Winslow Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Winslow

Maine Evergreen Hotel, an Ascend Collection Hotel

Maine Evergreen Hotel, an Ascend Collection Hotel

2.5 out of 5
65 Whitten Rd Augusta ME
Fully refundable
The price is 4.146.030 ₫ per night from 9 Aug to 10 Aug
4.146.030 ₫
4.519.173 ₫ total
9 Aug - 10 Aug
includes taxes & fees
9.2/10 Wonderful! (1,008 reviews)
"Great room - but small bathroom."

Reviewed on 25 Jul 2026

Maine Evergreen Hotel, an Ascend Collection Hotel
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 3.032.788 ₫ per night from 23 Aug to 24 Aug
3.032.788 ₫
3.305.739 ₫ total
23 Aug - 24 Aug
includes taxes & fees
Fireside Inn & Suites Waterville
Senator Inn & Spa

Senator Inn & Spa

3 out of 5
284 Western Ave Augusta ME
Fully refundableReserve now, pay when you stay
The price is 3.790.656 ₫ per night from 2 Aug to 3 Aug
3.790.656 ₫
4.131.815 ₫ total
2 Aug - 3 Aug
includes taxes & fees
8/10 Very good! (1,006 reviews)
"Loved it! Quiet. Beautiful. The best jetted tub and fireplace."

Reviewed on 24 Jul 2026

Senator Inn & Spa
See all 470 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.

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.
See properties

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?

  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.