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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Cottages in New Windsor and around

Mountain View escape
Guests can enjoy a cabin-style retreat surrounded by a wooded area and a common deck.

Mountain View escape

10.0 out of 10, Exceptional, (60)
"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
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Stroll through a serene residential setting surrounded by a lush lawn, a tree, and a picturesque bridge.

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (118)
"Nice view on the top of the mountain….I admired the river with the bridge and the surroundings until late in the night. The accommodation was excellent, we had everything we needed.… we are thinking of coming back sometime…."
The price is €282
includes taxes & fees
25 Aug - 26 Aug
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Charming Cottage in the Heart of the Shawangunks
Enjoy cooking in this well-lit kitchen with a double sink, toaster oven, and a window overlooking the surrounding trees.

Charming Cottage in the Heart of the Shawangunks

10.0 out of 10, Exceptional, (15)
"Wonderful stay, exactly as advertised, everything brand new and very cozy."
The price is €524
includes taxes & fees
24 Aug - 25 Aug
Charming Cottage in the Heart of the Shawangunks
Be in Nature at this Gorgeous Riverfront Cabin
Relax in this stylish living room with a sofa, armchair, and coffee table, offering a view of lush greenery.

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
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
10 Aug - 11 Aug
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Romantic retreat with stunning views of Croton River Gorge, a birder haven
Relax on the deck with a kayak nearby, surrounded by trees and a traditional building in the background.

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

9.8 out of 10, Exceptional, (6)
Romantic retreat with stunning views of Croton River Gorge, a birder haven
Hudson Valley Retreat w/ Pool Near Greenwood Lake
Enjoy cooking in this well-equipped kitchen with a refrigerator, oven, and granite countertops.

Hudson Valley Retreat w/ Pool Near Greenwood Lake

10.0 out of 10, Exceptional, (6)
"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
Cottage at Millpond Falls - Romantic Luxury Escape - Waterfall views in Warwick
Kitchen equipped with microwave, stove, and dishwasher, offering a view of the outdoors.

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

10.0 out of 10, Exceptional, (151)
"The property was very clean and the view atmosphere was amazing"
Cottage at Millpond Falls - Romantic Luxury Escape - Waterfall views in Warwick
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Enjoy cooking in this well-equipped kitchen with a stainless steel stove, black range hood, and ample storage.

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

9.8 out of 10, Exceptional, (11)
"We stayed one night, and it was splendid. The place is clean and quiet, and the sauna is a nice touch. "
The price is €249
includes taxes & fees
3 Sept - 4 Sept
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Magnificent Lake View
Property grounds

Magnificent Lake View

2.0 star property
Magnificent Lake View
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!
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
Cozy Haven: A Romantic Retreat in our Tiny House!
Cozy living room with a fireplace, comfortable sofa, and a potted plant.

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 €263
includes taxes & fees
13 Aug - 14 Aug
Cozy Haven: A Romantic Retreat in our Tiny House!
Charming 2-bedroom cottage in delightful Greenwood Lake with WiFi, AC
Relax in this stylish living room with a comfortable sofa, large mirror, and decorative artwork.

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

Charming 2-bedroom cottage in delightful Greenwood Lake with WiFi, AC
Charming Gardiner Home w/ Yard & Sunroom
House (4 Bedrooms) | Front of property

Charming Gardiner Home w/ Yard & Sunroom

3.0 star property
10.0 out of 10, Exceptional, (1)
Charming Gardiner Home w/ Yard & Sunroom
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!
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!
Pet-friendly Hopewell Junction Home w/ Pool
Enjoy cooking in this well-equipped kitchen with a sink, ample counter space, and a large island for extra workspace.

Pet-friendly Hopewell Junction Home w/ Pool

3.0 star property
10.0 out of 10, Exceptional, (1)
"This house was so incredible. Not only was it in a quiet nice neighborhood the inside was incredible too. Pool table as well as a pool it was perfect for my stay to have fun and enjoy our time. They were very communicative and welcoming to their house. Everything was comfortable and clean. Can’t say any bad things about this place. Definitely going to book again. I already miss it. "
Pet-friendly Hopewell Junction Home w/ Pool
Historic 1800s Cornwall-On-Hudson Cottage!
Charming single-story house with a gabled roof and symmetrical facade, set amidst lush greenery and mature trees.

Historic 1800s Cornwall-On-Hudson Cottage!

10.0 out of 10, Exceptional, (29)
"Best VRBO OUR FAMILY HAS RENTED .ABSOLUTELY PERFECT, THOUGHTFUL AND SUPER CLEAN,"
Historic 1800s Cornwall-On-Hudson Cottage!
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Children can play on the slide in this enclosed playground surrounded by trees.

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 - "
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
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

La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

10/10 Excellent
"Excellent!"
Latresha 2-night trip
Posted 1 day ago
La Quinta Inn & Suites by Wyndham Middletown-Goshen

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.