A large suspension bridge at night with illuminated cables and a central tower.

Search Cottages in New Windsor

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for New Windsor cottages

House (3 Bedrooms) | Interior

1. Bright Cornwall-on-hudson Vacation Rental!

Bright Cornwall-on-hudson Vacation Rental!
3.0 star property
Cornwall
10.0 out of 10, Exceptional, (1 review)
"Very nice property, very comfortable, close to multiple sightseeing location including bear mountain."
United States
Poyuk
The price is AED 1,363
AED 2,565 total
includes taxes & fees
22 Oct - 23 Oct
Bright Cornwall-on-hudson Vacation Rental!
Property grounds

2. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (146 reviews)
"We had a great stay!!"
United States
Jasmine
The price is AED 727
AED 1,215 total
includes taxes & fees
24 Sep - 25 Sep
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Exterior

3. Walk-to-Lake Cottage With Grill for Peaceful Fall Days

Walk-to-Lake Cottage With Grill for Peaceful Fall Days
Putnam Valley
9.8 out of 10, Exceptional, (25 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
Walk-to-Lake Cottage With Grill for Peaceful Fall Days
Exterior

4. Quiet Solitude with Firepit, Electric Stove & Private Deck

Quiet Solitude with Firepit, Electric Stove & Private Deck
Hopewell Junction
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our stay at Sara's place. Unfortunately due to all the rain we couldn't enjoy the outside facilities. The bedroom loft is charming and everything you need is there. Thanks for a great stay!"
United States
stephanie a.
The price is AED 600
AED 2,019 total
includes taxes & fees
1 Oct - 2 Oct
Quiet Solitude with Firepit, Electric Stove & Private Deck
Smart TV

5. Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.2 out of 10, Wonderful, (15 reviews)
"Great place to stay when visiting Legoland. Convenient location and comfortable and clean."
United States
Jessica C.
The price is AED 545
AED 1,075 total
includes taxes & fees
24 Sep - 25 Sep
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Property grounds

6. Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.

Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
Croton-on-Hudson
9.6 out of 10, Exceptional, (24 reviews)
"A lovely spot, very nice accommodations.Breakfast supples thoughtfully supplied as well as champagne to enjoy. "
United States
Eva C.
The price is AED 918
AED 1,563 total
includes taxes & fees
24 Sep - 25 Sep
Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
Property grounds

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

Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Bloomingburg
9.6 out of 10, Exceptional, (5 reviews)
"The place was as described, quaint, clean, no issues with communication or check in"
United States
Stephen H.
The price is AED 514
AED 793 total
includes taxes & fees
24 Sep - 25 Sep
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Exterior

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

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Kerhonkson
9.6 out of 10, Exceptional, (18 reviews)
"The cottage was welcoming, clean and cozy. We appreciated the special touches throughout. The indoor fireplace and sauna were a huge bonus "
United States
Anthony M.
The price is AED 492
AED 850 total
includes taxes & fees
5 Oct - 6 Oct
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
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.
View all properties
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

DoubleTree by Hilton Poughkeepsie Convention Center

DoubleTree by Hilton Poughkeepsie Convention Center

10/10 Excellent
"N/a"
Dayana 2-night trip
Posted 5 hours ago
DoubleTree by Hilton Poughkeepsie Convention Center

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.

Explore a world of travel with Expedia