley Inn by Coolvacay
$433
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Augusta (AUG)
8.2/10 Very Good! (188 reviews)
Very secluded and quiet If your looking for a little pice of Heaven look no further then here It was lovely Very friendly and very welcoming . I can’t wait to visit again
Reviewed on Aug 16, 2026
Mid-Town Motel
$448
per person
Oct 2 - Oct 4
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Augusta (AUG)
8.6/10 Excellent! (254 reviews)
We were looking for a quaint little motel and Mid Town Motel was perfect. We were able to grab the last room which only had twin beds, but we didn’t mind for our short stay. The beds and pillows were extremely comfortable. The employees were both helpful and friendly. We will definitely return.
Reviewed on Aug 17, 2026
Jordan Hotel
$611
per person
Sep 22 - Sep 27
found 21 hours ago
Roundtrip flight included
Chicago (CHI) to Augusta (AUG)
8.8/10 Excellent! (549 reviews)
Beautiful location. Hiking trails accessible from the property. Clean rooms. Large heated pool and 2 hot tubs. The staff were extremely friendly and helpful.
Reviewed on Aug 17, 2026
Stay near popular Winslow attractions
Fort Halifax
9.2/10 (15 reviews)
America's oldest wooden blockhouse stands as a riverside sentinel from the French and Indian War era. Explore this 1754 military relic while enjoying views of the converging Kennebec and Sebasticook rivers.
Winslow Hotel Deals
Maine Evergreen Hotel, an Ascend Collection Hotel
65 Whitten Rd Augusta ME
Fully refundable
$143 nightly
$156 total
Aug 30 - Aug 31
Total with taxes and fees
9.2/10 Wonderful! (1,003 reviews)
"We arrived kind of late, but check-in was quick. Our rooms were comfortable. Breakfast was great."
Reviewed on Aug 17, 2026
Fireside Inn & Suites Waterville
376 Main Street Waterville ME
Fully refundableReserve now, pay when you stay
$103 nightly
$112 total
Aug 27 - Aug 28
Total with taxes and fees
8.8/10 Excellent! (1,007 reviews)
"Place was spotless! Staff very friendly. The pool area was well laid out. Having a restaurant attached was very convenient."
Reviewed on Aug 17, 2026
Senator Inn & Spa
284 Western Ave Augusta ME
Fully refundableReserve now, pay when you stay
$118 nightly
$129 total
Aug 30 - Aug 31
Total with taxes and fees
8/10 Very Good! (1,018 reviews)
"Outdoor pool area was nice - didn’t swim just relaxed in the loungers .. convenient location walkable to stores and local things. Loud at times but overall comfortable stay"
Reviewed on Aug 17, 2026
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 Winslow Vacation Packages
Winslow Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Augusta State Airport (AUG) |
Population | 7,800 |
Top Sights | First Congregational Church, Colby College and Waterville Opera House |
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Frequently asked questions
How much does a Winslow vacation package cost?
Offering great value package deals from $433 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'd like to book a cheap Winslow vacation package, consider visiting in November, December and January. You'll typically find lower rates on flights and accommodations during these quieter months — ideal for a budget-friendly break.
How many days is enough for Winslow?
With a well-organized schedule, you can easily tick off the top Winslow sights in a few days. But if you want to discover hidden gems or go on day tours, consider booking your Winslow vacation for longer.
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.
Does Expedia offer Book Now, Pay Later Winslow vacation packages?
Jet off on your perfect escape to Winslow with help from Expedia's Book Now, Pay Later vacations. There's no need to scrimp and save or wait until the next payday — we've partnered with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans mean you can split the cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's easy to stay on budget and snap up bargains while they last.
Explore a world of travel with Expedia
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.