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New Windsor Holiday Rentals

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Holiday Rentals in New Windsor

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

10.0 out of 10, Exceptional, (302)
"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 NZ$998
includes taxes & fees
24 Aug - 25 Aug
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

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

9.8 out of 10, Exceptional, (27)
"Perfect for small family stay over for a wedding ! "
The price is NZ$557
includes taxes & fees
31 Aug - 1 Sept
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

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 NZ$1,149
includes taxes & fees
3 Sept - 4 Sept
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space

8.0 out of 10, Very good, (1)
7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space

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

10.0 out of 10, Exceptional, (86)
"We loved our stay. It was great for a family Thanksgiving"
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

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 NZ$994
includes taxes & fees
12 Aug - 13 Aug
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

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

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

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (118)
"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 NZ$549
includes taxes & fees
25 Aug - 26 Aug
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Cottage Suites

3.0 star property
6.6 out of 10, (7)
"It was a great place "
Cottage Suites

Magnificent Lake View

2.0 star property
Magnificent Lake View

Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town

10.0 out of 10, Exceptional, (1)
"My girlfriend and I loved our stay here! We stayed for one night and it was perfect for what we needed. Very clean with easy self-check-in. The host was very responsive with all inquiries. Short walk to nice downtown area as well!"
The price is NZ$300
includes taxes & fees
19 Aug - 20 Aug
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town

Cabin in the heart of the Hudson Valley, Cabin 4

9.0 out of 10, Wonderful, (24)
"Exactly as advertised "
The price is NZ$296
includes taxes & fees
13 Aug - 14 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, (21)
"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 NZ$296
includes taxes & fees
13 Aug - 14 Aug
Cabin in the heart of the Hudson Valley, Cabin 2

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

The price is NZ$866
includes taxes & fees
18 Aug - 19 Aug
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,

Apartment with Expansive Views; River & Mountains Walk to Train, Main St, DIA

8.8 out of 10, Excellent, (5)
"Had a wonderful, relaxing stay here. Convenient location allowed us to walk everywhere we wanted to go!"
Apartment with Expansive Views; River & Mountains Walk to Train, Main St, DIA

Cabin in the Heart of the Hudson Valley, Cabin 1

9.8 out of 10, Exceptional, (28)
"Really a nice place. Great for an overnight stop in the Hudson Valley"
The price is NZ$403
includes taxes & fees
12 Aug - 13 Aug
Cabin in the Heart of the Hudson Valley, Cabin 1

The House In Highland- Secluded Retreat

10.0 out of 10, Exceptional, (9)
"We had an absolutely wonderful stay at Highland House! This beautiful property is nestled in the woods, providing a serene and peaceful environment, yet it is conveniently close to town, making it easy to access local amenities and attractions. The kitchen was a standout feature, stocked with everything you could possibly need. From a Keurig and coffee pot to a tea kettle and KitchenAid mixer, it had all the appliances and utensils necessary for cooking up a storm. The variety of pots and pans...
The House In Highland- Secluded Retreat

Private lake escape

Private lake escape

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

10.0 out of 10, Exceptional, (22)
"Wonderful stay!"
The price is NZ$907
includes taxes & fees
13 Aug - 14 Aug
Modern penthouse suite in a restored grain tower with private roof deck.

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 NZ$490
includes taxes & fees
12 Aug - 13 Aug
A luxurious stay.
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.