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Check prices for these dates

In two weeks
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for Windsor cottages

Cottage (2 Bedrooms) | Interior

Private Dock on Messalonskee Lake: Cozy Cottage!

Private Dock on Messalonskee Lake: Cozy Cottage!
3.0 star property
Augusta
10.0 out of 10, Exceptional, (1 review)
"Great little lake cabin. Had everything we needed. Clean, comfortable, quite. Beautiful area and views. We had a wonderful stay and would stay again."
United States
John
$298 nightly
The price is $324
Jul 29 - Jul 30
Total with taxes and fees
Private Dock on Messalonskee Lake: Cozy Cottage!
Exterior

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, (19 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.
$464 nightly
The price is $506
Jul 29 - Jul 30
Total with taxes and fees
Maine river escape: free kayaks, paddle boards, tennis, cute rabbits and fun!
Exterior

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.
$278 nightly
The price is $294
Aug 5 - Aug 6
Total with taxes and fees
Cheerful Cottage with Loft 9
Exterior

Private Dock on Messalonskee Lake: Cozy Cottage!

Private Dock on Messalonskee Lake: Cozy Cottage!
Sidney
9.0 out of 10, Wonderful, (12 reviews)
"Great place to stay for our annual fishing weekend in the Belgrade Lakes region! "
United States
Shawn H.
$304 nightly
The price is $331
Jul 29 - Jul 30
Total with taxes and fees
Private Dock on Messalonskee Lake: Cozy Cottage!
Outdoor dining

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.
$303 nightly
The price is $322
Jul 27 - Jul 28
Total with taxes and fees
Spacious 1 Bedroom Close to Everything 4
Outdoor dining

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
$235 nightly
The price is $238
Aug 10 - Aug 11
Total with taxes and fees
Happy Cottage Near Everything 11
Exterior

Spacious 1 Bedroom Cottage Close to Everything 3

Spacious 1 Bedroom Cottage Close to Everything 3
Edgecomb
9.8 out of 10, Exceptional, (17 reviews)
"Great central location"
United States
Bruce O.
$293 nightly
The price is $311
Jul 28 - Jul 29
Total with taxes and fees
Spacious 1 Bedroom Cottage Close to Everything 3
Outdoor dining

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.
$379 nightly
The price is $413
Aug 16 - Aug 17
Total with taxes and fees
Rustic Retreat Across from Lake; Family Friendly!
Property grounds

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.
$591 nightly
The price is $645
Aug 14 - Aug 15
Total with taxes and fees
Boat launch and Trailer parking, Dog Friendly, Lake Great Pond
Outdoor dining

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
$253 nightly
The price is $267
Aug 11 - Aug 12
Total with taxes and fees
Spacious 1 Bedroom Cottage Close to Everything 5
Cottage (2 Bedrooms) | Interior

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
$370 nightly
The price is $404
Aug 16 - Aug 17
Total with taxes and fees
Rustic Retreat Across From Lake; Family Friendly!
Interior

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.
$259 nightly
The price is $274
Jul 27 - Jul 28
Total with taxes and fees
Cheerful Cottage with Loft Close to Everything 6
Outdoor dining

Cheerful Cottage Close to Everything 12

Cheerful Cottage Close to Everything 12
Edgecomb
9.6 out of 10, Exceptional, (15 reviews)
"Great experience, great location! Would highly recommend."
United States
Lynn R.
$246 nightly
The price is $260
Aug 3 - Aug 4
Total with taxes and fees
Cheerful Cottage Close to Everything 12
Exterior

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
$257 nightly
The price is $260
Aug 3 - Aug 4
Total with taxes and fees
Tiny Cottage Near Everything 10
Outdoor dining

Spacious 1 Bedroom Cottage Close to Everything 1

Spacious 1 Bedroom Cottage Close to Everything 1
Edgecomb
9.8 out of 10, Exceptional, (6 reviews)
"Comfortable cabin located in great area to all nearby towns and activities. Excellent host."
United States
john and michele j.
$301 nightly
The price is $320
Aug 9 - Aug 10
Total with taxes and fees
Spacious 1 Bedroom Cottage Close to Everything 1
House (3 Bedrooms) | Interior

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
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

Cod Cove Inn, BW Signature Collection

Cod Cove Inn, BW Signature Collection

8/10 Good
"Very good location and great sunsets out the balconies or just drive down to the water for beautiful shots. Room was clean and comfortable, if a bit basic. The loveseat was extremely uncomfortable. Breakfast was basic but staff were friendly."
CHARLENE 1-night trip
Posted 1 day ago
Cod Cove Inn, BW Signature Collection

Find out more about Windsor

Windsor Cottages information

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Frequently asked questions

How much do cottages in Windsor cost?
Prices for cottages in Windsor range between and 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 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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