Vacation rentals in Highland, NY

This Poughkeepsie apartment is conveniently located within walking distance of local restaurants, breweries, and the Walkway Over the Hudson, offering easy access to the city's attractions. The apartment consistently receives excellent ratings for its location, cleanliness, and overall user experience.
This two-bedroom, one-bathroom rental can comfortably accommodate up to six guests. Enjoy a fully equipped kitchen, two balconies, 125 cable TV channels, a Roku TV, and a relaxing ambiance, perfect for a comfortable and enjoyable stay.

This spacious waterfront estate is located in Highland, just 90 minutes from New York City, offering a peaceful escape from the hustle and bustle of the city. The property has earned excellent ratings for its cleanliness, location, and overall experience.
This 6-acre property features a large home with four bedrooms and two bathrooms, comfortably accommodating up to 10 guests. The estate boasts a private pool, a wood-fired pizza oven, a gas grill, a basketball court, a soccer net, a fire pit, and a deck with seating for 12, making it ideal for families and groups seeking a memorable vacation.

This charming cabin is located in the serene woods of the Hudson Valley, a short two-hour drive from New York City and a 15-minute drive from the Poughkeepsie train station. The cabin boasts excellent user, location, and cleanliness ratings, making it a highly recommended choice for travelers.
The cabin features three bedrooms and one bathroom, comfortably accommodating up to six guests. Guests can enjoy modern amenities like a fully equipped kitchen, a fitness center, a garden, and a spacious outdoor area with a fire pit, perfect for relaxing evenings under the stars.

This charming 1850s barn, located just 10 minutes from New Paltz and a short drive from I-87, offers a peaceful retreat in the Hudson Valley. Guests rave about the excellent location, cleanliness, and overall experience, making it a popular choice for travelers. The renovated barn features one bedroom and one bathroom, comfortably accommodating two guests. Amenities include a wood-burning stove, clawfoot tub, outdoor fire pit, and access to a shared farmhouse with a washer/dryer, as well as a treehouse and gazebo on the property.

This Fairview apartment is located in Hyde Park, New York, just north of Poughkeepsie and a short drive from Rhinebeck, offering easy access to the Hudson Valley's attractions. The apartment consistently receives excellent ratings for its cleanliness, location, and overall guest experience.
The apartment features a unique design that blends mid-century modern style with vintage accents, creating a stylish and eclectic atmosphere. It comfortably accommodates up to four guests and includes a fully equipped kitchen, a spacious living room, a screened-in porch with a hot tub, and a pet-friendly policy.

This Highland, NY A-frame log cabin boasts a secluded location on two wooded acres, a short 10-minute drive from both New Paltz and Poughkeepsie.
This four-bedroom, four-bathroom house sleeps eight guests and features a 100-inch screen theater room, game room, private gym, saltwater pool, cedar barrel sauna, hot tub, and multiple fireplaces.

This charming one-bedroom apartment is located in a central Poughkeepsie neighborhood, just a short drive from Vassar College, Marist College, the Walkway Over the Hudson, and the train station. Guests consistently rate the apartment excellent for its cleanliness, location, and overall experience.
The apartment comfortably sleeps two guests and includes a full-size bed, a kitchen, a living room, and a bathroom. Enjoy amenities like complimentary bicycles, a private entrance with French doors, and a garden, making it the perfect home base for exploring Poughkeepsie.

This Poughkeepsie residence is located near Franny Reese State Park and Vanderbilt Mansion National Historic Site, providing easy access to notable local attractions.
This spacious home accommodates up to 18 guests with five bedrooms and two bathrooms, featuring air conditioning, heating, and an iron for guest convenience.

This charming five-bedroom townhouse is located in the Poughkeepsie Historic District, just a short walk from the city's attractions, restaurants, and shops. The apartment consistently receives excellent ratings for cleanliness, location, and overall user experience.
The spacious home offers ample room for families or groups of friends, accommodating up to eight guests. Enjoy modern conveniences like air conditioning, a dishwasher, and a garden, perfect for relaxing or dining outdoors.

This studio apartment is located in Hyde Park, just a short walk from the Hudson River, the Vanderbilt Estate, and other local attractions. The studio has received excellent ratings for location, cleanliness, and overall user experience.
The unit is a spacious studio that comfortably accommodates two guests. It comes equipped with amenities like air conditioning, parking, internet, and a kitchen with a fridge. You can also enjoy keyless entry and a quiet second-floor location.

This Highland, NY apartment is conveniently located near the Mid-Hudson Bridge, offering easy access to Marist College and Vassar College, and the Walkway Over the Hudson.
This three-bedroom, three-bathroom rental sleeps six guests and features a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, plus air conditioning, parking, and internet access.

This luxurious mid-century house offers a waterfront bluff experience on the Hudson River, located two hours north of New York City in the heart of the Hudson Valley.
This designer retreat sleeps 8 guests and features 4 bedrooms, 3 bathrooms, air conditioning, and a kitchen equipped with a fridge, freezer, microwave, and dishwasher, all set on a property with a garden and deck providing direct river views.

This Highland, New York farmhouse offers a family-friendly escape, a 33-minute drive from Mohonk Lake and 12 minutes from the Walkway Over the Hudson State Historic Park.
The three-bathroom property sleeps eight guests and includes a fully equipped kitchen, Wi-Fi, laundry facilities, a private garden, and barbecue, with nearby access to Quartz Rock Vineyard and Franny Reese State Park.

This historic home is located in Milton, New York, directly across the street from Buttermilk Falls Resort & Spa and Henry's at the Farm Restaurant, with the Hudson River just a short walk away. It consistently receives excellent ratings for its location, cleanliness, and overall guest experience.
The house features a spacious kitchen, a full bath, a living room, a sunroom, and a large garden. It can accommodate up to four guests and allows one well-behaved dog per stay. Guests can enjoy amenities like a fire pit, Adirondack chairs, and Roku Guest Mode for streaming services.

This 2-bedroom, 1-bathroom apartment in Poughkeepsie is located in a district offering easy access to local attractions, including the Walkway Over the Hudson State Historic Park, a significant local landmark.
This well-appointed unit accommodates up to 6 guests and includes internet, a kitchen, and air conditioning, with convenient access to downtown Poughkeepsie businesses and transportation routes for exploring the Hudson Valley.

This charming 1850s barn, located just 10 minutes from New Paltz and a short drive from I-87, offers a peaceful retreat in the Hudson Valley. Guests rave about the excellent location, cleanliness, and overall experience, making it a popular choice for travelers. The renovated barn features one bedroom and one bathroom, comfortably accommodating two guests. Amenities include a wood-burning stove, clawfoot tub, outdoor fire pit, and access to a shared farmhouse with a washer/dryer, as well as a treehouse and gazebo on the property.

This historic home is located in Milton, New York, directly across the street from Buttermilk Falls Resort & Spa and Henry's at the Farm Restaurant, with the Hudson River just a short walk away. It consistently receives excellent ratings for its location, cleanliness, and overall guest experience.
The house features a spacious kitchen, a full bath, a living room, a sunroom, and a large garden. It can accommodate up to four guests and allows one well-behaved dog per stay. Guests can enjoy amenities like a fire pit, Adirondack chairs, and Roku Guest Mode for streaming services.

This charming cabin is located in the serene woods of the Hudson Valley, a short two-hour drive from New York City and a 15-minute drive from the Poughkeepsie train station. The cabin boasts excellent user, location, and cleanliness ratings, making it a highly recommended choice for travelers.
The cabin features three bedrooms and one bathroom, comfortably accommodating up to six guests. Guests can enjoy modern amenities like a fully equipped kitchen, a fitness center, a garden, and a spacious outdoor area with a fire pit, perfect for relaxing evenings under the stars.

This charming five-bedroom townhouse is located in the Poughkeepsie Historic District, just a short walk from the city's attractions, restaurants, and shops. The apartment consistently receives excellent ratings for cleanliness, location, and overall user experience.
The spacious home offers ample room for families or groups of friends, accommodating up to eight guests. Enjoy modern conveniences like air conditioning, a dishwasher, and a garden, perfect for relaxing or dining outdoors.