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Holiday Rentals in New Windsor

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Holiday Rentals in New Windsor

Our top choices for New Windsor holiday rentals

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

9.8 out of 10, Exceptional, (29)
"Great place for a quiet stay"
The price is €291
includes taxes & fees
31 Aug - 1 Sept
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (119)
"Nice view on the top of the mountain….I admired the river with the bridge and the surroundings until late in the night. The accommodation was excellent, we had everything we needed.… we are thinking of coming back sometime…."
The price is €273
includes taxes & fees
8 Sept - 9 Sept
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

10.0 out of 10, Exceptional, (303)
"The lake views at this house are absolutely worth the trip and the money. It's a beautiful spot. And the host, Don, is super responsive, thoughtful and accommodating. Highly recommend!"
The price is €474
includes taxes & fees
28 Aug - 29 Aug
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

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

9.8 out of 10, Exceptional, (6)
"Really liked that each room had it's own temperature control"
Our home is perfect for relaxing and having lots of fun, with near by activity’s

Ann Creek: Charming 2 BR fully renovated house at Greenwood Lake. Dog friendly

10.0 out of 10, Exceptional, (3)
"Awesome place. Cozy and great communication with owners. "
Ann Creek: Charming 2 BR fully renovated house at Greenwood Lake. Dog friendly

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

9.8 out of 10, Exceptional, (17)
"Clean, comfortable, beautiful views, cute little town. Super accommodating host. Couldn’t have asked for more. "
The price is €510
includes taxes & fees
15 Sept - 16 Sept
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

10.0 out of 10, Exceptional, (87)
"It was very nice "
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Cabin in the heart of the Hudson Valley, Cabin 4

9.2 out of 10, Wonderful, (25)
"Exactly as advertised "
The price is €156
includes taxes & fees
24 Aug - 25 Aug
Cabin in the heart of the Hudson Valley, Cabin 4

Cabin in the heart of the Hudson Valley, Cabin 2

9.6 out of 10, Exceptional, (22)
"Perfect for a getaway weekend for my wife and I! Easy check-in, clean, and although it's off a busy road, we found it peaceful and quiet. Would definitely stay again!"
The price is €156
includes taxes & fees
25 Aug - 26 Aug
Cabin in the heart of the Hudson Valley, Cabin 2

Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

9.8 out of 10, Exceptional, (11)
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

Modern penthouse suite in a restored grain tower with private roof deck.

10.0 out of 10, Exceptional, (23)
"Wonderful stay!"
The price is €477
includes taxes & fees
24 Aug - 25 Aug
Modern penthouse suite in a restored grain tower with private roof deck.

Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.

3.0 star property
10.0 out of 10, Exceptional, (2)
"It was great! We loved staying in this cute house. Proximity to the lake is great, and the backyard is quite beautiful."
The price is €252
includes taxes & fees
24 Aug - 25 Aug
Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

2.0 star property
9.8 out of 10, Exceptional, (12)
"A group of girlfriends stayed for a 2 night visit. Everything was just as listed, the home was in the perfect location, well stocked, and beautiful inside. We would definitely return again. "
The price is €454
includes taxes & fees
22 Sept - 23 Sept
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!

10.0 out of 10, Exceptional, (64)
"The property was just as pictured, and a convenient off site "
The price is €196
includes taxes & fees
27 Aug - 28 Aug
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!

Stylish & Peaceful Getaway on 3 Private Acres

2.0 star property
8.6 out of 10, Excellent, (7)
"The location is close to legoland which is nice. They had connect 4 and some playing cards otherwise the property isnt great for little ones due to some odd decor choices. There were ants and a spider and unsure about the cleaning. Thermostat didnt adjust and dishwasher didnt work. Tvs were hard to use. Wish there had been printed instructions for where to find things in the house, as well as recommendations in the town. Didnt use outdoor deck because too cold but also couldnt open the door and...
Stylish & Peaceful Getaway on 3 Private Acres

Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,

The price is €547
includes taxes & fees
1 Sept - 2 Sept
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,

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 €372
includes taxes & fees
25 Aug - 26 Aug
Rustic Cabin in Fishkill!

A luxurious stay.

6.0 out of 10, (2)
"If you want to go to a diagusting neighborhood then this is your place. We felt so unsafe we didn’t even stay there. We got a hotel. It is that bad. As nice as the inside is, the outside and neighborhood will have you running. Music blasting stinks of weed homeless people all over. Do not book this place. The owner didn’t even refund us our cleaning fee. Trust me STAY AWAY."
The price is €257
includes taxes & fees
24 Aug - 25 Aug
A luxurious stay.

Large,Cozy,Bright Apartment, Business Themed.

9.0 out of 10, Wonderful, (13)
"Very cozy stay with responsive host"
The price is €578
includes taxes & fees
23 Aug - 24 Aug
Large,Cozy,Bright Apartment, Business Themed.

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

7.0 out of 10, Good, (2)
"Nice to have top notch bar/restaurant downstairs!"
The price is €156
includes taxes & fees
16 Sept - 17 Sept
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
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

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?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This holiday home rental outside of New Windsor offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with an oven, a microwave and an electric kettle, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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 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 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.