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Check prices for these dates

In two weeks
10 Oct - 12 Oct
In two months
21 Nov - 23 Nov
In three months
19 Dec - 21 Dec
In four months
16 Jan - 18 Jan

Featured Cottages in New Windsor and around

Our top choices for New Windsor cottages

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Property grounds

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (122)
"It has an incredible mountain and water view. "
The price is €267
includes taxes & fees
30 Sept - 1 Oct
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Charming Cottage in the Heart of the Shawangunks
Exterior

Charming Cottage in the Heart of the Shawangunks

10.0 out of 10, Exceptional, (16)
"The gatehouse was a perfect spot for a girls trip getaway. Secluded enough, but close to some local activities and restaurants! Cozy vibe and place had everything we needed!"
Charming Cottage in the Heart of the Shawangunks
Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven
Property grounds

Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven

9.8 out of 10, Exceptional, (7)
"We loved our stay at the Carriage House. Patrick and Kathryn were wonderful hosts. They provided information in a timely manner, and were quick to respond to any questions. Our accommodations were clean, comfortable and well appointed, and Patrick and Kathryn included truly thoughtful touches. The location was perfect for exploring Croton-on-Hudson and the Hudson Valley. We'd love to come back!"
Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven
Be in Nature at this Gorgeous Riverfront Cabin
Exterior

Be in Nature at this Gorgeous Riverfront Cabin

10.0 out of 10, Exceptional, (21)
"An ideal retreat. The modern cabin offered serene surroundings with stunning views of the woods and creek. The property was well-maintained, and the property manager was highly responsive. A perfect choice for a peaceful and refreshing getaway."
Be in Nature at this Gorgeous Riverfront Cabin
Scenic Hudson Valley Getaway • Farms & Vineyards
Exterior

Scenic Hudson Valley Getaway • Farms & Vineyards

10.0 out of 10, Exceptional, (1)
"It was exactly what my family and I needed. A cozy, quiet place to stay with mountain views. The owner is responsive and communicates quickly. Will come back again."
Scenic Hudson Valley Getaway • Farms & Vineyards
Peaceful Cottage with Grill | Walk to Lake
Exterior

Peaceful Cottage with Grill | Walk to Lake

9.8 out of 10, Exceptional, (21)
"This property was great. Clean, roomy and about 1/2 hour from West Point."
Peaceful Cottage with Grill | Walk to Lake
Luxe Family Home on Orange Lake w/ Private Dock!
House (3 Bedrooms) | Interior

Luxe Family Home on Orange Lake w/ Private Dock!

3.0 star property
Luxe Family Home on Orange Lake w/ Private Dock!
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Exterior

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

The price is €185
includes taxes & fees
24 Sept - 25 Sept
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Magnificent Lake View
Property grounds

Magnificent Lake View

2.0 star property
Magnificent Lake View
Charming Victorian Retreat w/ Hudson River Views
House (3 Bedrooms) | Interior

Charming Victorian Retreat w/ Hudson River Views

3.0 star property
Charming Victorian Retreat w/ Hudson River Views
Mountain View escape
Exterior

Mountain View escape

10.0 out of 10, Exceptional, (66)
"It’s adorable exactly What’s on the photos and equipped with everything you need for your stay definitely will be visiting it again. "
Mountain View escape
Hudson Valley Retreat w/ Pool Near Greenwood Lake
Cottage (2 Bedrooms) | Interior

Hudson Valley Retreat w/ Pool Near Greenwood Lake

3.0 star property
10.0 out of 10, Exceptional, (1)
"Excelent House 👏👌👌"
Hudson Valley Retreat w/ Pool Near Greenwood Lake
A romantic cottage and artist's retreat looking down over an enchanted lake
Property grounds

A romantic cottage and artist's retreat looking down over an enchanted lake

9.4 out of 10, Exceptional, (99)
"It was an awesome stay we loved the couple days we got to spend there!!"
A romantic cottage and artist's retreat looking down over an enchanted lake
Cozy Haven: A Romantic Retreat in our Tiny House!
Exterior

Cozy Haven: A Romantic Retreat in our Tiny House!

7.0 out of 10, Good, (9)
"we enjoyed the cozy home it is a nice place to get away"
The price is €391
includes taxes & fees
23 Oct - 24 Oct
Cozy Haven: A Romantic Retreat in our Tiny House!
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Exterior

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

9.4 out of 10, Exceptional, (12)
"We stayed one night, and it was splendid. The place is clean and quiet, and the sauna is a nice touch. "
The price is €158
includes taxes & fees
24 Sept - 25 Sept
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Bright Cornwall-on-hudson Vacation Rental!
House (3 Bedrooms) | Interior

Bright Cornwall-on-hudson Vacation Rental!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Very nice property, very comfortable, close to multiple sightseeing location including bear mountain."
Bright Cornwall-on-hudson Vacation Rental!
Family Home Close to Warwick, 5 Mi to Lake!
House (4 Bedrooms) | Interior

Family Home Close to Warwick, 5 Mi to Lake!

3.0 star property
Family Home Close to Warwick, 5 Mi to Lake!
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Children’s area

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

9.8 out of 10, Exceptional, (10)
"Wonderful cottage - lots of natural light - well equipped - great shower- comfortable beds- near Legoland - affordable- beautiful surroundings with great sunsets and sunrises - "
The price is €254
includes taxes & fees
25 Sept - 26 Sept
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Charming 2-bedroom cottage in delightful Greenwood Lake with WiFi, AC
Exterior

Charming 2-bedroom cottage in delightful Greenwood Lake with WiFi, AC

Charming 2-bedroom cottage in delightful Greenwood Lake with WiFi, AC
Charcoal Chalet by Avantstay A+ Design w/ Firepit
House (4 Bedrooms) | Interior

Charcoal Chalet by Avantstay A+ Design w/ Firepit

3.0 star property
Charcoal Chalet by Avantstay A+ Design w/ Firepit
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
"Great hotel staff"
Charles 1-night trip
Posted 1 day ago
Sleep Inn & Suites Middletown - Goshen

Find out more about New Windsor

Find out more about New Windsor

New Windsor Cottages information

Number of reviews
351
Accommodation
85 Cottages
Lowest Price
€158
Highest Price
€391

Frequently asked questions

Why book your cottage in New Windsor with Expedia?
Reserving a cottage in New Windsor is as simple as clicking on your travel dates and picking an ideal place for outdoor fun and relaxation. From upmarket retreats to inexpensive properties and cottages that have amenities like laundry facilities, Expedia has something for all styles. As for epic deals? We've got them as well!
How can I find cheap cottages in New Windsor?
The simplest way to find cheap cottages in New Windsor is with Expedia's user-friendly filter tool. Refine your search by amenities, budget and star rating to access awesome bargains with only a few clicks.
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 travellers alike.

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Explore a world of travel with Expedia