Winslow Vacation Packages

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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.
Flagship Inn and Suites

Flagship Inn and Suites

2.5 out of 5
Price was CA $1,069, price is now CA $980 per person
CA $980
per person
Sep 27 - Sep 30
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Augusta (AUG)
8.2/10 Very Good! (1,011 reviews)
It was a nice place to stay! Quiet and clean. Agreeable personnel!

Reviewed on Aug. 20, 2025

Greenleaf Inn

Greenleaf Inn

2 out of 5
Price was CA $1,825, price is now CA $1,460 per person
CA $1,460
per person
Sep 27 - Sep 30
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Augusta (AUG)
9.4/10 Exceptional! (9 reviews)
The location and view of this property was excellent. The staff gave good dining recommendations. The fire pit at night with s’mores was nice. We were given a nice bouquet of flowers at time of check in. The morning breakfast was a bit different. The kitchen was stocked with eggs, cream cheese, yogurt and condiments and pastries. You were responsible to make your own breakfast in the kitchen.

Reviewed on Jul. 23, 2025

House near Acadia National Park

House near Acadia National Park

4 out of 5
Price was CA $2,175, price is now CA $1,901 per person
CA $1,901
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Augusta (AUG)
9.8/10 Exceptional! (18 reviews)
This house was perfect for my girls trip. Close to bar harbor and Acadia national park. The home was clean and full of everything we need for our stay. Highly recommend this house! When I return to Bar Harbor I will be staying here again!

Reviewed on Jun. 30, 2025

OneSixtyFive

OneSixtyFive

3 out of 5
Price was CA $1,731, price is now CA $1,551 per person
CA $1,551
per person
Oct 26 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Augusta (AUG)
9.4/10 Exceptional! (127 reviews)
Perfect for convenience, lovely staff and accommodation!

Reviewed on Aug. 17, 2025

The Brunswick Hotel

The Brunswick Hotel

3 out of 5
Price was CA $1,445, price is now CA $1,313 per person
CA $1,313
per person
Oct 26 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Augusta (AUG)
9.2/10 Wonderful! (816 reviews)
A lovely and comfortable inn with a nice continental breakfast and a fine restaurant. Walkable to a quaint town with super dining and shopping options! Friendly staff and convenient for exploring the area.

Reviewed on Aug. 18, 2025

Ready to book your vacation to Winslow?

 

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Winslow Hotel Deals

Maine Evergreen Hotel, Ascend Hotel Collection

Maine Evergreen Hotel, Ascend Hotel Collection

2.5 out of 5
65 Whitten Rd, Augusta, ME
Fully refundableReserve now, pay when you stay
The price is CA $215 per night from Sep 1 to Sep 2
CA $215
CA $234 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (1,010 reviews)
"Great little hotel. A bit dated but the hotel is clean and quiet and the breakfast was wonderful. Would stay again and recommend to family and friends."

Reviewed on Aug. 19, 2025

Maine Evergreen Hotel, Ascend Hotel Collection
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 $202 per night from Aug 24 to Aug 25
CA $202
CA $220 total
Aug 24 - Aug 25
includes taxes & fees
8.6/10 Excellent! (999 reviews)
Exceptional
"Everyone was so pleasant and pet friendly specially where I have a Service Dog."

Reviewed on Aug. 19, 2025

Fireside Inn & Suites Waterville
The Elmwood

The Elmwood

2.5 out of 5
455 Kennedy Memorial Dr, Waterville, ME
Fully refundableReserve now, pay when you stay
The price is CA $207 per night from Aug 24 to Aug 25
CA $207
CA $225 total
Aug 24 - Aug 25
includes taxes & fees
8.4/10 Very Good! (457 reviews)
"Amanda at check in was fantastic! Room recently refurbished, clean, and comfortable."

Reviewed on Aug. 16, 2025

The Elmwood
See all 437 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Winslow

Colby College

Colby College

Explore the campus of Colby College, during your trip to Waterville. While in this family-friendly area, you can savor the top-notch restaurants.

Colby College

Frequently asked questions

How much does a Winslow vacation package cost?
You can snap up a vacation package to this popular destination from CA $980 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.

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