A calm lake at sunset with trees and grass along the shore.

Search New Windsor Cottage Rentals from CA $302

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for New Windsor cottages

A house with a view of a bridge and mountains.

1. 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, (149 reviews)
"We had a great stay!!"
United States
Jasmine
The price is CA $277
CA $470 total
includes taxes & fees
Oct 28 - Oct 29
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
A grey sectional sofa with patterned cushions, a round wooden coffee table with a green plant, and a window with a view of trees.

2. Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.4 out of 10, Exceptional, (17 reviews)
"Great place to stay when visiting Legoland. Convenient location and comfortable and clean."
United States
Jessica C.
The price is CA $208
CA $415 total
includes taxes & fees
Nov 1 - Nov 2
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
A cottage with a wooden deck, a porch, and a staircase leading to the entrance.

3. Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Kerhonkson
9.6 out of 10, Exceptional, (18 reviews)
"Just what we needed .... place was spotless.....quiet.... peaceful."
United States
Victor M M.
The price is CA $205
CA $355 total
includes taxes & fees
Nov 12 - Nov 13
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
A small cabin with a porch, surrounded by dense forest and a clear night sky with a visible moon.

4. Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro

Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Bloomingburg
9.8 out of 10, Exceptional, (6 reviews)
"Tracy was an excellent host. The Mondrian Manor was cozy and perfect for two."
United States
Brandi A.
The price is CA $196
CA $302 total
includes taxes & fees
Oct 27 - Oct 28
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
A wooden deck with a railing overlooking a body of water and trees.

5. Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.

Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
Croton-on-Hudson
9.6 out of 10, Exceptional, (27 reviews)
"A lovely spot, very nice accommodations.Breakfast supples thoughtfully supplied as well as champagne to enjoy. "
United States
Eva C.
The price is CA $350
CA $596 total
includes taxes & fees
Oct 27 - Oct 28
Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
A bedroom with a large bed, a window with a view of trees, and a sliding glass door leading to an outdoor area.

6. Private Pool House - Pool · Jacuzzi · Fireplace

Private Pool House - Pool · Jacuzzi · Fireplace
Pine Bush
Private Pool House - Pool · Jacuzzi · Fireplace
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

Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury

10/10 Excellent
"Great stay, thanks"
Gina 1-night trip
Posted 1 hour ago
Sleep Inn & Suites Monroe - Woodbury

Find out more about New Windsor

New Windsor Cottages information

Number of reviews
217
Accommodation
83 Cottages
Lowest Price
CA $302
Highest Price
CA $596

Frequently asked questions

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What is there to do in New Windsor near my cottage?
If you want to discover the best of New Windsor, be sure to stop by New Windsor Cantonment State Historic Site. It's a winner with locals and travelers alike.

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