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Check prices for these dates

Next weekend
Mar 7 - Mar 9
In two weeks
Mar 14 - Mar 16
In one month
Mar 28 - Mar 30
In two months
Apr 25 - Apr 27

Browse Select Windsor Resorts

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

A Charming Waterfront Cottage with Touches of Elegance
Miscellaneous

A Charming Waterfront Cottage with Touches of Elegance

10.0 out of 10, Exceptional, (101)
"Manager David was very attentive and made sure I had everything I needed for a great stay. Property was beautiful and immaculately taken care of. Will definitely be back!"
A Charming Waterfront Cottage with Touches of Elegance
High End Apartment in Downtown Hallowell
Interior

High End Apartment in Downtown Hallowell

10.0 out of 10, Exceptional, (75)
"Property was very clean. Great location between Augustus and Gardner. Will definitely be staying there again when I go back."
The price is CA $149
CA $279 total
includes taxes & fees
Feb 26 - Feb 27
High End Apartment in Downtown Hallowell
March Special, Lake Great Pond, Dog Friendly
Outdoor dining

March Special, Lake Great Pond, Dog Friendly

10.0 out of 10, Exceptional, (31)
"Good space for 3 adults and two kids to stay, 25 min commute to Colby college and Quarry Road trails. Couch was comfy and nice for gathering. Beds also comfy and the double bunks were helpful for our group. Plow came quickly after snowstorm. We didn’t get out on the lake due to cold but nice to have it close by. "
The price is CA $187
CA $399 total
includes taxes & fees
Feb 25 - Feb 26
March Special, Lake Great Pond, Dog Friendly
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, Capitol Park, and Maine State House are a few interesting places to visit nearby. In the area, other attractions include Maine Veterans Memorial Cemetery and Damariscotta Lake.
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.