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Compare 339 Vacation Homes in New Windsor with updated reviews, rates, and availability.

Beautiful Private Stone Home in the Hudson Valley
10.0 out of 10, Exceptional, (138)
"home and amenities enjoyed by all age groups. the city-slickers were thrilled by the deer, and visiting the chickens and roosters. the location is beautiful and rural. easy drive from nyc and capital district."
Beautiful Private Stone Home in the Hudson Valley
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
10.0 out of 10, Exceptional, (74)
"This place was a great place for us to stay on our vacation. Secluded outside of the city, and a short drive down a gravel road, it really feels that you're lost in the woods, but in a good way. If you're up to visit the Gunks, Angry Orchard, the Hudson river, love the beauty of the outdoors, and have other family or friends to visit in the area, definitely consider this home. Host was very responsive and had everything ready for us."
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Red Barn Retreat - Shawangunk Mountains Getaway
10.0 out of 10, Exceptional, (30)
"This was an absolutely amazing stay. My husband and I hand an amazing time with our two dogs celebrating our anniversary. We plan on returning again because we hand such a lovely time. We were greeted by our host who was so kind and helpful. All the recommendations were amazing and really helped us plan out our short time there. I wish we were able to stay longer but again we will be returning in the future!"
Red Barn Retreat - Shawangunk Mountains Getaway
complete privacy vacation home [private pool]
9.6 out of 10, Exceptional, (4)
"Our family stayed here while visiting a nephew at West Point, around 35 min away. The house was very clean and check-in was flawless. The beds and pillows were comfortable. We spent a lot of time in the game room playing ping pong, air hockey, and pool. We did not swim in the pool but it looked amazing. A perfect place for us and we will definitely return if in the area again."
The price is AED 2,626
AED 4,068 total
includes taxes & fees
6 Nov - 7 Nov
complete privacy vacation home [private pool]
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
7.2 out of 10, Good, (11)
"Great space and very comfortable for a group "
The price is AED 1,485
AED 3,076 total
includes taxes & fees
6 Nov - 7 Nov
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.
10.0 out of 10, Exceptional, (10)
"We wanted to spend a night in cold spring after a hike but couldn't find anything last minute in the area, so ended up booking this lovely property a little bit away. At first I was skeptical because of the drive (about 40-45 mins if I remember correctly). But I'm so glad we ended up doing this. Cold spring was just so busy and crowded, we couldn't even get lunch easily. The property is located right across a lake and is on a rather quite street. We reached the property around 5pm just in time...
The price is AED 1,502
AED 2,917 total
includes taxes & fees
12 Nov - 13 Nov
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
9.8 out of 10, Exceptional, (43)
"Wonderful rental, clean, modern, and a beautiful location."
The price is AED 694
AED 1,376 total
includes taxes & fees
7 Nov - 8 Nov
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
'The Glabin’: Garrison Gem w/ Deck & Fire Pit!
10.0 out of 10, Exceptional, (22)
"House was beautifully furnished with lovely touches of art work and lovely succulent plants. The hot tub was a great touch, and we enjoyed it every morning. The children loved exploring the property. Thank you!"
'The Glabin’: Garrison Gem w/ Deck & Fire Pit!
Nature Getaway: Charming Villa Near Trails and Parks
7.2 out of 10, Good, (9)
"Really cool house. We has some issues with our stay. It took a bit to get in touch with the manager to resolve the issues. The next day the brought most if the items needed that the h"
Nature Getaway: Charming Villa Near Trails and Parks
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!
Lakeview with Mountain View, Nature seeker friendly. Greenwood Lake
9.0 out of 10, Wonderful, (4)
"The home was in a perfect spot with lake views and is nicely close to town. We picked the home for its closeness to the rein fair and I’m so glad we did, It was wonderfully quiet and relaxing after a long day of hanging out at the rein fair !"
Lakeview with Mountain View, Nature seeker friendly. Greenwood Lake
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
9.6 out of 10, Exceptional, (23)
"We enjoyed our stay. The property was very clean and had lots of nice amenities."
The price is AED 613
AED 1,141 total
includes taxes & fees
10 Nov - 11 Nov
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
Midcentury Modern Cabin Home in the Woods- Under 2 Hrs From NYC!
10.0 out of 10, Exceptional, (116)
"The home is nestled in the woods and surrounded by amazing boulders . The mid century home is comfortable and stunning . We stayed at the house for a quiet weekend visiting friends in the area. The home is well equipped and a joy to stay and relax in . The area is a hikers dream and there are many amazing places to explore . The working fireplace adds a magical atmosphere. We hope to visit this property again . "
Midcentury Modern Cabin Home in the Woods- Under 2 Hrs From NYC!
Perfect for families and large groups
9.4 out of 10, Exceptional, (9)
"I rented this property for my co-workers who were here for a retreat at my home in the area, and at the local community center. This home had everything we needed, and the host was easy to communicate with. We will definitely consider using this property again for future guests coming for work and family gatherings."
Perfect for families and large groups
Lakefront House on Breathtaking Greenwood Lake, NY Short Term Rental 33118
9.8 out of 10, Exceptional, (112)
"The house is right on the water and the outer area is very relaxing."
Lakefront House on Breathtaking Greenwood Lake, NY Short Term Rental 33118
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
9.0 out of 10, Wonderful, (31)
"This is a very nice home with a well equipped kitchen. The living room and dining areas are spacious. We could have used more closet space but it wasn’t that much of an issue. The driveway could use grading but had ample parking."
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Contemporary Cozy Cottage
10.0 out of 10, Exceptional, (12)
"An absolutely charming cottage with beautiful decor and peaceful neighborhood… close to shopping and resturants…. Also conveniece ti train station if traveling into Manhattan… A great perfect place to stay if visiting the area. "
The price is AED 918
AED 1,385 total
includes taxes & fees
10 Nov - 11 Nov
Contemporary Cozy Cottage
5 Acre Modern Mountain Farm
9.2 out of 10, Wonderful, (27)
"We were originally just looking for a house that was close to angry orchard for a quick couples trip. But after being there for a couple of hours we realized that this home was going to be the bright spot for the weekend. We ended up enjoying the outdoors for the first night and only ended up staying at the orchard for a couple hours and just wanted to get back to the hours and enjoy the outdoors. I highly recommend this home to any family or group of friends looking for an amazing home for the...
The price is AED 1,264
AED 2,216 total
includes taxes & fees
2 Dec - 3 Dec
5 Acre Modern Mountain Farm
Charming 2 Bed backyard guesthouse close to Peekskill, WestPoint, & trails.
9.0 out of 10, Wonderful, (23)
"The home was very clean and had everything we needed - snacks games and a cute patio. The internet was iffy and never worked to stream on the bedroom tv. They came and checked it , but it didn’t improve. The host was very responsive and offered to ship an item our daughter left. We would rent again. "
Charming 2 Bed backyard guesthouse close to Peekskill, WestPoint, & trails.
Hiking/Climbing Paradise- walking distance to Mohonk/Gunks/Minnewaska
9.8 out of 10, Exceptional, (87)
"My family (husband and 12 year-old daughter) rented Michele's beautiful home for four weeks in August as a complete getaway from the city. My daughter also had a friend up and her dad came for a bit, too; there was plenty of room for everyone to have their own comfortable space--it was great! We made great use of the hot tub and the girls loved the indoor pool and air hockey. I cooked multiple times on the big grill and we loved eating outside. It was a lovely, homey space to have as a home away...
Hiking/Climbing Paradise- walking distance to Mohonk/Gunks/Minnewaska
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 property types in New Windsor

Beautiful Cozy 2 br in-law apt, prime Hudson Valley location
9.6 out of 10, Exceptional, (14)
"Perfect location to USMA! Exactly what we needed for a short visit and a fully stocked kitchen to make a home cooked meal. "
Beautiful Cozy 2 br in-law apt, prime Hudson Valley location
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
10.0 out of 10, Exceptional, (38)
"This place was very clean and well maintained. We didn’t get to use the game room much but it was a nice touch. It had all of the essentials which was a nice touch. It is centrally located between all three Bethel locations. Overall, it was a very nice stay. Hope to stay there on our next trip. "
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (105)
"Super cozy apartment with a beautiful view. Very welcoming host and a great place for a short stay near Bear Mountain. "
The price is AED 617
AED 911 total
includes taxes & fees
11 Nov - 12 Nov
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
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.