
Winthrop Vacations from $609
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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.

OneSixtyFive
Price was $731, price is now $609 per person
$609
per person
Nov 21 - Nov 24
just found
Roundtrip flight included
Denver (DEN) to Augusta (AUG)
9.4/10 Exceptional! (133 reviews)
I can't say enough about my stay at OneSixtyFive. It was such a treat. The pub and library in the main house were so charming, and a great way to mingle with others. Arthur offered such great suggestions.
Reviewed on Oct 8, 2025

Greenleaf Inn
Price was $1,322, price is now $959 per person
$959
per person
Dec 19 - Dec 23
found 20 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Augusta (AUG)
9.4/10 Exceptional! (10 reviews)
Great spot in Boothbay Harbor Maine. Walkable area to restaurants, boat excursions, shops and waterfront. Easy parking on premises. Check in time on our Expedia booked reservation states 2:00pm-4:00pm check in. We received a text message from the Inn manager letting us know check in was at 4:00pm and to send him a text when we were close to arrival. Other than the time difference check in was seamless and informative. Property manager was friendly and accommodating and walked us around the common areas of both buildings Admirals Quarters where the main office is and the greenleaf building where we stayed. They both have a shared kitchen area and living room dining room areas.
Our room was advertised as a private penthouse king with direct access to the sky deck. The room was on the small side but worked for our short stay and had fold out luggage storage which was convenient for our belongings. We had a small refrigerator as well. Bed was on the soft side which didn’t work well for me but was fine for my husband. Lots of light comes in early morning but we are early risers so no issue for us. The view out of the windows from the bed was beautiful. All upgrades were well done. Neighbors sliding door was right next to ours which accesses the shared deck. You could hear your neighbor as well when inside.
The property is set up with a sense of community most areas are shared including decks, chairs, grounds both inside and out. Typical of most Inn’s.
Reviewed on Aug 11, 2025

Flagship Inn and Suites
Price was $948, price is now $764 per person
$764
per person
Dec 19 - Dec 23
found 20 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Augusta (AUG)
8.2/10 Very Good! (1,016 reviews)
Close to Boothbay Harbor with easy access to local attractions. Close to Botanical Gardens. Very pleasant stay. Nice outdoor area to sit and enjoy the evening.
Reviewed on Oct 15, 2025

Admirals Quarters Inn
Price was $1,435, price is now $1,166 per person
$1,166
per person
Dec 19 - Dec 23
found 20 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Augusta (AUG)
9.4/10 Exceptional! (26 reviews)
Admiral Quarters, and the Greenleaf are both very conveniently located. Although they are Inns that were built many years ago they are tastefully, renovated, and cozy. The Inn keeper, Jersey, goes above and beyond to make his guests feel comfortable. His hospitality was a highlight of our stay. He shared his knowledge of the area, places to eat, and things to do. He took us on a boat ride of the harbor area and had a fire pit with marshmallows and s’mores when weather permitted. We will be back.
Reviewed on Sep 9, 2025

Evergreen Valley Inn
Price was $1,100, price is now $910 per person
$910
per person
Dec 21 - Dec 26
found 7 hours ago
Roundtrip non-stop flight included
New York (LGA) to Augusta (AUG)
8/10 Very Good! (169 reviews)
This was a beautiful and cozy property in a remote part of Maine, yet the facilities were very well maintained and the staff was very friendly and helpful.
Reviewed on Oct 14, 2025
Winthrop Hotel Deals

Maine Evergreen Hotel, an Ascend Collection Hotel
65 Whitten Rd, Augusta, ME
Fully refundableReserve now, pay when you stay
$136 nightly
The price is $148 total per night from Nov 2 to Nov 3
$148 total
Nov 2 - Nov 3
Total with taxes and fees
9.2/10 Wonderful! (1,025 reviews)
""No Pets" is a wonderful thing for a person with severe animal allergies. Thank goodness! Also, the hotel is clean, well-maintained, quiet, and comfortable. We will definitely stay here again!!"
Reviewed on Oct 13, 2025

SureStay Hotel by Best Western Lewiston
516 Pleasant St, Lewiston, ME
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $117 total per night from Oct 26 to Oct 27
$117 total
Oct 26 - Oct 27
Total with taxes and fees
8/10 Very Good! (418 reviews)
"Property very clean and rate very reasonable. Near downtown area. Water pressure and facilities are great. Happy to have found this place late on a Friday night during peak leaf peeping season!!!"
Reviewed on Oct 11, 2025

Senator Inn & Spa
284 Western Ave, Augusta, ME
Fully refundableReserve now, pay when you stay
$120 nightly
The price is $131 total per night from Nov 16 to Nov 17
$131 total
Nov 16 - Nov 17
Total with taxes and fees
7.6/10 Good! (1,008 reviews)
"Very clean, comfortable rooms, fabulous pool, lovely restaurant for breakfast. Staff were very helpful."
Reviewed on Oct 14, 2025
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.
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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- Maranacook Lake
- Visit North Monmouth
- Theatre at Monmouth
- Visit Wayne
- Manchester Vacations
- Cobbossee Colony Golf Course
- Visit Manchester
- Purgatory Vacations
- Visit Purgatory
- Fayette Vacations
- Turnpike Mall
- Visit Fayette
- Kennebec Ice Arena
- Holocaust Human Rights Center of Maine
- Augusta Civic Center
- Harlow Gallery
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.