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 two-story house with a wooden exterior, a front porch, and a staircase leading to the entrance.

1. 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
Walk-to-Lake Cottage With Grill for Peaceful Fall Days
A house with a view of a bridge and mountains.

2. 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 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.
$457 nightly
The price is $517
Nov 17 - Nov 18
Total with taxes and fees
Quiet Solitude with Firepit, Electric Stove & Private Deck
A grey sectional sofa with patterned cushions, a round wooden coffee table with a green plant, and a window with a view of trees.

4. 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 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.
$209 nightly
The price is $211
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 16 - Nov 17
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)
"Beautiful setting and well appointed"
United States
Marianna H.
$353 nightly
The price is $404
Nov 16 - Nov 17
Total with taxes and fees
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.

8. Private Pool House - Pool · Jacuzzi · Fireplace

Private Pool House - Pool · Jacuzzi · Fireplace
Pine Bush
Private Pool House - Pool · Jacuzzi · Fireplace
A wooden deck with a 'COME IN' mat, white siding, and a view of dense green trees.

9. 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
$441 nightly
The price is $521
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.

10. 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
"Best stay great people great place pool was awesome clean the entire town was awesome!!! Breakfast was even wonderful. What a great selection. Thanks so much see you again for sure"
Teresa 1-night trip
Posted 1 hour 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
$211
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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