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Holiday Rentals in New Windsor

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Holiday Rentals in New Windsor

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

10.0 out of 10, Exceptional, (44)
"Good property. Game room was a very nice bonus."
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

Greenwoods of Warwick

9.8 out of 10, Exceptional, (8)
"Home was very clean. The host was very friendly & informative. The beds were very comfortable. We would highly recommend staying at this location. We will definitely stay here again. 👍 "
Greenwoods of Warwick

Spacious New Luxurious holiday house in lovely Hudson Valley

9.8 out of 10, Exceptional, (8)
"The house had room for all of us, spacious and comfortable with modern amenities. We enjoyed the large open kitchen, well equipped for making big meals, and especially loved the walk in pantry with sink, oven and coffee bar. The beds were comfy, the bathrooms deluxe. Large couch and huge TV in living room with cozy gas fireplace for us to gather and relax. Located on a quiet cul de sac, easy to get to local attractions. We enjoyed every minute of our stay."
The price is €797
includes taxes & fees
1 Mar - 2 Mar
Spacious New Luxurious holiday house in lovely Hudson Valley

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

9.8 out of 10, Exceptional, (50)
"Our family had a truly wonderful winter holiday stay - our kids (3 and 5) loved having the books and toys available to use. The location was super convenient to hiking, snow tubing and indoor playareas. House was clean and the beds were very comfortable - we slept great especially after using the hot tub!"
Renovated House w/Hot Tub, Deck, Grill & Fire Pit

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (107)
"Spectacular view and very convenient to USMA. "
The price is €239
includes taxes & fees
28 Feb - 1 Mar
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

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

10.0 out of 10, Exceptional, (2)
"Communication was easy, location and parking was great! Very clean and cozy!"
The price is €288
includes taxes & fees
1 Mar - 2 Mar
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

The Philip Johnson Wolfhouse

10.0 out of 10, Exceptional, (3)
"This house is an architectural gem with great views to the Hudson river and very close to Dia Beacon and really nice hikes. We were a group of 7 and really enjoyed our time together during our stay. Jeremy was really nice and accommodating. I highly recommend this house."
The Philip Johnson Wolfhouse

Luxurious 7 Bedroom Estate with Heated Pool and Hot Tub

2.0 out of 10, (1)
"There was rats inside the house and there was no amenities like toilet paper. And host was very unresponsive."
Luxurious 7 Bedroom Estate with Heated Pool and Hot Tub

Luxury 3-bedroom fully renovated house in Goshen with brand new furniture.

2.0 star property
9.4 out of 10, Exceptional, (3)
"This home was newly renovated and very clean. Would stay there again."
The price is €431
includes taxes & fees
28 Feb - 1 Mar
Luxury 3-bedroom fully renovated house in Goshen with brand new furniture.

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

2.0 star property
10.0 out of 10, Exceptional, (1)
"My husband and I had an amazing time. Absolutely beautiful home, great location, and overall amazing experience. "
The price is €386
includes taxes & fees
10 Mar - 11 Mar
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

Beautiful Private Stone Home in the Hudson Valley

10.0 out of 10, Exceptional, (139)
"We had a wonderful time together. Room for everyone. We were 11. Clean and spacious. We would stay there again."
Beautiful Private Stone Home in the Hudson Valley

Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View

10.0 out of 10, Exceptional, (281)
"Beautiful, quiet property that was a great getaway from the city. A pair of bald eagles were circling the lake which was a really amazing surprise! "
The price is €261
includes taxes & fees
11 Mar - 12 Mar
Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View

MODERN FARMHOUSE HOME ON 5-ACRE DREAM PROPERTY

9.6 out of 10, Exceptional, (9)
"We felt well taken care of- the house was warm with the fireplace going when we arrived and when it snowed the driveway was plowed and the sidewalk shoveled. The showers were hot and the beds so cozy! Would recommend to others! "
MODERN FARMHOUSE HOME ON 5-ACRE DREAM PROPERTY

The Cozy Goshen Home, 5mins from LEGOLAND and near skiing!

10.0 out of 10, Exceptional, (6)
"We enjoyed our stay! Very spacious, bigger than the pictures make it seem! Nice large backyard with a good amount of privacy. "
The Cozy Goshen Home, 5mins from LEGOLAND and near skiing!

BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.

10.0 out of 10, Exceptional, (2)
"My family and I had a fantastic stay! The house was even more beautiful and spacious than we expected, making it the perfect home base for our weekend trip to Mount Peter. It was clean, cozy, and had everything we needed for a comfortable and relaxing stay. My parents live nearby in Warwick and this will definitely be my go-to VRBO recommendation for anyone visiting the area. We can’t wait to come back!"
BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.

Mountain View escape

10.0 out of 10, Exceptional, (46)
"Can’t wait to go back, if I could move this home to Myrtle Beach I would. Fantastic communication with homeowner, great location. Homeowner keeps the home stocked with goodies, extra plus! Very cozy and Quiet it’s a 10 Star "
Mountain View escape

Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer

10.0 out of 10, Exceptional, (32)
"Nice."
The price is €220
includes taxes & fees
4 Mar - 5 Mar
Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer

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

10.0 out of 10, Exceptional, (75)
"We loved our stay. It was great for a family Thanksgiving"
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Contemporary Cozy Cottage

10.0 out of 10, Exceptional, (15)
"We had a wonderful stay at the Contemporary Cozy Cottage! Very modern amenities and appliances, and the kitchen had everything we needed!! Nadia always responded promptly, and answered all of my questions. The Cottage is located close to just about everything in the Peekskill, Cortlandt Manor, and Yorktown Heights area. And I would definitely recommend a short drive to the charming little town of Cold Spring which is not too far away. Thank you Nadia!"
The price is €364
includes taxes & fees
11 Mar - 12 Mar
Contemporary Cozy Cottage

Cozy Escape -Strong Wi-Fi -Prime Location

The price is €303
includes taxes & fees
19 Mar - 20 Mar
Cozy Escape -Strong Wi-Fi -Prime Location
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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Other types of properties in New Windsor you may be interested in

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

2.0 star property
8.4 out of 10, Very good, (1006)
"Had a restful night, very comfortable bed , felt safe , will stay again next time on the area."
The price is €101
includes taxes & fees
16 Mar - 17 Mar
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Homewood Suites Stewart Airport

3.0 star property
9.2 out of 10, Wonderful, (978)
"I loved the roominess and layout of the room. I loved the handicap accessible. Everything was clean and attractive. Staff was wonderful. Breakfast was nice. Thanks!"
The price is €145
includes taxes & fees
6 Mar - 7 Mar
Homewood Suites Stewart Airport

HYATT house Fishkill/Poughkeepsie

3.0 star property
8.8 out of 10, Excellent, (1004)
"Great service, clean facility, breakfast was excellent, very quiet. There was a pool that I didn't have a chance to use in my stay. Maybe the next time! I'd definitely recommend staying here."
The price is €111
includes taxes & fees
6 Mar - 7 Mar
HYATT house Fishkill/Poughkeepsie
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.

Frequently asked questions

Can I find a holiday rental in New Windsor?

Yes, there are holiday rentals close to the most popular sights in New Windsor, or you can select a more 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 coffee shops during your visit.

What are some of the best holiday rentals that New Windsor has to offer?

Spacious New Luxurious holiday house in lovely Hudson Valley: This holiday home rental outside of New Windsor offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, in addition to a kitchen with a dishwasher and kitchenware. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in New Windsor?

Choose from 4 Expedia holiday rentals in New Windsor for a memorable holiday.

What can I see and do in New Windsor?

Cultural attractions include National Purple Heart Hall of Honor and Knox's Headquarters State Historic Site, whereas Kristi Babcock Memorial Park is one spot to enjoy nature. Other places in town to visit include New Windsor Cantonment State Historic Site and Schunnemunk State Park.

What are holiday rentals like in New Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in New Windsor. Holiday rentals feature extras like kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a clean environment, a holiday rental can provide a sense of safety away from public hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for family trips.