Winthrop Vacations from $773
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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.
The Latest Winthrop vacation packages
Price found within the past 48 hours. Click for updated prices.
Stone Park
$1,306
per person
Nov 23 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) to Augusta (AUG)
9.4/10 Exceptional! (377 reviews)
There is no elevator so if you are in a third floor room you will be dragging all your luggage and belongings up two flights of stairs. There is only one window and that is in the bedroom. Kitchen utensils are pretty beat up we had to buy some and there is a fourteen day cancellation policy so by the time you find out all this it’s too late to change.
Reviewed on Oct 17, 2026
Stay near popular Winthrop attractions
Little Cobbossee Lake
Commune with nature and explore the great outdoors at Little Cobbossee Lake during your travels in Winthrop.
Mt Pisgah Conservation Area Trailhead
Climb to the historic 60-foot fire tower for panoramic views stretching to Mount Washington. The well-maintained trails wind through sugar maples and diverse flora, offering a serene escape into Maine's natural beauty.
Winthrop Hotel Deals
Escape to our cozy Winthrop cabin on Dexter Pond
Winthrop ME
10/10 Exceptional! (42 reviews)
"The cabin offers all the basics and is in a beautiful location. Dexter Pond is quiet and the cabin feels very private. Lovely space, very clean, and the location is perfect."
Reviewed on Oct 13, 2026
4-bedroom Direct Waterfront LAKEHOUSE in Maine. Fire pit, deck, private dock.
Winthrop ME
9.6/10 Exceptional! (8 reviews)
"Wonderful lake setting. We enjoyed outdoor activities, relaxing and indoors was roomy and comfortable. It was a great place to catch up with family and day trips to nearby Maine towns."
Reviewed on Oct 28, 2025
Discover your retreat - 3-bedroom cottage in Winthrop
Winthrop ME
9.8/10 Exceptional! (198 reviews)
"Second time staying here. Fits all my needs for a quick fishing trip. Place can use some upgrades. Water smell was really harsh when showering, I believe it needs a water softener. Over all I would recommend it ."
Reviewed on Oct 14, 2026
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.
Find the Best Winthrop Vacation Packages
Winthrop Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Augusta State Airport (AUG) |
Population | 2,700 |
Max Temp Winter | 30ºF |
Max Temp Summer | 75ºF |
Top Sights | Theatre at Monmouth, Maine State Museum and Johnson Hall |
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Frequently asked questions
How much does a Winthrop vacation package cost?
Offering excellent value package deals from $773 on Expedia, you'll be surprised at how little a vacation to Winthrop costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Winthrop?
If you're hoping to snag a cheap Winthrop vacation package, consider planning a trip in October, November and December. You're likely to find lower rates on flights and hotels during these quieter months — perfect for budget-conscious travelers.
How many days is enough for Winthrop?
With a well-planned schedule, you can easily tick off the top Winthrop sights in a few days. But if you want to discover hidden gems or take day trips, consider booking your Winthrop vacation for longer.
How to find the best Winthrop package deals?
Use Expedia's handy filters to help you find some unbeatable Winthrop package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or search for Winthrop package deals in the off-season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Winthrop vacation as a package?
You can enjoy significant savings on your next Winthrop getaway by booking a customized vacation package. Check the "Package" heading, then select your travel dates and destination to browse the best airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Winthrop?
If you're considering a spontaneous Winthrop adventure, check out 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 find sensational deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Winthrop vacation packages?
If you're anything like us, you love traveling but are not a fan of the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the total cost of your Winthrop vacation across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure cheap vacation packages with payment plans as soon as you spot them.
Explore a world of travel with Expedia
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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.
