Windsor Cottages

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Windsor cottages

A deck with a round table and chairs, a small potted plant, and a view of a house with a window and siding.

1. Rustic Retreat Across From Lake; Family Friendly!

Union

Lorraine

includes taxes & fees

2 Oct - 3 Oct

A residential house with a paved driveway, a small front porch, and a garage.

2. Maine river escape: free kayaks, paddle boards, tennis, cute rabbits and fun!

West Gardiner

Robert M.

includes taxes & fees

20 Oct - 21 Oct

A grassy area with two Adirondack chairs facing a body of water, a wooden fence, and a dock extending into the water.

3. Boat launch and Trailer parking, Dog Friendly, Lake Great Pond

Belgrade

Steve C.

includes taxes & fees

1 Oct - 2 Oct

4. Rustic Retreat Across from Lake; Family Friendly!

Union

Sallie S.

includes taxes & fees

6 Oct - 7 Oct

A small, single-story cabin with a front porch and a small attached shed, surrounded by dense trees and grass.

5. Tiny Cottage Near Everything 10

Edgecomb

Gene

includes taxes & fees

5 Oct - 6 Oct

A wooden deck with a round table and two chairs, surrounded by trees.

6. Cheerful Cottage Close to Everything 13

Edgecomb

Crystal B.

includes taxes & fees

4 Oct - 5 Oct

A row of small, single-story cabins with attached garages, surrounded by trees and a clear sky.

7. Cheerful Cottage with Loft 9

Edgecomb

Daniel B.

includes taxes & fees

5 Oct - 6 Oct

A small cabin with a wooden deck, surrounded by trees in a wooded area.

8. Spacious 1 Bedroom Cottage Close to Everything 3

Edgecomb

Bruce O.

includes taxes & fees

1 Oct - 2 Oct

A wooden deck with two chairs and a small table, surrounded by a wooden railing, set in a forested area.

9. Spacious 1 Bedroom Cottage Close to Everything 5

Edgecomb

Theresa

includes taxes & fees

4 Oct - 5 Oct

10. Cheerful Cottage Close to Everything 12

Edgecomb

Tom C.

includes taxes & fees

26 Oct - 27 Oct

A cabin with a deck, surrounded by dense forest.

11. Spacious 1 Bedroom Cottage Close to Everything 2

Edgecomb

jillian s.

includes taxes & fees

27 Oct - 28 Oct

A wooden deck with a round table and two chairs, surrounded by a wooden railing and trees.

12. Spacious 1 Bedroom Close to Everything 4

Edgecomb

Christine M.

includes taxes & fees

27 Oct - 28 Oct

13. Cheerful Cottage with Loft Close to Everything 6

Edgecomb

Yaoyubai

includes taxes & fees

27 Oct - 28 Oct

A deck with a table and chairs, overlooking a wooded area with trees and a house in the background.

14. Happy Cottage Near Everything 11

Edgecomb

George

includes taxes & fees

27 Oct - 28 Oct

View all properties

Find holiday rentals that suit your style

Apartments

Private holiday homes

Save an average of 15% on thousands of hotels when you're signed in

Top Windsor Hotel Reviews

Super 8 by Wyndham Augusta

8/10 Good

"A reasonable road-stop motel when making a long drive from Canada or from the south. Good dining in the Augusta area and closely located to the motel. 'Continental' breakfast clearly referred to some continent that man is not aware of. Otherwise, rooms are clean and functional with some minor maintenance issues that would be expected of an older property."

Fireside Inn & Suites Waterville

10/10 Excellent

"This was an amazing place!!!! We stayed a week in the king size fireplace suite. The room was awesome and the bed slept very good. The kicker and the most pleasant surprise was the MASSAGE CHAIR IN OUR ROOM!!!!! Do you know how fantastic it was to have that after 12 hours of traveling??????? AWESOME!!!!! The staff was just flat out kind and gracious. Enjoyed the grab and go breakfast. Had a lot of options if I didn't want to go to the restaurant. Thank you so much for the best week. See you next year!!!!"

Nature lovers Paradise your own island

10/10 Excellent

"I loved Little Paradise Island, but it’s definitely not for everyone. A shade above camping, but with more amenities and a solid roof over your head. The perfect getaway to unplug and reset from the world, if even for a short time and if you enjoy being out on the water then you can’t ask for more. Plenty of hiking trails nearby to enjoy and entertainment options if you’re willing to travel. I loved my stay and can’t wait to come back."

Find out more about Windsor