Book Holiday Homes in Windsor

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Featured Holiday Homes in Windsor

Downtown and secluded

Downtown and secluded

Manchester CT
Stay at this holiday home in Manchester. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Cheney Homestead Museum and Lutz Children's Museum ...
Opens in a new windowDowntown and secluded
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs

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

Coventry CT
The price is NZ$445 per night from 19 May to 20 May
NZ$445
19 May - 20 May
includes taxes & fees
Stay at this beach holiday home in Coventry. Enjoy free Wi-Fi, a beach locale and a garden. Popular attractions Nathan Hale Homestead and J. M. Sarnik & Sons' ...
Opens in a new windowLakefront - King - W&D - Fire Pit - Kayaks - SUPs
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 Windsor Arts Center are located nearby.
Opens in a new windowNEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
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Linny's Lakeview Cottage - updated

Linny's Lakeview Cottage - updated

Southwick MA
Stay at this family-friendly holiday home in Southwick. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Congamond Heights and Babbs Beach ...
Opens in a new windowLinny's Lakeview Cottage - updated
Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants

Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants

Somers CT
The price is NZ$635 per night from 8 June to 9 June
NZ$635
8 June - 9 June
includes taxes & fees
Stay at this holiday home in Somers. Enjoy laundry facilities and air conditioning. Popular attractions Sonny's Place and Scantic River State Park are located ...
Opens in a new windowSpacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
4 Bed, 3 Bath Urban Luxury in Central CT w/ free RV parking

4 Bed, 3 Bath Urban Luxury in Central CT w/ free RV parking

Newington CT
Stay at this family-friendly holiday home in Newington. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Brickyard Shopping Center and Dinosaur ...
Opens in a new window4 Bed, 3 Bath Urban Luxury in Central CT w/ free RV parking
Linny’s Lake House with dock

Linny’s Lake House with dock

West Suffield CT
Stay at this family-friendly holiday home in Southwick. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Congamond Heights and Suffield ...
Opens in a new windowLinny’s Lake House with dock
#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat

Middletown CT
The price is NZ$649 per night from 18 May to 19 May
NZ$649
18 May - 19 May
includes taxes & fees
Stay at this holiday home in Middletown. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Connecticut River State Wildlife Area and Brownstone ...
Opens in a new window#24 *Serenity* A Lakefront Cottage Retreat
Charming 4-bedroom house with AC in East Hartford

Charming 4-bedroom house with AC in East Hartford

East Hartford CT
Stay at this holiday home in East Hartford. Enjoy laundry facilities and air conditioning. Popular attractions Rentschler Field and Cabela's are located ...
Opens in a new windowCharming 4-bedroom house with AC in East 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
231 Holiday Homes
Lowest Price
NZ$219
Highest Price
NZ$649
Popular accommodation
Downtown and secluded, Lakefront - King - W&D - Fire Pit - Kayaks - SUPs, NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!, Linny's Lakeview Cottage - updated, Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants, 4 Bed, 3 Bath Urban Luxury in Central CT w/ free RV parking, Linny’s Lake House with dock, #24 *Serenity* A Lakefront Cottage Retreat, Charming 4-bedroom house with AC in East Hartford

Top trending hotels in Windsor

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$384 per night from 9 May to 10 May
NZ$384
9 May - 10 May
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
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$219 per night from 25 May to 26 May
NZ$219
25 May - 26 May
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
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$291 per night from 25 May to 26 May
NZ$291
25 May - 26 May
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
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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$246 per night from 25 May to 26 May
NZ$246
25 May - 26 May
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
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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.