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Search Vacation Homes in New Windsor

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Dec 19 - Dec 21
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Dec 26 - Dec 28
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Jan 9 - Jan 11
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Feb 6 - Feb 8

Our top choices for New Windsor vacation homes

Interior
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Vacation Home in Warwick

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
9.2 out of 10, Wonderful, (7)
"Nice to have top notch bar/restaurant downstairs!"
United States
John E
$131 nightly
The price is $148
Dec 12 - Dec 13
Total with taxes and fees
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
TV, fireplace
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Vacation Home in Carmel Hamlet

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
9.8 out of 10, Exceptional, (12)
"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."
United States
Hannah P.
$328 nightly
The price is $355
Dec 15 - Dec 16
Total with taxes and fees
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Interior
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

Vacation Home in Kerhonkson

Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
10.0 out of 10, Exceptional, (32)
"I love the place, very comfortable and cozy, Thank you so very much, Enjoyed a lot , Julia"
United States
Julia K.
$185 nightly
The price is $188
Dec 15 - Dec 16
Total with taxes and fees
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Property grounds
Sleek Escape: Modern 3 BR- 4 Min from West Point !

Vacation Home in Highland Falls

Sleek Escape: Modern 3 BR- 4 Min from West Point !
10.0 out of 10, Exceptional, (2)
"Looked like this property was recently renovated. Very clean and nice. "
United States
Ellie M.
$391 nightly
The price is $394
Dec 12 - Dec 13
Total with taxes and fees
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Private kitchen
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,

Vacation Home in new paltz

Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,
9.6 out of 10, Exceptional, (5)
"5 stars!!! 100% recommended and I will be coming back! Host is prompt, attentive, and is great with communication!! No complaints at all!!! "
United States
Fantasia
$634 nightly
The price is $710
Dec 12 - Dec 13
Total with taxes and fees
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,
Dining
Renovated House w/Hot Tub, Deck, Grill & Fire Pit

Vacation Home in Goshen

Renovated House w/Hot Tub, Deck, Grill & Fire Pit
10.0 out of 10, Exceptional, (58)
"Clean and comfortable accommodations, very close to Legoland and Castle Fun Center! The kids loved the room with bunk beds, and it had a big selection of children's books and some toys, which was a nice bonus!"
United States
Jennifer K.
$466 nightly
The price is $487
Jan 4 - Jan 5, 2026
Total with taxes and fees
Renovated House w/Hot Tub, Deck, Grill & Fire Pit
Exterior
House on the Babbling Brook- Quiet 2BR + King Bed!

Vacation Home in Highland Falls

House on the Babbling Brook- Quiet 2BR + King Bed!
10.0 out of 10, Exceptional, (5)
$393 nightly
The price is $418
Dec 21 - Dec 22
Total with taxes and fees
House on the Babbling Brook- Quiet 2BR + King Bed!
Exterior
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Vacation Home in Hopewell Junction

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
9.0 out of 10, Wonderful, (10)
"We had a great last minute visit to Hopewell Junction and enjoyed a lovely stay at the chapel! It’s a very unique experience and quiet and peaceful. We enjoyed the bbq and an evening fire with smores! "
United States
Esther P.
$228 nightly
The price is $258
Dec 12 - Dec 13
Total with taxes and fees
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Exterior detail
Cozy private suite in the heart of beautiful Gardiner.

Vacation Home in New Paltz

Cozy private suite in the heart of beautiful Gardiner.
10.0 out of 10, Exceptional, (7)
"Check-in was easy. Hosts very responsive to any questions and helpful to local recommendations. "
United States
Chanah B.
$229 nightly
The price is $256
Dec 12 - Dec 13
Total with taxes and fees
Cozy private suite in the heart of beautiful Gardiner.
Interior
5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!

Vacation Home in Warwick

5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!
2.0 star property
10.0 out of 10, Exceptional, (5)
$328 nightly
The price is $371
Dec 14 - Dec 15
Total with taxes and fees
5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!
Property grounds
Quaint & Cozy Cottage | Wood Stove, Pet Friendly

Vacation Home in New Paltz

Quaint & Cozy Cottage | Wood Stove, Pet Friendly
10.0 out of 10, Exceptional, (3)
"Lovely home in a beautiful area of New York state. Would stay here again! "
United States
Jason W.
$480 nightly
The price is $537
Dec 15 - Dec 16
Total with taxes and fees
Quaint & Cozy Cottage | Wood Stove, Pet Friendly
Interior
Lovely 3BR Home with parking-Walk to WP Gate!

Vacation Home in Highland Falls

Lovely 3BR Home with parking-Walk to WP Gate!
10.0 out of 10, Exceptional, (7)
"Convenient location. Nice to have 3 queen beds. One parking space is in a lot, but street for any additional. Plenty of availability though. Excellent washer and dryer, dishwasher. Internet worked well. "
United States
Matt D.
$263 nightly
The price is $295
Dec 22 - Dec 23
Total with taxes and fees
Lovely 3BR Home with parking-Walk to WP Gate!
Outdoor dining
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Vacation Home in Fishkill

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
9.6 out of 10, Exceptional, (49)
"Inside was very nice, outside could use some curb appeal. Enjoyed our stay "
United States
Karen K.
$280 nightly
The price is $316
Dec 12 - Dec 13
Total with taxes and fees
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fridge, microwave, oven, stovetop
Fabulous 3bdrm Home w/parking!

Vacation Home in Highland Falls

Fabulous 3bdrm Home w/parking!
9.0 out of 10, Wonderful, (4)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
$263 nightly
The price is $288
Dec 14 - Dec 15
Total with taxes and fees
Fabulous 3bdrm Home w/parking!
Fridge, microwave, oven, stovetop
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

Vacation Home in New Paltz

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
2.0 star property
9.4 out of 10, Exceptional, (24)
"Beautiful comfortable, clean "
United States
Michal G.
$405 nightly
The price is $410
Dec 14 - Dec 15
Total with taxes and fees
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
Interior
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Vacation Home in Poughkeepsie

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
10.0 out of 10, Exceptional, (2)
"Great host"
United States
Lindsey F.
$496 nightly
The price is $581
Dec 15 - Dec 16
Total with taxes and fees
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Private kitchen
Tranquil 4-bedroom house in welcoming Poughquag neighborhood

Vacation Home in Poughquag

Tranquil 4-bedroom house in welcoming Poughquag neighborhood
2.0 star property
$284 nightly
The price is $322
Dec 15 - Dec 16
Total with taxes and fees
Tranquil 4-bedroom house in welcoming Poughquag neighborhood
Property grounds
3BR West Point Retreat-3min to Back Gate+ King Bed

Vacation Home in Highland Falls

3BR West Point Retreat-3min to Back Gate+ King Bed
7.6 out of 10, Good, (5)
"We were supposed to check out at 10 AM, and everyone was still sleeping. But at 8 AM, very loud noises suddenly started. It felt like the whole roof was shaking and the house might fall down. We went outside and saw that workers were cleaning the roof. No one told us anything about this before. When we asked the cleaning manager, he said the landlord booked this cleaning two weeks ago, but we, the guests, were never informed. Also, our car was parked in the driveway, and the things falling from...
United States
Lixing
$463 nightly
The price is $524
Dec 21 - Dec 22
Total with taxes and fees
3BR West Point Retreat-3min to Back Gate+ King Bed
Pool
Spectacular Historic Mansion w/Pool&Tennis

Vacation Home in Goshen

Spectacular Historic Mansion w/Pool&Tennis
10.0 out of 10, Exceptional, (17)
"Truly amazing house, incredible pool, easy renting experience. Would definitely be back. "
United States
Aditya U.
$3,212 nightly
The price is $3,355
Dec 30 - Dec 31
Total with taxes and fees
Spectacular Historic Mansion w/Pool&Tennis
Outdoor dining
Stylish & Peaceful Getaway on 3 Private Acres

Vacation Home in Goshen

Stylish & Peaceful Getaway on 3 Private Acres
2.0 star property
9.0 out of 10, Wonderful, (12)
"Great location!"
United States
Alozie E.
$435 nightly
The price is $435
Dec 12 - Dec 13
Total with taxes and fees
Stylish & Peaceful Getaway on 3 Private Acres
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

Windrose On Hudson

Windrose On Hudson

10/10 Excellent
"Clean room, staff were very welcoming"
Semaj 1-night trip
Posted 2 days ago
Windrose On Hudson

Find out more about New Windsor

New Windsor Vacation Homes information

Number of reviews
252
Accommodation
383 Vacation Homes
Lowest Price
$148
Highest Price
$3,355

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