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.
Best Western Plus Augusta Civic Center Inn

Best Western Plus Augusta Civic Center Inn

2.5 out of 5
Price was CA $915, price is now CA $764 per person
CA $764
per person
Sep 25 - Sep 30
found 9 hours ago
Roundtrip flight included
Toronto (YTO) to Augusta (AUG)
7.8/10 Good! (1,000 reviews)
Seemed to be really run down to a degree. Air conditioning was on when we came into room and bedding/pillows damp.

Reviewed on Jul 5, 2026

Grand Summit Hotel

Grand Summit Hotel

3 out of 5
Price was CA $987, price is now CA $813 per person
CA $813
per person
Sep 25 - Sep 30
found 9 hours ago
Roundtrip flight included
Toronto (YTO) to Augusta (AUG)
8.4/10 Very good! (381 reviews)
Loved the pool and natural surroundings. Staff was friendly. Our room was very dated and in need of update. Patio door difficult to operate. Television did not work, no signal. Maintenance tried to fix but I don’t think there was a fix to it. Did not like the Murphy bed setup. No headboard to sit up in bed to read, watch tv. No end tables by the bed. We just felt this was a strange setup. Overall though we enjoyed our stay.

Reviewed on Jul 5, 2026

Jordan Hotel

Jordan Hotel

3 out of 5
Price was CA $975, price is now CA $804 per person
CA $804
per person
Sep 25 - Sep 30
found 9 hours ago
Roundtrip flight included
Toronto (YTO) to Augusta (AUG)
8.8/10 Excellent! (540 reviews)
Best experoence so far. We will be back again

Reviewed on Jul 6, 2026

Bluebird Ocean Point Inn

Bluebird Ocean Point Inn

3 out of 5
Ocean Point
Price was CA $1,291, price is now CA $1,084 per person
CA $1,084
per person
Sep 25 - Sep 30
found 9 hours ago
Roundtrip flight included
Toronto (YTO) to Augusta (AUG)
8.8/10 Excellent! (568 reviews)
The ocean views were perfect

Reviewed on Jul 8, 2026

Senator Inn & Spa

Senator Inn & Spa

3 out of 5
Price was CA $957, price is now CA $841 per person
CA $841
per person
Sep 25 - Sep 30
found 9 hours ago
Roundtrip flight included
Toronto (YTO) to Augusta (AUG)
7.8/10 Good! (1,003 reviews)
The spa and pools are awesome.

Reviewed on Jul 7, 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
The price is CA $228 per night from Jul 12 to Jul 13
CA $228
CA $249 total
Jul 12 - Jul 13
includes taxes & fees
9.2/10 Wonderful! (1,007 reviews)
"Un lugar muy acogedor. Limpio. Logares de comida y entretenimiento a pasos del lugar.. Lo recomiendo sin ningún repara."

Reviewed on Jul 7, 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
The price is CA $169 per night from Jul 12 to Jul 13
CA $169
CA $184 total
Jul 12 - Jul 13
includes taxes & fees
8.8/10 Excellent! (1,009 reviews)
"The place is very clean, the staff are super friendly, and the pool is sparkling clean. We really enjoyed our time here and will definitely be back! Highly recommended!"

Reviewed on Jul 7, 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 $165 per night from Jul 12 to Jul 13
CA $165
CA $180 total
Jul 12 - Jul 13
includes taxes & fees
7.8/10 Good! (1,004 reviews)
"Seemed to be really run down to a degree. Air conditioning was on when we came into room and bedding/pillows damp."

Reviewed on Jul 5, 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 $764 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.