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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Windsor cottages

Cottage (2 Bedrooms) | Interior

1. Rustic Retreat Across From Lake; Family Friendly!

Rustic Retreat Across From Lake; Family Friendly!
3.0 star property
Union
9.0 out of 10, Wonderful, (2 reviews)
"I liked that it was by the lake quiet and secluded. "
United States
Wilma
$358 nightly
The price is $391
Aug 3 - Aug 4
Total with taxes and fees
Rustic Retreat Across From Lake; Family Friendly!
Exterior

2. 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, (20 reviews)
"Very nice and clean place. We used this rental as a hub to go around and see lots that Maine had to offer. Hosts were very nice and kept a very clean place."
United States
Bruce J.
$466 nightly
The price is $508
Aug 4 - Aug 5
Total with taxes and fees
Maine river escape: free kayaks, paddle boards, tennis, cute rabbits and fun!
Outdoor dining

3. Spacious 1 Bedroom Cottage Close to Everything 5

Spacious 1 Bedroom Cottage Close to Everything 5
Edgecomb
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful, clean, small cottage close to the coast, shopping and dining."
United States
Theresa
$240 nightly
The price is $253
Aug 11 - Aug 12
Total with taxes and fees
Spacious 1 Bedroom Cottage Close to Everything 5
Exterior

4. Cheerful Cottage with Loft 9

Cheerful Cottage with Loft 9
Edgecomb
10.0 out of 10, Exceptional, (4 reviews)
"Immaculate, very cute - “tiny cottage”We loved it!"
United States
Daniel B.
$260 nightly
The price is $275
Aug 5 - Aug 6
Total with taxes and fees
Cheerful Cottage with Loft 9
Exterior

5. Tiny Cottage Near Everything 10

Tiny Cottage Near Everything 10
Edgecomb
8.0 out of 10, Very Good, (3 reviews)
"We recently stayed at the Tiny Cottage in Edgecomb, Maine, and truly enjoyed our visit. Except for a small initial issue, which was promptly and professionally addressed, everything was wonderful. The location is perfect for exploring the area, and the cottage itself was spotless, comfortable, and well-maintained. A lovely and relaxing getaway spot!"
United States
Elaine
$233 nightly
The price is $236
Aug 3 - Aug 4
Total with taxes and fees
Tiny Cottage Near Everything 10
Outdoor dining

6. Rustic Retreat Across from Lake; Family Friendly!

Rustic Retreat Across from Lake; Family Friendly!
Union
8.8 out of 10, Excellent, (19 reviews)
"Great location for visiting the coast."
United States
Sallie S.
$368 nightly
The price is $401
Aug 3 - Aug 4
Total with taxes and fees
Rustic Retreat Across from Lake; Family Friendly!
Outdoor dining

7. Cheerful Cottage Close to Everything 12

Cheerful Cottage Close to Everything 12
Edgecomb
9.4 out of 10, Exceptional, (16 reviews)
"Great experience, great location! Would highly recommend."
United States
Lynn R.
$230 nightly
The price is $242
Aug 5 - Aug 6
Total with taxes and fees
Cheerful Cottage Close to Everything 12
Outdoor dining

8. 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
$220 nightly
The price is $223
Aug 10 - Aug 11
Total with taxes and fees
Happy Cottage Near Everything 11
Interior

9. Cheerful Cottage with Loft Close to Everything 6

Cheerful Cottage with Loft Close to Everything 6
Edgecomb
9.2 out of 10, Wonderful, (10 reviews)
"It was so adorable!! Decorated beautifully and very clean- enjoyed it very much!! Hosts were fantastic and so easy to communicate with!!"
United States
Jackie A.
$263 nightly
The price is $278
Aug 5 - Aug 6
Total with taxes and fees
Cheerful Cottage with Loft Close to Everything 6
Outdoor dining

10. Spacious 1 Bedroom Close to Everything 4

Spacious 1 Bedroom Close to Everything 4
Edgecomb
9.8 out of 10, Exceptional, (24 reviews)
"This was a lovely little cabin. Everything was as described and my husband and I really enjoyed our stay."
Canada
Christine M.
$291 nightly
The price is $309
Aug 3 - Aug 4
Total with taxes and fees
Spacious 1 Bedroom Close to Everything 4
House (3 Bedrooms) | Interior

11. Near Lakes, Bay & Trails! Historic Waldoboro Gem

Near Lakes, Bay & Trails! Historic Waldoboro Gem
3.0 star property
Waldoboro
10.0 out of 10, Exceptional, (2 reviews)
"This home is such a gem! A historic home that is updated with many modern conveniences. We’ve been to MANY AirB&B’s and this home was probably the best equipped we’ve been in! Convenient to Boothbay and lots of downeast inlets and harbors. Very quiet, but close to groceries, food and farm stands. Our only regret was not staying longer- we would have loved to grill and use the fire pit!"
United States
Deborah
$450 nightly
The price is $491
Aug 9 - Aug 10
Total with taxes and fees
Near Lakes, Bay & Trails! Historic Waldoboro Gem
Property grounds

12. 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, (55 reviews)
"Great place, quiet neighborhood off the lake, very comfortable. Would definitely stay again!"
United States
Steve C.
$573 nightly
The price is $625
Aug 20 - Aug 21
Total with taxes and fees
Boat launch and Trailer parking, Dog Friendly, Lake Great Pond
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

10/10 Excellent
"We liked everything about. We only stayed 1 night but we will definitely be back."
Joe 1-night trip
Posted 4 hours ago
Senator Inn & Spa

Find out more about Windsor

Windsor Cottages information

Number of reviews
114
Accommodation
120 Cottages
Lowest Price
$223
Highest Price
$625

Frequently asked questions

How much do cottages in Windsor cost?
Prices for cottages in Windsor range between $223 and $625 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 120 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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