Book Holiday Homes in Windsor

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Featured Holiday Homes in Windsor

Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford

Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford

Manchester CT
The price is NZ$542 per night from 18 Mar to 19 Mar
NZ$542
18 Mar - 19 Mar
includes taxes & fees
Stay at this holiday home in Manchester. Enjoy laundry facilities, an in-room coffee maker and air conditioning. Popular attractions Charter Oak Park and Lutz ...
Opens in a new windowModern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Cozy Nest ~ 3.5BR & 2Bath Home ~ Manchester CT

Cozy Nest ~ 3.5BR & 2Bath Home ~ Manchester CT

Manchester CT
Stay at this family-friendly holiday home in Manchester. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Charter Oak Park and Cinemark Buckland ...
Opens in a new windowCozy Nest ~ 3.5BR & 2Bath Home ~ Manchester CT
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

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

Windsor CT
Stay at this holiday home in Windsor. Enjoy air conditioning. Popular attractions Loomis Chaffee School and Wintonbury Hills Playground are located nearby.
Opens in a new windowNEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
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The Bungalow at Eagleville Lake 
Under 3 miles to UCONN!

The Bungalow at Eagleville Lake Under 3 miles to UCONN!

Coventry CT
Stay at this family-friendly holiday home in Coventry. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions J. M. Sarnik & Sons' The Old General ...
Opens in a new windowThe Bungalow at Eagleville Lake Under 3 miles to UCONN!
Stylish & Luxurious 3 BDR Home with Play Station

Stylish & Luxurious 3 BDR Home with Play Station

Bristol CT
Stay at this holiday home in Bristol. Enjoy free Wi-Fi, laundry facilities and an in-room coffee maker. Popular attractions Leon J. Breen Memorial Field and ...
Opens in a new windowStylish & Luxurious 3 BDR Home with Play Station
Welcoming 3-bedroom house- Gardner home

Welcoming 3-bedroom house- Gardner home

Chicopee MA
Stay at this holiday home in Chicopee. Enjoy a garden, laundry facilities and air conditioning. Popular attractions MGM Springfield and Naismith Memorial Basketball ...
Opens in a new windowWelcoming 3-bedroom house- Gardner home
🌅A Lakefront Sunrise retreat for Couples or Families🌅

🌅A Lakefront Sunrise retreat for Couples or Families🌅

East Hampton CT
Stay at this family-friendly holiday home in East Hampton. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Lake Terramuggus and Marlborough ...
Opens in a new window🌅A Lakefront Sunrise retreat for Couples or Families🌅
Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires

Russell MA
The price is NZ$629 per night from 24 Mar to 25 Mar
NZ$629
24 Mar - 25 Mar
includes taxes & fees
Stay at this holiday home in Russell. Enjoy a garden, laundry facilities and patios. Popular attractions Tekoa Park and Westfield Wildlife Management Area are ...
Opens in a new windowBig farmhouse in the foothills of the Berkshires
Tranquil 3-bedroom house with AC in Hartford

Tranquil 3-bedroom house with AC in Hartford

Hartford CT
Stay at this holiday home in Hartford. Enjoy laundry facilities and air conditioning. Popular attractions Wintonbury Hills Playground and The Children's Museum ...
Opens in a new windowTranquil 3-bedroom house with AC in Hartford
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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
204 Holiday Homes
Lowest Price
NZ$222
Highest Price
NZ$629
Popular accommodation
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford, Cozy Nest ~ 3.5BR & 2Bath Home ~ Manchester CT, NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!, The Bungalow at Eagleville Lake Under 3 miles to UCONN! , Stylish & Luxurious 3 BDR Home with Play Station, Welcoming 3-bedroom house- Gardner home, 🌅A Lakefront Sunrise retreat for Couples or Families🌅, Big farmhouse in the foothills of the Berkshires, Tranquil 3-bedroom house with AC in Hartford

Top trending hotels in Windsor

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$236 per night from 3 Apr to 4 Apr
NZ$236
3 Apr - 4 Apr
includes taxes & fees
Stay at this business-friendly hotel in Windsor. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms in ...
Opens in a new windowHYATT house Hartford North/Windsor
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$222 per night from 1 Apr to 2 Apr
NZ$222
1 Apr - 2 Apr
includes taxes & fees
Stay at this business-friendly hotel in Windsor. Enjoy free breakfast, free Wi-Fi and an outdoor pool. Our guests praise the helpful staff in their reviews. ...
Opens in a new windowResidence Inn by Marriott Hartford/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$240 per night from 28 Mar to 29 Mar
NZ$240
28 Mar - 29 Mar
includes taxes & fees
Stay at this business-friendly hotel in Windsor. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Opens in a new windowHilton Garden Inn Hartford North/Bradley Int'l Airport
Save an average of 15% on thousands of hotels when you're signed in
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 NZ$277 per night from 3 Apr to 4 Apr
NZ$277
3 Apr - 4 Apr
includes taxes & fees
Stay at this business-friendly hotel in Windsor. Enjoy free parking, breakfast (surcharge) and a free airport shuttle. Our guests praise the helpful staff and ...
Opens in a new windowMarriott Hartford/Windsor Airport
Don't see what you're looking for?
See all available properties in 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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.