Book Holiday Homes in Windsor

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Featured Holiday Homes in Windsor

New!Quaint & Convenient Hideaway: Great Location

New!Quaint & Convenient Hideaway: Great Location

East Hartford
Stay at this vacation home in East Hartford. Enjoy an in-room coffeemaker and air conditioning. Popular attractions Xfinity Theatre and Cabela's are located ...
New!Quaint & Convenient Hideaway: Great Location
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 Xfinity Theatre and Loomis Chaffee School are located nearby.
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

Springfield
The price is NZ$570 per night from 30 Sept to 1 Oct
NZ$570
30 Sept - 1 Oct
includes taxes & fees
Book a stay at this family-friendly vacation home in Springfield. Enjoy free WiFi, a water park, and a fitness center. Popular attractions Six Flags New England ...
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
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Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

SPRINGFIELD
The price is NZ$576 per night from 8 Sept to 9 Sept
NZ$576
8 Sept - 9 Sept
includes taxes & fees
Stay at this vacation home in Springfield. Enjoy laundry facilities, an in-room coffeemaker, and air conditioning. Popular attractions MGM Springfield and Naismith ...
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove

Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove

Barkhamsted
Stay at this vacation home in Barkhamsted. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Canton Land Conservation Trust and Joan Kenney ...
Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove
Prime West Hartford Center Location: Historic Gem

Prime West Hartford Center Location: Historic Gem

West Hartford
Stay at this vacation home in West Hartford. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Xfinity Theatre and Blue Back Square are ...
Prime West Hartford Center Location: Historic Gem
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs

Lakefront - King - W&D - Fire Pit - Kayaks - SUPs

Coventry
The price is NZ$533 per night from 15 Sept to 16 Sept
NZ$533
15 Sept - 16 Sept
includes taxes & fees
Book a stay at this beach vacation home in Coventry. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Nathan Hale Homestead and J. M. Sarnik ...
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
Massive 5 Bedrooms: 3King 2Queen, 10 mins to Downtown Hartford

Massive 5 Bedrooms: 3King 2Queen, 10 mins to Downtown Hartford

Bloomfield
The price is NZ$1,053 per night from 8 Sept to 9 Sept
NZ$1,053
8 Sept - 9 Sept
includes taxes & fees
Stay at this vacation home in Bloomfield. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Xfinity Theatre and Bloomfield Crossing are located ...
Massive 5 Bedrooms: 3King 2Queen, 10 mins to Downtown Hartford
Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires

Russell
The price is NZ$606 per night from 7 Sept to 8 Sept
NZ$606
7 Sept - 8 Sept
includes taxes & fees
Stay at this vacation home in Russell. Enjoy a garden, laundry facilities, and patios. Our guests praise the property condition in our reviews. Popular attractions ...
Big farmhouse in the foothills of the Berkshires
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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
215 Holiday Homes
Lowest Price
NZ$269
Highest Price
NZ$1,053
Popular accommodation
New!Quaint & Convenient Hideaway: Great Location, NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!, Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!, Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield, Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove , Prime West Hartford Center Location: Historic Gem, Lakefront - King - W&D - Fire Pit - Kayaks - SUPs, Massive 5 Bedrooms: 3King 2Queen, 10 mins to Downtown Hartford, Big farmhouse in the foothills of the Berkshires

Top trending hotels in Windsor

Marriott Hartford/Windsor Airport

Marriott Hartford/Windsor Airport

3.5 out of 5
28 Day Hill Rd, Windsor, CT
The price is NZ$369 per night from 4 Oct to 5 Oct
NZ$369
4 Oct - 5 Oct
includes taxes & fees
Stay at this 3.5-star business-friendly hotel in Windsor. Enjoy free parking, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
Marriott Hartford/Windsor Airport
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$269 per night from 5 Oct to 6 Oct
NZ$269
5 Oct - 6 Oct
includes taxes & fees
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
The price is NZ$367 per night from 1 Oct to 2 Oct
NZ$367
1 Oct - 2 Oct
includes taxes & fees
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
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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$283 per night from 14 Sept to 15 Sept
NZ$283
14 Sept - 15 Sept
includes taxes & fees
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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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.

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^Subject to availability and chosen travel dates.