New Windsor Holiday Rentals

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Check prices for these dates

In two weeks
22 May - 24 May
In two months
3 Jul - 5 Jul
In three months
31 Jul - 2 Aug
In four months
28 Aug - 30 Aug

Our top choices for New Windsor holiday 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
The price is HK$2,026
HK$4,029 total
includes taxes & fees
10 May - 11 May
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.
The price is HK$1,473
HK$2,490 total
includes taxes & fees
10 May - 11 May
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.
The price is HK$838
HK$1,657 total
includes taxes & fees
11 May - 12 May
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, (65 reviews)
"Great spot! Very unique, has lots of charm!"
United States
Brian
The price is HK$1,939
HK$2,559 total
includes taxes & fees
13 May - 14 May
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)
"Cute, clean and perfect for our needs"
United States
Richard H.
The price is HK$1,324
HK$2,203 total
includes taxes & fees
10 May - 11 May
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.
The price is HK$1,324
HK$2,203 total
includes taxes & fees
12 May - 13 May
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.
The price is HK$1,587
HK$3,087 total
includes taxes & fees
10 May - 11 May
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.
The price is HK$1,570
HK$4,146 total
includes taxes & fees
11 May - 12 May
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
The price is HK$1,559
HK$1,868 total
includes taxes & fees
10 May - 11 May
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.
The price is HK$1,168
HK$3,287 total
includes taxes & fees
10 May - 11 May
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.
The price is HK$1,285
HK$3,762 total
includes taxes & fees
17 May - 18 May
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.
The price is HK$987
HK$1,801 total
includes taxes & fees
27 May - 28 May
Cozy 1-bedroom retreat minutes from West Point!
TV

Luxury House Near West Point

Luxury House Near West Point
Highland Falls
The price is HK$1,567
HK$2,544 total
includes taxes & fees
10 May - 11 May
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
The price is HK$1,763
HK$5,520 total
includes taxes & fees
13 May - 14 May
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.
The price is HK$1,164
HK$2,293 total
includes taxes & fees
17 May - 18 May
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.
The price is HK$1,058
HK$2,331 total
includes taxes & fees
18 May - 19 May
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.
The price is HK$901
HK$2,405 total
includes taxes & fees
11 May - 12 May
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.
The price is HK$2,037
HK$4,644 total
includes taxes & fees
12 May - 13 May
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, (16 reviews)
"Great weekend getaway to reconnect with old friends!"
United States
Lisa D.
The price is HK$1,625
HK$2,520 total
includes taxes & fees
20 May - 21 May
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.
The price is HK$2,673
HK$5,887 total
includes taxes & fees
12 May - 13 May
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

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury

2/10 Terrible
"The AC was dysfunctional (it would start with a big startling noise, and would stop after 5 min and keep going on this way all night long). The highway was in my window, horrible insulation, it felt like I was laying in the middle of the road. Also, every person walking, closing a door, or talking you could clearly hear. I slept poorly "
Laurie 1-night trip
Posted 1 hour ago
Hampton Inn Harriman Woodbury

Find out more about New Windsor

Search for holiday rentals in New Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in New Windsor using one of the methods below:

  • View our selection of featured holiday rentals in New Windsor
  • Use the map to find apartments and other holiday homes in the New Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in New Windsor while they last

Look no further and take a look at our great range of rental properties in New Windsor!

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?

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn. : This holiday home rental outside of New Windsor is located in the mountains, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. Make the most of garden in this rental home to help you unwind.

How many holiday rentals are there in New Windsor?

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

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 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.