Book Holiday Homes in Windsor

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Featured Holiday Homes in Windsor

Indoor Pool, 13 BR, Sleeps 39, 3 Luxury Homes

Indoor Pool, 13 BR, Sleeps 39, 3 Luxury Homes

Hancock
Located in Hancock, this vacation home is in the mountains, within a 10-minute drive of Hancock Town Hall and Hancock Hounds Dog Park.
Indoor Pool, 13 BR, Sleeps 39, 3 Luxury Homes
Waterfront Properties vacation rental

Waterfront Properties vacation rental

Windsor
The price is AU$493 per night from 28 Feb to 1 Mar
AU$493
includes taxes & fees
28 Feb - 1 Mar
A stay at this vacation home places you in the heart of Windsor, a 1-minute drive from Susquehanna River and 9 minutes from Animal Adventure Park.
Waterfront Properties vacation rental
Lakefront Gem: Hot Tub & Game Room in Hancock

Lakefront Gem: Hot Tub & Game Room in Hancock

Hancock
Located in Hancock, this vacation home is on the waterfront, within a 10-minute drive of West Branch Delaware River and Kerryville State Forest.
Lakefront Gem: Hot Tub & Game Room in Hancock
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11 Bedroom Lake House, 150 ft Lakefront, 1 Acre, Beach, Ski Elk Mountain Poconos

11 Bedroom Lake House, 150 ft Lakefront, 1 Acre, Beach, Ski Elk Mountain Poconos

Montrose
When you a stay at this vacation home in Montrose, you'll be on the waterfront, just steps from Endless Mountains and Heart Lake.
11 Bedroom Lake House, 150 ft Lakefront, 1 Acre, Beach, Ski Elk Mountain Poconos
Charming & Private Delaware Riverfront Home near Callicoon NY

Charming & Private Delaware Riverfront Home near Callicoon NY

Equinunk
When you a stay at this vacation home in Equinunk, you'll be on the waterfront, just steps from Upper Delaware Scenic and Recreational Area and Upper Delaware ...
Charming & Private Delaware Riverfront Home near Callicoon NY
Breathtaking 44+ Acre Country Estate

Breathtaking 44+ Acre Country Estate

Pleasant Mount
A stay at this vacation home places you in the heart of Pleasant Mount, a 1-minute drive from Lake Lorain and 12 minutes from Preston Township Municipal ...
Breathtaking 44+ Acre Country Estate
LARGE RUSTIC BRICK SCHOOL HOUSE  WITH MUSIC JAMSPACE /RECORDING STUDIO

LARGE RUSTIC BRICK SCHOOL HOUSE WITH MUSIC JAMSPACE /RECORDING STUDIO

hancock
When you stay at this vacation home in Hancock, you'll be on a river, within a 5-minute drive of East Branch Delaware River and Capitol Theatre.
LARGE RUSTIC BRICK SCHOOL HOUSE WITH MUSIC JAMSPACE /RECORDING STUDIO
Poconos Home w/ Private Hot Tub & Fireplace

Poconos Home w/ Private Hot Tub & Fireplace

Pleasant Mount
With a stay at this vacation home in Pleasant Mount, you'll be within a 15-minute drive of Lake Lorain and Preston Township Municipal Building.
Poconos Home w/ Private Hot Tub & Fireplace
New York Abode: 2 Mi to Binghamton University!

New York Abode: 2 Mi to Binghamton University!

Binghamton
With a stay at this vacation home in Binghamton, you'll be within a 5-minute drive of Binghamton University and Susquehanna River.
New York Abode: 2 Mi to Binghamton University!
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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
99 Holiday Homes
Lowest Price
AU$149
Highest Price
AU$493
Popular accommodation
Indoor Pool, 13 BR, Sleeps 39, 3 Luxury Homes , Waterfront Properties vacation rental, Lakefront Gem: Hot Tub & Game Room in Hancock, 11 Bedroom Lake House, 150 ft Lakefront, 1 Acre, Beach, Ski Elk Mountain Poconos, Charming & Private Delaware Riverfront Home near Callicoon NY, Breathtaking 44+ Acre Country Estate, LARGE RUSTIC BRICK SCHOOL HOUSE WITH MUSIC JAMSPACE /RECORDING STUDIO, Poconos Home w/ Private Hot Tub & Fireplace, New York Abode: 2 Mi to Binghamton University!

Top trending hotels in Windsor

Microtel Inn & Suites By Wyndham Binghamton

Microtel Inn & Suites By Wyndham Binghamton

2.5 out of 5
400 Prospect Street, Binghamton, NY
Fully refundableReserve now, pay when you stay
The price is AU$149 per night from 23 Feb to 24 Feb
AU$149
includes taxes & fees
23 Feb - 24 Feb
With a stay at Microtel Inn & Suites By Wyndham Binghamton in Binghamton, you'll be within a 10-minute drive of Binghamton University and C. Fred Johnson Park ...
Microtel Inn & Suites By Wyndham Binghamton
Holiday Inn Binghamton Downtown, an IHG Hotel

Holiday Inn Binghamton Downtown, an IHG Hotel

3 out of 5
2-8 Hawley Street, Binghamton, NY
Fully refundable
The price is AU$212 per night from 2 Mar to 3 Mar
AU$212
includes taxes & fees
2 Mar - 3 Mar
A stay at Holiday Inn Binghamton Downtown by IHG places you in the heart of Binghamton, within a 5-minute walk of Floyd L. Maines Veterans Memorial Arena and ...
Holiday Inn Binghamton Downtown, an IHG Hotel
Tru by Hilton Binghamton Vestal

Tru by Hilton Binghamton Vestal

2.5 out of 5
3504 Vestal Parkway East, Vestal, NY
Fully refundableReserve now, pay when you stay
The price is AU$184 per night from 3 Mar to 4 Mar
AU$184
includes taxes & fees
3 Mar - 4 Mar
When you stay at Tru by Hilton Binghamton Vestal in Vestal, you'll be near the airport, within a 5-minute drive of Binghamton University and Arnold Park.
Tru by Hilton Binghamton Vestal
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DoubleTree by Hilton Hotel Binghamton

DoubleTree by Hilton Hotel Binghamton

4 out of 5
225 Water St, Binghamton, NY
Fully refundableReserve now, pay when you stay
The price is AU$213 per night from 2 Mar to 3 Mar
AU$213
includes taxes & fees
2 Mar - 3 Mar
With a stay at DoubleTree by Hilton Hotel Binghamton, you'll be centrally located in Binghamton, steps from The Forum Theater and within a 10-minute walk of ...
DoubleTree by Hilton Hotel Binghamton
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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.