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Check prices for these dates

Next weekend
26 Sep - 28 Sep
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3 Oct - 5 Oct
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17 Oct - 19 Oct
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14 Nov - 16 Nov

Browse Select Windsor Cottages

Westfield Vacation Rental w/ Porch, Pets Welcome!
House (3 Bedrooms) | Interior

Westfield Vacation Rental w/ Porch, Pets Welcome!

3.0 star property
Westfield Vacation Rental w/ Porch, Pets Welcome!
Charming Windsor Home w/ Private Backyard!
House (3 Bedrooms) | Front of property

Charming Windsor Home w/ Private Backyard!

3.0 star property
8.0 out of 10, Very good, (1)
"The property was exactly as advertised and what we needed for a two night stay for a graduation. It was economical and accommodated 5 people comfortably. The interior is a bit dated, but clean. We did not spend much time at the property, so it worked well for us. The beds were a bit hard, but functional for two nights."
Charming Windsor Home w/ Private Backyard!
Cozy Springfield Vacation Rental Near Downtown
House (3 Bedrooms) | Interior

Cozy Springfield Vacation Rental Near Downtown

3.0 star property
Cozy Springfield Vacation Rental Near Downtown
Lakefront Connecticut Retreat Near Uconn
Cottage (2 Bedrooms) | Interior

Lakefront Connecticut Retreat Near Uconn

3.0 star property
Lakefront Connecticut Retreat Near Uconn
Lakefront Granby Escape w/ Private Dock & Kayaks!
House (2 Bedrooms) | Interior

Lakefront Granby Escape w/ Private Dock & Kayaks!

3.0 star property
Lakefront Granby Escape w/ Private Dock & Kayaks!
Charming Farmhouse w/ Pool & Fishing Pond!
House (5 Bedrooms) | Interior

Charming Farmhouse w/ Pool & Fishing Pond!

3.0 star property
Charming Farmhouse w/ Pool & Fishing Pond!
Cozy Lakefront Cottage w/ Fire Pit, Grill & Views!
Terrace/patio

Cozy Lakefront Cottage w/ Fire Pit, Grill & Views!

3.0 star property
Cozy Lakefront Cottage w/ Fire Pit, Grill & Views!
Lakefront Cottage w/ Covered Porch & Dock!
Cottage (3 Bedrooms) | Interior

Lakefront Cottage w/ Covered Porch & Dock!

3.0 star property
Lakefront Cottage w/ Covered Porch & Dock!
10 Mi to Hartford: Family Home w/ Yard
House (3 Bedrooms) | Interior

10 Mi to Hartford: Family Home w/ Yard

3.0 star property
10 Mi to Hartford: Family Home w/ Yard
Historic Farmhouse Near Mountains & Colleges!
House (4 Bedrooms) | Interior

Historic Farmhouse Near Mountains & Colleges!

3.0 star property
Historic Farmhouse Near Mountains & Colleges!
Springfield Vacation Rental: 1 Mi to Downtown
Interior

Springfield Vacation Rental: 1 Mi to Downtown

3.0 star property
Springfield Vacation Rental: 1 Mi to Downtown
Group Getaway w/ Outdoor Oasis in Southington!
House (4 Bedrooms) | Interior

Group Getaway w/ Outdoor Oasis in Southington!

3.0 star property
Group Getaway w/ Outdoor Oasis in Southington!
Lakefront Home: 2 Mi to Air Line State Park Trail!
Terrace/patio

Lakefront Home: 2 Mi to Air Line State Park Trail!

3.0 star property
Lakefront Home: 2 Mi to Air Line State Park Trail!
Modern Home w/ Spacious Yard in Springfield!
Interior

Modern Home w/ Spacious Yard in Springfield!

3.0 star property
Modern Home w/ Spacious Yard in Springfield!
Family Getaway in Bristol Near Trails & Parks!
Interior

Family Getaway in Bristol Near Trails & Parks!

3.0 star property
Family Getaway in Bristol Near Trails & Parks!
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

The Capitol Hotel

The Capitol Hotel

10/10 Excellent
"Good location."
Brian 1-night trip
Posted 1 day ago
The Capitol Hotel

Find out more about Windsor

Find out more about Windsor

Windsor Cottages information

Number of reviews
1
Accommodation
15 Cottages
Lowest Price
Highest Price

Frequently asked questions

Why book your cottage in Windsor with Expedia?
Expedia has some superb cottages in Windsor, so start packing for a memorable holiday 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 Centre 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.