New Windsor Vacation Rentals

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Check prices for these dates

In two weeks
May 15 - May 17
In two months
Jun 26 - Jun 28
In three months
Jul 24 - Jul 26
In four months
Aug 21 - Aug 23

Our top choices for New Windsor vacation rentals

Outdoor spa tub

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

Country House w/Hot Tub, Deck, Grill & Fire Pit
Goshen
10.0 out of 10, Exceptional, (62 reviews)
"Very good host "
United States
Binyomin
$481 nightly
The price is $502
May 4 - May 5
Total with taxes and fees
Country House w/Hot Tub, Deck, Grill & Fire Pit
Property grounds

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (135 reviews)
"Amazing place Thanks for the stay "
United States
Julien C.
$269 nightly
The price is $318
May 4 - May 5
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Exterior

Historic Cabin with Pool & Fire Pit

Historic Cabin with Pool & Fire Pit
Montgomery
10.0 out of 10, Exceptional, (3 reviews)
"This little cabin was exactly what we needed for our stay in NY. It looks just as described, was clean, and the location was perfect for all of the places we wanted to visit. Overall it was very cozy and relaxing and we can't wait to stay again! "
United States
Sarah A.
$187 nightly
The price is $211
May 5 - May 6
Total with taxes and fees
Historic Cabin with Pool & Fire Pit
Outdoor dining

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

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fishkill
9.2 out of 10, Wonderful, (64 reviews)
"For us it was in a great location, had a reasonable price and room for everyone."
United States
Gertrude (Gert) P.
$280 nightly
The price is $323
May 4 - May 5
Total with taxes and fees
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cabin in the Heart of the Hudson Valley, Cabin 1

Cabin in the Heart of the Hudson Valley, Cabin 1
Newburgh
10.0 out of 10, Exceptional, (32 reviews)
"Great overnight spot, especially with a dog."
United States
Ed C.
$236 nightly
The price is $279
May 4 - May 5
Total with taxes and fees
Cabin in the Heart of the Hudson Valley, Cabin 1
Terrace/patio

Cabin in the heart of the Hudson Valley, Cabin 3

Cabin in the heart of the Hudson Valley, Cabin 3
Newburgh
9.8 out of 10, Exceptional, (14 reviews)
"We had a great stay, everything you need is provided. Would recommend to anyone."
United States
Bill W.
$236 nightly
The price is $279
May 5 - May 6
Total with taxes and fees
Cabin in the heart of the Hudson Valley, Cabin 3
TV, fireplace

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Carmel Hamlet
9.8 out of 10, Exceptional, (13 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
$375 nightly
The price is $406
May 10 - May 11
Total with taxes and fees
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Exterior detail

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
Putnam Valley
9.8 out of 10, Exceptional, (23 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
$438 nightly
The price is $483
May 4 - May 5
Total with taxes and fees
Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
Exterior

Luxury home near West Point

Luxury home near West Point
Highland Falls
10.0 out of 10, Exceptional, (3 reviews)
"The accommodations are great—Very nice townhouse, lots of room, clean, comfortable, and pet-friendly."
United States
Suzy
$223 nightly
The price is $236
May 4 - May 5
Total with taxes and fees
Luxury home near West Point
Terrace/patio

House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
10.0 out of 10, Exceptional, (8 reviews)
"Good stay, awesome place"
United States
Scott G.
$367 nightly
The price is $389
May 4 - May 5
Total with taxes and fees
House on the Babbling Brook- Quiet 2BR + King Bed!
3 bedrooms, desk, iron/ironing board, free WiFi

Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
9.2 out of 10, Wonderful, (7 reviews)
"The host was prompt and attentive to any questions that arose. The home appeared exactly as depicted in the pictures and was perfect for a weekend stay close to family and The city!"
United States
Julio J.
$447 nightly
The price is $454
May 4 - May 5
Total with taxes and fees
Sleek Escape: Modern 3 BR- 4 Min from West Point !
TV

Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
10.0 out of 10, Exceptional, (1 review)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
$189 nightly
The price is $206
May 5 - May 6
Total with taxes and fees
Cozy 1-bedroom retreat minutes from West Point!
TV

Luxury House Near West Point

Luxury House Near West Point
Highland Falls
$310 nightly
The price is $325
May 7 - May 8
Total with taxes and fees
Luxury House Near West Point
Interior

Our home is perfect for relaxing and having lots of fun, with near by activity’s

Our home is perfect for relaxing and having lots of fun, with near by activity’s
Highland
9.6 out of 10, Exceptional, (12 reviews)
"We had was great time and the host Mary was amazing and excellent at communicating. Everything was perfect in the home. Thank you"
United States
Pinal
$629 nightly
The price is $704
May 4 - May 5
Total with taxes and fees
Our home is perfect for relaxing and having lots of fun, with near by activity’s
Smart TV

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.8 out of 10, Exceptional, (13 reviews)
"Great place to stay when visiting Legoland. Convenient location and comfortable and clean."
United States
Jessica C.
$281 nightly
The price is $293
May 4 - May 5
Total with taxes and fees
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Smart TV

Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (42 reviews)
"Great lil tranquil home. Had all the things you'd need with some bonus touches and Stan was very quick and easy to communicate with. "
United States
Jen G.
$260 nightly
The price is $294
May 4 - May 5
Total with taxes and fees
Grant - A Tranquil One Bedroom Steps from River
Fridge, oven, stovetop, coffee/tea maker

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.8 out of 10, Exceptional, (20 reviews)
"Very good communication and helpful. "
United States
Liam C.
$299 nightly
The price is $307
May 5 - May 6
Total with taxes and fees
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Outdoor spa tub

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Greenwood Lake
9.8 out of 10, Exceptional, (37 reviews)
"Second time staying here. Check in is a smooth process. House has everything we needed! "
United States
Lex S.
$460 nightly
The price is $520
May 4 - May 5
Total with taxes and fees
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Terrace/patio

Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna

Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
Gardiner
10.0 out of 10, Exceptional, (14 reviews)
"Great weekend getaway to reconnect with old friends!"
United States
Lisa D.
$250 nightly
The price is $253
May 13 - May 14
Total with taxes and fees
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
Interior

Entire Lakeview House ~ 1 hour to MetLife ~ Hot Tub~Firepit~Stunning View~Decks

Entire Lakeview House ~ 1 hour to MetLife ~ Hot Tub~Firepit~Stunning View~Decks
Greenwood Lake
10.0 out of 10, Exceptional, (7 reviews)
"We had lovely and relaxing stay at this property! The surrounding area is beautiful and the crowd are amazing!"
United States
Susan R.
$652 nightly
The price is $738
May 4 - May 5
Total with taxes and fees
Entire Lakeview House ~ 1 hour to MetLife ~ Hot Tub~Firepit~Stunning View~Decks
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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Top New Windsor Hotel Reviews

Studio 6 Extended Stay Fishkill Route 9 NY

Studio 6 Extended Stay Fishkill Route 9 NY

4/10 Poor
"When I arrived to check-in, there was no staff at reception. The police was there to get reports from other people that wanted to check-in. The police said the person working at the desk quit her job that night, and nobody else was working. Now i’m trying to get my money back from Expedia. I had to find another hotel for the night."
Louis 1-night trip
Posted 7 hours ago
Studio 6 Extended Stay Fishkill Route 9 NY

Find out more about New Windsor

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 $270 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.

Explore a world of travel with Expedia

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?

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn. : Visitors like this New Windsor vacation home rental. It is located in the mountains and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the garden in this rental home to help you unwind.

How many vacation rentals are there in New Windsor?

Choose from 10 Expedia vacation rentals in New Windsor for a memorable vacation.

What can I see and do in New Windsor?

Cultural attractions to visit include Knox's Headquarters State Historic Site and National Purple Heart Hall of Honor. Other places in town to visit include New Windsor Cantonment State Historic Site and Schunnemunk State Park.

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.