
Vacation rentals in New Windsor
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Top-rated vacation rentals in New Windsor
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for New Windsor vacation rentals
Other great vacation rentals in New Windsor
Guest favourite

Home in New Windsor
4.91 out of 5 average rating, 122 reviewsView House
Guest favourite

Cabin in Fishkill
4.96 out of 5 average rating, 108 reviewsSecluded Hilltop Cabin near Beacon & Cold Spring

Apartment in Newburgh
4.89 out of 5 average rating, 312 reviewsRomantic Riverfront Retreat | A Winter City Escape

Home in Philipstown
5 out of 5 average rating, 10 reviewsArkadia House Mid-century retreat with pool & view
Guest favourite

Apartment in Newburgh
4.96 out of 5 average rating, 80 reviewsCentrally Located in the Heart ❤ of Newburgh

Apartment in Newburgh
4.97 out of 5 average rating, 32 reviewsChic Design Studio for a History-Filled Visit
Guest favourite

Home in New Windsor
4.93 out of 5 average rating, 27 reviewsHudson Valley Hideaway

Apartment in Newburgh
4.7 out of 5 average rating, 10 reviewsCozy, high-ceiling apartment
Quick stats about vacation rentals in New Windsor
Total rentals
40 properties
Nightly prices starting at
$54 CAD 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
- MetLife Stadium
- Rye Beach
- Yankee Stadium
- Mountain Creek Resort
- Central Park Zoo
- Bethel Woods Center for the Arts
- Rockefeller Center
- Bronx Zoo
- Radio City Music Hall
- The Metropolitan Museum of Art
- Rye Playland Beach
- Astoria Park
- Minnewaska State Park Preserve
- The Kartrite Resort & Indoor Waterpark
- Jennings Beach
- Thunder Ridge Ski Area
- Hamilton Park
- Apollo Theater
- Calf Pasture Beach
- Seaside Beach