Default HTG hotel image

Search Windsor Cottage Rentals from CA $544

  • 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
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

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
The price is CA $184
CA $544 total
includes taxes & fees
Aug 18 - Aug 19
Rustic Retreat Across From Lake; Family Friendly!
Outdoor dining

2. Quiet & Lovely Lakefront Cottage for Families!

Quiet & Lovely Lakefront Cottage for Families!
Union
9.8 out of 10, Exceptional, (16 reviews)
"Evocative of my youth and going to the family lake camp in the summer. We had great weather and a great time. The cabin is a ‘Mainer’s’ memories wrapped in eclectic reminders. What a joy!"
United States
Venise B.
The price is CA $191
CA $715 total
includes taxes & fees
Aug 31 - Sep 1
Quiet & Lovely Lakefront Cottage for Families!
Exterior

3. 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.
The price is CA $348
CA $709 total
includes taxes & fees
Aug 17 - Aug 18
Maine river escape: free kayaks, paddle boards, tennis, cute rabbits and fun!
Exterior

4. The Little Grey Duck Cottage on Cobbossee Lake

The Little Grey Duck Cottage on Cobbossee Lake
Manchester
9.0 out of 10, Wonderful, (27 reviews)
"Location is amazing "
United States
Laura Q.
The price is CA $251
CA $523 total
includes taxes & fees
Aug 13 - Aug 14
The Little Grey Duck Cottage on Cobbossee Lake
Outdoor dining

5. Rustic Retreat Across from Lake; Family Friendly!

Rustic Retreat Across from Lake; Family Friendly!
Union
8.8 out of 10, Excellent, (20 reviews)
"Great location for visiting the coast."
United States
Sallie S.
The price is CA $138
CA $557 total
includes taxes & fees
Aug 18 - Aug 19
Rustic Retreat Across from Lake; Family Friendly!
Outdoor dining

6. 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
The price is CA $188
CA $384 total
includes taxes & fees
Aug 18 - Aug 19
Spacious 1 Bedroom Cottage Close to Everything 5
Outdoor dining

7. 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
The price is CA $156
CA $331 total
includes taxes & fees
Aug 19 - Aug 20
Happy Cottage Near Everything 11
Exterior

8. Cheerful Cottage with Loft 9

Cheerful Cottage with Loft 9
Edgecomb
10.0 out of 10, Exceptional, (5 reviews)
"Immaculate, very cute - “tiny cottage”We loved it!"
United States
Daniel B.
The price is CA $180
CA $373 total
includes taxes & fees
Sep 8 - Sep 9
Cheerful Cottage with Loft 9
Property grounds

9. 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, (56 reviews)
"Great place, quiet neighborhood off the lake, very comfortable. Would definitely stay again!"
United States
Steve C.
The price is CA $405
CA $756 total
includes taxes & fees
Sep 3 - Sep 4
Boat launch and Trailer parking, Dog Friendly, Lake Great Pond
Exterior

10. 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.
The price is CA $221
CA $425 total
includes taxes & fees
Sep 8 - Sep 9
Spacious 1 Bedroom Cottage Close to Everything 3
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
The price is CA $252
CA $683 total
includes taxes & fees
Aug 14 - Aug 15
Near Lakes, Bay & Trails! Historic Waldoboro Gem
Exterior

12. 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
The price is CA $156
CA $329 total
includes taxes & fees
Sep 8 - Sep 9
Tiny Cottage Near Everything 10
Outdoor dining

13. 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.
The price is CA $212
CA $413 total
includes taxes & fees
Sep 8 - Sep 9
Spacious 1 Bedroom Close to Everything 4
Outdoor dining

14. 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.
The price is CA $181
CA $375 total
includes taxes & fees
Sep 8 - Sep 9
Cheerful Cottage Close to Everything 12
Interior

15. 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.
The price is CA $217
CA $422 total
includes taxes & fees
Sep 1 - Sep 2
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor Hotel Reviews

Cod Cove Inn, BW Signature Collection

Cod Cove Inn, BW Signature Collection

10/10 Excellent
"My wife and I stayed here for our second time and both times we enjoyed very much. We love that they are dog friendly. Our 2 dogs had a wonderful time also. The staff was amazing! We very much enjoyed the breakfast and my wife had a nice time swimming in the pool. We didn’t get a balcony, we got a patio, which was perfect for our dogs. We will definitely be returning."
Nicholas 2-night trip
Posted 1 hour ago
Cod Cove Inn, BW Signature Collection

Find out more about Windsor

Windsor Cottages information

Number of reviews
4
Accommodation
111 Cottages
Lowest Price
CA $544
Highest Price
CA $683

Frequently asked questions

How much do cottages in Windsor cost?
Prices for cottages in Windsor range between CA $544 and CA $683 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 111 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.

Explore a world of travel with Expedia