Book Holiday Homes in Windsor

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Featured Holiday Homes in Windsor

Stylish & Luxurious 3 BDR Home with Play Station

Stylish & Luxurious 3 BDR Home with Play Station

Bristol
Stay at this vacation home in Bristol. Enjoy free WiFi, a water park, and an in-room coffeemaker. Popular attractions Seymour Park and Bristol Commons Shopping ...
Stylish & Luxurious 3 BDR Home with Play Station
PICON COZY

PICON COZY

Springfield
The price is NZ$294 per night from 7 Apr to 8 Apr
NZ$294
includes taxes & fees
7 Apr - 8 Apr
Stay at this vacation home in Springfield. Enjoy free WiFi, cable/satellite TV service, and an in-room coffeemaker. Popular attractions MGM Springfield and Naismith ...
PICON COZY
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

Windsor
Stay at this vacation home in Windsor. Enjoy air conditioning. Popular attractions XL Center and Windsor Meadows State Park are located nearby.
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
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Thomas's Cozy Duplex - Centrally Located

Thomas's Cozy Duplex - Centrally Located

Springfield
Stay at this vacation home in Springfield. Enjoy an in-room coffeemaker and air conditioning. Popular attractions MGM Springfield and Naismith Memorial Basketball ...
Thomas's Cozy Duplex - Centrally Located
The Bungalow at Eagleville Lake 
Under 3 miles to UCONN!

The Bungalow at Eagleville Lake Under 3 miles to UCONN!

Coventry
Book a stay at this family-friendly vacation home in Coventry. Enjoy free WiFi, a garden, and patios. Popular attractions J. M. Sarnik & Sons' The Old General ...
The Bungalow at Eagleville Lake Under 3 miles to UCONN!
Grammy's Lake House w/ Private Waterfront Access

Grammy's Lake House w/ Private Waterfront Access

East Hampton
Stay at this vacation home in East Hampton. Popular attractions Lake Terramuggus and Day Pond State Park are located nearby.
Grammy's Lake House w/ Private Waterfront Access
Owl's Nest - Cozy Westfield Home w/ Fire Pit

Owl's Nest - Cozy Westfield Home w/ Fire Pit

Westfield
Stay at this vacation home in Westfield. Enjoy a garden, an in-room coffeemaker, and in-room fireplaces. Popular attractions Elm Street Plaza and Westfield River ...
Owl's Nest - Cozy Westfield Home w/ Fire Pit
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university

Home away from home Hot Tub and Pool in Middletown home of Wesleyan university

Middletown
Book a stay at this family-friendly vacation home in Middletown. Enjoy free WiFi, a water park, and a fitness center. Popular attractions Lamentation Mountain ...
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
Charming 3BR Hilltop House, Newly Remodeled with Arcade

Charming 3BR Hilltop House, Newly Remodeled with Arcade

Plymouth
Book a stay at this family-friendly vacation home in Terryville. Enjoy free WiFi, a water park, and a garden. Popular attractions Witch's Dungeon Classic Movie ...
Charming 3BR Hilltop House, Newly Remodeled with Arcade
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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.

Windsor Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Windsor vacation homes are the perfect way for you to wing it.

Holiday houses in Windsor let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Windsor in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Windsor adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Windsor with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Windsor vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Windsor Holiday Homes essential information

Accommodation
208 Holiday Homes
Lowest Price
NZ$218
Highest Price
NZ$294
Popular accommodation
Stylish & Luxurious 3 BDR Home with Play Station, PICON COZY, NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!, Thomas's Cozy Duplex - Centrally Located, The Bungalow at Eagleville Lake Under 3 miles to UCONN! , Grammy's Lake House w/ Private Waterfront Access, Owl's Nest - Cozy Westfield Home w/ Fire Pit, Home away from home Hot Tub and Pool in Middletown home of Wesleyan university, Charming 3BR Hilltop House, Newly Remodeled with Arcade

Top trending hotels in Windsor

Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
555 Corporate Dr, Windsor, CT
Fully refundableReserve now, pay when you stay
The price is NZ$218 per night from 18 Apr to 19 Apr
NZ$218
includes taxes & fees
18 Apr - 19 Apr
Stay at this 3-star business-friendly hotel in Windsor. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Hilton Garden Inn Hartford North/Bradley Int'l Airport
HYATT house Hartford North/Windsor

HYATT house Hartford North/Windsor

3 out of 5
200 Corporate Dr, Windsor, CT
Fully refundableReserve now, pay when you stay
The price is NZ$266 per night from 13 Apr to 14 Apr
NZ$266
includes taxes & fees
13 Apr - 14 Apr
Stay at this 3-star business-friendly hotel in Windsor. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
HYATT house Hartford North/Windsor
Hampton Inn Hartford/Airport

Hampton Inn Hartford/Airport

2.5 out of 5
2168 Poquonock Ave, Windsor, CT
Fully refundableReserve now, pay when you stay
The price is NZ$235 per night from 13 Apr to 14 Apr
NZ$235
includes taxes & fees
13 Apr - 14 Apr
Book a stay at this business-friendly hotel in Windsor. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Hampton Inn Hartford/Airport
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Residence Inn by Marriott Hartford/Windsor

Residence Inn by Marriott Hartford/Windsor

3 out of 5
100 Dunfey Ln, Windsor, CT
Fully refundableReserve now, pay when you stay
The price is NZ$218 per night from 14 Apr to 15 Apr
NZ$218
includes taxes & fees
14 Apr - 15 Apr
Stay at this 3-star business-friendly hotel in Windsor. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
Residence Inn by Marriott Hartford/Windsor
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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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^Subject to availability and chosen travel dates.