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Check prices for these dates

Next weekend
28 Mar - 30 Mar
In two weeks
4 Apr - 6 Apr
In one month
18 Apr - 20 Apr
In two months
16 May - 18 May

Compare 3 Resorts in Windsor with updated reviews, rates, and availability.

Island Glamping in a Luxury Tent in Maine
Pet-friendly

Island Glamping in a Luxury Tent in Maine

10.0 out of 10, Exceptional, (2)
"Our stay at Hemlock Haven, was nothing short of magical. My fiancé, Jess, and I spent three unforgettable nights immersed in nature’s beauty. We loved the peaceful ambiance, especially the crisp fall air and foggy mornings by the lake. The hammocks were a favorite spot for us to relax, read, and craft. As two chefs, we had a blast cooking over the fire and experimenting with the smoky flavors. Each evening, we cozied up to the sounds of the night, even catching a haunting chorus from coyotes (or...
Island Glamping in a Luxury Tent in Maine
Eco-Island Resort:14 Private Acres, 5 Unique Stays
Pet-friendly

Eco-Island Resort:14 Private Acres, 5 Unique Stays

Eco-Island Resort:14 Private Acres, 5 Unique Stays
Island Tent Overlook in Maine
Pet-friendly

Island Tent Overlook in Maine

10.0 out of 10, Exceptional, (1)
Island Tent Overlook in Maine
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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Other property types in Windsor

The Modern Maine Retreat
Outdoor dining

The Modern Maine Retreat

10.0 out of 10, Exceptional, (3)
"Worked out perfectly for our needs. Owner responded immediately to assist us with minor issue. We would, and most likely will, rent this home again. Location was great for our purpose. Plenty of room."
The Modern Maine Retreat
Updated lake cottage right on Damariscotta Lake.
Property grounds

Updated lake cottage right on Damariscotta Lake.

10.0 out of 10, Exceptional, (135)
"My mid-October stay at Little Thumb was everything I hoped for and more: plenty of peace and quiet, an immaculate and comfortable place to stay, and beautiful surroundings in which to birdwatch from the dock, read, and take long walks. I especially enjoyed the well-stocked kitchen, comfy queen bed, and big gas heating stove in the living room that kept me toasty, even temps dipped into the 40s. And Natalie certainly deserves her rating as a top host!"
Updated lake cottage right on Damariscotta Lake.
High End Apartment in Downtown Hallowell
Interior

High End Apartment in Downtown Hallowell

10.0 out of 10, Exceptional, (76)
"It was so nice to have family visit us and stay just down the road "
High End Apartment in Downtown Hallowell
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.

Frequently asked questions

What can I expect from a resort vacation in Windsor?
You deserve a break, and a resort is the ideal place to find all the amenities and services you need for a relaxing trip to Windsor. One of the comfortable resorts in the surrounding area might be just what you’re looking for, whether you want a luxurious suite, a state-of-the-art fitness center, or fun activities to try.
What's a top resort in Windsor?
Our highest-rated resorts around Windsor: Island Glamping in a Luxury Tent in Maine - Beach resort. 20.1 mi (32.4 km) from Windsor. Features free self parking. Eco-Island Resort:14 Private Acres, 5 Unique Stays - Beach resort. 20.1 mi (32.3 km) from Windsor. Island Tent Overlook in Maine - Beach resort. 19.8 mi (31.9 km) from Windsor. Enjoy the garden.
What can I do in Windsor?
Old Fort Western, Kennebec River Rail Trail, and Maine State House are a few interesting places to visit nearby. In the area, other attractions include Damariscotta Lake and University of Maine at Augusta.
What's the seasonal weather like in Windsor?
The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 26°F. The snowiest months in Windsor are January, December, March, and February, with each month seeing an average of 10 inches of snowfall.
What's the best way to get to and around Windsor?
Fly into Augusta, ME (AUG-Augusta State), which is located 10.5 mi (16.9 km) away from the heart of the city. You can also search for flights into Waterville, ME (WVL-Robert Lafleur), which is 16.2 mi (26 km) away. If you’d like to venture out around the area, you may want a rental car for your journey.