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Search Vacation Homes in New Windsor

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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

Vacation Homes in New Windsor

Interior
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

Vacation Home in Kerhonkson

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.
The price is AED 290
AED 689 total
includes taxes & fees
11 Dec - 12 Dec
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Interior
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Vacation Home in Warwick

9.2 out of 10, Wonderful, (7)
"Nice to have top notch bar/restaurant downstairs!"
United States
John E
The price is AED 304
AED 544 total
includes taxes & fees
10 Dec - 11 Dec
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

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.
The price is AED 612
AED 1,304 total
includes taxes & fees
15 Dec - 16 Dec
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Property grounds
Sleek Escape: Modern 3 BR- 4 Min from West Point !

Vacation Home in Highland Falls

10.0 out of 10, Exceptional, (2)
"Looked like this property was recently renovated. Very clean and nice. "
United States
Ellie M.
The price is AED 345
AED 1,469 total
includes taxes & fees
10 Dec - 11 Dec
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Dining
Renovated House w/Hot Tub, Deck, Grill & Fire Pit

Vacation Home in Goshen

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.
The price is AED 909
AED 1,813 total
includes taxes & fees
4 Jan - 5 January 2026
Renovated House w/Hot Tub, Deck, Grill & Fire Pit
Private kitchen
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,

Vacation Home in new paltz

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
The price is AED 661
AED 2,608 total
includes taxes & fees
10 Dec - 11 Dec
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,
Property grounds
Quaint & Cozy Cottage | Wood Stove, Pet Friendly

Vacation Home in New Paltz

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.
The price is AED 601
AED 2,087 total
includes taxes & fees
14 Dec - 15 Dec
Quaint & Cozy Cottage | Wood Stove, Pet Friendly
Outdoor dining
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Vacation Home in Fishkill

9.6 out of 10, Exceptional, (49)
"Inside was very nice, outside could use some curb appeal. Enjoyed our stay "
United States
Karen K.
The price is AED 909
AED 1,161 total
includes taxes & fees
10 Dec - 11 Dec
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Interior
Lovely 3BR Home with parking-Walk to WP Gate!

Vacation Home in Highland Falls

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.
The price is AED 690
AED 1,269 total
includes taxes & fees
5 Jan - 6 January 2026
Lovely 3BR Home with parking-Walk to WP Gate!
Interior
5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!

Vacation Home in Warwick

2.0 star property
10.0 out of 10, Exceptional, (5)
The price is AED 518
AED 1,363 total
includes taxes & fees
17 Dec - 18 Dec
5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!
Exterior detail
Cozy private suite in the heart of beautiful Gardiner.

Vacation Home in New Paltz

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.
The price is AED 469
AED 941 total
includes taxes & fees
10 Dec - 11 Dec
Cozy private suite in the heart of beautiful Gardiner.
Exterior
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Vacation Home in Hopewell Junction

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.
The price is AED 559
AED 948 total
includes taxes & fees
10 Dec - 11 Dec
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Fridge, microwave, oven, stovetop
Fabulous 3bdrm Home w/parking!

Vacation Home in Highland Falls

9.0 out of 10, Wonderful, (4)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
The price is AED 667
AED 1,208 total
includes taxes & fees
5 Jan - 6 January 2026
Fabulous 3bdrm Home w/parking!
Fridge, microwave, oven, stovetop
Marvelous 6-bedroom house with AC in Monroe

Vacation Home in Monroe

Marvelous 6-bedroom house with AC in Monroe
Interior
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Vacation Home in Poughkeepsie

10.0 out of 10, Exceptional, (2)
"Great host"
United States
Lindsey F.
The price is AED 605
AED 2,133 total
includes taxes & fees
15 Dec - 16 Dec
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Property grounds
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!

Vacation Home in wallkill

9.8 out of 10, Exceptional, (57)
"Loved this property, clean, wonderful view of the river. Quite neighborhood. Great location "
United States
Mamie G.
The price is AED 727
AED 1,538 total
includes taxes & fees
18 Dec - 19 Dec
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
Smart TV, video games, DVD player, foosball
Spacious 4-bedroom home on 5 acre farm near Minnewaska State Park

Vacation Home in Pine Bush

9.4 out of 10, Exceptional, (43)
"Such a beautiful home and peaceful farm setting! We especially loved the game room and spacious living areas — perfect for relaxing and spending quality time together as a family. Good location as well! "
United States
Shachi S.
The price is AED 895
AED 1,944 total
includes taxes & fees
10 Dec - 11 Dec
Spacious 4-bedroom home on 5 acre farm near Minnewaska State Park
Property grounds
Fun, Friends, and Family Lakefront Home w/Dock and Beach

Vacation Home in Mahopac

10.0 out of 10, Exceptional, (12)
"Super convenient location :)"
United States
Sean M.
The price is AED 1,240
AED 2,649 total
includes taxes & fees
11 Dec - 12 Dec
Fun, Friends, and Family Lakefront Home w/Dock and Beach
Interior
Large,Cozy,Bright Apartment, Business Themed.

Vacation Home in Newburgh

9.0 out of 10, Wonderful, (15)
"Very cozy stay with responsive host"
United States
Adhith P.
The price is AED 1,322
AED 1,761 total
includes taxes & fees
10 Dec - 11 Dec
Large,Cozy,Bright Apartment, Business Themed.
Pool
Spectacular Historic Mansion w/Pool&Tennis

Vacation Home in Goshen

10.0 out of 10, Exceptional, (17)
"Truly amazing house, incredible pool, easy renting experience. Would definitely be back. "
United States
Aditya U.
The price is AED 8,099
AED 11,433 total
includes taxes & fees
30 Dec - 31 Dec
Spectacular Historic Mansion w/Pool&Tennis
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

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown

10/10 Excellent
"Clean room and easy check in. "
Melanie 2-night trip
Posted 2 days ago
Hampton Inn by Hilton Middletown

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