Book Holiday Homes in Windsor

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Featured Holiday Homes in Windsor

Tranquil River cottage w/hot tub, firepit , mins to a 18-holes golfing & fishing

Tranquil River cottage w/hot tub, firepit , mins to a 18-holes golfing & fishing

Conklin NY
This vacation home is 14.8 mi (23.9 km) from Binghamton University and 0.1 mi (0.1 km) from Susquehanna River.
Opens in a new windowTranquil River cottage w/hot tub, firepit , mins to a 18-holes golfing & fishing
Spacious Winter Retreat w/ Hot Tub, Games, Fire Pit & Scenic Hilltop Views!

Spacious Winter Retreat w/ Hot Tub, Games, Fire Pit & Scenic Hilltop Views!

Thompson PA
The price is AU$407 per night from 26 Apr to 27 Apr
AU$407
26 Apr - 27 Apr
includes taxes & fees
With a stay at this vacation home in Susquehanna, you'll be in the mountains, and 8.5 mi (13.6 km) from North Knob and 8.6 mi (13.8 km) from Snow Bowl.
Opens in a new windowSpacious Winter Retreat w/ Hot Tub, Games, Fire Pit & Scenic Hilltop Views!
Charming 3-bedroom house in peaceful Binghamton, close to downtown, with AC

Charming 3-bedroom house in peaceful Binghamton, close to downtown, with AC

Binghamton NY
With a stay at this vacation home in Binghamton, you'll be within a 10-minute drive of Binghamton University and Ross Park Carousel.
Opens in a new windowCharming 3-bedroom house in peaceful Binghamton, close to downtown, with AC
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FRENCH WOODS FARMHOUSE | TimeOut NY's Pick | Hot tub | Pond | Dogs OK | NYC=2hr

FRENCH WOODS FARMHOUSE | TimeOut NY's Pick | Hot tub | Pond | Dogs OK | NYC=2hr

Hancock NY
Located in Hancock, this vacation home is on the waterfront, within a 10-minute drive of West Branch Delaware River and Capitol Theatre.
Opens in a new windowFRENCH WOODS FARMHOUSE | TimeOut NY's Pick | Hot tub | Pond | Dogs OK | NYC=2hr
Binghamton's Beautiful Riverside Drive Living!

Binghamton's Beautiful Riverside Drive Living!

Binghamton NY
The price is AU$1,040 per night from 26 May to 27 May
AU$1,040
26 May - 27 May
includes taxes & fees
With a stay at this vacation home in Binghamton, you'll be within a 10-minute drive of Binghamton University and Susquehanna River.
Opens in a new windowBinghamton's Beautiful Riverside Drive Living!
Renovated Hancock NY house near Delaware River

Renovated Hancock NY house near Delaware River

Hancock NY
When you stay at this vacation home in Hancock, you'll be on a river, just steps from East Branch Delaware River and Hancock Town Square.
Opens in a new windowRenovated Hancock NY house near Delaware River
Breathtaking 44+ Acre Country Estate

Breathtaking 44+ Acre Country Estate

Pleasant Mount PA
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 ...
Opens in a new windowBreathtaking 44+ Acre Country Estate
Lakeside Gem: Hot Tub & Game Room in Hancock

Lakeside Gem: Hot Tub & Game Room in Hancock

Hancock NY
Located in Hancock, this vacation home is on the waterfront, within a 10-minute drive of West Branch Delaware River and Kerryville State Forest.
Opens in a new windowLakeside Gem: Hot Tub & Game Room in Hancock
Your Tranquil Oasis on the Susquehanna River

Your Tranquil Oasis on the Susquehanna River

Kirkwood NY
This vacation home is 18.1 mi (29.2 km) from Binghamton University and 0.1 mi (0.1 km) from Susquehanna River.
Opens in a new windowYour Tranquil Oasis on the Susquehanna River
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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
80 Holiday Homes
Lowest Price
AU$137
Highest Price
AU$1,040
Popular accommodation
Tranquil River cottage w/hot tub, firepit , mins to a 18-holes golfing & fishing, Spacious Winter Retreat w/ Hot Tub, Games, Fire Pit & Scenic Hilltop Views!, Charming 3-bedroom house in peaceful Binghamton, close to downtown, with AC, FRENCH WOODS FARMHOUSE | TimeOut NY's Pick | Hot tub | Pond | Dogs OK | NYC=2hr, Binghamton's Beautiful Riverside Drive Living! , Renovated Hancock NY house near Delaware River, Breathtaking 44+ Acre Country Estate, Lakeside Gem: Hot Tub & Game Room in Hancock, Your Tranquil Oasis on the Susquehanna River

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$137 per night from 30 Apr to 1 May
AU$137
30 Apr - 1 May
includes taxes & fees
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 ...
Opens in a new windowMicrotel Inn & Suites By Wyndham Binghamton
Spark by Hilton Vestal Binghamton University Area

Spark by Hilton Vestal Binghamton University Area

2.5 out of 5
3401 Vestal Parkway Vestal NY
Fully refundableReserve now, pay when you stay
The price is AU$149 per night from 3 May to 4 May
AU$149
3 May - 4 May
includes taxes & fees
A stay at Spark by Hilton Vestal Binghamton University Area places you in the heart of Vestal, within a 5-minute drive of Binghamton University and Arnold ...
Opens in a new windowSpark by Hilton Vestal Binghamton University Area
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$145 per night from 28 Apr to 29 Apr
AU$145
28 Apr - 29 Apr
includes taxes & fees
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.
Opens in a new windowTru by Hilton Binghamton Vestal
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Holiday Inn Binghamton Downtown by IHG

Holiday Inn Binghamton Downtown by IHG

3 out of 5
2-8 Hawley Street Binghamton NY
Fully refundable
The price is AU$226 per night from 24 May to 25 May
AU$226
24 May - 25 May
includes taxes & fees
With a stay at Holiday Inn Binghamton Downtown by IHG, you'll be centrally located in Binghamton, steps from Floyd L. Maines Veterans Memorial Arena and within ...
Opens in a new windowHoliday Inn Binghamton Downtown by IHG
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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.

Top Picks

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^Subject to availability and chosen travel dates.