Photo by Wanderlustfemale

New Windsor Vacation Rentals

Vacation 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, (29)
"Our stay was wonderful! The house was super clean and just what we needed. The bed was comfortable and the game room even better for the little ones and adults :) thank you so much!"
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
Property grounds
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
10.0 out of 10, Exceptional, (35)
"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."
The price is $80
$178 total
includes taxes & fees
May 31 - Jun 1
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
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. "
Cozy family-friendly home!
Property grounds
Luxury retreat w/ private deck, garden, firepit on organic farm
10.0 out of 10, Exceptional, (10)
"The property and the yurt were absolutely beautiful. And if you're looking to get AWAY, this is the place. It rained most of the weekend, and we still had an amazing time. Communication was terrific. Thank you so much, John."
Luxury retreat w/ private deck, garden, firepit on organic farm
Fridge, microwave, stovetop, dishwasher
Updated Getaway w/ Pool & Hot Tub on 2.5 Acres!
10.0 out of 10, Exceptional, (21)
"This is an attractive, well-laid out house with an extremely accommodating owner. The home is pretty small—great for two or three with very little play area inside for kids—but there are several great outside areas on the deck, around the pool and stream. In terms of accessibility, three steps up to the doorway, a step down to the master bedroom and a step up to the ensuite master bath."
Updated Getaway w/ Pool & Hot Tub on 2.5 Acres!
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
Outdoor dining
Black Walnut Tree Farm: Farmhouse on 50 Acres
10.0 out of 10, Exceptional, (13)
"Four friends had a wonderful time at Black Walnut Tree Farm. The space was amazing! There was plenty of spaces that we could hang out together, but also we each had areas that we could retreat to. The kitchen was well-stocked ands spacious, the large living room had many comfortable seats around the fire, and there was a great sunroom where we could sit and play games. The grounds were huge and one could easily get lost walking around the property. We all loved the place and are collectively...
Black Walnut Tree Farm: Farmhouse on 50 Acres
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.
Beach
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
10.0 out of 10, Exceptional, (34)
"We enjoyed staying here a few days. The place has been updated and was clean. We didn't use the fire pit but we did sit outside on the deck a couple times. The sound of the river is very relaxing."
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, (17)
"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 $157
$297 total
includes taxes & fees
May 28 - May 29
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
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!
1 bedroom, desk, iron/ironing board, travel crib
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 $184
$265 total
includes taxes & fees
May 20 - May 21
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fridge, microwave, oven, stovetop
Cozy country efficiency in the Hudson Valley
9.8 out of 10, Exceptional, (39)
"Quiet, clean and very comfortable. Beautiful property located just minutes from town. Will definitely stay here again."
The price is $150
$215 total
includes taxes & fees
Jun 4 - Jun 5
Cozy country efficiency in the Hudson Valley
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
Fridge, microwave, oven, stovetop
Spacious restored Victorian w/ wraparound porch
9.8 out of 10, Exceptional, (7)
"We had a very pleasant stay for a momentous occasion where my wife's family and my family met for the first time. The kitchen will always be the gathering spot as both our cultures enjoy food and this kitchen proved to be an excellent space. The billiards room was also a great hang out room and the porch areas were perfect for photo taking."
Spacious restored Victorian w/ wraparound porch
Property grounds
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
9.6 out of 10, Exceptional, (30)
"This place is wonderful!!!! It was a beautiful stay."
The price is $179
$363 total
includes taxes & fees
May 20 - May 21
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
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
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
Don't see what you're looking for?
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.

New Windsor Vacation Rental Travel Info

Number of vacation rentals
3
Popular accommodation
New Windsor private vacation homes
Known landmarks
Brotherhood Winery, Ritz Theater and Palaia Vineyards Winery
International airports
Newark, NJ (EWR-Liberty Intl.) and White Plains, NY (HPN-Westchester County)

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

Iron/ironing board, free cribs/infant beds, free WiFi, bed sheets
Homewood Suites Stewart Airport
3.0 star property
9.4 out of 10, Exceptional, (922)
"Always an amazing stay here!"
The price is $161
$182 total
includes taxes & fees
May 28 - May 29
Homewood Suites Stewart Airport
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils
HYATT house Fishkill/Poughkeepsie
3.0 star property
8.6 out of 10, Excellent, (1000)
"Great"
The price is $142
$159 total
includes taxes & fees
May 26 - May 27
HYATT house Fishkill/Poughkeepsie
Indoor pool
Red Roof Inn & Suites Newburgh – Stewart Airport
2.0 star property
8.4 out of 10, Very Good, (1005)
"It was clean and comfortable. Check inn was easy and the check-in person was very helpful in recommending places nearby to eat. It is also pet friendly with plenty of area to walk our dog. "
The price is $112
$127 total
includes taxes & fees
May 30 - May 31
Red Roof Inn & Suites Newburgh – Stewart Airport
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the New Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

New Windsor vacation 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 low season months. For more hustle and bustle, you may prefer to visit New Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $80 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on New Windsor rentals

At Expedia, we put the best New Windsor vacation 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 vacation.

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 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?

Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits: You might want to consider this vacation rental near New Windsor, which is located on a lake and has a fireplace, a patio, and a barbecue grill 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 a spa tub so you can immerse yourself in your vacation.

How many vacation rentals are there in New Windsor?

Choose from 5 Expedia vacation rentals in New Windsor for a memorable vacation.

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 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.

Recent reviews of New Windsor properties
Expedia verified reviews

Red Roof Inn & Suites Newburgh – Stewart Airport

Red Roof Inn & Suites Newburgh – Stewart Airport

5/5 Excellent
"It was clean and comfortable. Check inn was easy and the check-in person was very helpful in recommending places nearby to eat. It is also pet friendly with plenty of area to walk our dog. "
A verified traveler stayed at Red Roof Inn & Suites Newburgh – Stewart Airport
Posted 23 hours ago
Red Roof Inn & Suites Newburgh – Stewart Airport