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Browse Select New Windsor Holiday Homes

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
10.0 out of 10, Exceptional, (63)
"Stayed for West Point graduation. Beautiful home, scenic views, and everything we needed."
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Bright Cornwall-On-Hudson Vacation Rental!
10.0 out of 10, Exceptional, (4)
"We thoroughly enjoyed our stay at this beautiful and quaint home in the heart of the Cornwall village. The house was exactly as described, communication with the host was easy and quick, and we enjoyed being so close to everything Cornwall has to offer. We would absolutely recommend this beautiful home for your next visit to the Cornwall area"
Bright Cornwall-On-Hudson Vacation Rental!
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
9.8 out of 10, Exceptional, (37)
"it was excellent. exactly what I wanted. looking forward to coming back with family. the hot tub could have been slightly cleaner but it's like cold pizza, still good and hits the spot. honestly, a beautiful place. top notch Internet provided."
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
10.0 out of 10, Exceptional, (22)
"My family and I had a wonderful weekend at the property. It rained most of the time, but we made the best of it. It was all over too fast. It's a nice, relaxing property."
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
Renovated 1850's Cottage on Storm King Mountain
9.8 out of 10, Exceptional, (8)
"It was a beautiful setting with water fall. The home itself needs a little work. It is well used and needs some TLC. Photos look much better then actual home."
Renovated 1850's Cottage on Storm King Mountain
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
9.0 out of 10, Wonderful, (22)
"This house has an ideal location to see lots of local sites of interest in the Hyde Park and Poughkeepsie area. Easy trip from there to West Point, Hyde Park and the Culinary Institute from the location, and great restaurant, Tiramasu, is very close. The house is immaculate! The beds were very comfortable, linens were provided, the bathrooms were spacious and the five of us had plenty of room for our toiletries. The house has steps to its multiple levels for all essential rooms, not accessible....
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Beautiful Home - 4BR/2.5BA - Hot tub and Patio - Minutes from New Paltz
9.8 out of 10, Exceptional, (20)
"Several days with family for my Son’s West Point Graduation! House was perfect , located in a nice neighborhood. Hosts are super friendly and easy to communicate with. Prompt response and helpful information! Highly recommend for groups from 4-8! Thank you !"
Beautiful Home - 4BR/2.5BA - Hot tub and Patio - Minutes from New Paltz
CREATIVES DREAM GETAWAY
10.0 out of 10, Exceptional, (1)
"Our group of 4 adults spent 3 nights in Ezequiel's beautiful property. It was cozy, beautifully decorated, comfortable, and the kitchen had everything you could possibly need. We enjoyed the lovely, tranquil outdoor space, and we had easy access to the attractions we were there to visit (Mohank Nature Preserve, CIA -Culinary Institute of America, Storm King Sculpture Park, etc.). Highly recommend and would definitely stay here again."
CREATIVES DREAM GETAWAY
Pet-Friendly ‘Pond View Loft' w/ Private Pool!
9.6 out of 10, Exceptional, (11)
"Overall, it seemed like the property manager was not ready for guests. The toilet instantly broke, the pool hadn’t been cleaned in probably weeks, and the apartment had stained sheets. It’s a nice place but really not worth the money."
Pet-Friendly ‘Pond View Loft' w/ Private Pool!
Spacious restored Victorian w/ wraparound porch
9.4 out of 10, Exceptional, (10)
"Spacious house, beautiful setting. Perfect set up for a reunion with friends and family. Highlights were spending quality time on the wrap around porch and making s'mores in the fire pit. Kids loved the pool and exploring the property. Host was responsive and helpful. Highly recommend!"
Spacious restored Victorian w/ wraparound porch
Cozy family-friendly home!
10.0 out of 10, Exceptional, (3)
"Older manufactured home has been updated. We appreciated that each area had its own mini split unit for individual climate control. Area felt safe and quiet. Good hot water and water pressure. Kitchen was stocked for stovetop cooking but not much for baking, and no water glasses. (We just drank everything from the coffee cups.) Split bedroom layout was good for two couples. "
Cozy family-friendly home!
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
10.0 out of 10, Exceptional, (18)
"We had a very pleasant stay! We came for our son’s graduation from West Point. Pat was a gracious host and made sure that we had up to date info. There were lots of thoughtful amenities, the beds and couches were very comfortable, we used the grill and sat on the deck which overlooks a wooded hill. The location is peaceful and in the country just down the street from a horse pasture. You can hear the brook bubbling across the way. The WiFi worked great and although there is just a window air...
The price is £258
includes taxes & fees
17 Jun - 18 Jun
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
9.6 out of 10, Exceptional, (30)
"This place is wonderful!!!! It was a beautiful stay."
The price is £288
includes taxes & fees
18 Jun - 19 Jun
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
Newly Renovated Goshen Cottage
9.8 out of 10, Exceptional, (33)
"Lovely house, with very responsive and helpful owners. "
The price is £429
includes taxes & fees
3 Jul - 4 Jul
Newly Renovated Goshen Cottage
Sweet and spacious mountain view home w/fireplace!
9.8 out of 10, Exceptional, (14)
"Sweet space, well-stocked and nice open living and kitchen area. We enjoyed watching birds eat from the bird feeders and a family of deer graze in the meadow and along the edge of the woods! The location was situated well for accessing nearby hiking and is not far from scenic Hudson landmarks. Excellent quiet place to relax and take things at your own pace."
The price is £321
includes taxes & fees
17 Jun - 18 Jun
Sweet and spacious mountain view home w/fireplace!
Dream escape, new modern farmhouse, stunning views, game room & hot tub for 10+!
10.0 out of 10, Exceptional, (5)
"OUTSTANDING location! The views are incredible! Great outdoor area for a bonfire and family time! Hot tub! Grill! Not to mention the rooms are perfection with attention to detail. There is even a family room with a baby bed and play pen which was perfect for my daughter and her little family. The owners of the property answered our questions 24/7 and were always very gracious and kind. Constantly asking if we needed anything to make our stay better. The restrooms had towels with all kinds of...
The price is £803
includes taxes & fees
16 Jun - 17 Jun
Dream escape, new modern farmhouse, stunning views, game room & hot tub for 10+!
The Queen City Cottage
7.4 out of 10, Good, (16)
"My wife and I, along with my two daughters and grandchildren stayed at the Queen City Cottage for 4 nights. We needed to add an extra day at the last minute and Marissa was very responsive and accommodating. The house was clean upon our arrival and entry was a breeze. It's a bedroom, 1.5 bath, with extra bathroom in basement in laundry room. Location wa great! Restaurants and shopping minutes away. Outdoor space was tranquil with table and chairs under covered back porch. Wifi was fine, TV had...
The Queen City Cottage
Lake House, ONE HOUR from NYC
9.8 out of 10, Exceptional, (23)
"Great place and Rhona did a great job (great communication, timely, and adaptable). Well done!"
Lake House, ONE HOUR from NYC
Lovely Highland Home w/ Pool & Hot Tub!
9.4 out of 10, Exceptional, (3)
"I rented this house for my wife’s bridesmaids. Beautiful house."
Lovely Highland Home w/ Pool & Hot Tub!
The Woodbury Cottage
10.0 out of 10, Exceptional, (1)
"We really enjoyed relaxing on the front porch after a busy day out. Beds were very comfortable. So nice to be able to sit around and visit, instead being in a hotel, sitting on beds. We did miss having a microwave to use. Very nice and affordable."
The Woodbury Cottage
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See all available properties in New Windsor
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.

Other property types in New Windsor

Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
10.0 out of 10, Exceptional, (31)
"We came for West Point graduation. It was perfect in its location to West Point. Beds were good, its was very clean, and the hot tub was great! The owners communicated well and helped us with our scheduling. We highly recommend this place!"
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
Beautiful Cozy 2 br in-law apt, prime Hudson Valley location
9.4 out of 10, Exceptional, (10)
"Booked our stay over Ring Weekend at West Point. Quiet neighborhood, 15 minutes from Stoney Gate entrance to West Point. Wonderful well furnished clean and comfortable spot with 2 bedrooms. Friendly, prompt and kind communication during entire reservation and use process. Highly recommended!"
Beautiful Cozy 2 br in-law apt, prime Hudson Valley location
Cottage Suites
3.0 star property
9.0 out of 10, Wonderful, (2)
"The actual room was excellent, compfy bed. Shower door was hard to open. No handle on the outside. Loud cars going through the neighborhood and my room was up 3 flights of stairs. "
The price is £219
includes taxes & fees
16 Jun - 17 Jun
Cottage Suites
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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