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New Windsor Holiday Rentals

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Check prices for these dates

Tonight
31 Jul - 1 Aug
Tomorrow
1 Aug - 2 Aug
This weekend
1 Aug - 3 Aug
Next weekend
8 Aug - 10 Aug

Holiday Rentals in New Windsor

Cottage Suites
Private kitchen

Cottage Suites

3.0 star property
6.6 out of 10, (7)
"It was a great place "
Cottage Suites
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Stroll through a serene residential setting surrounded by a lush lawn, a tree, and a picturesque bridge.

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 HK$1,476
HK$2,380 total
includes taxes & fees
10 Aug - 11 Aug
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Relax on the serene deck, surrounded by bare trees and a frozen lake.

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

10.0 out of 10, Exceptional, (300)
"Beautiful, quiet property that was a great getaway from the city. A pair of bald eagles were circling the lake which was a really amazing surprise! "
The price is HK$3,172
HK$4,229 total
includes taxes & fees
3 Aug - 4 Aug
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Relax in a hot tub with a serene lake and forest view.

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

9.8 out of 10, Exceptional, (16)
"Clean, comfortable, beautiful views, cute little town. Super accommodating host. Couldn’t have asked for more. "
The price is HK$2,331
HK$4,964 total
includes taxes & fees
3 Aug - 4 Aug
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Relax in this serene outdoor seating area with a covered patio overlooking a lush garden.

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

9.8 out of 10, Exceptional, (26)
"Perfect for small family stay over for a wedding ! "
The price is HK$2,033
HK$2,611 total
includes taxes & fees
31 Aug - 1 Sept
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9
Terrace/patio

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

9.6 out of 10, Exceptional, (8)
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9
Magnificent Lake View
Property grounds

Magnificent Lake View

2.0 star property
Magnificent Lake View
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
Enjoy a serene view of lush greenery from the bay window, accompanied by a stylish seating area with a vase of flowers.

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 HK$749
HK$1,273 total
includes taxes & fees
12 Aug - 13 Aug
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
Enjoy cooking in this well-equipped kitchen with a large island, oven, and stainless steel range hood.

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

2.0 star property
9.8 out of 10, Exceptional, (11)
"My husband and I had an amazing time. Absolutely beautiful home, great location, and overall amazing experience. "
The price is HK$3,532
HK$5,099 total
includes taxes & fees
3 Aug - 4 Aug
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
Charming Inn Steps away from Downtown Warwick only an Hour away from NYC
Step into the grand lobby, featuring a stunning staircase, reception desk with a lighted panel, and elegant artwork on the walls.

Charming Inn Steps away from Downtown Warwick only an Hour away from NYC

8.8 out of 10, Excellent, (5)
The price is HK$600
HK$1,168 total
includes taxes & fees
11 Aug - 12 Aug
Charming Inn Steps away from Downtown Warwick only an Hour away from NYC
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel stove, and ample counter space.

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

10.0 out of 10, Exceptional, (85)
"We loved our stay. It was great for a family Thanksgiving"
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Indoor Pool Paradise | 6BR + Huge Decks
Enjoy dining or socializing on this covered deck with a table and chairs, surrounded by a serene landscape.

Indoor Pool Paradise | 6BR + Huge Decks

Indoor Pool Paradise | 6BR + Huge Decks
Charming 2-bedroom Guest Suite with Pool Access and Fitness Room
Relax by the serene pool surrounded by lush greenery and a children's play area.

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

6.0 out of 10, (1)
"Property was very clean and nicely decorated. There isn’t really a living room to hang out. Very difficult for 3 adults to all hang out together. When I booked I was more concerned about the sleeping area so I assumed there was a living room. The guest suite is in the basement of home in a nice neighborhood."
The price is HK$942
HK$1,980 total
includes taxes & fees
10 Aug - 11 Aug
Charming 2-bedroom Guest Suite with Pool Access and Fitness Room
New 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space
Relax in a hot tub surrounded by lush greenery and a wooden deck.

New 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space

10.0 out of 10, Exceptional, (26)
"A beautiful and bright cottage in a serene but convenient location. It was thoughtfully set up for a family getaway and was exceptionally clean. My entire family enjoyed the stay!"
The price is HK$4,702
HK$7,472 total
includes taxes & fees
10 Aug - 11 Aug
New 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space
Our home is perfect for relaxing and having lots of fun, with near by activity’s
Relax on the covered porch with comfortable seating and a small table, perfect for casual dining or unwinding.

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
The House In Highland- Secluded Retreat
Enjoy outdoor dining and relaxation on the spacious deck with comfortable seating and a barbecue grill.

The House In Highland- Secluded Retreat

10.0 out of 10, Exceptional, (9)
The House In Highland- Secluded Retreat
Cozy Cabin with Sauna & Firepit!
Enjoy a peaceful retreat on this serene property with a covered patio, perfect for relaxing with a seating area and umbrella.

Cozy Cabin with Sauna & Firepit!

9.2 out of 10, Wonderful, (34)
"We enjoyed our short stay at this comfy little cabin! It’s cozy and has a “lived-in” feel—definitely a bit worn, but still charming and functional. The outdoor space is the real highlight: the deck, fire pit, and sauna were perfect for relaxing. It’s also in a great location near wineries and some beautiful hikes.Just a heads-up: the cabin is at the end of a pretty rough dirt road, so be prepared for a bumpy ride in. It feels nicely tucked away, but it’s not completely isolated—there are...
Cozy Cabin with Sauna & Firepit!
7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space
Fridge, microwave, oven, stovetop

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

8.0 out of 10, Very good, (1)
The price is HK$9,419
HK$15,202 total
includes taxes & fees
28 Aug - 29 Aug
7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space
Simply Unforgettable HotTub, Pool, Pets, <1 Hr NYC
TV, fireplace, video games, ping pong

Simply Unforgettable HotTub, Pool, Pets, <1 Hr NYC

10.0 out of 10, Exceptional, (77)
"Lovely stay at large and clean home with great kitchen and pool area. Lots of room for everyone and attentive hosts"
Simply Unforgettable HotTub, Pool, Pets, <1 Hr NYC
Charming Cottage in the Heart of the Shawangunks
Enjoy cooking in this well-lit kitchen with a double sink, toaster oven, and a window overlooking the surrounding trees.

Charming Cottage in the Heart of the Shawangunks

10.0 out of 10, Exceptional, (15)
"Wonderful stay, exactly as advertised, everything brand new and very cozy."
The price is HK$2,159
HK$4,712 total
includes taxes & fees
24 Aug - 25 Aug
Charming Cottage in the Heart of the Shawangunks
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 & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie

10/10 Excellent
"Love the breakfast "
JACINTO 2-night trip
Posted 1 day ago
Hampton Inn & Suites Poughkeepsie

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 Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views: This holiday home rental outside of New Windsor is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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.