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.
Jordan Hotel
Price was CA $876, price is now CA $788 per person
CA $788
per person
Jul 31 - Aug 3
found 18 hours ago
Roundtrip flight included
Toronto (YYZ) to Augusta (AUG)
8.8/10 Excellent! (534 reviews)
Clean rooms and friendly staff. However I was there towards the end of the ski season and there was noticeably less staff around to help with bags and ski equipment when checking in, but I guess this is expected when visiting outside of peak season
Reviewed on Apr 11, 2026
Senator Inn & Spa
Price was CA $1,410, price is now CA $1,231 per person
CA $1,231
per person
Aug 2 - Aug 9
found 11 hours ago
Roundtrip flight included
Toronto (YYZ) to Augusta (AUG)
7.8/10 Good! (1,012 reviews)
The cloud 9 Restaurant which is attached to the Inn was ok. Not many options. Rooms were clean, beds are extremely hard.
Reviewed on May 9, 2026
OneSixtyFive
Price was CA $1,779, price is now CA $1,619 per person
CA $1,619
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Augusta (AUG)
9.4/10 Exceptional! (152 reviews)
Beautiful Inn. Excellent Breakfast. Lovely staff. Amenity comment: If you use conditioner, be sure to bring it as the property does not provide any in the rooms. Shampoo, soap and makeup wipes were given. We stayed in the Main House Suite.
Reviewed on May 21, 2026
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.
