New Windsor Holiday Rentals

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Check prices for these dates

In two weeks
20 Feb - 22 Feb
In two months
3 Apr - 5 Apr
In three months
1 May - 3 May
In four months
29 May - 31 May

Our top choices for New Windsor holiday rentals

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$730
HK$1,472 total
includes taxes & fees
3 Mar - 4 Mar
Cozy 1-bedroom retreat minutes from West Point!
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, (16 reviews)
"Great Unit."
United States
Rudy R.
The price is HK$625
HK$2,080 total
includes taxes & fees
9 Feb - 10 Feb
Quiet Apt with Coffee Bar, 1/2 Mile to 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, (6 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is HK$680
HK$2,685 total
includes taxes & fees
9 Feb - 10 Feb
House on the Babbling Brook- Quiet 2BR + King Bed!
Fireplace, books

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Kerhonkson
9.4 out of 10, Exceptional, (12 reviews)
"Charming and relaxing cottage. Perfect location for hiking or enjoying Lake Minnewaska or Mohonk Preserve. "
United States
Patrick S.
The price is HK$693
HK$1,532 total
includes taxes & fees
11 Feb - 12 Feb
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Interior

Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Kerhonkson
10.0 out of 10, Exceptional, (32 reviews)
"I love the place, very comfortable and cozy, Thank you so very much, Enjoyed a lot , Julia"
United States
Julia K.
The price is HK$425
HK$1,264 total
includes taxes & fees
8 Feb - 9 Feb
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Desk, WiFi, bed sheets

Rustic Lakefront Studio w/ Deck + Workspace

Rustic Lakefront Studio w/ Deck + Workspace
Monroe
The price is HK$555
HK$1,549 total
includes taxes & fees
8 Feb - 9 Feb
Rustic Lakefront Studio w/ Deck + Workspace
1 bedroom

Peaceful Lakeside Studio Fast Wifi Great WFH

Peaceful Lakeside Studio Fast Wifi Great WFH
2.0 star property
Monroe
The price is HK$646
HK$1,676 total
includes taxes & fees
8 Feb - 9 Feb
Peaceful Lakeside Studio Fast Wifi Great WFH
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, (8 reviews)
"Great weekend getaway to reconnect with old friends!"
United States
Lisa D.
The price is HK$857
HK$1,731 total
includes taxes & fees
10 Feb - 11 Feb
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
Interior

Dream getaway apartment in the foot of Gunks Ridge

Dream getaway apartment in the foot of Gunks Ridge
Wallkill
9.6 out of 10, Exceptional, (24 reviews)
"Serg’s place was comfortable and clean! It was a perfect location for me and my friends to stay while rock climbing in the Gunks. We did not feel cramped or unsafe and the complementary tea was a hit! One thing to note is that both of the beds were low to the ground (below knee level) so if someone has knee or back problems, it might be difficult to stand up out of bed. "
United States
Mary S.
The price is HK$425
HK$1,264 total
includes taxes & fees
8 Feb - 9 Feb
Dream getaway apartment in the foot of Gunks Ridge
Exterior

Cabin in the heart of the Hudson Valley, Cabin 2

Cabin in the heart of the Hudson Valley, Cabin 2
Newburgh
9.4 out of 10, Exceptional, (31 reviews)
"A very cute, convenient, and affordable stay with timely, friendly communication from the owner. Our dog loved it and we appreciated the ability to have a private place to stay."
United States
Sara B.
The price is HK$1,008
HK$1,560 total
includes taxes & fees
1 Mar - 2 Mar
Cabin in the heart of the Hudson Valley, Cabin 2
Interior

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Warwick
9.2 out of 10, Wonderful, (9 reviews)
"I really enjoyed my stay. The room was very clean, the inn is well located in town and it is great having the restaurant below. Would stay here again! "
United States
Erin R.
The price is HK$717
HK$1,236 total
includes taxes & fees
17 Feb - 18 Feb
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
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
10.0 out of 10, Exceptional, (3 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$977
HK$3,402 total
includes taxes & fees
10 Feb - 11 Feb
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Interior

Villa Verde B&B, bsm, Greenwood Lake NY

Villa Verde B&B, bsm, Greenwood Lake NY
Greenwood Lake
10.0 out of 10, Exceptional, (12 reviews)
"The breakfast was lovely!"
United States
Tara
The price is HK$1,226
HK$2,262 total
includes taxes & fees
6 Feb - 7 Feb
Villa Verde B&B, bsm, Greenwood Lake NY
Private kitchen

Charming 1-bedroom apartment in Carmel with WiFi, AC

Charming 1-bedroom apartment in Carmel with WiFi, AC
Carmel Hamlet
9.0 out of 10, Wonderful, (2 reviews)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
United States
Emmett
The price is HK$1,055
HK$2,150 total
includes taxes & fees
2 Mar - 3 Mar
Charming 1-bedroom apartment in Carmel with WiFi, AC
Dining

Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
Beacon
10.0 out of 10, Exceptional, (32 reviews)
"Great time and great place to stay "
United States
S S.
The price is HK$906
HK$1,952 total
includes taxes & fees
10 Feb - 11 Feb
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
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)
"Beautiful location. We really enjoyed seeing the deer in the field every morning. "
United States
Aaron M.
The price is HK$1,160
HK$2,286 total
includes taxes & fees
6 Feb - 7 Feb
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
1 bedroom

Boutique King Suite at Orchard Lake Private Farm

Boutique King Suite at Orchard Lake Private Farm
2.0 star property
Monroe
Boutique King Suite at Orchard Lake Private Farm
3 bedrooms, desk, iron/ironing board, travel cot

Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.4 out of 10, Exceptional, (11 reviews)
"Great place to stay if you have a West Point student - super close to all West Point related activities. The place itself needs some work but it’s functional."
United States
Jesse C.
The price is HK$891
HK$3,259 total
includes taxes & fees
10 Feb - 11 Feb
Local Artist Inspired | Walk to WestPoint + King Bed
Fridge, microwave, oven, stovetop

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Highland Falls
10.0 out of 10, Exceptional, (5 reviews)
"Very nice property. We have a son at West Point and approximately an hour from New York City. Host was quick to respond to questions and provided excellent information. We will stay here again. "
United States
Mark V.
The price is HK$1,321
HK$2,274 total
includes taxes & fees
2 Mar - 3 Mar
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
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)
"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."
United States
Hannah P.
The price is HK$1,445
HK$2,912 total
includes taxes & fees
3 Mar - 4 Mar
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
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

Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury

10/10 Excellent
"We had a very nice stay. The room was so clean. The staff was "
John T 3-night trip
Posted 2 days ago
Sleep Inn & Suites Monroe - 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
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  • 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?

Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel. : This highly rated holiday home rental in New Windsor is located on a river, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. 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 9 Expedia holiday rentals in New Windsor for a memorable holiday.

What can I see and do in New Windsor?

Cultural attractions to visit include National Purple Heart Hall of Honor and Knox's Headquarters State Historic Site. 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.