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New Windsor Vacation Rentals

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Jan 3 - Jan 4
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Jan 9 - Jan 11
In two weeks
Jan 16 - Jan 18

Our top choices for New Windsor vacation rentals

Fridge, oven, stovetop, cookware/dishes/utensils
Cozy 1-bedroom retreat minutes from West Point!

Apartment in Highland Falls

Cozy 1-bedroom retreat minutes from West Point!
10.0 out of 10, Exceptional, (1)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
$174 nightly
The price is $190
Feb 2 - Feb 3
Total with taxes and fees
Cozy 1-bedroom retreat minutes from West Point!
Children's area
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Cottage in Goshen

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
9.8 out of 10, Exceptional, (12)
"Beautiful location. We really enjoyed seeing the deer in the field every morning. "
United States
Aaron M.
$280 nightly
The price is $292
Jan 4 - Jan 5
Total with taxes and fees
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Exterior detail
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Apartment in Highland Falls

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
9.8 out of 10, Exceptional, (14)
"Great Unit."
United States
Rudy R.
$261 nightly
The price is $264
Jan 5 - Jan 6
Total with taxes and fees
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Exterior
House on the Babbling Brook- Quiet 2BR + King Bed!

Vacation Home in Highland Falls

House on the Babbling Brook- Quiet 2BR + King Bed!
10.0 out of 10, Exceptional, (5)
"Good stay, awesome place"
United States
Scott G.
$327 nightly
The price is $344
Jan 4 - Jan 5
Total with taxes and fees
House on the Babbling Brook- Quiet 2BR + King Bed!
Interior
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Vacation Home in Warwick

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
9.4 out of 10, Exceptional, (8)
"I really enjoyed my stay. The room was very clean, the inn is well located in town and it is great having the restaurant below. Would stay here again! "
United States
Erin R.
$131 nightly
The price is $148
Jan 27 - Jan 28
Total with taxes and fees
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Fridge, microwave, oven, stovetop
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

Cottage in Kerhonkson

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
9.4 out of 10, Exceptional, (12)
"Charming and relaxing cottage. Perfect location for hiking or enjoying Lake Minnewaska or Mohonk Preserve. "
United States
Patrick S.
$217 nightly
The price is $219
Feb 2 - Feb 3
Total with taxes and fees
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Interior
Walk-to-Lake Cottage With Office for Quiet Days and Easy Work

Cottage in Putnam Valley

Walk-to-Lake Cottage With Office for Quiet Days and Easy Work
9.8 out of 10, Exceptional, (23)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
$446 nightly
The price is $492
Jan 4 - Jan 5
Total with taxes and fees
Walk-to-Lake Cottage With Office for Quiet Days and Easy Work
Interior
Villa Verde B&B, bsm, Greenwood Lake NY

Aparthotel in Greenwood Lake

Villa Verde B&B, bsm, Greenwood Lake NY
10.0 out of 10, Exceptional, (12)
"The breakfast was lovely!"
United States
Tara
$256 nightly
The price is $290
Jan 4 - Jan 5
Total with taxes and fees
Villa Verde B&B, bsm, Greenwood Lake NY
Terrace/patio
Dream getaway apartment in the foot of Gunks Ridge

Apartment in Wallkill

Dream getaway apartment in the foot of Gunks Ridge
9.6 out of 10, Exceptional, (24)
"Over all the property was clean and staff was very cooperative. Only problems were the beds were very hard which made it hard for us to get a good nights sleep. The larger room had bugs but the owner took care of it right away. We enjoyed our stay."
United States
Harriet
$164 nightly
The price is $166
Jan 4 - Jan 5
Total with taxes and fees
Dream getaway apartment in the foot of Gunks Ridge
Fridge, microwave, oven, stovetop
Cabin in the heart of the Hudson Valley, Cabin 3

Cabin in Newburgh

Cabin in the heart of the Hudson Valley, Cabin 3
9.8 out of 10, Exceptional, (14)
"We had a great stay, everything you need is provided. Would recommend to anyone."
United States
Bill W.
$235 nightly
The price is $278
Jan 4 - Jan 5
Total with taxes and fees
Cabin in the heart of the Hudson Valley, Cabin 3
Terrace/patio
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna

Chalet in Gardiner

Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
2.0 star property
10.0 out of 10, Exceptional, (7)
"Great weekend getaway to reconnect with old friends!"
United States
Lisa D.
$277 nightly
The price is $281
Jan 12 - Jan 13
Total with taxes and fees
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
Interior
Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks

Vacation Home in Kerhonkson

Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks
10.0 out of 10, Exceptional, (14)
"Beautiful place tucked back in the woods. Very relaxing and incredibly clean. The free coffee was a nice touch too. Will 100% be returning to The Gunks because of this house. "
United States
Kyle T.
$193 nightly
The price is $195
Feb 2 - Feb 3
Total with taxes and fees
Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks
2 bedrooms, in-room safe, desk, iron/ironing board
Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food

Apartment in CROTON HDSN

Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food
9.8 out of 10, Exceptional, (90)
"I had a great stay at this extremely comfortable home in a quiet neighborhood. Maria was very welcoming and helpful. I hope to visit and stay here again soon."
United States
Jill D.
$234 nightly
The price is $268
Jan 4 - Jan 5
Total with taxes and fees
Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food
TV, fireplace
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Vacation Home in Carmel Hamlet

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
9.8 out of 10, Exceptional, (12)
"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."
United States
Hannah P.
$328 nightly
The price is $355
Jan 5 - Jan 6
Total with taxes and fees
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
1 bedroom, WiFi, bed sheets
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

Apartment in Beacon

Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
10.0 out of 10, Exceptional, (32)
"Great time and great place to stay "
United States
S S.
$209 nightly
The price is $241
Jan 4 - Jan 5
Total with taxes and fees
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
Exterior
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Vacation Home in Hopewell Junction

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
9.0 out of 10, Wonderful, (10)
"We had a great last minute visit to Hopewell Junction and enjoyed a lovely stay at the chapel! It’s a very unique experience and quiet and peaceful. We enjoyed the bbq and an evening fire with smores! "
United States
Esther P.
$228 nightly
The price is $258
Jan 4 - Jan 5
Total with taxes and fees
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Apartment | 1 bedroom
Hidden Lakefront Gem on a Gated Countryside Escape

Vacation Home in Monroe

Hidden Lakefront Gem on a Gated Countryside Escape
2.0 star property
$199 nightly
The price is $225
Jan 4 - Jan 5
Total with taxes and fees
Hidden Lakefront Gem on a Gated Countryside Escape
Outdoor dining
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro

Cottage in Bloomingburg

Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
10.0 out of 10, Exceptional, (1)
"The place was as described, quaint, clean, no issues with communication or check in"
United States
Stephen H.
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Exterior
TRANQUIL MOUNTAIN SOLITUDE

Mobile Home in Pine Bush

TRANQUIL MOUNTAIN SOLITUDE
10.0 out of 10, Exceptional, (4)
"Such a quaint & cozy little hideaway! Hosts could not be more hospitable. Thank you for a great stay!"
United States
Michelle H.
$214 nightly
The price is $239
Jan 24 - Jan 25
Total with taxes and fees
TRANQUIL MOUNTAIN SOLITUDE
Exterior
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

Apartment in Croton-on-Hudson

'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
10.0 out of 10, Exceptional, (2)
"Great stay!"
United States
Ann S.
$207 nightly
The price is $236
Jan 4 - Jan 5
Total with taxes and fees
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
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

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

10/10 Excellent
"clean super safe lady at front desk was very helpful "
guadalupe 1-night trip
Posted 1 day ago
Sleep Inn & Suites Middletown - Goshen

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 $239 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?

Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel. : Visitors give good reviews to this New Windsor vacation home rental, which is located on a river and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in New Windsor?

Choose from 8 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 Schunnemunk State Park.

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.