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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Windsor cottages

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

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

Maine river escape: free kayaks, paddle boards, tennis, cute rabbits and fun!
West Gardiner
9.8 out of 10, Exceptional, (22 reviews)
"This was the ideal Maine spot."
United States
Lisa W.
$388 nightly
The price is $423
Oct 15 - Oct 16
Total with taxes and fees
Maine river escape: free kayaks, paddle boards, tennis, cute rabbits and fun!
A grassy area with two Adirondack chairs facing a body of water, a wooden fence, and a dock extending into the water.

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

Boat launch and Trailer parking, Dog Friendly, Lake Great Pond
Belgrade
10.0 out of 10, Exceptional, (58 reviews)
"Great place, quiet neighborhood off the lake, very comfortable. Would definitely stay again!"
United States
Steve C.
$355 nightly
The price is $387
Nov 12 - Nov 13
Total with taxes and fees
Boat launch and Trailer parking, Dog Friendly, Lake Great Pond
A deck with a table and chairs, overlooking a wooded area with trees and a house in the background.

3. Happy Cottage Near Everything 11

Happy Cottage Near Everything 11
Edgecomb
6.8 out of 10, (3 reviews)
"Great quit little place, great accommodations with even better help and information about the local area."
United States
George
$190 nightly
The price is $192
Oct 14 - Oct 15
Total with taxes and fees
Happy Cottage Near Everything 11
A wooden deck with a round table and two chairs, surrounded by trees.

4. Cheerful Cottage Close to Everything 12

Cheerful Cottage Close to Everything 12
Edgecomb
9.4 out of 10, Exceptional, (18 reviews)
"Cute place and very clean will definitely stay again "
United States
Tom C.
$211 nightly
The price is $221
Nov 10 - Nov 11
Total with taxes and fees
Cheerful Cottage Close to Everything 12
A row of small, single-story cabins with attached garages, surrounded by trees and a clear sky.

5. Cheerful Cottage with Loft 9

Cheerful Cottage with Loft 9
Edgecomb
10.0 out of 10, Exceptional, (5 reviews)
$225 nightly
The price is $237
Nov 3 - Nov 4
Total with taxes and fees
Cheerful Cottage with Loft 9
A two-story cabin with a dock and a small boat.

6. New Lakefront Escape on Red Cedar Lane. Private Dock, Sunset Views & Family Fun

New Lakefront Escape on Red Cedar Lane. Private Dock, Sunset Views & Family Fun
Sidney
New Lakefront Escape on Red Cedar Lane. Private Dock, Sunset Views & Family Fun
A small, single-story cabin with a front porch and a small attached shed, surrounded by dense trees and grass.

7. Tiny Cottage Near Everything 10

Tiny Cottage Near Everything 10
Edgecomb
9.0 out of 10, Wonderful, (6 reviews)
"Great location awesome place to take it easy for a few"
United States
Gene
$214 nightly
The price is $216
Oct 20 - Oct 21
Total with taxes and fees
Tiny Cottage Near Everything 10
A small cabin with a wooden deck, surrounded by trees in a wooded area.

8. Spacious 1 Bedroom Cottage Close to Everything 3

Spacious 1 Bedroom Cottage Close to Everything 3
Edgecomb
9.6 out of 10, Exceptional, (18 reviews)
"Great central location"
United States
Bruce O.
$259 nightly
The price is $274
Nov 10 - Nov 11
Total with taxes and fees
Spacious 1 Bedroom Cottage Close to Everything 3
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

Spacious 1 Bedroom Cottage Close to Everything 5
Edgecomb
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful, clean, small cottage close to the coast, shopping and dining."
United States
Theresa
$220 nightly
The price is $231
Nov 10 - Nov 11
Total with taxes and fees
Spacious 1 Bedroom Cottage Close to Everything 5
A cabin with a deck, surrounded by dense forest.

10. Spacious 1 Bedroom Cottage Close to Everything 2

Spacious 1 Bedroom Cottage Close to Everything 2
Edgecomb
9.4 out of 10, Exceptional, (22 reviews)
"Easy to find, very near the highway. Entry code sent promptly to access the property. Cottage was cozy and welcoming. Nicely thought out outdoor areas. Would highly recommend."
United States
jillian s.
$236 nightly
The price is $249
Nov 10 - Nov 11
Total with taxes and fees
Spacious 1 Bedroom Cottage Close to Everything 2
A wooden deck with a round table and two chairs, surrounded by a wooden railing and trees.

11. Spacious 1 Bedroom Close to Everything 4

Spacious 1 Bedroom Close to Everything 4
Edgecomb
9.8 out of 10, Exceptional, (25 reviews)
"This was a lovely little cabin. Everything was as described and my husband and I really enjoyed our stay."
Canada
Christine M.
$247 nightly
The price is $261
Nov 9 - Nov 10
Total with taxes and fees
Spacious 1 Bedroom Close to Everything 4
Interior

12. Cheerful Cottage with Loft Close to Everything 6

Cheerful Cottage with Loft Close to Everything 6
Edgecomb
9.4 out of 10, Exceptional, (11 reviews)
"Very clean and comfortable little cottage. Host responds and communicates effectively. Very nice experience."
United States
Yaoyubai
$223 nightly
The price is $235
Nov 3 - Nov 4
Total with taxes and fees
Cheerful Cottage with Loft Close to Everything 6
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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Top Windsor Hotel Reviews

Senator Inn & Spa

Senator Inn & Spa

8/10 Good
"yes"
Eric 1-night trip
Posted 2 hours ago
Senator Inn & Spa

Find out more about Windsor

Windsor Cottages information

Number of reviews
184
Accommodation
124 Cottages
Lowest Price
$192
Highest Price
$423

Frequently asked questions

How much do cottages in Windsor cost?
Prices for cottages in Windsor range between $192 and $423 per night. No matter your budget, you're sure to find an ideal place to reconnect with nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Windsor?
Pack your suitcase and choose from 124 cottages in Windsor. Dreaming of a place where you can relax and connect with nature? Expedia can help you find your ideal getaway in a few simple clicks.
Why book your cottage in Windsor with Expedia?
Expedia has some superb cottages in Windsor, so start packing your bags for an unforgettable vacay on nature's doorstep. If you have a budget, click on how much you want to spend and your preferred property star rating. Or, make use of our filters to search for cottages with a kitchen or a pool. We'll help you find the perfect fit whatever your getaway looks like.
How can I find cheap cottages in Windsor?
Expedia can help you easily locate cheap cottages in Windsor. To find a terrific stay in just a few clicks, try out our convenient filter tool to refine your search by budget, amenities and star rating.

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