Winthrop Vacation Packages
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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.
Top Winthrop Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Topside Inn
Price was CA $1,781, price is now CA $1,516 per person
CA $1,516
per person
Jul 23 - Jul 25
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Augusta (AUG)
10/10 Exceptional! (91 reviews)
Would definitely visit again. Staff was very welcoming, has a great attention to detail.
Breakfast was spectacular, a savory or sweet morning!! And the cookie of the day!! Always coffee and tea and plenty of snacks available!!!
The location, at the top of the hill, made for great viewing of the area, not only from our room but the main building as well. It was only a short walk to enjoy the downtown shops and restaurants.
Reviewed on May 16, 2026
Sunset Chalet-amazing Views Private hot tub
Price was CA $4,242, price is now CA $3,583 per person
CA $3,583
per person
Jul 8 - Jul 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Augusta (AUG)
10/10 Exceptional! (2 reviews)
Easy to find, amenties were great for kitchen, bathroom, and game room. We look forward to going again but try one of the treehouses.
Reviewed on Nov 3, 2024
Little Landing Cottage-gorgeous View BBQ Wi-fi
Price was CA $4,012, price is now CA $3,399 per person
CA $3,399
per person
Jul 8 - Jul 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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
Winthrop Hotel Deals
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
Cozy cottage in the Winthrop Lakes Area
Winthrop ME
The price is CA $158 per night from Jun 1 to Jun 2
CA $158
CA $273 total
Jun 1 - Jun 2
includes taxes & 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
Escape to our cozy Winthrop cabin on Dexter Pond
Winthrop ME
10/10 Exceptional! (26 reviews)
This is an amazing property. We stayed for 3 nights, right on Dexter pond. Cabin is quaint and beautiful. Lovely stay and highly recommend for a weekend getaway. We fished, had an outdoor fire. Visited a couple of local restaurants. The cabin was fully stocked as noted in the description. Very comfortable ...
Reviewed on May 17, 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.
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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.
