Winthrop Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Your Winthrop Vacation

With all the details organized before you head off, our Winthrop vacation packages mean you can focus more on having a great time. Whether you're staying in the neighborhood of Readfield, which is good for culture, or someplace else in town, this city offers a wealth of discoveries. Fill your days with tours of Cobbosseecontee Lake, Augusta Country Club and Maranacook Lake, some of the top attractions you really should see during your trip to Winthrop. A couple of quick clicks is all it takes to create a tailored Winthrop vacation on Expedia.

Top Winthrop 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
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Augusta (AUG)
8.2/10 Very Good! (1,007 reviews)
Staff are very friendly and helpful. Pratik was very accommodating and so helpful. Went above and beyond

Reviewed on Jul. 12, 2025

Greenleaf Inn

Greenleaf Inn

2 out of 5
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Augusta (AUG)
10/10 Exceptional! (7 reviews)
Hawthorn Extended Stay by Wyndham Ellsworth / Bar Harbor

Hawthorn Extended Stay by Wyndham Ellsworth / Bar Harbor

3 out of 5
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Augusta (AUG)
8.2/10 Very Good! (1,000 reviews)
Average hotel cross the board

Reviewed on Jul. 3, 2025

Best Western Plus Brunswick Bath

Best Western Plus Brunswick Bath

2.5 out of 5
per person
Aug 18 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Augusta (AUG)
8.2/10 Very Good! (1,005 reviews)
Close to where we had to be.

Reviewed on Jul. 12, 2025

Pressey House Lakeside Bed & Breakfast

Pressey House Lakeside Bed & Breakfast

3 out of 5
per person
Aug 14 - Aug 20
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Augusta (AUG)
No reviews

Ready to book your vacation to Winthrop?

 

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Winthrop Hotel Deals

Fantastic Lakefront Cabin W/ Free WiFi, Three Kayaks, Private Dock, & Firepit
Fantastic Lakefront Cabin W/ Free WiFi, Three Kayaks, Private Dock, & Firepit
Winthrop
Tranquil and beautiful waterfront spot
"Well kept with all the right amenities. Beautiful views."

Reviewed on Jul. 23, 2024

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Fantastic Lakefront Cabin W/ Free WiFi, Three Kayaks, Private Dock, & Firepit
Escape to our cozy Winthrop cabin on Dexter Pond
Escape to our cozy Winthrop cabin on Dexter Pond
Winthrop
10/10 Exceptional! (12 reviews)
So relaxing!
"The cabin was so clean and welcoming. Our hosts were friendly and helpful. The views of the pond were wonderful. We were looking for a peaceful get away and it was just that! Will go back next year."

Reviewed on Jun. 30, 2025

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Escape to our cozy Winthrop cabin on Dexter Pond
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 $245 per night from Jul 13 to Jul 14
CA $245
CA $267 total
Jul 13 - Jul 14
includes taxes & fees
9/10 Wonderful! (1,009 reviews)
"Excellent"

Reviewed on Jul. 9, 2025

Maine Evergreen Hotel, Ascend Hotel Collection
See all 495 properties in Winthrop
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

Frequently asked questions

How much does a Winthrop vacation package cost?
Offering excellent value package deals from CA $1,175 on Expedia, you'll be thrilled with how little a vacation to Winthrop costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Winthrop?
To pick up cheap Winthrop vacation packages, organize your getaway outside of busy periods such as public holidays. You'll typically find better availability and lower prices for hotels and flights.
How many days is enough for Winthrop?
You can easily explore all the top attractions in Winthrop in a few days, including the popular Annabessacook Lake. If you're after a longer Winthrop vacation, look at what kind of day trips and activities are available close by.
How to find the best Winthrop package deals?
Use Expedia's filter tool to help you find some unbeatable Winthrop package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or search for Winthrop package deals in the low season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book a Winthrop vacation as a package?
You can enjoy significant savings on your next Winthrop getaway by booking a personalized vacation package. Click on the "Package" heading, then enter your travel dates and destination to browse some great hotel prices and airfares. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Winthrop?
Land amazing discounts by reserving your flights in advance with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Winthrop getaway.
How to plan a trip to Winthrop?

  1. Pick your travel dates: What you plan to do in Winthrop and your favourite season can help you decide when to go.
  2. Calculate your budget: Make sure you have enough money to pay for everything from meals and transportation to airfares and activities. Your hotel will likely be the largest expense during your trip to Winthrop.
  3. Work out your trip length: Think about how long you want to spend exploring Winthrop. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to find a Winthrop vacation package that brings all your bookings together.

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