Book Holiday Homes in Windsor
More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)
We keep it easy with the option to pay now or later on select accommodation
Book up 'til the last second - millions of rooms to crash tonight^
Featured Holiday Homes in Windsor

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
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 |
More accommodations in Windsor
Top trending hotels in Windsor

Hilton Garden Inn Hartford North/Bradley Int'l Airport

HYATT house Hartford North/Windsor

Hampton Inn Hartford/Airport

Marriott Hartford/Windsor Airport
More ways to explore Windsor
Top picks
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.