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.
Jordan Hotel
CA $1,049
per person
Oct 11 - Oct 17
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Augusta (AUG)
8.8/10 Excellent! (549 reviews)
Beautiful location. Hiking trails accessible from the property. Clean rooms. Large heated pool and 2 hot tubs. The staff were extremely friendly and helpful.
Reviewed on Aug 17, 2026
Bluebird Ocean Point Inn
Ocean Point
CA $1,412
per person
Sep 21 - Sep 28
found 24 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Augusta (AUG)
8.8/10 Excellent! (597 reviews)
the staff were so kind & attentive! We felt so welcomed. We had help offered at every turn. We also ate breakfast at the restaurant and it was SOOOO delicious!!
Reviewed on Aug 18, 2026
Fairfield Inn & Suites by Marriott Brunswick Freeport
CA $1,983
per person
Sep 21 - Sep 28
found 24 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Augusta (AUG)
8.8/10 Excellent! (492 reviews)
It was perfect for our needs. Close to Freeport, Bath, Wiscasset and Brunswick.
It was clean and well maintained. Breakfast was very nice. Parking was on site and convenient. Staff were very helpful
Reviewed on Aug 18, 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 $199
CA $216 total
Aug 30 - Aug 31
includes taxes & fees
9.2/10 Wonderful! (1,004 reviews)
"Everything about this hotel is excellent including breakfast"
Reviewed on Aug 18, 2026
Fireside Inn & Suites Waterville
376 Main Street Waterville ME
Fully refundableReserve now, pay when you stay
CA $150
CA $164 total
Aug 23 - Aug 24
includes taxes & fees
8.8/10 Excellent! (1,009 reviews)
"Good stay"
Reviewed on Aug 18, 2026
Senator Inn & Spa
284 Western Ave Augusta ME
Fully refundableReserve now, pay when you stay
CA $178
CA $195 total
Aug 31 - Sep 1
includes taxes & fees
8/10 Very good! (1,019 reviews)
"It was a very pleasant stay"
Reviewed on Aug 18, 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 $758 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.
