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
This vacation home is 14.8 mi (23.9 km) from Binghamton University and 0.1 mi (0.1 km) from Susquehanna River.
Tranquil River cottage w/hot tub, firepit , mins to a 18-holes golfing & fishing
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
Charming 3-bedroom 2 Bath house in wonderful Endicott with AC, WiFi!

Charming 3-bedroom 2 Bath house in wonderful Endicott with AC, WiFi!

Endicott
With a stay at this vacation home in Endicott, you'll be next to a golf course, within a 15-minute drive of Binghamton University and En-Joie Golf Course.
Charming 3-bedroom 2 Bath house in wonderful Endicott with AC, WiFi!
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Waterfront house on the upper most portion of the West Branch Delaware.

Waterfront house on the upper most portion of the West Branch Delaware.

Deposit
With a stay at this vacation home in Deposit, you'll be on the waterfront, just steps from West Branch Delaware River and a 4-minute drive from Warner ...
Waterfront house on the upper most portion of the West Branch Delaware.
Cozy ranch 3-bedroom house with WiFi, AC in brilliant Vestal

Cozy ranch 3-bedroom house with WiFi, AC in brilliant Vestal

Vestal
The price is AU$455 per night from 23 Apr to 24 Apr
AU$455
includes taxes & fees
23 Apr - 24 Apr
With a stay at this vacation home in Vestal, you'll be within a 10-minute drive of Binghamton University and Endicott Riverside Cemetery.
Cozy ranch 3-bedroom house with WiFi, AC in brilliant Vestal
Spacious 6-bedroom house with AC, fitness room, pool, WiFi in charming Vestal

Spacious 6-bedroom house with AC, fitness room, pool, WiFi in charming Vestal

Vestal
With a stay at this vacation home in Vestal, you'll be within a 10-minute drive of Binghamton University and Endicott Riverside Cemetery.
Spacious 6-bedroom house with AC, fitness room, pool, WiFi in charming Vestal
Binghamton's Beautiful Riverside Drive Living!

Binghamton's Beautiful Riverside Drive Living!

Binghamton
With a stay at this vacation home in Binghamton, you'll be within a 10-minute drive of Binghamton University and Susquehanna River.
Binghamton's Beautiful Riverside Drive Living!
Scenic Home on the Delaware River, Pet-Friendly!

Scenic Home on the Delaware River, Pet-Friendly!

Hancock
When you stay at this vacation home in Hancock, you'll be on the waterfront, within a 10-minute walk of Hancock Town Square and Hancock-Chehocton Historical ...
Scenic Home on the Delaware River, Pet-Friendly!
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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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
109 Holiday Homes
Lowest Price
AU$152
Highest Price
AU$494
Popular accommodation
Tranquil River cottage w/hot tub, firepit , mins to a 18-holes golfing & fishing, Breathtaking 44+ Acre Country Estate, Charming 3-bedroom 2 Bath house in wonderful Endicott with AC, WiFi!, Waterfront house on the upper most portion of the West Branch Delaware., Cozy ranch 3-bedroom house with WiFi, AC in brilliant Vestal, Spacious 6-bedroom house with AC, fitness room, pool, WiFi in charming Vestal, Binghamton's Beautiful Riverside Drive Living! , Scenic Home on the Delaware River, Pet-Friendly!, Lakefront Gem: Hot Tub & Game Room in Hancock

Top trending hotels in Windsor

Waterfront Properties vacation rental

Waterfront Properties vacation rental

Windsor
The price is AU$494 per night from 1 May to 2 May
AU$494
includes taxes & fees
1 May - 2 May
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
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$186 per night from 30 Apr to 1 May
AU$186
includes taxes & fees
30 Apr - 1 May
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 by IHG

Holiday Inn Binghamton Downtown by IHG

3 out of 5
2-8 Hawley Street, Binghamton, NY
Fully refundable
The price is AU$220 per night from 20 Apr to 21 Apr
AU$220
includes taxes & fees
20 Apr - 21 Apr
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 by IHG
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Comfort Inn Binghamton I-81

Comfort Inn Binghamton I-81

2.5 out of 5
1000 Upper Front St, Binghamton, NY
Fully refundableReserve now, pay when you stay
The price is AU$152 per night from 27 Apr to 28 Apr
AU$152
includes taxes & fees
27 Apr - 28 Apr
A stay at Comfort Inn Binghamton I-81 places you in the heart of Binghamton, within a 10-minute drive of Municipal Stadium and Mirabito Stadium.
Comfort Inn Binghamton I-81
Don't see what you're looking for?
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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.