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New Windsor Vacation Rentals

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Oct 29 - Oct 30
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Oct 31 - Nov 2
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Nov 7 - Nov 9

Vacation Rentals in New Windsor

Fridge, microwave, oven, stovetop
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
10.0 out of 10, Exceptional, (60)
"Beautiful home - just as pictured. Many nice touches that made it a great stay. Would definitely stay at this home again. "
United States
Stacey H.
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
Outdoor dining
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
9.6 out of 10, Exceptional, (42)
"Plenty of seating & comfortable beds were a plus! The theatre room was really fun for grandkids!"
United States
Lisa B.
$292 nightly
The price is $330
Nov 3 - Nov 4
Total with taxes and fees
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (123)
"It has an incredible mountain and water view. "
United States
MIHYUN
$271 nightly
The price is $307
Oct 30 - Oct 31
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Property grounds
Cabin in the heart of the Hudson Valley, Cabin 2
Cabin in the heart of the Hudson Valley, Cabin 2
9.4 out of 10, Exceptional, (27)
"We stayed here a few years ago and loved the convenience of this property. When we returned to the area, we immediately started by looking for this property again. It’s clean, no fuss, easy check in, and precisely what we needed!"
United States
Erika S.
$149 nightly
The price is $176
Nov 2 - Nov 3
Total with taxes and fees
Cabin in the heart of the Hudson Valley, Cabin 2
Interior
Large,Cozy,Bright Apartment, Business Themed.
Large,Cozy,Bright Apartment, Business Themed.
9.0 out of 10, Wonderful, (15)
"Very cozy stay with responsive host"
United States
Adhith P.
$585 nightly
The price is $691
Oct 30 - Oct 31
Total with taxes and fees
Large,Cozy,Bright Apartment, Business Themed.
Children's area
Hickory on Willow Lake
Hickory on Willow Lake
9.6 out of 10, Exceptional, (4)
"Cute cottage on nice grounds with a small lake. Kayaks and life jackets available for use was a big plus"
United States
Rachel C.
$536 nightly
The price is $610
Oct 30 - Oct 31
Total with taxes and fees
Hickory on Willow Lake
Terrace/patio
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9
9.8 out of 10, Exceptional, (19)
"Great host, amazing area, perfect get away!"
United States
Gianna W.
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9
Exterior
Rustic Cabin in Fishkill!
Rustic Cabin in Fishkill!
10.0 out of 10, Exceptional, (2)
"The place was very nice, we met the owner and he was also bery accommodating. This is definitely a family friendly spot. "
United States
Arron T.
$367 nightly
The price is $417
Oct 30 - Oct 31
Total with taxes and fees
Rustic Cabin in Fishkill!
Outdoor dining
Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven
Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven
9.6 out of 10, Exceptional, (14)
"Lovely two weeks in the carriage house on the Croton River. Hosts Patrick and Kathryn were attentive and helpful, the area was full of fun adventures for my husband, a cyclist, and me (jogger and kayaker). Swimming in the Croton from the dock was so great, especially on warm days. Kayaking in the Croton was peaceful and full of fun water birds."
United States
Ann M.
Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven
Fridge, microwave, oven, stovetop
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
10.0 out of 10, Exceptional, (92)
"My family and I loved this property! We enjoyed walking around the woods and exploring. The house was well equipped and was really charming. We also loved sightseeing around the near by towns. Definitely a place to come back to stay again. "
United States
Hector L.
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Interior
Contemporary Cozy Cottage
Contemporary Cozy Cottage
10.0 out of 10, Exceptional, (29)
"Very clean comfortable quiet place"
United States
Mauro C.
$370 nightly
The price is $423
Oct 30 - Oct 31
Total with taxes and fees
Contemporary Cozy Cottage
Exterior
Modern penthouse suite in a restored grain tower with private roof deck.
Modern penthouse suite in a restored grain tower with private roof deck.
10.0 out of 10, Exceptional, (25)
"Wonderful stay!"
United States
Lisi M.
$478 nightly
The price is $540
Nov 2 - Nov 3
Total with taxes and fees
Modern penthouse suite in a restored grain tower with private roof deck.
Smart TV, books
Be in Nature at this Gorgeous Riverfront Cabin
Be in Nature at this Gorgeous Riverfront Cabin
10.0 out of 10, Exceptional, (21)
"We had a wonderful stay. The Cabin is ideally situated in a very tranquil spot. Perfectly appointed, we couldn't have been happier with our stay."
United States
Phoebe J.
Be in Nature at this Gorgeous Riverfront Cabin
Outdoor dining
Cabin in the heart of the Hudson Valley, Cabin 4
Cabin in the heart of the Hudson Valley, Cabin 4
9.2 out of 10, Wonderful, (25)
"Enjoyable "
United States
Lisa M.
$149 nightly
The price is $176
Nov 2 - Nov 3
Total with taxes and fees
Cabin in the heart of the Hudson Valley, Cabin 4
Outdoor dining
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
10.0 out of 10, Exceptional, (311)
"Excellent communication with great host. Pleasant, peaceful stay."
United States
Frank D.
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Smart TV, fireplace, books, computer monitors
Entire Lakeview House ~ Hot Tub ~ Firepit ~ Stunning View ~ Spacious Deck
Entire Lakeview House ~ Hot Tub ~ Firepit ~ Stunning View ~ Spacious Deck
10.0 out of 10, Exceptional, (3)
"We had lovely and relaxing stay at this property! The surrounding area is beautiful and the crowd are amazing!"
United States
Susan R.
$699 nightly
The price is $790
Nov 4 - Nov 5
Total with taxes and fees
Entire Lakeview House ~ Hot Tub ~ Firepit ~ Stunning View ~ Spacious Deck
Dining
Pool, Fire Pit Bedroom & Alaska King – Sleeps 16
Pool, Fire Pit Bedroom & Alaska King – Sleeps 16
2.0 star property
$696 nightly
The price is $781
Nov 3 - Nov 4
Total with taxes and fees
Pool, Fire Pit Bedroom & Alaska King – Sleeps 16
Outdoor dining
Stylish & Peaceful Getaway on 3 Private Acres
Stylish & Peaceful Getaway on 3 Private Acres
2.0 star property
9.0 out of 10, Wonderful, (12)
"The owner was extremely responsive and the home was very clean."
United States
Christine C.
$438 nightly
The price is $438
Oct 30 - Oct 31
Total with taxes and fees
Stylish & Peaceful Getaway on 3 Private Acres
1 bedroom, WiFi, bed sheets
Charming 1-bedroom apartment in Carmel with WiFi, AC
Charming 1-bedroom apartment in Carmel with WiFi, AC
9.0 out of 10, Wonderful, (2)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
United States
Emmett
$218 nightly
The price is $236
Oct 30 - Oct 31
Total with taxes and fees
Charming 1-bedroom apartment in Carmel with WiFi, AC
Smart TV, video games, DVD player, foosball
Spacious 4-bedroom home on 5 acre farm near Minnewaska State Park
Spacious 4-bedroom home on 5 acre farm near Minnewaska State Park
9.2 out of 10, Wonderful, (42)
"Such a beautiful home and peaceful farm setting! We especially loved the game room and spacious living areas — perfect for relaxing and spending quality time together as a family. Good location as well! "
United States
Shachi S.
Spacious 4-bedroom home on 5 acre farm near Minnewaska State Park
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

Americas Best Value Inn New Paltz

Americas Best Value Inn New Paltz

10/10 Excellent
"Hotel was clean perfect for Over night stay"
Nick 1-night trip
Posted 1 day ago
Americas Best Value Inn New Paltz

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 $176 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 7 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. Woodbury Common Premium Outlets and LEGOLAND® New York are other popular places to visit in the area.

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.