Photo by Eugenio Ruiz

Holiday Homes in Peekskill

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Featured Holiday Homes in Peekskill

Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
10.0 out of 10, Exceptional, (7)
"Absolutely loved our stay! The house was cozy, comfortable, and well-equipped. The host was responsive and made sure everything was just right. Highly recommend!!"
The price is NZ$1,443
includes taxes & fees
3 Oct - 4 Oct
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
6.6 out of 10, (8)
"My family was in the area for an event. We had a very pleasant time and the house is spacious and perfect for a weekend getaway!"
The price is NZ$1,343
includes taxes & fees
3 Oct - 4 Oct
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
9.0 out of 10, Wonderful, (26)
"The house was just as pictured. Past reviews were helpful. Knowing about the driveway in advance was helpful. It is an odd floorplan, but it worked out fine for us. The kitchen is lovely and had everything we needed. We were in the area for the Stormville antique show. The house is in a great location, central to many great attractions. "
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
The Woodbury Cottage
8.4 out of 10, Very good, (7)
"This property and rental exceeded my expectations by far! The pictures do not do justice. Has everything you need and more to have a perfect stay. Everything was clean and it felt like home. Me and my sister stayed here 3 nights and did not want to leave. The property is beautiful! I read the reviews before coming here and I have to say there were two things said, that there was no microwave and not enough lighting. The host immediately got a microwave and updated the lighting! I found that so...
The Woodbury Cottage
Historic Newburgh Home w/ Hudson River Views!
2.0 out of 10, (1)
Historic Newburgh Home w/ Hudson River Views!
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
10.0 out of 10, Exceptional, (29)
"Awesome girls weekend. Great layout of the house and the pool got a lot of use! Didn’t explore much but can’t wait to come back and stay next year! Thanks for renting out your home."
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
Nature Getaway: Charming Villa Near Trails & 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 & Parks
Family Friendly Fun + Easy Walk to Main Street Center
9.8 out of 10, Exceptional, (9)
"We have a cadet at West Point and were visiting for A-Day. This home proved to be the perfect spot for hosting our group of five ranging in ages from 20-83. The home was spotless and so well-appointed. The hosts truly thought through everything that a guest might need and it was right where you would expect it to be. All of the rooms were comfortable and the cute town of Beacon is within easy walking distance. The entire process was smooth and the hosts were super responsive. They even provided...
Family Friendly Fun + Easy Walk to Main Street Center
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
10.0 out of 10, Exceptional, (71)
"Hoyse is in a beautiful location and was very clean. The host was responsive and helpful. I would give it 5 stars if it actually had 3 bedrooms."
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Charming 2 Bed backyard guesthouse close to Peekskill, WestPoint, & trails.
9.0 out of 10, Wonderful, (22)
"Stay was absolutely wonderful, property was lovely and super easy to get to and from sleepy hollow. Definitely recommended."
Charming 2 Bed backyard guesthouse close to Peekskill, WestPoint, & trails.
'The Glabin’: Garrison Gem w/ Deck & Fire Pit!
10.0 out of 10, Exceptional, (20)
"We had a wonderful stay, the property is gorgeous and pristine. Wonderful communication! We'll definitely be back, thank you!"
'The Glabin’: Garrison Gem w/ Deck & Fire Pit!
Ossining Vacation Rental Near River, Trails & MTA!
6.0 out of 10, (2)
"The house was nice & spacious. I do feel like it could use more seating in the living room, considering it can hold up to 11 guests. It would aslo be nice if there were tv's in the guest rooms upstairs. Also, maybe make sure the cleaning crew removes cobweks. "
Ossining Vacation Rental Near River, Trails & MTA!
Waterfront Lake House. Near NYC and hiking trials. Complimentary kayaks provided
2.0 star property
10.0 out of 10, Exceptional, (1)
"It is a small property but an excellent location on the lake. Kayaks and paddle boat provided were an added bonus. Owner is very responsive and helpful. Kitchen could be better equipped. Overall a very pleasant and enjoyable stay."
Waterfront Lake House. Near NYC and hiking trials. Complimentary kayaks provided
Hudson Valley's Nature Experience with Incredible Views!
9.0 out of 10, Wonderful, (2)
"We stayed here for A - Day to give our cadet time away from post to decompress. Beautiful property with an amazing patio. Great food choices nearby as well as Walmart to stock up our cadet before he started his Academic Year. "
Hudson Valley's Nature Experience with Incredible Views!
Renovated 1850's Cottage on Storm King Mountain
9.8 out of 10, Exceptional, (12)
"House and property were amazing. Extremely serene. Our son is at West Point and your property was the perfect location for him to hang out with us and relax."
Renovated 1850's Cottage on Storm King Mountain
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
10.0 out of 10, Exceptional, (35)
"Communication and accommodations were great!! Clean place and friendly hosts. "
The price is NZ$863
includes taxes & fees
27 Oct - 28 Oct
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
Majestic RiverView Estate - Breathtaking Views
10.0 out of 10, Exceptional, (2)
"This house was beautiful and perfect for a weekend with friends. There is plenty of space for everyone to spread out and we enjoyed the scenic view from the back deck all weekend. Dan was very responsive from start to finish and we did not encounter any problems throughout our stay. I would highly recommend!"
Majestic RiverView Estate - Breathtaking Views
Contemporary Cozy Cottage
10.0 out of 10, Exceptional, (11)
"We had a fantastic stay at this house! The place is cozy, contemporary, and immaculately clean. The comfort level was top-notch, making it easy to relax and enjoy our time there. Nadia, the host, was wonderful with communication, ensuring all our needs were met promptly. The house was well stocked with everything we needed. The neighborhood is very cute and added to the overall charm of our stay. Checking in and out was a breeze. Highly recommended!"
The price is NZ$594
includes taxes & fees
2 Oct - 3 Oct
Contemporary Cozy Cottage
Amazing Home Near West Point, Shopping, Skiing and Legoland
10.0 out of 10, Exceptional, (11)
"Very nice property in a nice neighborhood . Had all the amenities we needed and Ruth was super responsive. If we are in the area again, we will def stay at this location. "
Amazing Home Near West Point, Shopping, Skiing and Legoland
Duplex WATERFRONT HOME
10.0 out of 10, Exceptional, (5)
"This place is much more spacious than it looks in the pictures. When you walk through the front door, you are immediately greeted with an amazing view of the Hudson River. The sunrise over the river is beautiful. We easily went back and forth over the bridge to Sleepy Hollow and there are great restaurants right near the house. Would definitely stay here again."
Duplex WATERFRONT HOME
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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 Peekskill

Global Luxury Suites White Plains
3.5 star property
6.8 out of 10, (24)
"Central property within walking distance of nearby shops. "
Global Luxury Suites White Plains
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (99)
"Wonderful hilltop location. Beautiful view. Nice apartment. Great hosts. Wish we could have stayed longer! "
The price is NZ$403
includes taxes & fees
2 Oct - 3 Oct
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
10.0 out of 10, Exceptional, (47)
"This property was very comfortable, clean and had everything we needed. I was able to visit with my West Point Cadet for a weekend and cook a meal for her and we had a lovely time. "
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
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.