Winslow Vacations from $518

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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.
Flagship Inn and Suites

Flagship Inn and Suites

2.5 out of 5
per person
Oct 24 - Oct 28
found 1 hour ago
Roundtrip non-stop flight included
Dallas (DFW) to Augusta (AUG)
8.2/10 Very Good! (1,011 reviews)
The free breakfast was great and convenient to town

Reviewed on Aug 8, 2025

House near Acadia National Park

House near Acadia National Park

4 out of 5
Save 100% on your flight
per person
Oct 24 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Augusta (AUG)
9.8/10 Exceptional! (18 reviews)
This house was perfect for my girls trip. Close to bar harbor and Acadia national park. The home was clean and full of everything we need for our stay. Highly recommend this house! When I return to Bar Harbor I will be staying here again!

Reviewed on Jun 30, 2025

Topside Inn

Topside Inn

3 out of 5
Save 100% on your flight
per person
Oct 15 - Oct 18
found 24 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Augusta (AUG)
10/10 Exceptional! (30 reviews)
One of the best stays I have ever had.

Reviewed on Aug 8, 2025

Newly Renovated Acadia Apartment Maple Street

Newly Renovated Acadia Apartment Maple Street

3 out of 5
per person
Oct 24 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Augusta (AUG)
No reviews
The Brunswick Hotel

The Brunswick Hotel

3 out of 5
per person
Oct 10 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Augusta (AUG)
9.2/10 Wonderful! (816 reviews)
Very clean and quiet place, next door to the grocery store and walkable to Main Street shops!

Reviewed on Aug 6, 2025

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Discover the most popular places to visit in Winslow

Sunsets in Colby

Colby College

4.5/5(37 reviews)

Explore the campus of Colby College, during your trip to Waterville. While in this family-friendly area, you can savor the top-notch restaurants.

Colby College

Waterville Opera House

4.5/5(7 reviews)

You can get tickets for a performance at Waterville Opera House on your trip to Waterville. While in this family-friendly area, you can savor the top-notch restaurants.

Waterville Opera House

Thomas College

4.5/5(2 reviews)

Explore the campus of Thomas College, during your trip to Waterville. While in this family-friendly area, you can savor the top-notch restaurants.

Thomas College

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
$159 nightly
The price is $173 total per night from Sep 7 to Sep 8
$173 total
Sep 7 - Sep 8
Total includes taxes and fees
9/10 Wonderful! (1,000 reviews)
"The hotel premises was very clean and neat."

Reviewed on Aug 7, 2025

Maine Evergreen Hotel, Ascend Hotel Collection
Holiday Inn Express & Suites Waterville - North by IHG

Holiday Inn Express & Suites Waterville - North by IHG

2.5 out of 5
332 Main St, Waterville, ME
Fully refundable
$135 nightly
The price is $147 total per night from Sep 4 to Sep 5
$147 total
Sep 4 - Sep 5
Total includes taxes and fees
8.6/10 Excellent! (780 reviews)
"Was really impressed. Had not stayed at a Holiday Inn in years and always thought that Express was a second great. Was shocked with the great condition of this hotel"

Reviewed on Aug 8, 2025

Holiday Inn Express & Suites Waterville - North by IHG
The Elmwood

The Elmwood

2.5 out of 5
455 Kennedy Memorial Dr, Waterville, ME
Fully refundableReserve now, pay when you stay
$149 nightly
The price is $162 total per night from Aug 11 to Aug 12
$162 total
Aug 11 - Aug 12
Total includes taxes and fees
8.6/10 Excellent! (439 reviews)
"I liked that it was quite qnd out of ghe way"

Reviewed on Aug 6, 2025

The Elmwood
See all 448 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.

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Frequently asked questions

How much does a Winslow vacation package cost?
Offering great value package deals from $518 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.