Vacation rentals in Highland

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Popular amenities for Highland vacation rentals

Stay near Highland's top sights

Walkway Over the Hudson State Historic Park158 locals recommend
The Culinary Institute of America70 locals recommend
Mid-Hudson Children's Museum31 locals recommend
Marist College17 locals recommend
Shadows on the Hudson20 locals recommend
Poughkeepsie Station Parking47 locals recommend

Other great vacation rentals in Highland

Guest favorite
Home in Windham
5 out of 5 average rating, 22 reviews

Cozy Mountain Cabin Near Windham Slopes

MardaRating, 5 stars2 weeks ago
Impressed by the attention to detail! Communication was seamless! The host was responsive and considerate, ensuring our stay was comfortable from start to finish The host stocked the kitchen with essentials. Highly recommend to anyone looking for a cozy and clean place to stay!
Top guest favorite
An outdoor deck area is shown featuring several light-colored Adirondack chairs arranged around a stone fire pit. A neatly stacked pile of firewood is positioned against a backdrop of trees, creating a natural setting for relaxation and gatherings.
Home in Millerton
4.97 out of 5 average rating, 184 reviews

Vacation Home In Millerton

BettyRating, 5 stars2 weeks ago
We wanted to get away from the city for some peace and quiet and Corina’s place was exactly what we were looking for. It felt very tucked away. The home was stocked with pretty much anything I think one would need. The outdoor space is huge, nice and safe for our dog to frolic. Loved the large firepit - wish we had more time to sit outside. Corina was super friendly, accommodating, and extremely quick to respond to any inquiries, so you should be in good hands if you need any help. I like to try a new airbnb whenever I can, but when we return to Millerton, we’ll be going back to Corina’s!
Guest favorite
A functional laundry area is presented, featuring stacked washer and dryer units in sleek white. A door leads to the outside, and a small rug covers the floor, providing traction. Shelves above hold extra linens, enhancing the space's practicality.
Home in Hensonville
5 out of 5 average rating, 10 reviews

Perfect Windham & Hunter Ski House 2 Miles to Mntn

PeterRating, 5 stars2 months ago
One of the best Airbnbs I've stayed at. The house is amazing - spacious, cozy, ad each room had their own temperature control! Plenty of communal space and the kitchen was very functional. The hosts were so responsive and nice and even offered to mail a piece of clothing we had left at the house afterwards. Definitely would come back again and highly recommended.
Guest favorite
A wooden home is surrounded by lush greenery and manicured gardens. Flower beds with colorful blooms are visible in the foreground, while the house features a large deck. Mature trees provide a natural backdrop, enhancing the serene outdoor atmosphere.
Cottage in Greenwood Lake
4.96 out of 5 average rating, 48 reviews

5 bedroom 7 beds Cottage Sauna, Hike, Winery & Ski

JasonRating, 5 stars2 weeks ago
We had a great time at Carmine's place, highly recommend.
Top guest favorite
A spacious outdoor deck features black lounge chairs set beside a low wooden table. A contemporary black chiminea stands as a focal point, surrounded by trees and open land, creating a relaxing atmosphere for outdoor gatherings.
Home in Athens
5 out of 5 average rating, 16 reviews

Lake house with arcade games

AdrienneRating, 5 stars3 months ago
Rosane and Daniel's place was great. Very clean and comfortable. It was well stocked with everything we needed.
Guest favorite
A spacious outdoor terrace is shown, featuring a wooden railing and gray flooring. Two colorful Adirondack chairs are positioned alongside a picnic table. Lush greenery surrounds the area, and a grill is visible in the corner, adding to the outdoor living space.
Home in Tannersville
4.93 out of 5 average rating, 28 reviews

Luxury Spacious Private Home w/tub! Enjoy Spring

SantiagoRating, 5 stars2 months ago
It’s a fantastic place to stay—a well-designed, private home with a great layout. Conveniently located near the mountain, it’s perfect for skiing while still offering a peaceful retreat.
Superhost
An outdoor deck area features a circular table surrounded by six chairs. Two lounge chairs are positioned nearby, offering a comfortable seating arrangement. A gas grill is visible at the edge of the deck, set against a backdrop of lush greenery.
Chalet in Fleischmanns
4.73 out of 5 average rating, 158 reviews

Sauna equipped Belleayre Cozy Cabin

ChloeRating, 5 stars2 months ago
Perfect for a ski weekend. Sauna is great, and location cannot be beat.
Guest favorite
Home in Monticello
4.87 out of 5 average rating, 15 reviews

Luxurious & Newly Renovated Catskills Lakehouse

ShelbyRating, 5 stars1 month ago
We had a weekend youth retreat and stayed at Alan’s spacious home. We had a great time together. the home was as described, the hosts were very friendly and accommodating, and everything was clean and in good condition. Would definitely recommend for a big group!

Quick stats about vacation rentals in Highland

  • Total rentals

    10 properties

  • Nightly prices starting at

    $40 before taxes and fees

  • Total number of reviews

    600 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    10 properties include access to wifi

Destinations to explore

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