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Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sept - 14 Sept

Featured Cottages in New Windsor and around

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, (116)
"The greatest spot anyone could imagine. We will be back in the fall for the beautiful colors. "
The price is €261
includes taxes & fees
22 Jul - 23 Jul
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Charming Cottage in the Heart of the Shawangunks
Fridge, microwave, oven, stovetop

Charming Cottage in the Heart of the Shawangunks

10.0 out of 10, Exceptional, (12)
"Wonderful stay, exactly as advertised, everything brand new and very cozy."
The price is €493
includes taxes & fees
23 Jul - 24 Jul
Charming Cottage in the Heart of the Shawangunks
Be in Nature at this Gorgeous Riverfront Cabin
Smart TV, books

Be in Nature at this Gorgeous Riverfront Cabin

10.0 out of 10, Exceptional, (18)
"Property was as advertised. Clean and nearby places we wanted to visit while, still being out of the way and quiet."
Be in Nature at this Gorgeous Riverfront Cabin
Hudson Valley Retreat w/ Pool Near Greenwood Lake
Fridge, microwave, stovetop, dishwasher

Hudson Valley Retreat w/ Pool Near Greenwood Lake

10.0 out of 10, Exceptional, (5)
"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!"
Hudson Valley Retreat w/ Pool Near Greenwood Lake
Cozy Retreat w/ Pool, Cinema Room & Fire Pit
Smart TV, fireplace

Cozy Retreat w/ Pool, Cinema Room & Fire Pit

9.6 out of 10, Exceptional, (13)
"The house was exactly as advertised. It was clean, well maintained and comfortable! The location was beautiful and private yet close to nearby stores and activities."
Cozy Retreat w/ Pool, Cinema Room & Fire Pit
Romantic retreat with stunning views of Croton River Gorge, a birder haven
Outdoor dining

Romantic retreat with stunning views of Croton River Gorge, a birder haven

10.0 out of 10, Exceptional, (3)
"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!"
Romantic retreat with stunning views of Croton River Gorge, a birder haven
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Outdoor dining

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

The price is €189
includes taxes & fees
18 Jul - 19 Jul
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
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
Charming 2-bedroom cottage in delightful Greenwood Lake with WiFi, AC
Living area

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

Charming 2-bedroom cottage in delightful Greenwood Lake with WiFi, AC
Mountain View escape
Exterior

Mountain View escape

10.0 out of 10, Exceptional, (58)
"This was such a lovely place to stay! Great location and beautiful setting. "
Mountain View escape
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!
Historic 1800s Cornwall-On-Hudson Cottage!
Outdoor dining

Historic 1800s Cornwall-On-Hudson Cottage!

10.0 out of 10, Exceptional, (27)
"Best VRBO OUR FAMILY HAS RENTED .ABSOLUTELY PERFECT, THOUGHTFUL AND SUPER CLEAN,"
Historic 1800s Cornwall-On-Hudson Cottage!
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!
Charming Gardiner Home w/ Yard & Sunroom
House (3 Bedrooms) | Interior

Charming Gardiner Home w/ Yard & Sunroom

3.0 star property
Charming Gardiner Home w/ Yard & Sunroom
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
Cottage at Millpond Falls - Romantic Luxury Escape - Waterfall views in Warwick
Fridge, microwave, oven, stovetop

Cottage at Millpond Falls - Romantic Luxury Escape - Waterfall views in Warwick

10.0 out of 10, Exceptional, (149)
"The property was very clean and the view atmosphere was amazing"
Cottage at Millpond Falls - Romantic Luxury Escape - Waterfall views in Warwick
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
Cozy Haven: A Romantic Retreat in our Tiny House!
TV, fireplace

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 €262
includes taxes & fees
16 Jul - 17 Jul
Cozy Haven: A Romantic Retreat in our Tiny House!
Serene Holmes Cottage Near Lakes & Trails!
Interior

Serene Holmes Cottage Near Lakes & Trails!

3.0 star property
Serene Holmes Cottage Near Lakes & Trails!
Waterfront Wallkill Duplex Home w/ Fire Pits!
House (3 Bedrooms) | Interior

Waterfront Wallkill Duplex Home w/ Fire Pits!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Great for my kids and family for options to play outdoors and indoors games together. Loved the coffee bar and the details in the bathrooms with all the little things we could use down to the qtips and things. Really great for our family trip memories!!"
Waterfront Wallkill Duplex Home w/ Fire Pits!
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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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.