Winthrop Vacations from $585

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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.
Comfort Inn Ellsworth - Bar Harbor

Comfort Inn Ellsworth - Bar Harbor

2.5 out of 5
Price was $637, price is now $585 per person
$585
per person
Mar 30 - Apr 3
found 16 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Augusta (AUG)
9/10 Wonderful! (879 reviews)
I stay here often. Its consistent in quality and condition.

Reviewed on Feb 20, 2026

Greenleaf Inn

Greenleaf Inn

2 out of 5
Price was $951, price is now $680 per person
$680
per person
May 1 - May 4
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Augusta (AUG)
9/10 Wonderful! (13 reviews)
Our host is the best! Such a beautiful property.

Reviewed on Nov 16, 2025

The Brunswick Hotel

The Brunswick Hotel

3 out of 5
Price was $1,013, price is now $872 per person
$872
per person
May 1 - May 6
found 17 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Augusta (AUG)
9.4/10 Exceptional! (868 reviews)
The location was perfect, rooms were clean and waitstaff was courteous.

Reviewed on Feb 22, 2026

Admirals Quarters Inn

Admirals Quarters Inn

2 out of 5
Price was $1,428, price is now $1,287 per person
$1,287
per person
Apr 23 - Apr 26
found 8 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Augusta (AUG)
9.4/10 Exceptional! (28 reviews)
The room was great. Lots of space. The bed was super comfortable. The breakfast items were delicious. We enjoyed the many selections of tea and coffee. The proprietor,Jersey was terrific. He explained the property and area Had a wonderful time

Reviewed on Dec 1, 2025

OneSixtyFive

OneSixtyFive

3 out of 5
Price was $829, price is now $761 per person
$761
per person
Mar 30 - Apr 3
found 16 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Augusta (AUG)
9.4/10 Exceptional! (142 reviews)
Clean, quiet, and comfortable. Very nice setting in the carriage house, enjoyable stay.

Reviewed on Nov 1, 2025

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Winthrop Hotel Deals

Spacious 5-bedroom lakefront home on pristine Lower Narrows Pond in Winthrop

Spacious 5-bedroom lakefront home on pristine Lower Narrows Pond in Winthrop

Winthrop ME
10/10 Exceptional! (9 reviews)
We visited for the weekend of our wedding and used the house and garage/apartment for the rehearsal dinner and to get ready. Every single person loved the home and commented on how clean and homey it was. We 100% recommend staying here and would love to come back in the future

Reviewed on Oct 6, 2025

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Spacious 5-bedroom lakefront home on pristine Lower Narrows Pond in Winthrop
Discover your retreat - 3-bedroom cottage in Winthrop

Discover your retreat - 3-bedroom cottage in Winthrop

Winthrop ME
10/10 Exceptional! (179 reviews)
Great host - we got a pretty big snow storm the host was making sure everything was ok. 2nd time staying here and won’t be our last. House is very clean and the host is great

Reviewed on Feb 24, 2026

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Discover your retreat - 3-bedroom cottage in Winthrop
Maine Evergreen Hotel, an Ascend Collection Hotel

Maine Evergreen Hotel, an Ascend Collection Hotel

2.5 out of 5
65 Whitten Rd Augusta ME
Fully refundable
$106 nightly
The price is $116 total per night from Mar 8 to Mar 9
$116 total
Mar 8 - Mar 9
Total with taxes and fees
9.2/10 Wonderful! (1,000 reviews)
Great staff

Reviewed on Feb 25, 2026

Maine Evergreen Hotel, an Ascend Collection Hotel
See all 490 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.

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 $585 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.

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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.