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Holiday Homes in Cortlandt

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Featured Holiday Homes in Cortlandt

LUXE 3BD/2BA 29 min>NYC w/Parking & deck

10.0 out of 10, Exceptional, (13)
"The listing is accurate, perfect location to walk to train, restaurants and so much more! We were delighted to stay there and we look forward to staying in the future!! Thanks Dan"
LUXE 3BD/2BA 29 min>NYC w/Parking & deck

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

Charming 3-bedroom Newly Renovated house in Highland Falls with AC, WiFi

Charming 3-bedroom Newly Renovated house in Highland Falls with AC, WiFi

Charming Highland Falls Home < 2 Mi to West Point!

10.0 out of 10, Exceptional, (3)
"Beautiful cozy home. Well stocked. Good communication with management/owners Overall great experience!!! ❤️"
Charming Highland Falls Home < 2 Mi to West Point!

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.

PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

9.0 out of 10, Wonderful, (18)
"Great space. Clean sheets and towels. Wonderful shower. Great balcony I highly recommend!"
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

Updated Getaway w/ Pool & Hot Tub on < 3 Acres!

10.0 out of 10, Exceptional, (28)
"Beautiful property, with cozy linens in every room, incredibly well maintained property, and lovely views. The welcome book had clear instructions, there were great lawn games, lots of suggestions to eat too. The icing on the cake was the welcome basket, complete with Halloween treat bag for our little one! "
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!

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

9.0 out of 10, Wonderful, (32)
"We enjoyed our stay however, the listing states all the beds are king sized and only 2 are. The other 2 are queen. Also (note for host) we forgot a pair of sunglasses and would like to have them mailed back if they are found, could you contact me if possible."
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

'The Glabin’: Garrison Gem w/ Deck & Fire Pit!

10.0 out of 10, Exceptional, (23)
"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!

Ossining Vacation Rental Near River, Trails & MTA!

7.6 out of 10, Good, (5)
"Family funeral brought us to the area. House was excellent for us "
Ossining Vacation Rental Near River, Trails & MTA!

Amazing 3BR/3BA! Croton on Hudson!

7.0 out of 10, Good, (2)
"We found the house pleasant and centrally located"
Amazing 3BR/3BA! Croton on Hudson!

Cozy House 3 Blocks From West Pt

9.8 out of 10, Exceptional, (6)
"Perfect location very close to Thayer Gate, West Point Museum, Visitors Center and local restaurants in Highland Falls. Host is an excellent communicator and has put a lot of thought into this clean and comfortable home. Cannot wait to visit again soon. "
Cozy House 3 Blocks From West Pt

Mountain house perfect winter getaway near skilling

8.0 out of 10, Very good, (13)
"The place was perfect for the occasion! My partner and two friends were in town for a wedding. The wedding venue was only 6 minutes away so it was the ideal location! The place was clean and communication with the host was great! Would recommend to anyone. "
The price is AU$411
includes taxes & fees
3 Dec - 4 Dec
Mountain house perfect winter getaway near skilling

Up-to-date Home w/ Pool, Playground & Fireplace!

Up-to-date Home w/ Pool, Playground & Fireplace!

Our Rockbound Highland Home - 2 Blocks from Thayer Gate - 1/2 Block to Main St.

10.0 out of 10, Exceptional, (37)
"Review of VRBO Home - Our Rockbound Highland Rating: ⭐⭐⭐⭐⭐ (5/5) - Exceeded Expectations I recently stayed at a VRBO home that completely surpassed my expectations! The home was not only beautiful but incredibly comfortable, offering all the amenities promised in the listing. It felt like a home away from home and matched the online photos perfectly, which made our stay even more enjoyable. The check-in process was seamless, and the communication with the property manager was top-notch. This...
Our Rockbound Highland Home - 2 Blocks from Thayer Gate - 1/2 Block to Main St.

Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.

10.0 out of 10, Exceptional, (11)
"This property was even more beautiful than it appeared in the photos. The wooded backyard was also spacious and lovely. We were so happy with the view of the lake and how peaceful the space was. The owners are easy to communicate with and prompt to respond. We will absolutely be going back. "
The price is AU$1,325
includes taxes & fees
3 Dec - 4 Dec
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.

Renovated 1850's Cottage on Storm King Mountain

9.8 out of 10, Exceptional, (14)
"Great place!"
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, (40)
"We loved our two nights here! Space was spotless and comfortable for 4 of us. Location was central to everything. "
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

Contemporary Cozy Cottage

10.0 out of 10, Exceptional, (14)
"Secluded and filled with every conveniece you might desire. We especially appreciated the air fryer for our leftovers!"
The price is AU$581
includes taxes & fees
3 Dec - 4 Dec
Contemporary Cozy Cottage

New 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space

10.0 out of 10, Exceptional, (22)
"Easy 30 minute drive to West Point. In the country, yet outlet mall, restaurants and things to do all within 30 minutes. Very responsive when I text as the keypad didn’t work. They let us in remotely. We had several in our family and we were all comfortable. Nice fire pit, swim spa, and clean. "
The price is AU$1,111
includes taxes & fees
3 Dec - 4 Dec
New 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space
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 Cortlandt

Charming 2 Bed backyard guesthouse close to Peekskill, WestPoint, & trails.

9.0 out of 10, Wonderful, (23)
"Homeowner responded promptly to inquiries. Property was well prepared. "
Charming 2 Bed backyard guesthouse close to Peekskill, WestPoint, & trails.

Global Luxury Suites White Plains

3.5 star property
6.8 out of 10, (26)
"Great location, friendly people, great apartment "
Global Luxury Suites White Plains

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 AU$382
includes taxes & fees
3 Dec - 4 Dec
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.