
Holiday rentals in New Windsor
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Top-rated holiday rentals in New Windsor
Guests agree: these stays are highly rated for location, cleanliness and more.
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Other great holiday rentals in New Windsor
Guest favourite

Home in New Windsor
4.91 out of 5 average rating, 121 reviewsView House
JamieRating, 5 stars1 week ago
A fantastic stay: totally private yet with expansive views. Birds galore, June was the perfect time to spot them all. House is gorgeous and unique. Fantastic hosts, stayed here 8 years ago and I very much hope to be back before another 8 years passes. Thank you to Lisa and Nafeeza!

Flat in Salisbury Mills
4.83 out of 5 average rating, 6 reviewsCharming 3BR/2BA Attic Retreat!
IanRating, 5 stars1 month ago
Mel was a great host, responded within a few minutes to text messages. It was very thoughtful of her to share her cell numbers with us. One thing the listing does not tell you is how comfortable the beds are! We slept so well, it was a great holiday for the family. The apartment is in a very beautiful part of the state, you are surrounded by forested areas everywhere with a lot of walking trails. The apartment has a gas station/ convenience store a 2 min walk away which has lots of snacks and treats if you have a late night craving. Thanks Mel!
Superhost

Farm stay in Salisbury Mills
4.84 out of 5 average rating, 68 reviewsCozy Getaway on a 50 Acre Historic Ranch
LynnRating, 5 stars3 weeks ago
I didn’t realize, until we were leaving, that America’s oldest winery was three miles away. I would have loved to have visited .
Guest favourite

Cabin in Fishkill
4.96 out of 5 average rating, 106 reviewsSecluded Hilltop Cabin near Beacon & Cold Spring
AvrahamRating, 5 stars2 weeks ago
The cabin was exactly as listed and MORE! The nature and privacy you have will make you feel as though you've been transported to a different universe. Paul was an excellent host, providing clear instructions and recommendations, as well as proactively checking in to make sure the stay was going well! 10/10 recommend!!

Flat in Newburgh
4.89 out of 5 average rating, 308 reviewsRomantic Riverfront Retreat | A Winter City Escape
KirkRating, 5 stars2 weeks ago
33 or so steps up to lovely room Great view Very Comfy bed—Casper brand Shower curtain strangely inadequate but totally useful tub

Home in Philipstown
5 out of 5 average rating, 9 reviewsArkadia House Mid-century retreat with pool & view
AriRating, 5 stars71 months ago
Dan and Andrew were great hosts and very easy to communicate with. The location was beautiful and the views were amazing. The house was stocked with everything you could possibly need; towels, bedsheets, blankets cookware, a bunch of basic food necessities & more. The pool was refreshing after laying in the sun and watching the sunset from the pool is truly a must when visiting this home. We would love to stay here again and highly recommend to others looking for a gorgeous getaway home.
Guest favourite

Home in New Windsor
4.93 out of 5 average rating, 27 reviewsHudson Valley Hideaway
ThomasRating, 5 stars1 week ago
The home is beautiful, clean and very well equipped. We did run into a bit of problem when Julio told us there were going to be some emergency repairs, while we understand the occasional emergency I was questioning how much it would effect us he was complaining how it was effecting him I responded that I was concerned about my situation, he responded quite vehemently that he didn’t like my attitude and might cancel on us ( he had offered to us to cancel). I had never encountered that from a host before. We were able to get past that situation and were ultimately satisfied with the stay.
Superhost

Home in Newburgh
4.89 out of 5 average rating, 97 reviewsLady Montgomery
ShaunRating, 5 stars2 weeks ago
My wife and I stayed along with another couple and had a perfectly wonderful trip. We traveled to the area to visit Storm King and Dia Beacon, and we were less than 15 minutes to both museums by car. The house was very comfortable, the kitchen was comfortable to cook in and it made hanging out between outings very enjoyable. Loved the neighborhood, everyone was very friendly! Also enjoyed a brilliant dawn across the bridge over the Hudson -- only 4 miles there and back. Would definitely stay again when we're in the area.
Quick stats about holiday rentals in New Windsor
Total rentals
40 properties
Nightly prices starting at
$51 SGD before taxes and fees
Total number of reviews
2.8K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Times Square
- Hunter Mountain
- Columbia University
- Fairfield Beach
- Rye Beach
- MetLife Stadium
- Yankee Stadium
- Mountain Creek Resort
- Bethel Woods Center for the Arts
- Central Park Zoo
- Rockefeller Center
- Radio City Music Hall
- Rye Playland Beach
- Bronx Zoo
- The Metropolitan Museum of Art
- Astoria Park
- Minnewaska State Park Preserve
- Thunder Ridge Ski Area
- The Kartrite Resort & Indoor Waterpark
- Rye Town Beach
- Ringwood State Park
- Hamilton Park
- Apollo Theater
- Jennings Beach