New Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Feb 6 - Feb 8
In two months
Mar 20 - Mar 22
In three months
Apr 17 - Apr 19
In four months
May 15 - May 17

Our top choices for New Windsor vacation rentals

Interior

Vacation Home in Kerhonkson

Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
10.0 out of 10, Exceptional, (32 reviews)
"I love the place, very comfortable and cozy, Thank you so very much, Enjoyed a lot , Julia"
United States
Julia K.
$159 nightly
The price is $162
Jan 26 - Jan 27
Total with taxes and fees
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Interior

Apartment in Wallkill

Dream getaway apartment in the foot of Gunks Ridge
9.6 out of 10, Exceptional, (24 reviews)
"Serg’s place was comfortable and clean! It was a perfect location for me and my friends to stay while rock climbing in the Gunks. We did not feel cramped or unsafe and the complementary tea was a hit! One thing to note is that both of the beds were low to the ground (below knee level) so if someone has knee or back problems, it might be difficult to stand up out of bed. "
United States
Mary S.
$159 nightly
The price is $162
Jan 25 - Jan 26
Total with taxes and fees
Dream getaway apartment in the foot of Gunks Ridge
Terrace/patio

Vacation Home in Highland Falls

House on the Babbling Brook- Quiet 2BR + King Bed!
10.0 out of 10, Exceptional, (6 reviews)
"Good stay, awesome place"
United States
Scott G.
$305 nightly
The price is $319
Jan 26 - Jan 27
Total with taxes and fees
House on the Babbling Brook- Quiet 2BR + King Bed!
Fridge, oven, stovetop, coffee/tea maker

Apartment in Highland Falls

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
9.8 out of 10, Exceptional, (16 reviews)
"Great Unit."
United States
Rudy R.
$254 nightly
The price is $258
Jan 25 - Jan 26
Total with taxes and fees
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Interior

Vacation Home in Warwick

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
9.2 out of 10, Wonderful, (9 reviews)
"I really enjoyed my stay. The room was very clean, the inn is well located in town and it is great having the restaurant below. Would stay here again! "
United States
Erin R.
$134 nightly
The price is $152
Feb 9 - Feb 10
Total with taxes and fees
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Interior

Aparthotel in Ossining

1BR Queen near NYC | Trails, Biking & Sauna Bliss
$316 nightly
The price is $352
Feb 12 - Feb 13
Total with taxes and fees
1BR Queen near NYC | Trails, Biking & Sauna Bliss
TV

Apartment in Highland Falls

Cozy 1-bedroom retreat minutes from West Point!
10.0 out of 10, Exceptional, (1 review)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
$175 nightly
The price is $191
Feb 4 - Feb 5
Total with taxes and fees
Cozy 1-bedroom retreat minutes from West Point!
3 bedrooms, desk, iron/ironing board, free WiFi

Vacation Home in Highland Falls

Sleek Escape: Modern 3 BR- 4 Min from West Point !
10.0 out of 10, Exceptional, (3 reviews)
"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.
$439 nightly
The price is $446
Feb 10 - Feb 11
Total with taxes and fees
Sleek Escape: Modern 3 BR- 4 Min from West Point !
3 bedrooms, desk, iron/ironing board, travel crib

Apartment in Highland Falls

Local Artist Inspired | Walk to WestPoint + King Bed
9.4 out of 10, Exceptional, (11 reviews)
"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.
$362 nightly
The price is $366
Jan 25 - Jan 26
Total with taxes and fees
Local Artist Inspired | Walk to WestPoint + King Bed
Interior

Vacation Home in Highland Falls

Lovely 3BR Home with parking-Walk to WP Gate!
10.0 out of 10, Exceptional, (7 reviews)
"Lovely home, great location and space for my family to have privacy. Enjoyed the deck for morning coffee. Would book again. "
United States
Briana T.
$308 nightly
The price is $348
Feb 4 - Feb 5
Total with taxes and fees
Lovely 3BR Home with parking-Walk to WP Gate!
Terrace/patio

Chalet in Gardiner

Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
10.0 out of 10, Exceptional, (7 reviews)
"Great weekend getaway to reconnect with old friends!"
United States
Lisa D.
$201 nightly
The price is $204
Jan 26 - Jan 27
Total with taxes and fees
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
Apartment | 1 bedroom

Apartment in Monroe

Bright Studio Retreat w Deck Nature Views
2.0 star property
$276 nightly
The price is $313
Jan 26 - Jan 27
Total with taxes and fees
Bright Studio Retreat w Deck Nature Views
Dining

Apartment in Beacon

Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
10.0 out of 10, Exceptional, (32 reviews)
"Great time and great place to stay "
United States
S S.
$216 nightly
The price is $249
Feb 10 - Feb 11
Total with taxes and fees
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
TV, fireplace

Vacation Home in Carmel Hamlet

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
9.8 out of 10, Exceptional, (12 reviews)
"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."
United States
Hannah P.
$327 nightly
The price is $354
Jan 25 - Jan 26
Total with taxes and fees
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Interior

Apartment in Warwick

Luxe Loft on Main St.ZeroG King Bed, Designer Kitchen, Elevator!
10.0 out of 10, Exceptional, (42 reviews)
"This loft is great! Well appointed with everything you need. "
United States
Jean L.
$219 nightly
The price is $248
Jan 26 - Jan 27
Total with taxes and fees
Luxe Loft on Main St.ZeroG King Bed, Designer Kitchen, Elevator!
Desk, free WiFi, bed sheets

Apartment in Croton-on-Hudson

'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
10.0 out of 10, Exceptional, (2 reviews)
"Great stay!"
United States
Ann S.
$211 nightly
The price is $242
Jan 25 - Jan 26
Total with taxes and fees
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
TV

Apartment in Highland Falls

Walk to WP Gate + Free Parking!
9.8 out of 10, Exceptional, (21 reviews)
"This place was awesome for the location to Thayer gate, close to restaurants, and a parking spot next to the building. We will return to this place!"
United States
Pamela
$288 nightly
The price is $319
Feb 4 - Feb 5
Total with taxes and fees
Walk to WP Gate + Free Parking!
Exterior detail

Vacation Home in Highland Falls

Fabulous 3bdrm Home w/parking!
9.0 out of 10, Wonderful, (4 reviews)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
$297 nightly
The price is $327
Feb 4 - Feb 5
Total with taxes and fees
Fabulous 3bdrm Home w/parking!
Exterior

Apartment in Monroe

Studio Retreat | Near Woodbury Commons & Legoland
$194 nightly
The price is $197
Jan 25 - Jan 26
Total with taxes and fees
Studio Retreat | Near Woodbury Commons & Legoland
Exterior

Cabin in Fishkill

Rustic Cabin in Fishkill!
10.0 out of 10, Exceptional, (3 reviews)
"Ideal cabin getaway. "
United States
Nadja E.
$395 nightly
The price is $449
Jan 26 - Jan 27
Total with taxes and fees
Rustic Cabin in Fishkill!
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 & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie

10/10 Excellent
"Everything was great . "
Jason 1-night trip
Posted 2 days ago
Hampton Inn & Suites Poughkeepsie

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 $152 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?

Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel. : Visitors give good reviews to this New Windsor vacation home rental, which is located on a river and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in New Windsor?

Choose from 9 Expedia vacation rentals in New Windsor for a memorable vacation.

What can I see and do in New Windsor?

Cultural attractions to visit include National Purple Heart Hall of Honor and Knox's Headquarters State Historic Site. 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.