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New Windsor Vacation Rentals

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Check prices for these dates

Tonight
Jul 13 - Jul 14
Tomorrow
Jul 14 - Jul 15
Next weekend
Jul 18 - Jul 20
In two weeks
Jul 25 - Jul 27

Vacation Rentals in New Windsor

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Cozy living room with a comfortable seating area, dining table, and fireplace.

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

9.8 out of 10, Exceptional, (7)
"Great spot, wonderful host. Would recommend to anyone!"
$369 nightly
The price is $399
Jul 16 - Jul 17
Total includes taxes and fees
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.
Enjoy cooking in this well-equipped kitchen with a sink, ample counter space, and a large window offering a view of the surrounding landscape.

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

10.0 out of 10, Exceptional, (15)
"We had a great stay and had everything we needed!"
$746 nightly
The price is $809
Jul 16 - Jul 17
Total includes taxes and fees
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Situated in a wooded area, this cabin features a steeply pitched roof, chimney, and three windows with shutters.

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

9.0 out of 10, Wonderful, (9)
"Truly a hidden gem. The property and home were nothing short of extraordinary. For those looking for a great location with access to hiking and a one of a kind experience this is the place."
$165 nightly
The price is $186
Jul 16 - Jul 17
Total includes taxes and fees
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Contemporary Cozy Cottage
Cozy retreat with a natural touch, featuring a large artificial tree and potted plants.

Contemporary Cozy Cottage

10.0 out of 10, Exceptional, (23)
"Our stay was lovely. Nadia was a wonderful host and the property was so welcoming."
$371 nightly
The price is $424
Jul 14 - Jul 15
Total includes taxes and fees
Contemporary Cozy Cottage
Rustic Cabin in Fishkill!
Relax by the serene lake with a dock and outdoor seating areas amidst lush greenery and mature trees.

Rustic Cabin in Fishkill!

10.0 out of 10, Exceptional, (1)
"Beautiful property with many different areas to explore. We originally intended to spend more time in beacon but decided it was more fun hanging out here. "
$367 nightly
The price is $417
Jul 17 - Jul 18
Total includes taxes and fees
Rustic Cabin in Fishkill!
Chestnut on Willow Lake
Enjoy cooking in this well-equipped kitchen with a stove, sink, and refrigerator.

Chestnut on Willow Lake

9.0 out of 10, Wonderful, (2)
"We absolutely loved our stay in Chestnut—the home was spotless and comfortable, the property was terrific (the lake was perfect for swimming, boating, and fishing), and the owners/management were all very friendly and helpful. We definitely plan to return!"
$508 nightly
The price is $578
Jul 17 - Jul 18
Total includes taxes and fees
Chestnut on Willow Lake
Hickory on Willow Lake
Escape to a serene oasis beneath a triangular gazebo, surrounded by lush greenery and a tranquil hillside setting.

Hickory on Willow Lake

9.0 out of 10, Wonderful, (2)
"Cute cottage on nice grounds with a small lake. Kayaks and life jackets available for use was a big plus"
$536 nightly
The price is $610
Jul 17 - Jul 18
Total includes taxes and fees
Hickory on Willow Lake
Red Cottage - Lakeside Property!
Situated in a natural setting, this standalone structure offers easy access and visibility with its large glass door and windows.

Red Cottage - Lakeside Property!

$514 nightly
The price is $585
Jul 17 - Jul 18
Total includes taxes and fees
Red Cottage - Lakeside Property!
Spacious New Luxurious holiday house in lovely Hudson Valley
Enjoy expansive mountain views from this sunroom with a sofa, table, and wicker chair.

Spacious New Luxurious holiday house in lovely Hudson Valley

10.0 out of 10, Exceptional, (11)
"We loved our stay at this gorgeous home & we will definitely book it again in the future!"
$661 nightly
The price is $767
Jul 16 - Jul 17
Total includes taxes and fees
Spacious New Luxurious holiday house in lovely Hudson Valley
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Relax in this serene outdoor seating area with a covered patio overlooking a lush garden.

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

9.8 out of 10, Exceptional, (22)
"Plenty of room for my family"
$292 nightly
The price is $330
Jul 20 - Jul 21
Total includes taxes and fees
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
West Point Family Retreat, 5 min walk to Thayer!
Meet the team at this charming two-story building with a welcoming porch and a classic chimney.

West Point Family Retreat, 5 min walk to Thayer!

2.0 star property
10.0 out of 10, Exceptional, (4)
"Nice houseAwesome kitchen Granddaughter loved the bunk bed and the many games"
$731 nightly
The price is $827
Jul 14 - Jul 15
Total includes taxes and fees
West Point Family Retreat, 5 min walk to Thayer!
Lovely 3BR Home with parking-Walk to WP Gate!
Enjoy a comfortable stay with a flat-screen TV and convenient table for your belongings.

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

10.0 out of 10, Exceptional, (4)
"Easy booking, arrival, and departure. Very nice home. Very Clean and comfortable. Host was very kind and clear on everything for stay. Will book again!"
$294 nightly
The price is $337
Jul 29 - Jul 30
Total includes taxes and fees
Lovely 3BR Home with parking-Walk to WP Gate!
Fabulous 3bdrm Home w/parking!
Enjoy cooking in this well-equipped kitchen with a stovetop, sink, and appliances.

Fabulous 3bdrm Home w/parking!

6.0 out of 10, (1)
"The proximity to Westpoint was great. Trashy neighborhood. Very loud construction early in the morning. The cooking supplies were limited and one of the handles on the pans fell off while we were there. It was okay, but probably wouldn't return."
$305 nightly
The price is $335
Aug 6 - Aug 7
Total includes taxes and fees
Fabulous 3bdrm Home w/parking!
Room for Everyone: Spacious 6BR West Point Retreat
Kitchen features a stainless steel stove, microwave, and sink, with a window above and a chair in the corner.

Room for Everyone: Spacious 6BR West Point Retreat

10.0 out of 10, Exceptional, (1)
"Great location for Westpoint visit. As described. Clean with new updates. "
Room for Everyone: Spacious 6BR West Point Retreat
Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat
Relax on the patio with a round table and two chairs, surrounded by a white railing and overlooking a serene grassy area with trees.

Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat

10.0 out of 10, Exceptional, (4)
"Our stay was only a couple nights but it was what we expected. I would recommend this property. Had a great stay."
$539 nightly
The price is $626
Jul 27 - Jul 28
Total includes taxes and fees
Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat
Cozy Escape -Strong Wi-Fi -Prime Location
Enjoy cooking in this well-equipped kitchen with a double sink, microwave, oven, and coffee maker.

Cozy Escape -Strong Wi-Fi -Prime Location

7.4 out of 10, Good, (3)
"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."
$299 nightly
The price is $350
Jul 29 - Jul 30
Total includes taxes and fees
Cozy Escape -Strong Wi-Fi -Prime Location
Family friendly Spacious 4 bedroom 3 bathroom getaway
Relax in this stylish living room with a sofa, armchair, and ottoman, surrounded by a clean, minimalist design.

Family friendly Spacious 4 bedroom 3 bathroom getaway

10.0 out of 10, Exceptional, (4)
"Very easy checkin, great communication from owner. Bring your own travel soap shampoo etc. Store was right down the road for these things so not a big deal. Would rent again in a heartbeat."
$422 nightly
The price is $489
Jul 22 - Jul 23
Total includes taxes and fees
Family friendly Spacious 4 bedroom 3 bathroom getaway
Large, Cozy, Bright Business Class Corporate Retreat
Enjoy a serene forest view from the large window in this cozy hotel room.

Large, Cozy, Bright Business Class Corporate Retreat

9.0 out of 10, Wonderful, (13)
"Very cozy stay with responsive host"
$577 nightly
The price is $682
Jul 14 - Jul 15
Total includes taxes and fees
Large, Cozy, Bright Business Class Corporate Retreat
complete privacy vacation home [private pool]
Relax by the indoor pool with a hot tub, surrounded by natural light and wooden accents.

complete privacy vacation home [private pool]

9.8 out of 10, Exceptional, (8)
"Our family thoroughly enjoyed our stay. The pool was so big and so much fun!"
$964 nightly
The price is $1,138
Jul 15 - Jul 16
Total includes taxes and fees
complete privacy vacation home [private pool]
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Relax on the serene deck, surrounded by bare trees and a frozen lake.

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

10.0 out of 10, Exceptional, (298)
"Beautiful, quiet property that was a great getaway from the city. A pair of bald eagles were circling the lake which was a really amazing surprise! "
$500 nightly
The price is $591
Aug 3 - Aug 4
Total includes taxes and fees
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
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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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 Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views: Visitors like this New Windsor vacation home rental. It is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in New Windsor?

Choose from 6 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. Woodbury Common Premium Outlets and LEGOLAND® New York are other popular places to visit in the area.

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.