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.
Topside Inn

Topside Inn

3 out of 5
per person
Oct 17 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Augusta (AUG)
10/10 Exceptional! (13 reviews)
This is a beautiful, five star in with beautiful views, impeccable rooms, and wonderful service. Morning breakfast was also wonderful.

Reviewed on Jul. 26, 2025

Flagship Inn and Suites

Flagship Inn and Suites

2.5 out of 5
per person
Aug 28 - Aug 31
found 23 hours ago
Roundtrip non-stop flight included
Charlottetown (YYG) to Augusta (AUG)
8.2/10 Very Good! (1,005 reviews)
We only stayed one night and left before breakfast so we have little to say about our stay. It was a comfortable, clean room and the pool was enjoyable. I would recommend others to consider staying here.

Reviewed on Jul. 28, 2025

Mid-Town Motel

Mid-Town Motel

2 out of 5
per person
Aug 28 - Aug 31
found 23 hours ago
Roundtrip non-stop flight included
Charlottetown (YYG) to Augusta (AUG)
9/10 Wonderful! (161 reviews)
Clean, very friendly staff and great location. The bathroom was small but clean. Walkable to town for restaurants and our boat tour. Never had to worry about parking.

Reviewed on Jul. 28, 2025

Jordan Hotel

Jordan Hotel

3 out of 5
per person
Aug 28 - Aug 31
found 23 hours ago
Roundtrip non-stop flight included
Charlottetown (YYG) to Augusta (AUG)
8.8/10 Excellent! (366 reviews)
The staff was extremely helpful and friendly. Will definitely be back.

Reviewed on Jul. 27, 2025

Grand Summit Hotel

Grand Summit Hotel

3 out of 5
per person
Aug 28 - Aug 31
found 23 hours ago
Roundtrip non-stop flight included
Charlottetown (YYG) to Augusta (AUG)
8.2/10 Very Good! (265 reviews)
We hadn’t visited Grand Summit for a while, but upon our return improvements to the facility made our visit very enjoyable. In particular, the upgrade to the pool area with resurfacing and the addition of a new hot tub was a major improvement. Staff were very helpful. Breakfast in Camp was outstanding!!

Reviewed on Jul. 17, 2025

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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 $232 per night from Aug 17 to Aug 18
CA $232
CA $253 total
Aug 17 - Aug 18
includes taxes & fees
9/10 Wonderful! (1,005 reviews)
Paintings by local artists
"My sister, niece and I stayed here for one night in July. The hotel was comfortable and clean, and the front desk staff member who checked us in was very friendly. Also, we loved all the paintings by local artists that were displayed throughout the hotel."

Reviewed on Jul. 21, 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 $200 per night from Aug 3 to Aug 4
CA $200
CA $219 total
Aug 3 - Aug 4
includes taxes & fees
8.6/10 Excellent! (1,010 reviews)
"Squeaky clean hotel has a nice grab and go breakfast and a lovely outdoor pool."

Reviewed on Jul. 27, 2025

Fireside Inn & Suites Waterville
Senator Inn & Spa

Senator Inn & Spa

3 out of 5
284 Western Ave, Augusta, ME
Fully refundableReserve now, pay when you stay
The price is CA $224 per night from Aug 28 to Aug 29
CA $224
CA $245 total
Aug 28 - Aug 29
includes taxes & fees
7.6/10 Good! (1,006 reviews)
"The hotel was fine and we liked the upgrade they gave us. What we didn't like was driving in the area. It was all one way streets. We had a very hard time finding a good place to have dinner and ended up with fast food."

Reviewed on Jul. 25, 2025

Senator Inn & Spa
See all 458 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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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 $944 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.