Winthrop Vacations from $439

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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.
Flagship Inn and Suites
Greenleaf Inn
Newagen Seaside Inn
Spruce Point Inn
Topside Inn
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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

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

Escape to our cozy Winthrop cabin on Dexter Pond
Located directly in central downtown and beach area, fish or kayak from backyard
Located directly in central downtown and beach area, fish or kayak from backyard
Winthrop
Lake Region Charmer
"We stayed at this home while in town for Maine 70.3. The location was great. Winthrop is a cute little town. Home was close to two beautiful lakes. The backyard was very peaceful, right next to a stream. The home was well appointed and had everything we needed. The communication with the host was ..."

Reviewed on Aug 4, 2024

Located directly in central downtown and beach area, fish or kayak from backyard
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 $439 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.