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 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

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
$257 nightly
The price is $304
Nov 16 - Nov 17
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
A two-story house with a wooden exterior, a front porch, and a staircase leading to the entrance.

2. Walk-to-Lake Cottage With Grill for Peaceful Fall Days

Walk-to-Lake Cottage With Grill for Peaceful Fall Days
Putnam Valley
9.8 out of 10, Exceptional, (25 reviews)
"Absolute comfortable stay. Everything you need and fantastic host!! Will be back."
United States
Lisa
$472 nightly
The price is $521
Nov 15 - Nov 16
Total with taxes and fees
Walk-to-Lake Cottage With Grill for Peaceful Fall Days
A grey sectional sofa with patterned cushions, a round wooden coffee table with a green plant, and a window with a view of trees.

3. 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.
$268 nightly
The price is $280
Nov 16 - Nov 17
Total with taxes and fees
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
A two-story house with a balcony, surrounded by lush greenery.

4. 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.
$470 nightly
The price is $532
Nov 17 - Nov 18
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.

5. 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)
"A cozy little cabin. A great place to enjoy in itself and a relaxing place to come back to after a day out. Stayed two nights and went hiking, great location for the mountains. Host was very responsive."
United States
Devon Q.
$222 nightly
The price is $224
Dec 1 - Dec 2
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.

6. 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.
$194 nightly
The price is $219
Nov 15 - Nov 16
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.

7. 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.
$353 nightly
The price is $404
Nov 15 - Nov 16
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.

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

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

10/10 Excellent
"Room was excellent service great customer service front desk breakfast was excellent highly recommended. Five stars"
hector 1-night trip
Posted 10 hours ago
Sleep Inn & Suites Middletown - Goshen

Find out more about New Windsor

New Windsor Cottages information

Number of reviews
225
Accommodation
83 Cottages
Lowest Price
$219
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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