Winslow Holidays

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    Better together

    Save up to S$134 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

Winslow Flight & Hotel Packages

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

Comfort Inn Brunswick

2.5 out of 5
per person
17 Oct - 22 Oct
found 1 day ago
Return flight included
Minneapolis (MSP) to Augusta (AUG)
9/10 Wonderful! (1,001 reviews)
It served my purpose.

Reviewed on 14 Aug, 2025

Top hotels in Winslow

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 S$223 per night from 14 Sept to 15 Sept
S$223
14 Sept - 15 Sept
includes taxes & fees
9/10 Wonderful! (1,006 reviews)
"The staff was very friendly."

Reviewed on 13 Aug, 2025

Maine Evergreen Hotel, Ascend Hotel Collection
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 S$208 per night from 17 Aug to 18 Aug
S$208
17 Aug - 18 Aug
includes taxes & fees
8.4/10 Very Good! (449 reviews)
Very nice for the price
"Room was clean and modern, staff was very friendly and helpful."

Reviewed on 10 Aug, 2025

The Elmwood
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 S$199 per night from 17 Aug to 18 Aug
S$199
17 Aug - 18 Aug
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"Attached to the hotel is the Governor's restaurant (the pictures that show bakery items under glass). Pool and hot tub are well maintained, I see maintenance and staff all around the property from early hours until late. Grab and Go breakfast choices on par with many breakfast options from most hotel ..."

Reviewed on 13 Aug, 2025

Fireside Inn & Suites Waterville
See all 437 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 holiday package cost?
Offering great value package deals from S$964 on Expedia, you'll be pleasantly surprised at how much a holiday 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 holiday 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 holiday. 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 customise 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 travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Winslow holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to arranging accommodation and flights individually. Better still, you can customise 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 holiday 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 favourite 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 personalised Winslow holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.