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Search Vacation Homes in New Windsor

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Next weekend
Dec 26 - Dec 28
In two weeks
Jan 2 - Jan 4
In one month
Jan 16 - Jan 18
In two months
Feb 13 - Feb 15

Our top choices for New Windsor vacation homes

Exterior
House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
10.0 out of 10, Exceptional, (5)
"A clean and convenient place to stay for visiting our cadet at West Point. Our hosts were very communicative and helpful. The home and parking situation was just as described. Nice quiet neighborhood, well maintained home. Hearing the babbling broom outside the living room window was very relaxing. Plan on staying here again!"
United States
Maria L.
$333 nightly
The price is $350
Dec 21 - Dec 22
Total with taxes and fees
House on the Babbling Brook- Quiet 2BR + King Bed!
Interior
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
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.
$181 nightly
The price is $183
Jan 8 - Jan 9, 2026
Total with taxes and fees
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Fridge, microwave, oven, stovetop
Bright Contemporary Near The Best Hiking Trails

Bright Contemporary Near The Best Hiking Trails

Bright Contemporary Near The Best Hiking Trails
Pine Bush
10.0 out of 10, Exceptional, (3)
"Nice property, very close to Sam’s Point trailheads. We were there to hike, so this was perfect. We would definitely book again."
United States
Amy L.
$435 nightly
The price is $487
Jan 14 - Jan 15, 2026
Total with taxes and fees
Bright Contemporary Near The Best Hiking Trails
Fridge, microwave, oven, stovetop
Cozy Escape -Strong Wi-Fi -Prime Location

Cozy Escape -Strong Wi-Fi -Prime Location

Cozy Escape -Strong Wi-Fi -Prime Location
Poughkeepsie
6.8 out of 10, (5)
"The property was perfect for our little weekend getaway. It was very clean and cozy and the host Christina made it so easy for check in and was available for any questions. We would definitely stay again."
United States
Andrea C.
$255 nightly
The price is $299
Dec 21 - Dec 22
Total with taxes and fees
Cozy Escape -Strong Wi-Fi -Prime Location
Interior
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

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

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Warwick
9.4 out of 10, Exceptional, (8)
"The room was clean, the staff at the restaurant were friendly. Truely enjoyed our stay."
United States
Milo M.
$135 nightly
The price is $153
Jan 6 - Jan 7, 2026
Total with taxes and fees
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Property grounds
Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
10.0 out of 10, Exceptional, (3)
"The host was prompt and attentive to any questions that arose. The home appeared exactly as depicted in the pictures and was perfect for a weekend stay close to family and The city!"
United States
Julio J.
$426 nightly
The price is $432
Jan 13 - Jan 14, 2026
Total with taxes and fees
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Dining
Renovated House w/Hot Tub, Deck, Grill & Fire Pit

Renovated House w/Hot Tub, Deck, Grill & Fire Pit

Renovated House w/Hot Tub, Deck, Grill & Fire Pit
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.
$456 nightly
The price is $477
Jan 4 - Jan 5, 2026
Total with taxes and fees
Renovated House w/Hot Tub, Deck, Grill & Fire Pit
Exterior detail
Cozy private suite in the heart of beautiful Gardiner.

Cozy private suite in the heart of beautiful Gardiner.

Cozy private suite in the heart of beautiful Gardiner.
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.
$229 nightly
The price is $256
Dec 21 - Dec 22
Total with taxes and fees
Cozy private suite in the heart of beautiful Gardiner.
Interior
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Poughkeepsie
10.0 out of 10, Exceptional, (2)
"Great host"
United States
Lindsey F.
$550 nightly
The price is $644
Jan 5 - Jan 6, 2026
Total with taxes and fees
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Outdoor dining
Stylish & Peaceful Getaway on 3 Private Acres

Stylish & Peaceful Getaway on 3 Private Acres

Stylish & Peaceful Getaway on 3 Private Acres
2.0 star property
Goshen
9.0 out of 10, Wonderful, (12)
"Great location!"
United States
Alozie E.
$436 nightly
The price is $436
Dec 21 - Dec 22
Total with taxes and fees
Stylish & Peaceful Getaway on 3 Private Acres
Property grounds
3BR West Point Retreat-3min to Back Gate+ King Bed

3BR West Point Retreat-3min to Back Gate+ King Bed

3BR West Point Retreat-3min to Back Gate+ King Bed
Highland Falls
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
$377 nightly
The price is $427
Dec 21 - Dec 22
Total with taxes and fees
3BR West Point Retreat-3min to Back Gate+ King Bed
Fridge, microwave, oven, stovetop
Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.0 out of 10, Wonderful, (4)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
$253 nightly
The price is $276
Dec 21 - Dec 22
Total with taxes and fees
Fabulous 3bdrm Home w/parking!
Outdoor dining
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fishkill
9.6 out of 10, Exceptional, (50)
"Inside was very nice, outside could use some curb appeal. Enjoyed our stay "
United States
Karen K.
$280 nightly
The price is $316
Dec 21 - Dec 22
Total with taxes and fees
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Pool
complete privacy vacation home [private pool]

complete privacy vacation home [private pool]

complete privacy vacation home [private pool]
Newburgh
10.0 out of 10, Exceptional, (11)
"Our family thoroughly enjoyed our stay. The pool was so big and so much fun!"
United States
Devin O.
$1,038 nightly
The price is $1,226
Jan 11 - Jan 12, 2026
Total with taxes and fees
complete privacy vacation home [private pool]
Private kitchen
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,

Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,

Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,
new paltz
9.4 out of 10, Exceptional, (6)
"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 21 - Dec 22
Total with taxes and fees
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,
TV, fireplace
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
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.
$328 nightly
The price is $355
Dec 21 - Dec 22
Total with taxes and fees
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Fridge, microwave, oven, stovetop
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
2.0 star property
New Paltz
9.4 out of 10, Exceptional, (24)
"Beautiful comfortable, clean "
United States
Michal G.
$319 nightly
The price is $323
Dec 22 - Dec 23
Total with taxes and fees
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
Property grounds
Fun, Friends, and Family Lakefront Home w/Dock and Beach

Fun, Friends, and Family Lakefront Home w/Dock and Beach

Fun, Friends, and Family Lakefront Home w/Dock and Beach
Mahopac
10.0 out of 10, Exceptional, (12)
"Super convenient location :)"
United States
Sean M.
$714 nightly
The price is $774
Jan 12 - Jan 13, 2026
Total with taxes and fees
Fun, Friends, and Family Lakefront Home w/Dock and Beach
Fridge, microwave, oven, stovetop
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.

Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.

Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.
Carmel Hamlet
10.0 out of 10, Exceptional, (17)
"Fabulous property! Everything was as advertised with a great kitchen and grill. Tastefully decorated and comfortable. Great game room! "
United States
Rachel F.
$790 nightly
The price is $856
Dec 29 - Dec 30
Total with taxes and fees
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.
Private kitchen
3-bedroom house in marvelous Goshen. Luxury cabin vibes for your getaway.

3-bedroom house in marvelous Goshen. Luxury cabin vibes for your getaway.

3-bedroom house in marvelous Goshen. Luxury cabin vibes for your getaway.
Goshen
8.0 out of 10, Very Good, (1)
"The check-in process went smoothly. The property was very clean and comfortable. Location was close to many different small towns. "
United States
Kelly M.
$399 nightly
The price is $491
Dec 21 - Dec 22
Total with taxes and fees
3-bedroom house in marvelous Goshen. Luxury cabin vibes for your getaway.
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

Holiday Inn Express Hotel & Suites Chester by IHG

10/10 Excellent
"Clean Clean Clean!!! "
Jose 1-night trip
Posted 7 hours ago
Holiday Inn Express Hotel & Suites Chester by IHG

Find out more about New Windsor

New Windsor Vacation Homes information

Number of reviews
261
Accommodation
375 Vacation Homes
Lowest Price
$153
Highest Price
$1,226

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