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New Windsor Holiday Rentals

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Holiday Rentals in New Windsor

Woodland Sanctuary - 6000ft retreat for pure relaxation!

The price is NZ$4,466
includes taxes & fees
1 July - 2 July
Woodland Sanctuary - 6000ft retreat for pure relaxation!

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

9.8 out of 10, Exceptional, (7)
"Great spot, wonderful host. Would recommend to anyone!"
The price is NZ$707
includes taxes & fees
2 July - 3 July
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.

10.0 out of 10, Exceptional, (15)
"Wonderful, comfortable home! Clean, user-friendly with great views!"
The price is NZ$1,433
includes taxes & fees
30 June - 1 July
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

8.8 out of 10, Excellent, (8)
"Truly a hidden gem. The property and home were nothing short of extraordinary. For those looking for a great location with access to hiking and a one of a kind experience this is the place."
The price is NZ$345
includes taxes & fees
27 June - 28 June
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Contemporary Cozy Cottage

10.0 out of 10, Exceptional, (23)
"Our stay was lovely. Nadia was a wonderful host and the property was so welcoming."
The price is NZ$669
includes taxes & fees
27 June - 28 June
Contemporary Cozy Cottage

Rustic Cabin in Fishkill!

10.0 out of 10, Exceptional, (1)
"Beautiful property with many different areas to explore. We originally intended to spend more time in beacon but decided it was more fun hanging out here. "
The price is NZ$687
includes taxes & fees
30 June - 1 July
Rustic Cabin in Fishkill!

Chestnut on Willow Lake

8.0 out of 10, Very good, (1)
"We had a very nice stay!Chestnut on Willow Lake worked well for us!We loved the property and campfire on Friday evening! I wish we had had time to go over to the fire to enjoy it!"
The price is NZ$952
includes taxes & fees
30 June - 1 July
Chestnut on Willow Lake

Hickory on Willow Lake

8.0 out of 10, Very good, (1)
The price is NZ$1,016
includes taxes & fees
1 July - 2 July
Hickory on Willow Lake

Red Cottage - Lakeside Property!

The price is NZ$963
includes taxes & fees
1 July - 2 July
Red Cottage - Lakeside Property!

Charming 2-bedroom Guest Suite with Pool Access and Fitness Room

The price is NZ$382
includes taxes & fees
20 July - 21 July
Charming 2-bedroom Guest Suite with Pool Access and Fitness Room

Gorgeous Garrison Gem Pool Sauna Hot Tub More

2.0 star property
The price is NZ$2,655
includes taxes & fees
6 July - 7 July
Gorgeous Garrison Gem Pool Sauna Hot Tub More

Spacious New Luxurious holiday house in lovely Hudson Valley

9.8 out of 10, Exceptional, (10)
"We had a wonderful time in this beautiful home with lots of room and amenities!"
The price is NZ$1,338
includes taxes & fees
16 July - 17 July
Spacious New Luxurious holiday house in lovely Hudson Valley

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

9.8 out of 10, Exceptional, (18)
"Communication was easy, location and parking was great! Very clean and cozy!"
The price is NZ$552
includes taxes & fees
1 July - 2 July
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

West Point Family Retreat, 5 min walk to Thayer!

2.0 star property
10.0 out of 10, Exceptional, (4)
"Nice houseAwesome kitchen Granddaughter loved the bunk bed and the many games"
The price is NZ$1,354
includes taxes & fees
6 July - 7 July
West Point Family Retreat, 5 min walk to Thayer!

Lovely 3BR Home with parking-Walk to WP Gate!

10.0 out of 10, Exceptional, (4)
"Easy booking, arrival, and departure. Very nice home. Very Clean and comfortable. Host was very kind and clear on everything for stay. Will book again!"
The price is NZ$579
includes taxes & fees
1 July - 2 July
Lovely 3BR Home with parking-Walk to WP Gate!

Fabulous 3bdrm Home w/parking!

6.0 out of 10, (1)
"The proximity to Westpoint was great. Trashy neighborhood. Very loud construction early in the morning. The cooking supplies were limited and one of the handles on the pans fell off while we were there. It was okay, but probably wouldn't return."
The price is NZ$716
includes taxes & fees
27 July - 28 July
Fabulous 3bdrm Home w/parking!

Room for Everyone: Spacious 6BR West Point Retreat

10.0 out of 10, Exceptional, (1)
"Great location for Westpoint visit. As described. Clean with new updates. "
The price is NZ$1,798
includes taxes & fees
6 July - 7 July
Room for Everyone: Spacious 6BR West Point Retreat

Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat

10.0 out of 10, Exceptional, (4)
"Our stay was only a couple nights but it was what we expected. I would recommend this property. Had a great stay."
The price is NZ$1,030
includes taxes & fees
1 July - 2 July
Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat

Cozy Escape -Strong Wi-Fi -Prime Location

7.4 out of 10, Good, (3)
"The property was perfect for our little weekend getaway. It was very clean and cozy and the host Christina made it so easy for check in and was available for any questions. We would definitely stay again."
The price is NZ$637
includes taxes & fees
27 July - 28 July
Cozy Escape -Strong Wi-Fi -Prime Location

The Huron- large family friendly home with unforgettable views

10.0 out of 10, Exceptional, (16)
"Six adult family members stayed here to attend a memorial service. It was a very attractive and comfortable house. The views of the Hudson were fabulous and watching the river was a calming distraction for us. We also watched movies on comfy sofa and listened to a few records.ii totogetheri.p.oethe lower level of thehouse"
The price is NZ$912
includes taxes & fees
27 June - 28 June
The Huron- large family friendly home with unforgettable views
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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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?

Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 8: This holiday home rental outside of New Windsor is located on a lake, and offers a BBQ, air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in New Windsor?

Choose from 6 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. 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.