Winslow Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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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.
Evergreen Valley Inn by Coolvacay

Evergreen Valley Inn by Coolvacay

3 out of 5
Price was CA $1,239, price is now CA $997 per person
CA $997
per person
Aug 15 - Aug 22
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Augusta (AUG)
8/10 Very good! (184 reviews)
I met three staff members here. They could not have been nicer or more accommodating. Seriously...the most friendly staff I have encountered in all of my travel days.

Reviewed on Jun 24, 2026

Spruce Point Inn

Spruce Point Inn

3.5 out of 5
Price was CA $3,213, price is now CA $2,471 per person
CA $2,471
per person
Aug 15 - Aug 22
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Augusta (AUG)
8.8/10 Excellent! (408 reviews)
Nice place to stay but rooms can use an upgrade. Remove rugs and upgrade television sets. Also resort fee is expensive especially during off season.

Reviewed on Jun 29, 2026

Grand Summit Hotel

Grand Summit Hotel

3 out of 5
Price was CA $1,294, price is now CA $1,052 per person
CA $1,052
per person
Aug 15 - Aug 22
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Augusta (AUG)
8.4/10 Very good! (380 reviews)
Easy ski in ski out access very nice staff that were always willing to help

Reviewed on Jul 1, 2026

Best Western Plus Rumford Falls

Best Western Plus Rumford Falls

2.5 out of 5
Price was CA $1,448, price is now CA $1,178 per person
CA $1,178
per person
Aug 15 - Aug 22
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Augusta (AUG)
9.4/10 Exceptional! (284 reviews)
Clean updated room, decent breakfast. Nice for family overnight stay

Reviewed on Jun 25, 2026

Jordan Hotel

Jordan Hotel

3 out of 5
Price was CA $1,248, price is now CA $1,017 per person
CA $1,017
per person
Aug 15 - Aug 22
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Augusta (AUG)
8.8/10 Excellent! (539 reviews)
Great pool and we loved the balct

Reviewed on Jun 29, 2026

Ready to book your vacation to Winslow?

 

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Winslow Hotel Deals

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 CA $216 per night from Jul 9 to Jul 10
CA $216
CA $236 total
Jul 9 - Jul 10
includes taxes & fees
9.2/10 Wonderful! (1,010 reviews)
"Great staff. Great vibe. Great experience."

Reviewed on Jul 1, 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 CA $160 per night from Jul 4 to Jul 5
CA $160
CA $175 total
Jul 4 - Jul 5
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"I booked a double room. When I checked in I was told I was being upgraded to a suite at no extra cost. When I went to the room they assigned and as far as I’m concerned it was not a suite. It was the room I booked a double. If that was a suite I hate to see what a regular double room is."

Reviewed on Jun 30, 2026

Fireside Inn & Suites Waterville
Best Western Plus Augusta Civic Center Inn

Best Western Plus Augusta Civic Center Inn

2.5 out of 5
110 Community Drive Augusta ME
Fully refundableReserve now, pay when you stay
The price is CA $154 per night from Jul 5 to Jul 6
CA $154
CA $167 total
Jul 5 - Jul 6
includes taxes & fees
7.8/10 Good! (1,000 reviews)
"The carpet in our room was damp and the room smelled moldy. The breakfast was ok. Easy parking."

Reviewed on Jun 30, 2026

Best Western Plus Augusta Civic Center Inn
See all 473 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.
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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.
See properties

Frequently asked questions

How much does a Winslow vacation package cost?
You can snap up a vacation package to this popular destination from CA $997 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?

  1. 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.
  2. 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.
  3. 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.
  4. Combine your airfare and accommodations: Once you've settled on your dates and duration, lock in the ideal Winslow vacation package for you.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.