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
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for New Windsor vacation rentals

A living room with a fireplace, a painting, shelves with decorative items, and a television.

1. Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (48 reviews)
"We enjoyed our stay, property was as described. It's convenient to many of the Hudson Valley small towns, including West Point."
United States
Mike W.
$261 nightly
The price is $295
Sep 21 - Sep 22
Total with taxes and fees
Grant - A Tranquil One Bedroom Steps from River
A modern kitchen with grey cabinets, stainless steel appliances, a granite countertop, and a wooden floor.

2. 2-bedroom apartment in excellent Newburgh with AC and charm

2-bedroom apartment in excellent Newburgh with AC and charm
Newburgh
10.0 out of 10, Exceptional, (3 reviews)
"We have stayed here once before overnight while in the area for an event. It is close to where we needed to be and a great value for the price"
United States
Nick L.
$215 nightly
The price is $243
Sep 24 - Sep 25
Total with taxes and fees
2-bedroom apartment in excellent Newburgh with AC and charm
A two-story house with a porch, a red door, and a small outdoor seating area with chairs and a table.

3. House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
10.0 out of 10, Exceptional, (11 reviews)
"We had a very comfortable stay. Nice quaint village. Area was quiet and easy to get to."
United States
Leann M.
$378 nightly
The price is $404
Sep 20 - Sep 21
Total with taxes and fees
House on the Babbling Brook- Quiet 2BR + King Bed!
A small, two-story house with a red and gray exterior, a front porch with blue chairs, and a table.

4. Cabin in the heart of the Hudson Valley, Cabin 4

Cabin in the heart of the Hudson Valley, Cabin 4
Newburgh
9.2 out of 10, Wonderful, (28 reviews)
"Pet-friendly and easily accessible."
United States
Brigitte
$191 nightly
The price is $226
Sep 20 - Sep 21
Total with taxes and fees
Cabin in the heart of the Hudson Valley, Cabin 4
A cozy living room with a sofa, a dining table, and a bed.

5. Cozy country efficiency in the Hudson Valley

Cozy country efficiency in the Hudson Valley
Newburgh
10.0 out of 10, Exceptional, (74 reviews)
"Comfy cozy weekend retreat"
United States
Michael M.
$301 nightly
The price is $356
Sep 18 - Sep 19
Total with taxes and fees
Cozy country efficiency in the Hudson Valley
A brick building with a sign reading 'Lobby' in front.

6. Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Fishkill
9.2 out of 10, Wonderful, (19 reviews)
"Great place to stay,"
United States
Anonymous traveler
$81 nightly
The price is $94
Oct 5 - Oct 6
Total with taxes and fees
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
A compact living space with a kitchenette, a sofa, a bed, and a colorful rug.

7. 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, (36 reviews)
"Great place! Nicely decorated with attention to detail. My wife and I would stay again if we are back in the area."
United States
Tim G.
$236 nightly
The price is $279
Sep 20 - Sep 21
Total with taxes and fees
Cabin in the Heart of the Hudson Valley, Cabin 1
A deck with Adirondack chairs, a fire pit, and a grill.

8. 3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
Cornwall
10.0 out of 10, Exceptional, (15 reviews)
"Everything you could ask for!!"
United States
Elisabeth
$357 nightly
The price is $422
Sep 22 - Sep 23
Total with taxes and fees
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
A hotel lobby with a reception desk, seating area, and a fire extinguisher on the wall.

9. 1 King Bed | Non-Smoking, Kitchen, Shower

1 King Bed | Non-Smoking, Kitchen, Shower
Fishkill
9.6 out of 10, Exceptional, (18 reviews)
"Great rooms and service,"
United States
Anonymous traveler
$73 nightly
The price is $82
Oct 13 - Oct 14
Total with taxes and fees
1 King Bed | Non-Smoking, Kitchen, Shower
A wooden cabin with a covered deck, outdoor seating, and a fire pit.

10. Historic Cabin with Pool & Fire Pit

Historic Cabin with Pool & Fire Pit
Montgomery
9.8 out of 10, Exceptional, (6 reviews)
"This little cabin was exactly what we needed for our stay in NY. It looks just as described, was clean, and the location was perfect for all of the places we wanted to visit. Overall it was very cozy and relaxing and we can't wait to stay again! "
United States
Sarah A.
$187 nightly
The price is $221
Sep 24 - Sep 25
Total with taxes and fees
Historic Cabin with Pool & Fire Pit
A house with a view of a bridge and mountains.

11. 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, (145 reviews)
"We had a great stay!!"
United States
Jasmine
$280 nightly
The price is $331
Sep 21 - Sep 22
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
A fire pit with four Adirondack chairs arranged around it, set on a gravel surface with a lake and trees in the background.

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

Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Wallkill
10.0 out of 10, Exceptional, (99 reviews)
"We were very happy with the house and location, but what made it amazing was how great host was. Very accommodating and helpful with helping us out last minute. Would absolutely recommend working with this host again."
United States
Chris W.
$217 nightly
The price is $242
Sep 27 - Sep 28
Total with taxes and fees
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
A blue house with a white porch, a welcome sign, and a mailbox.

13. 3BR West Point Retreat-3min to Back Gate+ King Bed

3BR West Point Retreat-3min to Back Gate+ King Bed
Highland Falls
8.4 out of 10, Very good, (7 reviews)
"Space was excellent, the multiple bedrooms with the extra bathroom was great. Kitchen was stocked with utensils, bathrooms were clean, living space was comfortable and cozy."
United States
Christine T.
3BR West Point Retreat-3min to Back Gate+ King Bed

14. Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
9.0 out of 10, Wonderful, (4 reviews)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
$238 nightly
The price is $264
Sep 28 - Sep 29
Total with taxes and fees
Cozy 1-bedroom retreat minutes from West Point!
A small blue house with two blue Adirondack chairs, a small table, and a potted plant.

15. Cabin in the heart of the Hudson Valley, Cabin 2

Cabin in the heart of the Hudson Valley, Cabin 2
Newburgh
9.6 out of 10, Exceptional, (40 reviews)
"This was a great place to stay with our cats for a night on our way to Vermont."
United States
George J.
$192 nightly
The price is $227
Sep 21 - Sep 22
Total with taxes and fees
Cabin in the heart of the Hudson Valley, Cabin 2
A single-story house with a front porch, two blue chairs, a white chair, and a potted plant with pink flowers.

16. 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.
$236 nightly
The price is $279
Sep 20 - Sep 21
Total with taxes and fees
Cabin in the heart of the Hudson Valley, Cabin 3
A rural landscape with a barn, a silo, and a bridge with rocks and purple flowers in the foreground.

17. A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail

A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail
Wallkill
9.0 out of 10, Wonderful, (14 reviews)
"The room was super cute and clean. It had everything that I needed."
United States
Carrie
$125 nightly
The price is $140
Sep 29 - Sep 30
Total with taxes and fees
A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail
A bedroom with a bed, a ceiling fan, a window, and a painting on the wall.

18. Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.4 out of 10, Exceptional, (20 reviews)
"Great location! Easy checkin, checkout process. We would stay again"
United States
Morgan S.
$430 nightly
The price is $441
Sep 21 - Sep 22
Total with taxes and fees
Local Artist Inspired | Walk to WestPoint + King Bed
A modern kitchen with stainless steel appliances, wooden cabinets, and a marble countertop.

19. Modern Hudson Valley Apt 202 - King/Queen/Twin

Modern Hudson Valley Apt 202 - King/Queen/Twin
Montgomery
9.8 out of 10, Exceptional, (20 reviews)
"Great hosts and great location!"
United States
Shelby A.
$256 nightly
The price is $294
Sep 20 - Sep 21
Total with taxes and fees
Modern Hudson Valley Apt 202 - King/Queen/Twin
An outdoor patio area with a covered seating area, a pool, and potted plants.

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

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fishkill
9.2 out of 10, Wonderful, (76 reviews)
"It’s was nice, clean and the outdoor out area was really nice."
United States
Roger S.
$295 nightly
The price is $341
Sep 20 - Sep 21
Total with taxes and fees
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
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

SureStay Plus Hotel by Best Western Highland Poughkeepsie

SureStay Plus Hotel by Best Western Highland Poughkeepsie

8/10 Good
"Very clean room. Hotel stairs carpets were okay. Nice breakfast and very friendly staff. Nice comfortable bed and large pillow selection."
morgan 3-night trip
Posted 11 hours ago
SureStay Plus Hotel by Best Western Highland Poughkeepsie

Find out more about New Windsor

Everything you need to know about New Windsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the New Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect New Windsor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

New Windsor vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in New Windsor. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit New Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $94 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on New Windsor rentals

At Expedia, we put the best New Windsor vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top New Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream New Windsor vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around New Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: Visitors like this New Windsor vacation home rental. It 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 kitchenware, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in New Windsor?

Choose from 9 Expedia vacation rentals in New Windsor for a memorable vacation.

What can I see and do in New Windsor?

Cultural attractions to visit include National Purple Heart Hall of Honor and Knox's Headquarters State Historic Site. 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.