Best Vacation rentals and Airbnb offers in Highland, NY
10 1 review
Highland, NY
07/15 – 07/27
$468/nighttotal: $5616 (12 )
Two Tillson
1 2
apartment , Highland
This apartment is located on the grounds of the Inn at Twaalfskill in Highland, adjacent to the Hudson Valley Rail Trail and within minutes of Vassar College, Marist University, and the Culinary Institute of America. This 2-bedroom, 2-bathroom residence accommodates up to 5 guests and features air conditioning, a kitchen with a fridge and dishwasher, and garden and parking access.
Highland, NY
07/15 – 07/27
$839/nighttotal: $10068 (12 )
Views On Hudson River / Luxury Modern Home
4 2
apartment , Highland
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.
9.6 11 reviews
Highland, NY
07/15 – 07/27
$411/nighttotal: $4932 (12 )
Pleasant Lane Family Retreat
1 2
apartment , Red Oaks Mill
This three-bedroom, two-bathroom Poughkeepsie apartment rental, located on Pleasant Lane near Red Oaks Mill, offers easy access to local attractions, though precise distances aren't provided. The 3-bedroom dwelling boasts a finished basement with a large TV, full kitchen, patio with fire pit, in-unit laundry, and kid-friendly amenities like a crib and bunk bed, comfortably sleeping seven guests.
9.9 98 reviews
Highland, NY
07/15 – 07/27
$239/nighttotal: $2868 (12 )
Magical Charming 1850s Barn On Idyllic Former Farm
1 2
farm , Rifton
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.
Highland, NY
07/15 – 07/27
$283/nighttotal: $3396 (12 )
Industry Style Open Concept Downtown
2 2
apartment , Poughkeepsie
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.
9.9 153 reviews
Highland, NY
07/15 – 07/27
$188/nighttotal: $2256 (12 )
Historic Hyde Park Studio | Minutes From Fdr & Cia
1 2
apartment , Hyde Park
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.
8.9 11 reviews
Highland, NY
07/15 – 07/27
$284/nighttotal: $3408 (12 )
Quiet Hudson Valley Escape
1 2
apartment , Highland
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.
9.7 111 reviews
Highland, NY
07/15 – 07/27
$148/nighttotal: $1776 (12 )
Your Own Pied-a-terre "Walkway Over The Hudson"#2
1 2
apartment , Poughkeepsie
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.
10 47 reviews
Highland, NY
07/15 – 07/27
$1602/nighttotal: $19224 (12 )
Hudson Valley Estate 90 Min From Nyc Pet Friendly
4 2
apartment , Highland
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.
9.7 27 reviews
Highland, NY
07/15 – 07/27
$1387/nighttotal: $16644 (12 )
Modern Designer Cabin In Woods W/ 5-star Amenities
1 2
cabin , Highland
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.
9.5 191 reviews
Highland, NY
07/15 – 07/27
$235/nighttotal: $2820 (12 )
Historic 1 Br Family Home Near Buttermilk Falls
1 2
apartment , Milton
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.
9.6 4 reviews
Highland, NY
07/15 – 07/27
$595/nighttotal: $7140 (12 )
Stunning 5-bedroom House With Ac / Heat In Charming Poughkeepsie Ny
5 2
apartment , 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.
Discover Family-Friendly Vacation Rentals in Highland, NY
The right family vacation rental in Highland, NY makes all the difference, keeping you close to top city attractions.
9.4 3 reviews
Highland, NY
07/15 – 07/27
$542/nighttotal: $6504 (12 )
Black Walnut Tree Farm: 50-acres + Private Pond
4 2
apartment , Clintondale
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.
Best Highland, NY vacation rentals with parking
9.9 146 reviews
Highland, NY
07/15 – 07/27
$257/nighttotal: $3084 (12 )
2br|1 King 1 Queen Bed|balcony|parking|strong Wifi
2 2
apartment , Poughkeepsie
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.
9.7 52 reviews
Highland, NY
07/15 – 07/27
$692/nighttotal: $8304 (12 )
Charming Townhouse In Historic District
5 2
apartment , Poughkeepsie
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.
Frequently Asked Questions about vacation rentals in Highland, NY
What sports or outdoor activites can visitors enjoy in and around Highland, NY?
You can enjoy hiking, biking, and fishing at Minnewaska State Park Preserve, or try kayaking or canoeing on the Hudson River.
What are the best Airbnb and vacation rentals in Highland, NY?
What amenities are commonly available in vacation rentals in Highland, NY?
Vacation rentals in Highland typically offer amenities like kitchens, laundry facilities, and Wi-Fi. Some may also have outdoor space, like a patio or balcony.
What are the best vacation rentals with a pool in Highland, NY?
Top Vacation Rentals with Balconies in Highland, NY
Enjoy a Highland, NY vacation rental with a balcony and stunning city skyline views for a truly memorable stay.
10 74 reviews
Highland, NY
07/15 – 07/27
$557/nighttotal: $6684 (12 )
Wooded Rhinebeck-beacon Area Escape W/outdoor Spa
1 2
apartment , Fairview
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.
Find the Best Dog-Friendly Vacation Rentals in Highland, NY
Travel with ease to Highland, NY with pet-friendly rentals located near local dog parks and scenic city walks.
9.8 78 reviews
Highland, NY
07/15 – 07/27
$588/nighttotal: $7056 (12 )
Luxurious Private Log Cabin Retreat In Nature
1 2
cabin , Haviland
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.