Photo by Wanderlustfemale

Search Cottages in New Windsor

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 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, (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 €269
includes taxes & fees
30 Jul - 31 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, (15)
"Wonderful stay, exactly as advertised, everything brand new and very cozy."
The price is €523
includes taxes & fees
24 Aug - 25 Aug
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
Magnificent Lake View
Property grounds

Magnificent Lake View

2.0 star property
Magnificent Lake View
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, (5)
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 €190
includes taxes & fees
30 Jul - 31 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, (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
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, (28)
"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
10.0 out of 10, Exceptional, (1)
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, (150)
"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 €256
includes taxes & fees
13 Aug - 14 Aug
Cozy Haven: A Romantic Retreat in our Tiny House!
Serene Holmes Cottage Near Lakes & Trails!
Cottage (2 Bedrooms) | Front of property

Serene Holmes Cottage Near Lakes & Trails!

3.0 star property
Serene Holmes Cottage Near Lakes & Trails!
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top New Windsor Hotel Reviews

La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

10/10 Excellent
"I knew it would be a great experience when I pulled up and it was very clean outside. I was met by Tatiana at the front desk. She was super friendly and a pleasure to have check me in after a long ride to the hotel. She even knew where the closest Dunkin Donuts was-yayy. The hallways, the elevator, the waiting area..very very clean. My room was everything I wanted it to be. Very roomy. Big closet to stow away luggage. The bathroom was HUGE. Also very clean. No bumping in to the walls or the sink. You can actually move around comfortably. And more than enough towels were in there. Major plus. I honestly have nothing negative to say about this visit. Anthony checked me out. Another awesome front desk person. I have even booked my next trip with this very same hotel. I wasnt disappointed at all..Well worth it. "
Sharon 1-night trip
Posted 23 hours 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.