Vacation rentals in Highland

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Popular amenities for Highland vacation rentals

Other great vacation rentals in Highland

Top guest favorite
A modern kitchen corner features a Keurig coffee maker alongside a selection of coffee pods arranged in a tray. A pale pink vase holds delicate flowers, and a woven basket contains snacks, creating an inviting space for preparing morning beverages.
Apartment in Clintondale
5 out of 5 average rating, 30 reviews

Cozy Cottage Getaway in Clintondale Near New Paltz

SankalpRating, 5 stars6 days ago
5 stars all the way. The location, the interiors, the equipment, linens, provisions were all top notch. Nick and Mar were generous and responsive hosts. One of the best stays I’ve had!
Guest favorite
A fire pit, surrounded by log seating, emits a warm glow in a natural setting. Green foliage and trees provide a serene backdrop, while the evening sky transitions to dusk, enhancing the peaceful atmosphere of the outdoor space.
Home in Pleasant Valley
5 out of 5 average rating, 27 reviews

The Wildflower House

MatthewRating, 5 stars1 month ago
Loved every part of our stay with Kristine. Perfect for a romantic weekend away - gorgeous cabin, well appointed, and great kitchen for cooking-in. Her recommendations for local spots were also so thoughtful. Thank you again!
Top guest favorite
A charming exterior view of the apartment showcases a white wood-paneled building framed by blooming pink trees. The front porch features a small seating area, while the surrounding greenery adds a touch of nature to the setting.
Apartment in Poughkeepsie
4.98 out of 5 average rating, 66 reviews

Charming Getaway in Historic Poughkeepsie

ElizabethRating, 5 stars1 week ago
This was a wonderful, comfortable apartment with a nice backyard area, close to the train station and a very short drive to Vassar College. A lovely spot to enjoy exploring the Hudson Valley from! The hosts are communicative, had a bottle of wine waiting for us, and everything was very clean. They were also kindly flexible about adjusting our check in time. Thank you for a great stay!
Guest favorite
An outdoor area is featured, illuminated by string lights overhead. A hot tub is positioned under a shelter with slatted roofing, surrounded by wooden fencing for privacy. The paved floor offers a clean and spacious setting for relaxation.
Home in Highland
4.9 out of 5 average rating, 42 reviews

Beautiful Home - 4BR/2.5BA - Hot Tub and Patio

EvanRating, 5 stars5 days ago
This was a beautiful home in a great location! The home was very clean and the hosts were very responsive and flexible with us when an unexpected situation arose with our car!
Guest favorite
A serene riverside view showcases still waters reflecting a clear blue sky. A modern bridge spans across the river, with mountains visible in the distance. The waterfront path is lined with rocks, and trees provide gentle shade along the edge.
Apartment in Poughkeepsie
4.93 out of 5 average rating, 30 reviews

Sunny Apartment in Historic Home

SageRating, 5 stars2 weeks ago
I had a very nice stay at Heather's place! The apartment was lovely and a comfortable place to spend time between different activities in Poughkeepsie. Very walkable to the convention center and to a main drag with restaurants and coffee shops. Definitely recommend and would stay there again if I found myself in the area!
Superhost
A private entrance is showcased with a black door featuring glass panes, flanked by two green chairs on a concrete step. A welcome mat lies on the ground, and fallen leaves surround the area, adding a natural element.
Guest suite in New Paltz
4.83 out of 5 average rating, 18 reviews

Private Suite in the Village - walk to all!

JoanneRating, 5 stars4 days ago
Great location and perfect for what we needed to bike in the area. We would recommend it!
Guest favorite
An expansive wooden deck features a smooth surface with ample space for seating. The A-frame structure, with its sleek black roof, showcases large glass panels that reflect the surrounding greenery. Lush trees cover the background, creating a serene outdoor setting.
Home in New Paltz
5 out of 5 average rating, 38 reviews

Stunning 4 bed A-Frame Holiday Retreat

FaigyRating, 5 stars1 week ago
Beautiful home, super clean, Great host! Would definitely return!
Guest favorite
A charming street scene showcases a row of colorful historic buildings featuring red, pink, and green façades. The architecture is complemented by modern storefronts and benches along the sidewalk. A tall church spire is visible in the background against a partly cloudy blue sky.
Home in Highland
4.92 out of 5 average rating, 75 reviews

Vintage Farmhouse in the heart of Hudson Valley

AlexandraRating, 5 stars5 days ago
We had a great stay at this Airbnb. Good staring point for day trips and beautiful setting for relaxing after a busy day.

Quick stats about vacation rentals in Highland

  • Total rentals

    10 properties

  • Nightly prices starting at

    G$8,372 GYD 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

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  3. New York
  4. Ulster County
  5. Highland