Winslow Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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
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.
Top Winslow Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Five Gables Inn
CA $1,095
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Augusta (AUG)
10/10 Exceptional! (2 reviews)
We loved the view, along with the kindness and attentiveness of all who worked there. The location was great and made it easy to get to other places of interest in the area, great restaurants, botannical gardens, etc.
Reviewed on Sep 7, 2026
Maine Evergreen Hotel, an Ascend Collection Hotel
CA $1,055
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Augusta (AUG)
9.4/10 Exceptional! (1,009 reviews)
Beautiful hotel, with all sorts of artwork on the hallway walls. Service was very friendly and efficient at all times. The included breakfast buffet was good, especially the cute and tasty pastries. Vibrant atmosphere in the evenings in the bar. Love the decor all around. Did not end up using the pool due to a busy schedule and chilly temps, but it looked inviting. Room was a little cozy for a family of four, but the bathroom was spacious. Great access to the Maine turnpike, not far from the Capitol, downtown Hallowell, or nearby Farmingdale and Gardiner. Would stay again!
Reviewed on Sep 20, 2026
Ready to book your vacation to Winslow?
Winslow Hotel Deals
Maine Evergreen Hotel, an Ascend Collection Hotel
65 Whitten Rd Augusta ME
Fully refundable
CA $207
CA $226 total
Oct 18 - Oct 19
includes taxes & fees
9.4/10 Exceptional! (1,005 reviews)
"Beautiful hotel, with all sorts of artwork on the hallway walls. Service was very friendly and efficient at all times. The included breakfast buffet was good, especially the cute and tasty pastries. Vibrant atmosphere in the evenings in the bar. Love the decor all around. Did not end up using the ..."
Reviewed on Sep 20, 2026
Fireside Inn & Suites Waterville
376 Main Street Waterville ME
Fully refundableReserve now, pay when you stay
CA $164
CA $179 total
Oct 4 - Oct 5
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
"Room was clean and the shower was hot! What more to ask! Lol"
Reviewed on Sep 20, 2026
Senator Inn & Spa
284 Western Ave Augusta ME
Fully refundableReserve now, pay when you stay
CA $183
CA $200 total
Oct 19 - Oct 20
includes taxes & fees
8/10 Very good! (1,002 reviews)
"Clean room, excellent staff. Restaurant and fitness equipment were a nice surprise."
Reviewed on Sep 19, 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)
Learn about the local history of Winslow when you spend time at Fort Halifax. Stroll along the riverfront or experience the area's entertainment venues.
Frequently asked questions
How much does a Winslow vacation package cost?
You can snap up a vacation package to this popular destination from CA $682 on Expedia. But how much your vacation to Winslow costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Winslow?
You can typically find lower prices and greater availability in January, February and March. Take a look at our cheap Winslow vacation packages and you could land some great off-season discounts.
How many days is enough for Winslow?
With a well-planned itinerary, you can easily visit the top Winslow sights in a few days. But if you prefer to venture off the beaten track or go on day tours, think about booking your Winslow vacation for longer.
How to find the best Winslow package deals?
Start your search for a Winslow package deal by entering your destination and preferred trip dates under our "Packages" tab. Then add a few filters, like "Property type" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Winslow package deal straight away, just change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Winslow escape underway.
Is it cheaper to book a Winslow vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll typically land a better deal than booking each component separately. And you'll still get the freedom to create a tailored Winslow vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Winslow?
If you're considering a spontaneous Winslow trip, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can land sensational deals on your hotels and flights by booking well in advance.
How to plan a trip to Winslow?
- Pick the perfect time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to visit Winslow.
- Figure out your budget: Ensure you have enough money to cover everything from meals and transportation to activities and flights. Your hotel will probably be the biggest expense during your trip to Winslow.
- Work out your trip length: Think about how much time you want to spend exploring Winslow. Plan your days so you can get to all the experiences and attractions you're interested in at a comfortable pace.
- Combine your airfare and accommodations: Once you've settled on your dates and duration, lock in the ideal Winslow vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
