Winthrop Vacations from $747

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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.
The Brunswick Hotel

The Brunswick Hotel

3 out of 5
Price was $919, price is now $747 per person
$747
per person
Jun 23 - Jun 27
found 14 hours ago
Roundtrip flight included
Chicago (CHI) to Augusta (AUG)
9.4/10 Exceptional! (937 reviews)
Fantastic location in town. Hotel is very clean and rooms were comfortable. Def will return.

Reviewed on Apr 26, 2026

Topside Inn

Topside Inn

3 out of 5
Save 100% on your flight
Price was $1,730, price is now $1,230 per person
$1,230
per person
Jun 23 - Jun 27
found 14 hours ago
Roundtrip flight included
Chicago (CHI) to Augusta (AUG)
10/10 Exceptional! (90 reviews)
Outstanding facility. Elegant and classy. Gourmet breakfast. Great view. Incredibly friendly staff. Intimate bar. Wonderful.

Reviewed on May 7, 2026

Greenleaf Inn

Greenleaf Inn

2 out of 5
Save 100% on your flight
Price was $1,983, price is now $1,513 per person
$1,513
per person
Jul 19 - Jul 25
found 22 hours ago
Roundtrip flight included
Chicago (CHI) to Augusta (AUG)
9.2/10 Wonderful! (15 reviews)
Our host is the best! Such a beautiful property.

Reviewed on Nov 16, 2025

Little Landing Cottage-gorgeous View BBQ Wi-fi

Little Landing Cottage-gorgeous View BBQ Wi-fi

3.5 out of 5
Save 100% on your flight
Price was $3,634, price is now $2,944 per person
$2,944
per person
Jul 18 - Jul 25
found 18 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Augusta (AUG)
10/10 Exceptional! (1 review)
I love this little cottage. I will definitely be staying again. Thank you.!!!!!

Reviewed on May 26, 2025

Sheepscot Harbour Village Resort

Sheepscot Harbour Village Resort

2.5 out of 5
Price was $1,753, price is now $1,423 per person
$1,423
per person
Jul 19 - Jul 25
found 22 hours ago
Roundtrip flight included
Chicago (CHI) to Augusta (AUG)
9/10 Wonderful! (232 reviews)
We were surprised that we couldn’t get a hot coffee in the mornings. They never came to make up our room. The towels were like sandpaper. The bed and comforter were great. Though they have a restaurant they couldn’t even give us real milk for the in room coffee maker, just lightener! I don’t think I’d stay again.

Reviewed on Dec 16, 2025

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Winthrop Hotel Deals

Discover your retreat - 3-bedroom cottage in Winthrop

Discover your retreat - 3-bedroom cottage in Winthrop

Winthrop ME
10/10 Exceptional! (181 reviews)
Lovely house with a a beautiful view! Very clean and tidy, easy to find what you need in the home. A perfect relaxing and quiet retreat

Reviewed on Mar 30, 2026

Get rates
Discover your retreat - 3-bedroom cottage in Winthrop
Cozy cottage in the Winthrop Lakes Area

Cozy cottage in the Winthrop Lakes Area

Winthrop ME
$171 nightly
The price is $187 total per night from May 18 to May 19
$187 total
May 18 - May 19
Total with taxes and fees
9.6/10 Exceptional! (5 reviews)
My only regret is that we were only there for one night & didn’t have time to enjoy the surroundings.

Reviewed on May 2, 2026

Cozy cottage in the Winthrop Lakes Area
Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters

Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters

Winthrop ME
$251 nightly
The price is $274 total per night from May 25 to May 26
$274 total
May 25 - May 26
Total with taxes and fees
Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters
See all 525 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 $747 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.