A rustic barn surrounded by autumn foliage and a field.

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Windsor cottages

Exterior

1. Lakeview Carriage House with Spectacular Sunset Views

Lakeview Carriage House with Spectacular Sunset Views
Lake Pocotopaug
10.0 out of 10, Exceptional, (19 reviews)
"Clean, quiet, beautiful surroundings and a great host"
United States
Jennifer J.
The price is CA $208
CA $447 total
includes taxes & fees
Sep 7 - Sep 8
Lakeview Carriage House with Spectacular Sunset Views
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

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

10/10 Excellent
"Very clean place. And staff was amazing"
Kaleb 1-night trip
Posted 2 hours ago
Holiday Inn Express Southington by IHG

Find out more about Windsor

Windsor Cottages information

Number of reviews
19
Accommodation
40 Cottages
Lowest Price
CA $447
Highest Price
CA $447

Frequently asked questions

Why book your cottage in Windsor with Expedia?
Expedia has some superb cottages in Windsor, so start packing for a memorable vacay close to nature. If you have a certain budget, select how much you want to spend and your preferred property star rating. Or take advantage of our filters to search for cottages with a pool or a hot tub. We'll help you find the perfect digs whatever your getaway looks like.
How can I find cheap cottages in Windsor?
The best way to locate cheap cottages in Windsor is with Expedia's convenient filter tool. Refine your search results by star rating, amenities and budget to take advantage of awesome prices in a couple of clicks.
What is there to do in Windsor near my cottage?
Windsor has enough activities and sights to keep you entertained for weeks (or months!), starting with Windsor Historical Society. Northwest Park, Windsor Arts Center and Vintage Radio and Communications Museum of Connecticut are other renowned attractions. If you're lingering longer, Oliver Ellsworth Homestead and Windsor Meadows State Park will round off your itinerary nicely.

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