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New Windsor Vacation Rentals

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Vacation Rentals in New Windsor

Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

10.0 out of 10, Exceptional, (48)
"This is an adorable cottage. It is very clean and well appointed. The kids (and adults) really enjoyed the detached game room. The hot tub and fire pit made for very relaxing evenings. We really enjoyed our time here. "
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

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

9.6 out of 10, Exceptional, (5)
"Plenty of room for my family"
The price is CA $365
CA $465 total
includes taxes & fees
Apr 6 - Apr 7
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (108)
"Awesome "
The price is CA $237
CA $393 total
includes taxes & fees
Apr 6 - Apr 7
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

9.2 out of 10, Wonderful, (33)
"Perfect spot for a get together with friends... kitchen, dining room and living room all connected so you're always together and not missing out on the fun. Comfy couches and plenty of space for large board games."
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

Hillcrest Glasshouse - a minimalist modern retreat

10.0 out of 10, Exceptional, (10)
"I found this place after countless hours of research looking for the perfect getaway where I would eventually propose to my girlfriend. This place stunned us in every aspect. Their home was impeccably clean and intricately decorated, their amenities were awesome and easy to use thanks to their clear instructions (Highlights were: Sonos speakers, hot tub with bathrobes, Miele coffee machine, and the fire pit), and the view is unmatched. Seeing the reaction of my now fiancée as she walked around...
Hillcrest Glasshouse - a minimalist modern retreat

Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC

9.8 out of 10, Exceptional, (57)
"Clean and welcoming. Deck is a great attraction. Price point is what attracted me as we were visiting Beacon & couldn’t find a place that didn’t break the bank. Was a little surprised to discover that this is an apartment addition to an existing house; we could hear the family members inside, and I hope we weren’t too noisy for them. Overall cozy and a nice respite. Thank you."
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC

Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View

10.0 out of 10, Exceptional, (284)
"I visited my college aged son over the weeend for a special event and wanted to stay somewhere with a little something special rather than a hotel. This property exceeded my expectations. Even with winter still lingering, the lake view was spectacular and was highlighted by the home's back wall of windows. Also, Don is a very responsive host and made sure the home had everything you could need - grill, grill tools, pots/pans, appliances, etc. I truly appreciated the hospitality. I hope to stay...
The price is CA $387
CA $512 total
includes taxes & fees
Apr 11 - Apr 12
Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View

Hiking & Climbing Paradise- walking distance to Mohonk,Gunks,Minnewaska

9.8 out of 10, Exceptional, (93)
"We had a wonderful family long weekend at Michele’s beautiful home in the Hudson Valley. We were there to celebrate the birthdays of my husband, son, and grandson. The house was comfortable and well equipped to make meals. Michele the host couldn’t be more responsive. There are many great hikes and wineries close by. This was a 5 star expereince enjoyed by all."
Hiking & Climbing Paradise- walking distance to Mohonk,Gunks,Minnewaska

BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.

10.0 out of 10, Exceptional, (2)
"My family and I had a fantastic stay! The house was even more beautiful and spacious than we expected, making it the perfect home base for our weekend trip to Mount Peter. It was clean, cozy, and had everything we needed for a comfortable and relaxing stay. My parents live nearby in Warwick and this will definitely be my go-to VRBO recommendation for anyone visiting the area. We can’t wait to come back!"
BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.

Red Barn Retreat - Shawangunk Mountains Getaway

10.0 out of 10, Exceptional, (36)
"Needed rest and quiet away from the city! Not only was this the perfect location, but William is a fantastic host. Great communication before and after, from directions to access and operation with kindness and generosity of spirit. Will return! "
Red Barn Retreat - Shawangunk Mountains Getaway

Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick

Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick

Mountain View escape

10.0 out of 10, Exceptional, (50)
"We had a lovely weekend staying at MVE. The host was communicative and thoughtful and the home was beautiful and clean upon arrival. We look forward to coming back soon! "
Mountain View escape

Cabin in the heart of the Hudson Valley, Cabin 4

9.0 out of 10, Wonderful, (21)
"The cabin was great. We drove to Beacon (15min) and spent a day. We plan to return in the Spring/Summer. "
The price is CA $153
CA $248 total
includes taxes & fees
Apr 6 - Apr 7
Cabin in the heart of the Hudson Valley, Cabin 4

Expansive Views; Miles of River & Mountains Walk to Train, Main St, DIA

10.0 out of 10, Exceptional, (1)
"Had a wonderful, relaxing stay here. Convenient location allowed us to walk everywhere we wanted to go!"
Expansive Views; Miles of River & Mountains Walk to Train, Main St, DIA

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

10.0 out of 10, Exceptional, (76)
"The house was super clean and very easy to take care of while we were here. It was perfect for a remote getaway, hiking and just being quiet. "
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons

2.0 star property
9.0 out of 10, Wonderful, (6)
"This property is great, our stay here was just amazing from start to finish. Communication with the host was great, we left some items there and the host was super accommodating. Would recommend this property very highly."
Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons

Spacious New Luxurious holiday house in lovely Hudson Valley

9.8 out of 10, Exceptional, (8)
"The house had room for all of us, spacious and comfortable with modern amenities. We enjoyed the large open kitchen, well equipped for making big meals, and especially loved the walk in pantry with sink, oven and coffee bar. The beds were comfy, the bathrooms deluxe. Large couch and huge TV in living room with cozy gas fireplace for us to gather and relax. Located on a quiet cul de sac, easy to get to local attractions. We enjoyed every minute of our stay."
The price is CA $767
CA $1,298 total
includes taxes & fees
May 1 - May 2
Spacious New Luxurious holiday house in lovely Hudson Valley

Catskills mountain gateway house.

9.8 out of 10, Exceptional, (17)
"The house comfortably slept the six of us."
Catskills mountain gateway house.

Contemporary Cozy Cottage

10.0 out of 10, Exceptional, (17)
"This is a fully decked out house with cozy beds, full kitchen, completely up to date amenities. The host is very accessible, polite, and helpful."
The price is CA $352
CA $585 total
includes taxes & fees
Apr 9 - Apr 10
Contemporary Cozy Cottage

Waterfront Modern Home with Fast Wifi & Hot Tub

9.8 out of 10, Exceptional, (13)
"Family time, hiking, visiting and touring the area. Views are great - saw a bald eagle on day 1! The home is very comfortable and had everything we needed. The owner has thought out all the details - extra toilet paper to spices! Nicely appointed home. Greenwood Lake is a nice area to relax. "
The price is CA $253
CA $682 total
includes taxes & fees
Apr 7 - Apr 8
Waterfront Modern Home with Fast Wifi & Hot Tub
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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Other types of properties in New Windsor you may be interested in

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

2.0 star property
8.4 out of 10, Very good, (1007)
"Very nice stay, friendly staff and clean room. There is a nice balcony on the second floor overlooking a nearby lake. I would definitely stay again."
The price is CA $153
CA $174 total
includes taxes & fees
Apr 6 - Apr 7
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Homewood Suites Stewart Airport

3.0 star property
9.4 out of 10, Exceptional, (990)
"great"
The price is CA $190
CA $215 total
includes taxes & fees
Apr 13 - Apr 14
Homewood Suites Stewart Airport

Overlook Lodge at Bear Mountain

2.5 star property
8.2 out of 10, Very good, (1007)
"Will return, loved the place so close to NYC, West Point and Woodbury Commons"
The price is CA $166
CA $188 total
includes taxes & fees
Apr 16 - Apr 17
Overlook Lodge at Bear Mountain
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.

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 4 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.