A large suspension bridge at night with illuminated cables and a central tower.

New Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for New Windsor vacation rentals

Lake view

Jellystone Park Gardiner

Jellystone Park Gardiner
3.0 star property
Gardiner
The price is ￥57,620
￥64,535 total
includes taxes & fees
Jul 9 - Jul 10
Jellystone Park Gardiner
Cottage (2 Bedrooms) | Interior

Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
3.0 star property
Monroe
10.0 out of 10, Exceptional, (3 reviews)
"fantastic accommodations"
United States
David
The price is ￥34,289
￥83,555 total
includes taxes & fees
Jul 2 - Jul 3
Hudson Valley Retreat w/ Pool Near Greenwood Lake
Design Apartment, Patio, Garden View | View from room

Historic Horse Barn Apartment in Goshen

Historic Horse Barn Apartment in Goshen
4.0 star property
Goshen
The price is ￥39,366
￥48,470 total
includes taxes & fees
Jun 30 - Jul 1
Historic Horse Barn Apartment in Goshen
Apartment, 3 Bedrooms, Kitchen | Living area

Hay Loft Apartment in Barn - Goshen

Hay Loft Apartment in Barn - Goshen
2.0 star property
Goshen
The price is ￥62,155
￥76,529 total
includes taxes & fees
Jun 29 - Jun 30
Hay Loft Apartment in Barn - Goshen
Fridge, microwave, oven, stovetop

Luxury 3BR with King Beds in Montgomery Village

Luxury 3BR with King Beds in Montgomery Village
Montgomery
10.0 out of 10, Exceptional, (3 reviews)
"Excellent location! Very clean and the hosts were quick to respond to communication. We would definitely stay here again. "
United States
Barbara M.
The price is ￥50,406
￥85,300 total
includes taxes & fees
Jun 29 - Jun 30
Luxury 3BR with King Beds in Montgomery Village
Smart TV

Thoughtfully restored Victorian-Walk to Main st and Train

Thoughtfully restored Victorian-Walk to Main st and Train
Beacon
10.0 out of 10, Exceptional, (7 reviews)
"Very well designed and listed place. Had everything we needed, and the host was friendly!"
United States
Jesse L.
The price is ￥59,844
￥110,606 total
includes taxes & fees
Jul 1 - Jul 2
Thoughtfully restored Victorian-Walk to Main st and Train
Fridge, microwave, oven, stovetop

Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (34 reviews)
"Very clean comfortable quiet place"
United States
Mauro C.
The price is ￥36,392
￥67,892 total
includes taxes & fees
Jun 29 - Jun 30
Contemporary Cozy Cottage
Romantic Duplex, 3 Bedrooms, Kitchen | Private kitchen | Coffee/tea maker, toaster, spices, cleaning supplies

Carriage House Apartment Goshen NY

Carriage House Apartment Goshen NY
4.0 star property
Goshen
The price is ￥70,470
￥86,766 total
includes taxes & fees
Jul 13 - Jul 14
Carriage House Apartment Goshen NY
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cabin in the Heart of the Hudson Valley, Cabin 1

Cabin in the Heart of the Hudson Valley, Cabin 1
Newburgh
10.0 out of 10, Exceptional, (35 reviews)
"Cute, clean and perfect for our needs"
United States
Richard H.
The price is ￥27,334
￥45,281 total
includes taxes & fees
Jun 29 - Jun 30
Cabin in the Heart of the Hudson Valley, Cabin 1
Exterior

Chestnut on Willow Lake

Chestnut on Willow Lake
Fishkill
9.6 out of 10, Exceptional, (5 reviews)
"We really enjoyed the privacy of the grounds, lake, dock , swimming, boats and paddle boards. The kitchen was well equipped and the beds were comfy. We had a great stay, thanks."
United States
Doria W.
The price is ￥80,061
￥113,805 total
includes taxes & fees
Jun 29 - Jun 30
Chestnut on Willow Lake
Terrace/patio

Cabin in the heart of the Hudson Valley, Cabin 3

Cabin in the heart of the Hudson Valley, Cabin 3
Newburgh
9.8 out of 10, Exceptional, (14 reviews)
"We had a great stay, everything you need is provided. Would recommend to anyone."
United States
Bill W.
The price is ￥27,334
￥45,281 total
includes taxes & fees
Jun 29 - Jun 30
Cabin in the heart of the Hudson Valley, Cabin 3
House | 7 bedrooms

West Point Summer Pool Jacuzzi Events Pets OK

West Point Summer Pool Jacuzzi Events Pets OK
2.0 star property
Cornwall
The price is ￥152,285
￥267,007 total
includes taxes & fees
Jun 29 - Jun 30
West Point Summer Pool Jacuzzi Events Pets OK
Terrace/patio

Luxury Lakefront | Beach • Hot Tub • Dock

Luxury Lakefront | Beach • Hot Tub • Dock
Greenwood Lake
9.8 out of 10, Exceptional, (29 reviews)
"Great house! Beautiful inside and out! Will stay again "
United States
kurt b.
The price is ￥121,116
￥224,288 total
includes taxes & fees
Jul 8 - Jul 9
Luxury Lakefront | Beach • Hot Tub • Dock
Fridge, oven, stovetop, dishwasher

Charming 2-bedroom house in Greenwood Lake with Central AC/Heat

Charming 2-bedroom house in Greenwood Lake with Central AC/Heat
Greenwood Lake
10.0 out of 10, Exceptional, (7 reviews)
"Very clean and really cute place. "
United States
Katie C.
The price is ￥46,743
￥95,692 total
includes taxes & fees
Jul 12 - Jul 13
Charming 2-bedroom house in Greenwood Lake with Central AC/Heat
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, (38 reviews)
"Clean, welcoming, great location."
United States
Nicolae P.
The price is ￥19,975
￥36,634 total
includes taxes & fees
Jul 6 - Jul 7
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Interior

Entire Lakeview House ~ 1 hour to MetLife ~ Hot Tub~Firepit~Stunning View~Decks

Entire Lakeview House ~ 1 hour to MetLife ~ Hot Tub~Firepit~Stunning View~Decks
Greenwood Lake
10.0 out of 10, Exceptional, (8 reviews)
"We had lovely and relaxing stay at this property! The surrounding area is beautiful and the crowd are amazing!"
United States
Susan R.
The price is ￥88,722
￥164,772 total
includes taxes & fees
Jun 30 - Jul 1
Entire Lakeview House ~ 1 hour to MetLife ~ Hot Tub~Firepit~Stunning View~Decks
Smart TV, offices

River Views & Hot Tub | Riverview on Washington

River Views & Hot Tub | Riverview on Washington
Newburgh
The price is ￥142,538
￥249,964 total
includes taxes & fees
Jul 4 - Jul 5
River Views & Hot Tub | Riverview on Washington
Exterior

Charming Cabin in Fishkill!

Charming Cabin in Fishkill!
Fishkill
9.6 out of 10, Exceptional, (4 reviews)
"What a sweet little spot in a gorgeous area - clean, simple, and beautiful. Thanks for a great stay! "
United States
Julia T.
The price is ￥52,485
￥71,769 total
includes taxes & fees
Jun 29 - Jun 30
Charming Cabin in Fishkill!
Exterior

Mountain View Retreat w/ Hot Tub, Theater, and Gym

Mountain View Retreat w/ Hot Tub, Theater, and Gym
Warwick
10.0 out of 10, Exceptional, (3 reviews)
"Amazing stay on a beautiful place!"
United States
Dorian G.
The price is ￥107,913
￥195,631 total
includes taxes & fees
Jul 1 - Jul 2
Mountain View Retreat w/ Hot Tub, Theater, and Gym
Property grounds

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (139 reviews)
"The space was comfortable and clean with a great view of the Hudson River valley. Perfect for 2 people on a weekend getaway. "
United States
Meredith C.
The price is ￥32,025
￥53,496 total
includes taxes & fees
Jul 6 - Jul 7
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
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

Quality Inn & Suites Fishkill South near I-84

Quality Inn & Suites Fishkill South near I-84

8/10 Good
"The property was very clean and well maintained. It was exactly what we expect from a hotel."
Edward 1-night trip
Posted 5 hours ago
Quality Inn & Suites Fishkill South near I-84

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 vacation rental in New Windsor?

Yes, we have vacation rentals near the most popular local attractions in New Windsor, or you can select a 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 coffeehouses during your visit.

What's the top vacation rental in New Windsor?

Lakefront Paradise Pool + Paddle Boats Sleeps 12: Visitors like this New Windsor vacation home rental. It offers an outdoor pool, a balcony, and air-conditioning to help you feel perfectly comfortable in your new surroundings. You can relax into your vacation with a garden and a pool table.

How many vacation rentals are there in New Windsor?

Choose from 10 Expedia vacation rentals in New Windsor for a memorable vacation.

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. Other places in town to visit include New Windsor Cantonment State Historic Site and New Windsor Little League.

What are vacation rentals like in New Windsor?

Vacation rentals are private accommodations you can stay in for a short or long stay in New Windsor. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can offer a sense of privacy away from public hotel elevators and busy reception areas while still allowing you to travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for a family trip or a small group gathering.