Winslow Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Winslow
Maine Evergreen Hotel, an Ascend Collection Hotel
65 Whitten Rd Augusta ME
Fully refundable
S$209
13 Sept - 14 Sept
includes taxes & fees
9.2/10 Wonderful! (1,009 reviews)
"Everything"
Reviewed on 24 Aug, 2026
Fireside Inn & Suites Waterville
376 Main Street Waterville ME
Fully refundableReserve now, pay when you stay
S$178
20 Sept - 21 Sept
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"Rooms were clean, beds comfortable. Children enjoyed the pool. Disappointed that the hotel does not clean during multiple days stay."
Reviewed on 25 Aug, 2026
Senator Inn & Spa
284 Western Ave Augusta ME
Fully refundableReserve now, pay when you stay
S$182
31 Aug - 1 Sept
includes taxes & fees
8/10 Very good! (1,026 reviews)
"A new vendor for hand soap should be on order"
Reviewed on 22 Aug, 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.
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.
Frequently asked questions
How much does a Winslow holiday package cost?
Offering great value package deals 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?
- 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.
- 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.
- 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.
- 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.
