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New Windsor Holiday Rentals

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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, (42)
"The perfect spot for a Beacon/Newburgh getaway! Great access to the towns, Storm King State Park, and Storm King Art Center! Lovely house, great game room (played so much ping pong and darts), and the hot tub was perfect."
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

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 AU$390
includes taxes & fees
17 Feb - 18 Feb
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

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

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

9.8 out of 10, Exceptional, (49)
"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!"
The price is AU$793
includes taxes & fees
17 Feb - 18 Feb
Renovated House w/Hot Tub, Deck, Grill & Fire Pit

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 AU$631
includes taxes & fees
10 Mar - 11 Mar
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

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 AU$461
includes taxes & fees
18 Feb - 19 Feb
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

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

Luxurious 7 Bedroom Estate with Heated Pool and Hot Tub

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 AU$715
includes taxes & fees
17 Feb - 18 Feb
Luxury 3-bedroom fully renovated house in Goshen with brand new furniture.

MODERN FARMHOUSE HOME ON 5-ACRE DREAM PROPERTY

9.6 out of 10, Exceptional, (9)
"Great property nice and cozy for a group of 6. Rooms and house were clean and very organized host provided coffee and bath basics. House was equipped with family games and kitchen and living room and deck all open floor plan. Working jacuzzi which was great after hitting the slopes and a lot of backyard space for kids to roam around. The host was communicative throughout the stay. Warwick town was 20 mins away and mount Peter was 15 mins away Woodbury commons are 20 mins away . Overall would...
MODERN FARMHOUSE HOME ON 5-ACRE DREAM PROPERTY

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 AU$1,300
includes taxes & fees
1 Mar - 2 Mar
Spacious New Luxurious holiday house in lovely Hudson Valley

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

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 AU$591
includes taxes & fees
17 Feb - 18 Feb
Contemporary Cozy Cottage

Kick back & relax in this peaceful, stylish place to stay with the whole family.

10.0 out of 10, Exceptional, (22)
"Our family went to the Hudson Valley area for a wedding. Pre stay communication with Malka was excellent and we all had a wonderful time. Lots of room for the kids to play and be entertained downstairs as well as upstairs in the Projection Room. The backyard was a great soccer area and the fire pit was great to sit around at night. Firewood on site was a real plus! I do recommend to anyone doing substantial cooking for many people to bring their own favorite pots and pans if possible though...
Kick back & relax in this peaceful, stylish place to stay with the whole family.

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

10.0 out of 10, Exceptional, (1)
"Alexis was a great host and she was super communicative and easy to reach. The house was clean and prefect size for my group of 6. Most things were stocked but I’d reach out to the host in advance so you can buy anything that isn’t ahead of time. One important thing to note is that the driveway can only fit 2 cars and there isn’t really any street parking. "
BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.

Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons

2.0 star property
9.0 out of 10, Wonderful, (4)
"Just what we needed with lots of space very clean and comfortable"
Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons

Spectacular ~10k sqft Mansion w/Pool&Tennis

10.0 out of 10, Exceptional, (6)
"I reserved the house for a family reunion of about 20 people and had a great time. What I really liked about coming here:1. The house - It was spacious and elegant, had multiple living rooms, and had many bathrooms. This was perfect for our large group.2. The grounds - Although we did not use the tennis or pickleball courts because of the weather, we could see how nice it is to have right next to the house. Folks from our group went walking and running on the roads around the house and those...
Spectacular ~10k sqft Mansion w/Pool&Tennis

Catskills mountain gateway house.

9.8 out of 10, Exceptional, (14)
"House is spacious and clean. The little touches like the Christmas decorations, games, books etc. were greatly appreciated. Beautiful property. Would definitely return. "
Catskills mountain gateway house.

Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!

7.0 out of 10, Good, (15)
"This home was just what our group of 16 needed to find rest, reconvene from the day’s activities, and prepare for all the next day’s activities. The town of Monroe was a great place to stay as it was centrally located for all the places we visited. "
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!

Hiking/Climbing Paradise- walking distance to Mohonk/Gunks/Minnewaska

9.8 out of 10, Exceptional, (92)
"This property was spectacular. Immaculately clean and every detail done well. From a fully stocked and ready to go kitchen, to comfortable beds, sheets and towels. I’ll be back to stay here again and the host Michelle couldn’t have done more. Having had a few disappointing stays in other properties of late, this was a welcome game changer!!!"
Hiking/Climbing Paradise- walking distance to Mohonk/Gunks/Minnewaska
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, (1012)
"The staff is fantastic The room is always clean and in good working order"
The price is AU$176
includes taxes & fees
17 Feb - 18 Feb
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Homewood Suites Stewart Airport

3.0 star property
9.2 out of 10, Wonderful, (977)
"Large rooms, clean and quiet."
The price is AU$241
includes taxes & fees
23 Feb - 24 Feb
Homewood Suites Stewart Airport

HYATT house Fishkill/Poughkeepsie

3.0 star property
8.8 out of 10, Excellent, (1005)
"We had a family 1 night stay. Bed was comfy, multiple tvs is the 2 bedroom. Only negative was too much chlorine in the pool and a bit cold. "
The price is AU$183
includes taxes & fees
22 Feb - 23 Feb
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?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: 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. Kitchen amenities include an oven, a microwave and an electric kettle. Kick off your shoes and enjoy yourself with a garden and 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?

Enjoy the outdoors at Kristi Babcock Memorial Park and Schunnemunk State Park, or simply take in cultural attractions like National Purple Heart Hall of Honor and Knox's Headquarters State Historic Site. In the wider area, you’ll find New Windsor Cantonment State Historic Site and Woodbury Common Premium Outlets.

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.