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 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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, (49 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.
The price is ￥21,233
￥44,482 total
includes taxes & fees
Oct 5 - Oct 6
Grant - A Tranquil One Bedroom Steps from River
A two-story house with a porch, a red door, and a small outdoor seating area with chairs and a table.

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

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
9.8 out of 10, Exceptional, (13 reviews)
"We had a very comfortable stay. Nice quaint village. Area was quiet and easy to get to."
United States
Leann M.
The price is ￥19,660
￥59,530 total
includes taxes & fees
Sep 30 - Oct 1
House on the Babbling Brook- Quiet 2BR + King Bed!
A modern kitchen with grey cabinets, stainless steel appliances, a granite countertop, and a wooden floor.

3. 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.
The price is ￥29,726
￥37,187 total
includes taxes & fees
Oct 5 - Oct 6
2-bedroom apartment in excellent Newburgh with AC and charm
A modern kitchen with white cabinets, a wooden countertop, and a refrigerator.

4. Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.4 out of 10, Exceptional, (24 reviews)
"Exactly what we needed for two people prior to an early morning touring West Point. "
United States
Andrew L.
The price is ￥18,087
￥45,553 total
includes taxes & fees
Oct 1 - Oct 2
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
A small blue house with two blue Adirondack chairs, a small table, and a potted plant.

5. 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.
The price is ￥23,435
￥35,115 total
includes taxes & fees
Sep 30 - Oct 1
Cabin in the heart of the Hudson Valley, Cabin 2
A compact living space with a kitchenette, a sofa, a bed, and a colorful rug.

6. 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.
The price is ￥26,580
￥42,545 total
includes taxes & fees
Sep 30 - Oct 1
Cabin in the Heart of the Hudson Valley, Cabin 1
A cozy living room with a sofa, a dining table, and a bed.

7. 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.
The price is ￥29,097
￥52,950 total
includes taxes & fees
Sep 30 - Oct 1
Cozy country efficiency in the Hudson Valley
A fire pit with four Adirondack chairs arranged around it, set on a gravel surface with a lake and trees in the background.

8. 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, (101 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.
The price is ￥21,675
￥41,025 total
includes taxes & fees
Oct 8 - Oct 9
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
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
The price is ￥11,359
￥12,850 total
includes taxes & fees
Oct 25 - Oct 26
1 King Bed | Non-Smoking, Kitchen, Shower
A brick building with a sign reading 'Lobby' in front.

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

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Fishkill
9.2 out of 10, Wonderful, (20 reviews)
"Great place to stay,"
United States
Anonymous traveler
The price is ￥12,623
￥14,596 total
includes taxes & fees
Oct 26 - Oct 27
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
A deck with Adirondack chairs, a fire pit, and a grill.

11. 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
The price is ￥33,371
￥63,035 total
includes taxes & fees
Oct 6 - Oct 7
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
A house with a view of a bridge and mountains.

12. 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, (146 reviews)
"We had a great stay!!"
United States
Jasmine
The price is ￥31,141
￥49,791 total
includes taxes & fees
Sep 30 - Oct 1
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
A modern kitchen with white cabinets, a central island with stools, a stainless steel refrigerator, and a staircase leading to another level.

13. Bright Cornwall-On-Hudson Vacation Rental!

Bright Cornwall-On-Hudson Vacation Rental!
Cornwall-On-Hudson
10.0 out of 10, Exceptional, (34 reviews)
"We had a girlfriend get away long weekend. This was a great house and really convenient location. Two really good restaurants were within walking distance just around the corner. I would highly recommend staying here!"
United States
Dawn H.
The price is ￥48,285
￥106,085 total
includes taxes & fees
Oct 22 - Oct 23
Bright Cornwall-On-Hudson Vacation Rental!
A modern kitchen with white cabinets, a central island with stools, a stainless steel refrigerator, and a staircase leading to another level.

14. Bright Cornwall-on-hudson Vacation Rental!

Bright Cornwall-on-hudson Vacation Rental!
3.0 star property
Cornwall
10.0 out of 10, Exceptional, (1 review)
"Very nice property, very comfortable, close to multiple sightseeing location including bear mountain."
United States
Poyuk
The price is ￥58,399
￥109,927 total
includes taxes & fees
Oct 22 - Oct 23
Bright Cornwall-on-hudson Vacation Rental!
A bedroom with a bed, a ceiling fan, a window, and a painting on the wall.

15. 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.
The price is ￥21,870
￥66,031 total
includes taxes & fees
Oct 6 - Oct 7
Local Artist Inspired | Walk to WestPoint + King Bed
A wooden cabin with a covered deck, outdoor seating, and a fire pit.

16. 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.
The price is ￥19,364
￥37,739 total
includes taxes & fees
Oct 7 - Oct 8
Historic Cabin with Pool & Fire Pit
A bedroom with a bed, a ceiling fan, a nightstand, a window with curtains, and a wall with framed pictures.

17. Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
9.4 out of 10, Exceptional, (8 reviews)
"Great location and super host. "
United States
James U.
The price is ￥22,195
￥67,375 total
includes taxes & fees
Oct 6 - Oct 7
Sleek Escape: Modern 3 BR- 4 Min from West Point !
A rural landscape with a barn, a silo, and a bridge with rocks and purple flowers in the foreground.

18. 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
9.2 out of 10, Wonderful, (15 reviews)
"The room was super cute and clean. It had everything that I needed."
United States
Carrie
The price is ￥11,010
￥22,020 total
includes taxes & fees
Oct 20 - Oct 21
A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail
A single-story house with a front porch, two blue chairs, a white chair, and a potted plant with pink flowers.

19. 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, (15 reviews)
"We had a great stay, everything you need is provided. Would recommend to anyone."
United States
Bill W.
The price is ￥26,580
￥42,545 total
includes taxes & fees
Sep 30 - Oct 1
Cabin in the heart of the Hudson Valley, Cabin 3
Living area

20. 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.
The price is ￥20,808
￥36,876 total
includes taxes & fees
Sep 30 - Oct 1
Cozy 1-bedroom retreat minutes from West Point!
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

10/10 Excellent
"Perfect room. Very clean and new hotel. Quiet and convenient. Decent breakfast. Very nice and helpful front desk staff."
Michael 1-night trip
Posted 1 hour ago
SureStay Plus Hotel by Best Western Highland Poughkeepsie

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
  • Use the map to find apartments and other holiday homes in the New Windsor neighbourhood you prefer
  • 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?

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views: Visitors like this New Windsor vacation home rental. It is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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 Knox's Headquarters State Historic Site and National Purple Heart Hall of Honor. Other places in town to visit include New Windsor Little League and New Windsor Cantonment State Historic Site.

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.