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Check prices for these dates

In two weeks
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

Our top choices for New Windsor vacation homes

TV, fireplace

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Carmel Hamlet
9.8 out of 10, Exceptional, (13 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is ￥35,741
￥66,968 total
includes taxes & fees
May 27 - May 28
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Outdoor dining

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fishkill
9.2 out of 10, Wonderful, (65 reviews)
"Great spot! Very unique, has lots of charm!"
United States
Brian
The price is ￥39,315
￥51,705 total
includes taxes & fees
May 27 - May 28
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fridge, microwave, oven, stovetop

Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (34 reviews)
"Very clean comfortable quiet place"
United States
Mauro C.
The price is ￥35,741
￥67,223 total
includes taxes & fees
Jun 2 - Jun 3
Contemporary Cozy Cottage
TV

Luxury House Near West Point

Luxury House Near West Point
Highland Falls
The price is ￥31,770
￥51,561 total
includes taxes & fees
Jun 3 - Jun 4
Luxury House Near West Point
Terrace/patio

House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
10.0 out of 10, Exceptional, (8 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is ￥19,856
￥61,781 total
includes taxes & fees
May 27 - May 28
House on the Babbling Brook- Quiet 2BR + King Bed!
Outdoor spa tub

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Greenwood Lake
9.8 out of 10, Exceptional, (37 reviews)
"Great communication with the host and its a beautiful home. Very clean and a great location with wonderful views."
United States
Frank M.
The price is ￥31,800
￥80,941 total
includes taxes & fees
May 26 - May 27
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Interior

Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Kerhonkson
10.0 out of 10, Exceptional, (37 reviews)
"I was very happy with the property. I shared the place with my adult children for a family wedding. It was wonderful to have some quality, screenfree, engaging time with them. We took full advantage of the games and cards provided. The bedding was sooo comfy that I came home and ordered the same pillows that were there. I would definitely add the fact that the water is “well water” to the listing so people know in advance to bring water. All in all a great experience."
United States
Kim
The price is ￥12,510
￥27,997 total
includes taxes & fees
May 25 - May 26
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Interior

Lovely 3BR Home with parking-Walk to WP Gate!

Lovely 3BR Home with parking-Walk to WP Gate!
Highland Falls
10.0 out of 10, Exceptional, (7 reviews)
"Lovely home, great location and space for my family to have privacy. Enjoyed the deck for morning coffee. Would book again. "
United States
Briana T.
The price is ￥39,530
￥69,521 total
includes taxes & fees
May 27 - May 28
Lovely 3BR Home with parking-Walk to WP Gate!
Interior

Our home is perfect for relaxing and having lots of fun, with near by activity’s

Our home is perfect for relaxing and having lots of fun, with near by activity’s
Highland
9.6 out of 10, Exceptional, (12 reviews)
"We had was great time and the host Mary was amazing and excellent at communicating. Everything was perfect in the home. Thank you"
United States
Pinal
The price is ￥35,741
￥111,906 total
includes taxes & fees
May 26 - May 27
Our home is perfect for relaxing and having lots of fun, with near by activity’s
Outdoor spa tub

Country House w/Hot Tub, Deck, Grill & Fire Pit

Country House w/Hot Tub, Deck, Grill & Fire Pit
Goshen
10.0 out of 10, Exceptional, (62 reviews)
"Very good host "
United States
Binyomin
The price is ￥52,262
￥91,530 total
includes taxes & fees
May 27 - May 28
Country House w/Hot Tub, Deck, Grill & Fire Pit
Fridge, microwave, oven, stovetop

5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!

5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!
Warwick
10.0 out of 10, Exceptional, (5 reviews)
"Had a lovely weekend in the little red barn. And the little market next door has the best breakfast egg and bacon sandwich."
United States
michelle d.
5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!
Fridge, microwave, oven, stovetop

Secluded Warwick Retreat on 3 Acres Next to Winery- 1 Hr from NYC!

Secluded Warwick Retreat on 3 Acres Next to Winery- 1 Hr from NYC!
Warwick
10.0 out of 10, Exceptional, (8 reviews)
"We enjoy our stay at this beautiful home. The house is very spacious and clean. It is located in a great area and was very quiet."
United States
matthew l.
The price is ￥42,307
￥106,084 total
includes taxes & fees
Jun 1 - Jun 2
Secluded Warwick Retreat on 3 Acres Next to Winery- 1 Hr from NYC!
Property grounds

Glamping Tent & Campsite by Minnewaska State Park

Glamping Tent & Campsite by Minnewaska State Park
Kerhonkson
8.8 out of 10, Excellent, (3 reviews)
"This is an "upgraded" camping experience! A peaceful setting for outdoor living, exceptionally private. Super convenient to Minnewaska. Everything you need amd exactly as described, plenty of seating for a larger group and sleeping tent/yurt makes inclement weather less of a concern than a regular tent or backpacking setup. Definitely stay here!"
United States
Megan
The price is ￥13,582
￥24,107 total
includes taxes & fees
May 26 - May 27
Glamping Tent & Campsite by Minnewaska State Park
Exterior detail

Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.4 out of 10, Exceptional, (6 reviews)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
The price is ￥38,696
￥66,407 total
includes taxes & fees
May 27 - May 28
Fabulous 3bdrm Home w/parking!
Exterior

Luxury home near West Point

Luxury home near West Point
Highland Falls
10.0 out of 10, Exceptional, (3 reviews)
"The accommodations are great—Very nice townhouse, lots of room, clean, comfortable, and pet-friendly."
United States
Suzy
The price is ￥66,082
￥78,911 total
includes taxes & fees
Jun 8 - Jun 9
Luxury home near West Point
Property grounds

3BR West Point Retreat-3min to Back Gate+ King Bed

3BR West Point Retreat-3min to Back Gate+ King Bed
Highland Falls
8.0 out of 10, Very Good, (6 reviews)
"Space was excellent, the multiple bedrooms with the extra bathroom was great. Kitchen was stocked with utensils, bathrooms were clean, living space was comfortable and cozy."
United States
Christine T.
The price is ￥19,856
￥72,062 total
includes taxes & fees
May 27 - May 28
3BR West Point Retreat-3min to Back Gate+ King Bed
Exterior

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.2 out of 10, Wonderful, (11 reviews)
"The chapel was just as it was pictured. It has been beautifully restored. It was a very unique experience."
United States
Stella
The price is ￥24,161
￥41,350 total
includes taxes & fees
May 27 - May 28
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
3 bedrooms, desk, iron/ironing board, free WiFi

Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
9.2 out of 10, Wonderful, (7 reviews)
"Very nice apartment in Highland Falls. Each bedroom has nice closet space and the master is very large. Remodeled very well and comfortable. "
United States
chris f.
The price is ￥21,604
￥71,097 total
includes taxes & fees
May 27 - May 28
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Fridge, microwave, oven, stovetop

Luxury 3BR with King Beds in Montgomery Village

Luxury 3BR with King Beds in Montgomery Village
Montgomery
10.0 out of 10, Exceptional, (2 reviews)
"Excellent location! Very clean and the hosts were quick to respond to communication. We would definitely stay here again. "
United States
Barbara M.
The price is ￥49,506
￥83,598 total
includes taxes & fees
May 27 - May 28
Luxury 3BR with King Beds in Montgomery Village
Interior

Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks

Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks
Kerhonkson
10.0 out of 10, Exceptional, (15 reviews)
"Beautiful place tucked back in the woods. Very relaxing and incredibly clean. The free coffee was a nice touch too. Will 100% be returning to The Gunks because of this house. "
United States
Kyle T.
The price is ￥10,513
￥24,410 total
includes taxes & fees
May 28 - May 29
Art Studio Retreat with Sauna Fireplace Forest Views | 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.
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Top New Windsor Hotel Reviews

Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen

8/10 Good
"The room was clean but staff was not as friendly as expected for a hotel they didn’t even greet you unless you greeted them first."
Elsie 7-night trip
Posted 6 hours ago
Courtyard by Marriott Middletown Goshen

Find out more about New Windsor

New Windsor Vacation Homes information

Number of reviews
341
Accommodation
375 Vacation Homes
Lowest Price
￥24,107
Highest Price
￥111,906