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New Windsor Holiday Rentals

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Holiday Rentals in New Windsor

Fridge, microwave, oven, stovetop
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
10.0 out of 10, Exceptional, (31)
"As a family of 4 the house was perfect to relax at the end of the day. The kids really enjoyed the game room. Thank you 😊 Chris and Ed."
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
Fridge, microwave, oven, stovetop
Beautiful Cozy 2 br in-law apt, prime Hudson Valley location
9.4 out of 10, Exceptional, (10)
"Booked our stay over Ring Weekend at West Point. Quiet neighborhood, 15 minutes from Stoney Gate entrance to West Point. Wonderful well furnished clean and comfortable spot with 2 bedrooms. Friendly, prompt and kind communication during entire reservation and use process. Highly recommended!"
Beautiful Cozy 2 br in-law apt, prime Hudson Valley location
Luxury Studio | Private kitchen
Cottage Suites
3.0 star property
Cottage Suites
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1 bedroom, desk, iron/ironing board, travel cot
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
9.8 out of 10, Exceptional, (35)
"This is a cozy property in a very rural setting. The host is extremely responsive and very thorough. It is quiet and private. The furniture and bed are very comfortable. The wood burning stove is a pellet stove which provides enough heat to take the edge off. The hot tub could comfortably fit 4 people. The Village of Cold Spring is less than 10 minutes away, as is the Interstate 84 bridge across the Hudson. If you want to make your own food, bring it. There is no grocery store nearby."
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (96)
"Comfortable apartment with a phenomenal view! The space could use a deep clean and some decluttering, but that view!!! Did I mention that the view was A-mazing?!?"
The price is NZ$430
includes taxes & fees
29 May - 30 May
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Property grounds
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
9.6 out of 10, Exceptional, (35)
"Three nights here as we toured the area. Check in was easy. We were able to access the VRBO app 30 minutes prior to our arrival. By the time we reached the driveway, Ruben had sent the access code.The road to the house is gravel and only wide enough for one car. We were glad we had arrived during the day.The house has an antique store vibe. Lots of books for a rainy day activity. FYI, the photos on the listing are a bit different from what we saw in the rooms. The dining table is larger with...
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
Property grounds
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
10.0 out of 10, Exceptional, (36)
"This sweet little apartment was perfect for my solo stay. Comfortable, quiet, and very easy to get to. Lovely view from the deck. It had a feeling of security and privacy. Vicky was quick with answering my emails."
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
Fridge, microwave, stovetop, dishwasher
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
10.0 out of 10, Exceptional, (22)
"My family and I had a wonderful weekend at the property. It rained most of the time, but we made the best of it. It was all over too fast. It's a nice, relaxing property."
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
Exterior
Cabin in the heart of the Hudson Valley, Cabin 4
8.4 out of 10, Very good, (11)
"Everything was as it says it was. Place was spotless. In the evening and morning you didn’t hear any traffic noise at all. Was quiet and peaceful. Communication with the property owner was outstanding."
The price is NZ$265
includes taxes & fees
29 May - 30 May
Cabin in the heart of the Hudson Valley, Cabin 4
Property grounds
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC!
10.0 out of 10, Exceptional, (168)
"If you need a relaxing few days in the winter, very good place. Great views and quiet is the key."
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC!
Property grounds
Renovated 1850's Cottage on Storm King Mountain
9.8 out of 10, Exceptional, (8)
"It was a beautiful setting with water fall. The home itself needs a little work. It is well used and needs some TLC. Photos look much better then actual home."
Renovated 1850's Cottage on Storm King Mountain
Exterior
Cabin in the heart of the Hudson Valley, Cabin 2
9.4 out of 10, Exceptional, (3)
"Great tiny house for a stay upstate. Check in was easy and the place is clean!"
The price is NZ$265
includes taxes & fees
3 Jun - 4 Jun
Cabin in the heart of the Hudson Valley, Cabin 2
Smart TV
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
9.0 out of 10, Wonderful, (21)
"This house has an ideal location to see lots of local sites of interest in the Hyde Park and Poughkeepsie area. Easy trip from there to West Point, Hyde Park and the Culinary Institute from the location, and great restaurant, Tiramasu, is very close. The house is immaculate! The beds were very comfortable, linens were provided, the bathrooms were spacious and the five of us had plenty of room for our toiletries. The house has steps to its multiple levels for all essential rooms, not accessible....
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Fridge, microwave, oven, stovetop
Cozy family-friendly home!
10.0 out of 10, Exceptional, (3)
"Older manufactured home has been updated. We appreciated that each area had its own mini split unit for individual climate control. Area felt safe and quiet. Good hot water and water pressure. Kitchen was stocked for stovetop cooking but not much for baking, and no water glasses. (We just drank everything from the coffee cups.) Split bedroom layout was good for two couples. "
The price is NZ$440
includes taxes & fees
29 May - 30 May
Cozy family-friendly home!
Property grounds
Spectacular Log Home Estate North Wing Apt
10.0 out of 10, Exceptional, (25)
"All as represented. Had everything we needed for a lovely home away from home!"
Spectacular Log Home Estate North Wing Apt
Interior
Royal Garden Main Cabin
Royal Garden Main Cabin
Fridge, microwave, oven, stovetop
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
6.4 out of 10, (5)
"This host is very irresponsible knowing 8 months in advanced about the reservation and not having the pool ready or even communicating that the pool would not be ready for use is just unexceptable. Also property has many things wrong with it. The oven doesn't work, the gas tank for the grill was left empty, all shower heads need to be replaced, the tv and mini Fridge in the basement bedroom dont work, the power outlet in the master bedroom doesn't work and the wall fixture above jacuzzi is just...
The price is NZ$1,572
includes taxes & fees
30 May - 31 May
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
Beach
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
10.0 out of 10, Exceptional, (35)
"I needed a place in Wallkill NY to stay. This VRBO was perfect!"
The price is NZ$380
includes taxes & fees
24 Jun - 25 Jun
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Outdoor pool
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
10.0 out of 10, Exceptional, (18)
"House is very cute. The scenery in early spring was amazing. Very quiet neighborhood. Conveniently located. Very clean. Beds were very comfortable. Had everything we needed."
The price is NZ$505
includes taxes & fees
3 Jun - 4 Jun
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
Fridge, microwave, oven, stovetop
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
10.0 out of 10, Exceptional, (61)
"The property and house were beautiful, out of the way but beautiful. The fire pit, sunroom, and porch were amazing. It was great for decompressing after a West Point graduation. Thank you for sharing your little piece of heaven."
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
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See all available properties in New Windsor
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.

Other types of properties in New Windsor you may be interested in

Indoor pool
Red Roof Inn & Suites Newburgh – Stewart Airport
2.0 star property
8.4 out of 10, Very good, (1002)
"Enjoyed our short stay!"
The price is NZ$219
includes taxes & fees
29 May - 30 May
Red Roof Inn & Suites Newburgh – Stewart Airport
Iron/ironing board, free cots/infant beds, free WiFi, bed sheets
Homewood Suites Stewart Airport
3.0 star property
9.4 out of 10, Exceptional, (927)
"It was clean nice and quiet. "
The price is NZ$321
includes taxes & fees
5 Jun - 6 Jun
Homewood Suites Stewart Airport
Exterior
La Quinta Inn & Suites by Wyndham Middletown
2.5 star property
9.2 out of 10, Wonderful, (388)
"The staff was nice. Checking in was very quick and the place is clean. "
The price is NZ$243
includes taxes & fees
3 Jun - 4 Jun
La Quinta Inn & Suites by Wyndham Middletown
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our New Windsor holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up New Windsor. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in New Windsor. Seeing all the best attractions is bound to make you fall in love with New Windsor. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in New Windsor short-term rentals, that won’t be hard to do.

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?

Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits: This holiday home rental outside of New Windsor is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in New Windsor?

Choose from 6 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 Knox's Headquarters State Historic Site and National Purple Heart Hall of Honor. Woodbury Common Premium Outlets and LEGOLAND® New York are other popular places to visit in the area.

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.

Recent reviews of New Windsor properties
Expedia verified reviews