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Our top choices for New Windsor vacation homes

Vacation Home in Highland Falls
House on the Babbling Brook- Quiet 2BR + King Bed!10.0 out of 10, Exceptional, (5)
$327 nightly
The price is $344
Dec 21 - Dec 22
Total with taxes and fees

Vacation Home in Highland Falls
Fabulous 3bdrm Home w/parking!9.0 out of 10, Wonderful, (4)
$253 nightly
The price is $276
Dec 21 - Dec 22
Total with taxes and fees

Vacation Home in Highland Falls
3BR West Point Retreat-3min to Back Gate+ King Bed7.6 out of 10, Good, (5)
$377 nightly
The price is $427
Dec 21 - Dec 22
Total with taxes and fees

Vacation Home in Warwick
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town9.4 out of 10, Exceptional, (8)
$135 nightly
The price is $153
Jan 6 - Jan 7, 2026
Total with taxes and fees

Vacation Home in Carmel Hamlet
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.9.8 out of 10, Exceptional, (12)
$328 nightly
The price is $355
Dec 21 - Dec 22
Total with taxes and fees

Vacation Home in Kerhonkson
Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks10.0 out of 10, Exceptional, (14)
$185 nightly
The price is $188
Jan 8 - Jan 9, 2026
Total with taxes and fees

Vacation Home in Highland Falls
Sleek Escape: Modern 3 BR- 4 Min from West Point !10.0 out of 10, Exceptional, (3)
$426 nightly
The price is $432
Jan 13 - Jan 14, 2026
Total with taxes and fees

Vacation Home in Goshen
Spectacular Historic Mansion w/Pool&Tennis10.0 out of 10, Exceptional, (17)
$3,052 nightly
The price is $3,195
Dec 30 - Dec 31
Total with taxes and fees
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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Top New Windsor Hotel Reviews

Holiday Inn Express Hotel & Suites Chester by IHG
10/10 Excellent
Find out more about New Windsor
New Windsor Vacation Homes information
Number of reviews | 261 |
|---|---|
Accommodation | 375 Vacation Homes |
Lowest Price | $153 |
Highest Price | $3,501 |
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