New Windsor Vacation Rentals

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Our top choices for New Windsor vacation rentals

Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer

Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer
Beacon
10.0 out of 10, Exceptional, (47 reviews)
"Great place!"
United States
Sara B.
The price is CA $150
CA $332 total
includes taxes & fees
Feb 11 - Feb 12
Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer

Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
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.
The price is CA $123
CA $252 total
includes taxes & fees
Feb 9 - Feb 10
Cozy 1-bedroom retreat minutes from West Point!

Cabin in the heart of the Hudson Valley, Cabin 3

Cabin in the heart of the Hudson Valley, Cabin 3
Newburgh
9.8 out of 10, Exceptional, (14 reviews)
"We had a great stay, everything you need is provided. Would recommend to anyone."
United States
Bill W.
The price is CA $231
CA $386 total
includes taxes & fees
Feb 19 - Feb 20
Cabin in the heart of the Hudson Valley, Cabin 3

Villa Verde B&B, bsm, Greenwood Lake NY

Villa Verde B&B, bsm, Greenwood Lake NY
Greenwood Lake
10.0 out of 10, Exceptional, (12 reviews)
"The breakfast was lovely!"
United States
Tara
The price is CA $215
CA $401 total
includes taxes & fees
Feb 9 - Feb 10
Villa Verde B&B, bsm, Greenwood Lake NY

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, (13 reviews)
"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."
United States
Hannah P.
The price is CA $253
CA $514 total
includes taxes & fees
Mar 5 - Mar 6
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

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 reviews)
"I love the place, very comfortable and cozy, Thank you so very much, Enjoyed a lot , Julia"
United States
Julia K.
The price is CA $63
CA $210 total
includes taxes & fees
Feb 8 - Feb 9
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.8 out of 10, Exceptional, (16 reviews)
"Great Unit."
United States
Rudy R.
The price is CA $110
CA $365 total
includes taxes & fees
Feb 10 - Feb 11
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Charming 1-bedroom apartment in Carmel with WiFi, AC

Charming 1-bedroom apartment in Carmel with WiFi, AC
Carmel Hamlet
9.0 out of 10, Wonderful, (2 reviews)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
United States
Emmett
The price is CA $185
CA $379 total
includes taxes & fees
Feb 9 - Feb 10
Charming 1-bedroom apartment in Carmel with WiFi, AC

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, (6 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is CA $125
CA $477 total
includes taxes & fees
Feb 8 - Feb 9
House on the Babbling Brook- Quiet 2BR + King Bed!

Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna

Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
Gardiner
10.0 out of 10, Exceptional, (8 reviews)
"Great weekend getaway to reconnect with old friends!"
United States
Lisa D.
The price is CA $281
CA $462 total
includes taxes & fees
Feb 26 - Feb 27
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (131 reviews)
"Amazing place Thanks for the stay "
United States
Julien C.
The price is CA $257
CA $416 total
includes taxes & fees
Feb 9 - Feb 10
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Highland Falls
10.0 out of 10, Exceptional, (5 reviews)
"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.
The price is CA $215
CA $392 total
includes taxes & fees
Feb 10 - Feb 11
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

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
9.2 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.
The price is CA $128
CA $219 total
includes taxes & fees
Feb 17 - Feb 18
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen

Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
Warwick
10.0 out of 10, Exceptional, (34 reviews)
"Great location within walking distance of boutiques and restaurants. Enjoyed our stay. "
United States
Cynthia W.
The price is CA $148
CA $347 total
includes taxes & fees
Feb 8 - Feb 9
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen

Cabin in the Heart of the Hudson Valley, Cabin 1

Cabin in the Heart of the Hudson Valley, Cabin 1
Newburgh
10.0 out of 10, Exceptional, (32 reviews)
"Great overnight spot, especially with a dog."
United States
Ed C.
The price is CA $231
CA $386 total
includes taxes & fees
Feb 9 - Feb 10
Cabin in the Heart of the Hudson Valley, Cabin 1

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.8 out of 10, Exceptional, (13 reviews)
"Beautiful location. We really enjoyed seeing the deer in the field every morning. "
United States
Aaron M.
The price is CA $203
CA $404 total
includes taxes & fees
Feb 9 - Feb 10
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

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 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.
The price is CA $160
CA $589 total
includes taxes & fees
Feb 10 - Feb 11
Sleek Escape: Modern 3 BR- 4 Min from West Point !

Dream getaway apartment in the foot of Gunks Ridge

Dream getaway apartment in the foot of Gunks Ridge
Wallkill
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.
The price is CA $74
CA $221 total
includes taxes & fees
Feb 8 - Feb 9
Dream getaway apartment in the foot of Gunks Ridge

Cozy Cabin Gateway I 1.5 Acres w. Pool & Firepit

Cozy Cabin Gateway I 1.5 Acres w. Pool & Firepit
Montgomery
10.0 out of 10, Exceptional, (3 reviews)
"This little cabin was exactly what we needed for our stay in NY. It looks just as described, was clean, and the location was perfect for all of the places we wanted to visit. Overall it was very cozy and relaxing and we can't wait to stay again! "
United States
Sarah A.
The price is CA $167
CA $285 total
includes taxes & fees
Feb 19 - Feb 20
Cozy Cabin Gateway I 1.5 Acres w. Pool & Firepit

Lovely 3BR Home with parking-Walk to WP Gate!

Lovely 3BR Home with parking-Walk to WP Gate!
Highland Falls
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.
The price is CA $223
CA $445 total
includes taxes & fees
Feb 10 - Feb 11
Lovely 3BR Home with parking-Walk to WP Gate!
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

Find out more about New Windsor

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with New Windsor. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.