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New Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for New Windsor vacation rentals

Fridge, oven, stovetop, cookware/dishes/utensils
Cozy 1-bedroom retreat minutes from West Point!

Apartment in Highland Falls

Cozy 1-bedroom retreat minutes from West Point!
10.0 out of 10, Exceptional, (1)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
$157 nightly
The price is $169
Dec 18 - Dec 19
Total with taxes and fees
Cozy 1-bedroom retreat minutes from West Point!
Apartment, 2 Bedrooms, Balcony, Garden View | Exterior
2Br Private Victorian Apartment in City Location on Half Acre Sleeps 5

Apartment in Poughkeepsie

2Br Private Victorian Apartment in City Location on Half Acre Sleeps 5
2.0 star property
10.0 out of 10, Exceptional, (5)
"My friends and I rented this property for a long girls weekend to attend an event in the area. We liked the historical aspect of the property and Gary was an excellent host. His banana bread was amazing! We would definitely stay again. "
United States
Sara
$232 nightly
The price is $272
Dec 14 - Dec 15
Total with taxes and fees
2Br Private Victorian Apartment in City Location on Half Acre Sleeps 5
Interior
Modern Hudson Valley Retreat Near Mohonk

Apartment in Plattekill

Modern Hudson Valley Retreat Near Mohonk
2.0 star property
10.0 out of 10, Exceptional, (2)
"Beautiful location and great stay! Would come here again in a heartbeat. "
United States
Gavin
$234 nightly
The price is $262
Dec 13 - Dec 14
Total with taxes and fees
Modern Hudson Valley Retreat Near Mohonk
1 bedroom, WiFi, bed sheets
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

Apartment in Beacon

Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
10.0 out of 10, Exceptional, (32)
"Great time and great place to stay "
United States
S S.
$211 nightly
The price is $243
Dec 14 - Dec 15
Total with taxes and fees
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
Interior
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town

Vacation Home in Warwick

Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
9.4 out of 10, Exceptional, (6)
"My girlfriend and I loved our stay here! We stayed for one night and it was perfect for what we needed. Very clean with easy self-check-in. The host was very responsive with all inquiries. Short walk to nice downtown area as well!"
United States
Jay D.
$133 nightly
The price is $150
Dec 15 - Dec 16
Total with taxes and fees
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
1 bedroom, WiFi, bed sheets
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen

Apartment in Beacon

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
9.8 out of 10, Exceptional, (42)
"Adorable place to stay in an adorable town! "
United States
Mary L.
$205 nightly
The price is $236
Dec 14 - Dec 15
Total with taxes and fees
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Terrace/patio
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna

Chalet in Gardiner

Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
2.0 star property
10.0 out of 10, Exceptional, (7)
"Great weekend getaway to reconnect with old friends!"
United States
Lisa D.
$218 nightly
The price is $220
Dec 15 - Dec 16
Total with taxes and fees
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
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
Exterior
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

Apartment in Croton-on-Hudson

'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
10.0 out of 10, Exceptional, (2)
"Great stay!"
United States
Ann S.
$204 nightly
The price is $233
Dec 14 - Dec 15
Total with taxes and fees
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
Exterior detail
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Apartment in Highland Falls

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
9.8 out of 10, Exceptional, (14)
"Great Unit."
United States
Rudy R.
$260 nightly
The price is $263
Dec 13 - Dec 14
Total with taxes and fees
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Terrace/patio
Dream getaway apartment in the foot of Gunks Ridge

Apartment in Wallkill

Dream getaway apartment in the foot of Gunks Ridge
9.6 out of 10, Exceptional, (24)
"Over all the property was clean and staff was very cooperative. Only problems were the beds were very hard which made it hard for us to get a good nights sleep. The larger room had bugs but the owner took care of it right away. We enjoyed our stay."
United States
Harriet
$173 nightly
The price is $175
Dec 14 - Dec 15
Total with taxes and fees
Dream getaway apartment in the foot of Gunks Ridge
Fridge, microwave, oven, stovetop
Luxe Loft on Main St.- Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!

Apartment in Warwick

Luxe Loft on Main St.- Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!
10.0 out of 10, Exceptional, (40)
"This was the best place to stay. Host was so nice to us. If we are in the area again we would definitely stay here again. "
United States
Eileen H.
$216 nightly
The price is $244
Jan 4 - Jan 5, 2026
Total with taxes and fees
Luxe Loft on Main St.- Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!
Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.

Cabin in Carmel

Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.
3.0 star property
10.0 out of 10, Exceptional, (3)
"It was great! We loved staying in this cute house. Proximity to the lake is great, and the backyard is quite beautiful."
United States
Varuna S.
$217 nightly
The price is $235
Dec 14 - Dec 15
Total with taxes and fees
Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.
Game room
Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food

Apartment in CROTON HDSN

Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food
9.8 out of 10, Exceptional, (90)
"I had a great stay at this extremely comfortable home in a quiet neighborhood. Maria was very welcoming and helpful. I hope to visit and stay here again soon."
United States
Jill D.
$239 nightly
The price is $274
Dec 14 - Dec 15
Total with taxes and fees
Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food
Fridge, microwave, oven, stovetop
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Apartment in Highland Falls

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
10.0 out of 10, Exceptional, (5)
"Very nice property. We have a son at West Point and approximately an hour from New York City. Host was quick to respond to questions and provided excellent information. We will stay here again. "
United States
Mark V.
$217 nightly
The price is $238
Dec 14 - Dec 15
Total with taxes and fees
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
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 13 - Dec 14
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)
$323 nightly
The price is $365
Dec 14 - Dec 15
Total with taxes and fees
5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!
Outdoor dining
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro

Cottage in Bloomingburg

Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
10.0 out of 10, Exceptional, (1)
"The place was as described, quaint, clean, no issues with communication or check in"
United States
Stephen H.
$190 nightly
The price is $214
Dec 13 - Dec 14
Total with taxes and fees
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Smart TV
Grant - A Tranquil One Bedroom Steps from River

Apartment in Newburgh

Grant - A Tranquil One Bedroom Steps from River
9.6 out of 10, Exceptional, (39)
"Stan is really nice and helpful. The apartment is really well designed, spacious and clean, very well equipped with a nice porch. Stan is really thoughtful. Recommended!"
United States
Zohar
$241 nightly
The price is $273
Dec 25 - Dec 26
Total with taxes and fees
Grant - A Tranquil One Bedroom Steps from River
Fridge, microwave, oven, stovetop
Local Artist Inspired | Walk to WestPoint + King Bed

Apartment in Highland Falls

Local Artist Inspired | Walk to WestPoint + King Bed
9.2 out of 10, Wonderful, (9)
"Great place to stay if you have a West Point student - super close to all West Point related activities. The place itself needs some work but it’s functional."
United States
Jesse C.
$377 nightly
The price is $382
Dec 14 - Dec 15
Total with taxes and fees
Local Artist Inspired | Walk to WestPoint + King Bed
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 4 days ago
Windrose On Hudson

Find out more about New Windsor

Everything you need to know about New Windsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the New Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect New Windsor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

New Windsor vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in New Windsor. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit New Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $148 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on New Windsor rentals

At Expedia, we put the best New Windsor vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top New Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream New Windsor vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around New Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in New Windsor?

Yes, we have vacation rentals near the most popular local attractions in New Windsor, or you can select a secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and shops in New Windsor. Allow lots of time to check out the lakeside and coffeehouses during your visit.

What's the top vacation rental in New Windsor?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: Visitors like this New Windsor vacation home rental. It offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with an oven, a microwave, and kitchenware, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in New Windsor?

Choose from 7 Expedia vacation rentals in New Windsor for a memorable vacation.

What can I see and do in New Windsor?

Cultural attractions to visit include Knox's Headquarters State Historic Site and National Purple Heart Hall of Honor. Other places in town to visit include New Windsor Cantonment State Historic Site and Schunnemunk State Park.

What are vacation rentals like in New Windsor?

Vacation rentals are private accommodations you can stay in for a short or long stay in New Windsor. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can offer a sense of privacy away from public hotel elevators and busy reception areas while still allowing you to travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for a family trip or a small group gathering.