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

Our top choices for New Windsor vacation rentals

Lake view

Jellystone Park Gardiner

Jellystone Park Gardiner
3.0 star property
Gardiner
The price is AED 1,309
AED 1,466 total
includes taxes & fees
8 Jul - 9 Jul
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 AED 779
AED 1,897 total
includes taxes & fees
28 Jun - 29 Jun
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 AED 1,127
AED 1,387 total
includes taxes & fees
30 Jun - 1 Jul
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 AED 1,736
AED 2,138 total
includes taxes & fees
29 Jun - 30 Jun
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 AED 1,174
AED 1,983 total
includes taxes & fees
28 Jun - 29 Jun
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, (6 reviews)
"Very well designed and listed place. Had everything we needed, and the host was friendly!"
United States
Jesse L.
The price is AED 1,359
AED 2,512 total
includes taxes & fees
1 Jul - 2 Jul
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 AED 826
AED 1,554 total
includes taxes & fees
28 Jun - 29 Jun
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 AED 1,544
AED 1,901 total
includes taxes & fees
13 Jul - 14 Jul
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 AED 621
AED 1,024 total
includes taxes & fees
28 Jun - 29 Jun
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 AED 1,818
AED 2,584 total
includes taxes & fees
29 Jun - 30 Jun
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 AED 621
AED 1,024 total
includes taxes & fees
28 Jun - 29 Jun
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 AED 3,458
AED 6,064 total
includes taxes & fees
29 Jun - 30 Jun
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 AED 3,219
AED 5,682 total
includes taxes & fees
9 Jul - 10 Jul
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 AED 1,080
AED 2,198 total
includes taxes & fees
19 Jul - 20 Jul
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 AED 499
AED 890 total
includes taxes & fees
5 Jul - 6 Jul
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 AED 1,794
AED 3,459 total
includes taxes & fees
30 Jun - 1 Jul
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
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 AED 1,192
AED 1,630 total
includes taxes & fees
29 Jun - 30 Jun
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 AED 2,461
AED 4,450 total
includes taxes & fees
1 Jul - 2 Jul
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 AED 727
AED 1,215 total
includes taxes & fees
8 Jul - 9 Jul
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

Spark by Hilton Fishkill

Spark by Hilton Fishkill

8/10 Good
"The room was clean. The mattress is very comfortable. Staff was nice. It’s a cheap hotel so it’s not fancy but it has everything you need and it’s clean."
Ryan 2-night trip
Posted 21 hours ago
Spark by Hilton Fishkill

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.