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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

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 €283
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
Surrounded by a forest, this cabin features a stone chimney and a cozy porch.

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 €522
includes taxes & fees
24 Aug - 25 Aug
Charming Cottage in the Heart of the Shawangunks
Be in Nature at this Gorgeous Riverfront Cabin
Steps lead to a front door flanked by large windows, set amidst a beautifully manicured lawn and 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
Hudson Valley Retreat w/ Pool Near Greenwood Lake
Property grounds

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
Cozy Retreat w/ Pool, Cinema Room & Fire Pit
Enjoy al fresco dining in this outdoor space, complete with a grill and comfortable seating for two.

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
Magnificent Lake View
Property grounds

Magnificent Lake View

2.0 star property
The price is €559
includes taxes & fees
9 Aug - 10 Aug
Magnificent Lake View
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 €191
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
Walk along the weathered boardwalk to a serene body of water surrounded by lush trees and vibrant flowers.

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

10.0 out of 10, Exceptional, (5)
Romantic retreat with stunning views of Croton River Gorge, a birder haven
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!
Escape to a secluded cabin nestled among the trees, accessible via a stone staircase.

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 €260
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
Stunning single-story home with a garage and inviting front porch.

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 (3 Bedrooms) | Interior

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!
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
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 a meal or relax on the deck with a table and six chairs, surrounded by a grassy area with trees.

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
Cottage at Millpond Falls - Romantic Luxury Escape - Waterfall views in Warwick
Enjoy a serene outdoor space with a deck, table, and chair overlooking a tranquil landscape with trees and a body of water.

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
Historic 1800s Cornwall-On-Hudson Cottage!
Stately home surrounded by a well-manicured lawn and lush trees, featuring a charming front porch and a small garden.

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 - "
The price is €262
includes taxes & fees
6 Aug - 7 Aug
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

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury

10/10 Excellent
"The room was in quiet area no kids making noise thank you will request same area next time I visit"
Denise 1-night trip
Posted 1 day ago
Hampton Inn Harriman Woodbury

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.