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
With a stay at this vacation home in Bristol, you'll be within a 5-minute drive of Seymour Park and Bristol Commons Shopping Center.
Stylish & Luxurious 3 BDR Home with Play Station
PICON COZY

PICON COZY

Springfield
The price is AU$274 per night from 1 Apr to 2 Apr
AU$274
includes taxes & fees
1 Apr - 2 Apr
With a stay at this vacation home in Springfield (Sixteen Acres), you'll be within a 10-minute drive of MassMutual Center and MGM Springfield.
PICON COZY
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

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

Windsor
With a stay at this vacation home in Windsor, you'll be within a 10-minute drive of Connecticut Convention Center and XL Center.
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
With a stay at this vacation home in Springfield, you'll be within a 5-minute drive of MassMutual Center and MGM Springfield.
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
With a stay at this vacation home in Coventry, you'll be on the waterfront, within a 5-minute drive of University of Connecticut and J. M. Sarnik & Sons' The ...
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
Located in East Hampton, this vacation home is on the waterfront, a 4-minute drive from Day Pond State Park and 8 minutes from Lake Terramuggus.
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
With a stay at this vacation home in Westfield, you'll be a 4-minute walk from Elm Street Plaza and 13 minutes by foot from Baystate Noble Hospital.
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
Located in Middletown, this vacation home is in the mountains, within a 10-minute drive of Falcon Field and Cedar Park.
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
Located in Terryville, this vacation home is a 5-minute drive from Witch's Dungeon Classic Movie Museum and 5 minutes from Muzzy Field.
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
216 Holiday Homes
Lowest Price
AU$201
Highest Price
AU$291
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 AU$201 per night from 18 Apr to 19 Apr
AU$201
includes taxes & fees
18 Apr - 19 Apr
A stay at Hilton Garden Inn Hartford North/Bradley Int'l Airport places you in the heart of Windsor, within a 10-minute drive of Xfinity Theatre and Connecticut ...
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 AU$245 per night from 6 Apr to 7 Apr
AU$245
includes taxes & fees
6 Apr - 7 Apr
When you stay at HYATT house Hartford North/Windsor in Windsor, you'll be in the business district, within a 10-minute drive of XL Center and Connecticut Convention ...
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 AU$216 per night from 13 Apr to 14 Apr
AU$216
includes taxes & fees
13 Apr - 14 Apr
Located in Windsor, Hampton Inn Hartford/Airport is in the business district, within a 10-minute drive of Northwest Park and Connecticut Trolley Museum.
Hampton Inn Hartford/Airport
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Marriott Hartford/Windsor Airport

Marriott Hartford/Windsor Airport

3.5 out of 5
28 Day Hill Rd, Windsor, CT
Fully refundableReserve now, pay when you stay
The price is AU$291 per night from 18 Apr to 19 Apr
AU$291
includes taxes & fees
18 Apr - 19 Apr
Located in Windsor, Marriott Hartford/Windsor Airport is in the business district, within a 10-minute drive of Windsor Arts Center and Windsor Historical ...
Marriott Hartford/Windsor Airport
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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.