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Holiday Rentals in New Windsor

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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, (27)
"Weather was not so great to be outside but the game room made up for it!"
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
Fridge, microwave, oven, stovetop
Downtown Loft. In Poughkeepsie. Walking distance to Civic Center. Pet friendly
The price is €189
per night
7 May - 8 May
Downtown Loft. In Poughkeepsie. Walking distance to Civic Center. Pet friendly
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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 €258
per night
7 May - 8 May
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
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."
The price is €248
per night
6 May - 7 May
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
Luxury Studio
Cottage Suites
3.0 star property
The price is €239
per night
3 May - 4 May
Cottage Suites
Property grounds
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
9.6 out of 10, Exceptional, (29)
"Family trip with teens and grandma. Beautiful home but unprepared for the gnats outside. Quiet location. Peaceful to sit outside around the fire pit. Kelly quickly responded to all questions and concerns. Kids enjoyed the ping pong table and grandma enjoyed the sunsets. Thank you for a great getaway!"
The price is €380
per night
7 May - 8 May
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
Fridge, microwave, oven, stovetop
Cozy country efficiency in the Hudson Valley
9.8 out of 10, Exceptional, (37)
"This property is beautiful!! Spotless, functional and private. We absolutely loved the experience and will DEFINITELY be back again."
Cozy country efficiency in the Hudson Valley
Exterior
Cabin in the heart of the Hudson Valley, Cabin 4
8.4 out of 10, Very good, (10)
"Pleasant overbite getaway. Cabin fit the bill!"
The price is €157
per night
5 May - 6 May
Cabin in the heart of the Hudson Valley, Cabin 4
Property grounds
Renovated 1850's Cottage on Storm King Mountain
10.0 out of 10, Exceptional, (7)
"Great location, very clean. Check in was easy and convenient. Will stay there again. Perfect for a family gathering."
Renovated 1850's Cottage on Storm King Mountain
Property grounds
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
9.6 out of 10, Exceptional, (34)
"Comfy place and great communication. Would stay again!"
The price is €332
per night
7 May - 8 May
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
Fridge, microwave, oven, stovetop
Cozy family-friendly home!
10.0 out of 10, Exceptional, (2)
"The property was beautiful and just as pictured. The host was more than attentive and helpful. He went above and beyond to make sure my stay was fantastic. I highly recommend this property!"
Cozy family-friendly home!
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 €815
per night
6 May - 7 May
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
Property grounds
Hudson River View Suite-romantic getaway with fireplace/private deck-75 min NYC
10.0 out of 10, Exceptional, (33)
"Very nice property, immaculately clean and very close to the Riverside Art Venue. Both quiet and convenient for my time in Newburgh. I would definitely stay here again."
The price is €168
per night
27 May - 28 May
Hudson River View Suite-romantic getaway with fireplace/private deck-75 min NYC
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.
Property grounds
Spectacular Log Home Estate North Wing Apt
10.0 out of 10, Exceptional, (24)
"The place was amazing! It was a very beautiful place and was close to everything I was needing to do. It was extremely clean and cozy and I would stay again for sure!"
Spectacular Log Home Estate North Wing Apt
Property grounds
Quaint village, walk to restaurants and shops.
The price is €293
per night
3 May - 4 May
Quaint village, walk to restaurants and shops.
Exterior
Mountain View escape
10.0 out of 10, Exceptional, (24)
"We've stayed in a number of VRBOs and none have been as well-appointed and welcoming as this Mountain View Escape home. Privacy and space, while close to wonderful towns and places to explore. Highly recommend!"
Mountain View escape
Outdoor pool
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
10.0 out of 10, Exceptional, (16)
"This house is located minutes from the highway making it easy to get to. Its a very scenic and country area so you feel farther away then you are. The house is extremely clean and well appointed it sits up high on a hill so you can enjoy the veiw of the country house across the street which has a small creek and gardens to enjoy theres even a pool to enjoy in summer months and a fire pit .this house was peaceful and perfect for the quick weekend getaway that we all needed. The host Pat was...
The price is €245
per night
7 May - 8 May
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
3 bedrooms, iron/ironing board, WiFi, bed sheets
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
10.0 out of 10, Exceptional, (1)
"We went to the area to celebrate my husbands 30th birthday with some friends and absolutely loved the home. It was brand new and decorated immaculately. It comfortably fit our group and we thoroughly enjoyed our time there. The hosts were super accommodating and quick to respond. Would absolutely reccomend and go again!"
The price is €867
per night
5 May - 6 May
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
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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, (1004)
"Clean, and check-in is quick. Pillows are not comfortable. Toilet and shower system are so noisy. Heater is too strong, can’t adjust the temperature "
The price is €138
per night
7 May - 8 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, (921)
"Always an amazing stay here!"
The price is €170
per night
13 May - 14 May
Homewood Suites Stewart Airport
Exterior
La Quinta Inn & Suites by Wyndham Middletown
2.5 star property
9.2 out of 10, Wonderful, (366)
"Clean, friendly staff Only negative: Breakfast! Only a few items available. Most everything needed to be restocked. Coffee too weak...tasted like hot water."
The price is €140
per night
14 May - 15 May
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.

Everything you need to know about New Windsor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the New Windsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect New Windsor holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

New Windsor holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in New Windsor. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A New Windsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of New Windsor holiday rentals we have selected for you start as low as €157 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on New Windsor rentals

At Expedia, we put the best New Windsor holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top New Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream New Windsor holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around New Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 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 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
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