Compare vacation rentals in Highlands, NY from 100+ sites!

This Cold Spring apartment is located in a historic district, perched atop a hill, within walking distance of the village's restaurants, shops, and hiking trails.
The two-bedroom apartment features a private patio, a cozy living room with a gas fireplace, and a fully equipped kitchen.

This Fort Montgomery vacation home is nestled near Bear Mountain State Park, offering easy access to West Point, Garrison, Cold Spring, and Storm King Mountain.
The 4-bedroom, 2-bathroom house sleeps 8 comfortably, features a private pool, and includes family-friendly amenities like a crib, children's books, and toys.

This charming apartment is located in the Ondaora Park community in Highland Falls, just a short distance from Thayer Gates and West Point. It has received excellent ratings for its cleanliness, location, and overall experience.
The entire house is available for rent, accommodating up to six guests. The apartment offers a range of amenities including a swimming pool, garden, parking, and a fully equipped kitchen with a refrigerator and dishwasher.

This 100-year-old house in Cornwall, New York is a short drive from the Storm King Art Center, Woodbury Commons, and the Cornwall town center. The property is highly rated by guests, receiving excellent scores for location, cleanliness, and overall experience.
The house has five bedrooms and two bathrooms, comfortably accommodating up to nine guests. Enjoy amenities like a swimming pool, a garden, and a fireplace, perfect for relaxation and entertainment.

This Stony Point house rental, located in Tomkins Cove, offers easy access to Bear Mountain State Park (10 miles) and Palisades Center mall (13 miles).
The 1300-square-foot home features one bedroom, one bathroom, and can comfortably accommodate up to 15 guests, boasting a fully equipped kitchen, free Wi-Fi, private parking, and a terrace.

This charming house is located in Cortlandt, a short drive from Peekskill, offering easy access to attractions like Mohansic Golf Course, Bear Mountain State Park, and Michie Stadium. The cozy home features three bedrooms, a comfortable living space, and can accommodate up to six guests. This Peekskill rental offers amenities like a fully equipped kitchen, air conditioning, a private garden, and parking.

This 3-bedroom apartment is located in Fort Montgomery, about an hour north of New York City, offering stunning views of the Hudson River and mountains. It has excellent user, location, and cleanliness ratings.
The apartment is spacious and modern, accommodating up to 8 guests. It features a private hiking trail, a private deck and backyard, and is close to West Point Academy, the Appalachian Trail, Bear Mountain, and Cold Springs, offering access to numerous outdoor activities.

This family-friendly vacation home is located in Cortlandt, just a short distance from Peekskill, within 2 miles of NewYork-Presbyterian Hudson Valley Hospital, Hudson Valley Center for Contemporary Art, and Paramount Hudson Valley Theater, offering easy access to attractions and amenities. This property has received excellent ratings for location, cleanliness, and overall user experience.
The home features 2 bedrooms and 1 bathroom, comfortably accommodating up to 4 guests. Enjoy a relaxing stay with amenities like a private patio, garden, and barbecue grills, along with a fully equipped kitchen, free Wi-Fi, a fireplace, and air conditioning.

This Highland Falls vacation home is a 15-minute walk from the West Point Museum and a 4-minute drive from Bear Mountain State Park.
The 970-square-foot property features two bedrooms, one bathroom, and accommodates four guests, offering amenities such as a fully equipped kitchen, Wi-Fi, air conditioning, and on-site parking.

This Highland Mills vacation house is located 9.4 miles from Metro-North Harriman Station and 18 miles from Bear Mountain State Park, offering proximity to Woodbury Commons and Storm King State Park.
This 1210 sq ft, 3-bedroom rental home accommodates up to 8 guests with amenities including a full kitchen, air conditioning, free WiFi, and a terrace, ideal for outdoor enthusiasts with nearby skiing, cycling, and hiking.

The Abbey Inn & Spa is conveniently located in Peekskill, within walking distance of attractions like the Lincoln Depot Museum, Dramatic Hall, and Peekskill Landing Park. This makes it easy to explore Peekskill's history and enjoy the scenic views. The hotel features a range of amenities including a bar, restaurant, fitness center, sauna, steam bath, and spa center. Guests can also enjoy free parking and Wi-Fi access.

This Garrison cottage is located in Philipstown, just a short drive from the Bear Mountain Bridge, 15 minutes from West Point, and 60 minutes from NYC. This property has excellent user ratings and is a great choice for families and groups. The home has 3 bedrooms and 3 bathrooms, comfortably accommodating up to 8 guests. Enjoy amenities such as a fully equipped kitchen, a private terrace, and a garden, perfect for relaxing after a day of hiking or exploring the nearby attractions.

This 3-bedroom, 1-bathroom apartment in Woodbury offers a unique Narnia-esque setting with mountain views, located minutes from the Storm King Art Center and within easy reach of local breweries, distilleries, and farm-to-table dining.
This rental accommodates up to 4 guests and features a wrap-around deck, air conditioning, internet, a kitchen, and parking, with convenient access to vista-packed hiking trails and situated just over an hour from New York City.

This Highland Falls apartment rental is centrally located, offering easy access to Hudson Valley attractions.
The two-bedroom unit, sleeping up to six guests, features a fully equipped kitchen, in-unit laundry, free high-speed Wi-Fi, and free on-site parking.

This 3-bedroom, 2-bathroom condo in Fort Montgomery offers a peaceful retreat with a guest capacity of 6, featuring essential amenities such as a full kitchen with a dishwasher, air conditioning, and parking. Located in Fort Montgomery, this dwelling is conveniently situated for exploring local attractions, providing a calm and comfortable atmosphere for travelers.

This Cold Spring stone house, a short walk from the Hudson River beach and Metro-North train station, offers easy access to Cold Spring's shops, restaurants, and hiking trails.
The three-bedroom, two-bathroom home includes air conditioning, Wi-Fi, a kitchen, parking, and accommodates up to four guests, perfect for families or small groups exploring the Hudson Valley.