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

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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, (150 reviews)
"We had a great stay!!"
United States
Jasmine
$260 nightly
The price is $307
Nov 19 - Nov 20
Total with taxes and fees
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.
$261 nightly
The price is $273
Nov 12 - Nov 13
Total with taxes and fees
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
A two-story house with a balcony, surrounded by lush greenery.

3. Quiet Solitude with Firepit, Electric Stove & Private Deck

Quiet Solitude with Firepit, Electric Stove & Private Deck
Hopewell Junction
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our stay at Sara's place. Unfortunately due to all the rain we couldn't enjoy the outside facilities. The bedroom loft is charming and everything you need is there. Thanks for a great stay!"
United States
stephanie a.
$465 nightly
The price is $526
Nov 9 - Nov 10
Total with taxes and fees
Quiet Solitude with Firepit, Electric Stove & Private Deck
A cottage with a wooden deck, a porch, and a staircase leading to the entrance.

4. 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.
$242 nightly
The price is $243
Nov 25 - Nov 26
Total with taxes and fees
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.

5. 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.
$189 nightly
The price is $213
Nov 9 - Nov 10
Total with taxes and fees
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
A wooden deck with a railing overlooking a body of water and trees.

6. 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, (28 reviews)
"A lovely spot, very nice accommodations.Breakfast supples thoughtfully supplied as well as champagne to enjoy. "
United States
Eva C.
$343 nightly
The price is $392
Nov 9 - Nov 10
Total with taxes and fees
Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
A wooden deck with a 'COME IN' mat, white siding, and a view of dense green trees.

7. Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
Monroe
10.0 out of 10, Exceptional, (9 reviews)
"We loved our stay! It was the perfect size for our small family. The property was extremely well maintained and there was a lot to do near by. We would definitely book here again!"
United States
Marc
$428 nightly
The price is $506
Nov 30 - Dec 1
Total with taxes and fees
Hudson Valley Retreat w/ Pool Near Greenwood Lake
A wooden deck with a 'COME IN' mat, white siding, and a view of dense green trees.

8. Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
3.0 star property
Monroe
10.0 out of 10, Exceptional, (4 reviews)
"The house was very quiet and exactly as advertised. Would stay again!"
United States
Scott
$457 nightly
The price is $539
Nov 30 - Dec 1
Total with taxes and fees
Hudson Valley Retreat w/ Pool Near Greenwood Lake
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

Hampton Inn by Hilton New Paltz

Hampton Inn by Hilton New Paltz

10/10 Excellent
"The breakfast was amazing and staff was responsive and the pool is open early and closed late .. location is great"
Ani 2-night trip
Posted 4 hours ago
Hampton Inn by Hilton New Paltz

Find out more about New Windsor

New Windsor Cottages information

Number of reviews
225
Accommodation
83 Cottages
Lowest Price
$213
Highest Price
$698

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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