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New Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Nov 28 - Nov 30
In two months
Jan 9 - Jan 11
In three months
Feb 6 - Feb 8
In four months
Mar 6 - Mar 8

Vacation Rentals in New Windsor

Fridge, microwave, oven, stovetop
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

New Windsor
10.0 out of 10, Exceptional, (61)
"Good property. Game room was a very nice bonus."
United States
Marela F.
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
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
9.6 out of 10, Exceptional, (45)
"Plenty of seating & comfortable beds were a plus! The theatre room was really fun for grandkids!"
United States
Lisa B.
The price is ￥40,028
￥51,576 total
includes taxes & fees
Nov 30 - Dec 1
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Property grounds
Cabin in the heart of the Hudson Valley, Cabin 2

Cabin in the heart of the Hudson Valley, Cabin 2

Newburgh
9.4 out of 10, Exceptional, (27)
"My partner and I stayed at the cabin for a writing retreat/getaway. It served us well and was perfect for our short trip. The host, Julie was very kind and helpful throughout our stay!"
United States
Thani B.
The price is ￥16,846
￥27,202 total
includes taxes & fees
Nov 17 - Nov 18
Cabin in the heart of the Hudson Valley, Cabin 2
Interior
Large,Cozy,Bright Apartment, Business Themed.

Large,Cozy,Bright Apartment, Business Themed.

Newburgh
9.0 out of 10, Wonderful, (15)
"Very cozy stay with responsive host"
United States
Adhith P.
The price is ￥66,766
￥106,799 total
includes taxes & fees
Nov 17 - Nov 18
Large,Cozy,Bright Apartment, Business Themed.
Property grounds
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, (126)
"Everything was super clean and the hosts are very easy to deal with. They came and took care of an issue with wasps for us. The view is phenomenal and having the patio to enjoy it from was great. "
United States
Samantha W.
The price is ￥29,055
￥47,556 total
includes taxes & fees
Nov 17 - Nov 18
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Exterior
Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!

Fishkill
10.0 out of 10, Exceptional, (3)
"Ideal cabin getaway. "
United States
Nadja E.
The price is ￥46,751
￥69,861 total
includes taxes & fees
Nov 17 - Nov 18
Rustic Cabin in Fishkill!
Outdoor dining
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

Newburgh
10.0 out of 10, Exceptional, (311)
"Beautiful location- owner was very responsive to any questions we had."
United States
Richard K.
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Fridge, microwave, oven, stovetop
7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space

7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space

Monroe
6.8 out of 10, (5)
The price is ￥87,483
￥174,668 total
includes taxes & fees
Nov 17 - Nov 18
7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space
Outdoor dining
Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven

Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven

Croton-on-Hudson
9.6 out of 10, Exceptional, (15)
"Nice secluded place to get away"
United States
Orion O.
Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven
Exterior
Modern penthouse suite in a restored grain tower with private roof deck.

Modern penthouse suite in a restored grain tower with private roof deck.

Warwick
10.0 out of 10, Exceptional, (26)
"Wonderful stay!"
United States
Lisi M.
The price is ￥52,161
￥83,487 total
includes taxes & fees
Nov 17 - Nov 18
Modern penthouse suite in a restored grain tower with private roof deck.
Fridge, microwave, oven, stovetop
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Carmel Hamlet
10.0 out of 10, Exceptional, (94)
"We loved our stay. It was great for a family Thanksgiving"
United States
Edmund F.
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Interior
Luxury 9BR Retreat w/Pool & Hot Tub

Luxury 9BR Retreat w/Pool & Hot Tub

Chester
7.0 out of 10, Good, (2)
"House fit our needs but felt like it needed better maintaining. Many doors didn’t open to the outside. Leaves were everywhere. We had to sweep and clean off the outdoor furniture and porch to make it usable. Downstairs basement had a strong chemical smell and pool table was very small. "
United States
Melanie F.
Luxury 9BR Retreat w/Pool & Hot Tub
Smart TV
Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River

Newburgh
9.6 out of 10, Exceptional, (37)
"Was great. A Beautiful place!"
United States
Bryan S.
The price is ￥16,691
￥40,037 total
includes taxes & fees
Nov 18 - Nov 19
Grant - A Tranquil One Bedroom Steps from River
Interior
Contemporary Cozy Cottage

Contemporary Cozy Cottage

Lake Peekskill
10.0 out of 10, Exceptional, (30)
"Very clean comfortable quiet place"
United States
Mauro C.
The price is ￥34,774
￥64,874 total
includes taxes & fees
Nov 17 - Nov 18
Contemporary Cozy Cottage
Outdoor dining
The House In Highland- Secluded Retreat

The House In Highland- Secluded Retreat

Highland
10.0 out of 10, Exceptional, (16)
"Nice secluded location. Very comfortable house. Climate control was a bit finicky, but our overall stay was outstanding. "
United States
Lee K.
The House In Highland- Secluded Retreat
Interior
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Poughkeepsie
10.0 out of 10, Exceptional, (2)
"House worked perfectly for our needs. Newly renovated home. Parking was plentiful behind the home. "
United States
Wayne S.
The price is ￥25,593
￥89,890 total
includes taxes & fees
Nov 19 - Nov 20
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Terrace/patio
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

Newburgh
9.8 out of 10, Exceptional, (20)
"The house was really clean! We will definitely try to stay here again!"
United States
Ellie M.
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9
Terrace/patio
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
9.4 out of 10, Exceptional, (9)
"We enjoyed our stay. The host is very responsive. The location is 30 minutes from Beacon, 10 minutes from Poughkeepsie and 2 hrs from NYC. The office was a nice feature and the house has great WiFi. "
United States
Debora R.
Our home is perfect for relaxing and having lots of fun, with near by activity’s
Terrace/patio
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!

Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!

Holmes
10.0 out of 10, Exceptional, (196)
"A sweet little cabin on a quiet lake was exactly what I was looking for. My overall experience was absolutely wonderful."
United States
Janine H.
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!
Exterior
Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!

Highland Falls
9.8 out of 10, Exceptional, (19)
"Well equipped space and great communication from the host"
United States
Beth
The price is ￥22,354
￥40,130 total
includes taxes & fees
Nov 17 - Nov 18
Walk to WP Gate + Free Parking!
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
"Great"
Gregg 1-night trip
Posted 22 hours ago
Hampton Inn Harriman Woodbury

Find out more about New Windsor

Search for holiday rentals in New Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in New Windsor using one of the methods below:

  • View our selection of featured holiday rentals in New Windsor
  • Use the map to find apartments and other holiday homes in the New Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in New Windsor while they last

Look no further and take a look at our great range of rental properties in New Windsor!

Frequently asked questions

Can I find a vacation rental in New Windsor?

Yes, we have vacation rentals near the most popular local attractions in New Windsor, or you can select a secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and shops in New Windsor. Allow lots of time to check out the lakeside and coffeehouses during your visit.

What's the top vacation rental in New Windsor?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: Visitors like this New Windsor vacation home rental. It offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with an oven, a microwave, and a coffee maker, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in New Windsor?

Choose from 7 Expedia vacation rentals in New Windsor for a memorable vacation.

What can I see and do in New Windsor?

Cultural attractions to visit include National Purple Heart Hall of Honor and Knox's Headquarters State Historic Site. Other places in town to visit include New Windsor Cantonment State Historic Site and Schunnemunk State Park.

What are vacation rentals like in New Windsor?

Vacation rentals are private accommodations you can stay in for a short or long stay in New Windsor. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can offer a sense of privacy away from public hotel elevators and busy reception areas while still allowing you to travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for a family trip or a small group gathering.