
Vacation rentals in Highland
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Top-rated vacation rentals in Highland
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Popular amenities for Highland vacation rentals
Other great vacation rentals in Highland
Top guest favorite

Apartment in Clintondale
5 out of 5 average rating, 30 reviewsCozy 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

Home in Pleasant Valley
5 out of 5 average rating, 27 reviewsThe 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

Apartment in Poughkeepsie
4.98 out of 5 average rating, 66 reviewsCharming 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

Home in Highland
4.9 out of 5 average rating, 42 reviewsBeautiful 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

Apartment in Poughkeepsie
4.93 out of 5 average rating, 30 reviewsSunny 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

Guest suite in New Paltz
4.83 out of 5 average rating, 18 reviewsPrivate 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

Home in New Paltz
5 out of 5 average rating, 38 reviewsStunning 4 bed A-Frame Holiday Retreat
FaigyRating, 5 stars1 week ago
Beautiful home, super clean, Great host! Would definitely return!
Guest favorite

Home in Highland
4.92 out of 5 average rating, 75 reviewsVintage 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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- Hunter Mountain
- Mountain Creek Resort
- Bethel Woods Center for the Arts
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- Thunder Ridge Ski Area
- The Kartrite Resort & Indoor Waterpark
- Ringwood State Park
- Taconic State Park
- Resorts World Catskills
- Catamount Mountain Ski Resort
- Zoom Flume
- Windham Mountain
- Kent Falls State Park
- Rockland Lake State Park
- Walkway Over the Hudson State Historic Park
- Bash Bish Falls State Park
- Hudson Highlands State Park
- Brotherhood, America's Oldest Winery
- Wawayanda State Park
- Sterling Forest State Park
- Tallman Mountain State Park
- The Stanwich Club
- The Connecticut Golf Club