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Vacation Rentals in Highland, New York

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Search vacation deals on homes, villas, cabins, cottages, apartments and condos in destinations all over the world. Click the "rental results" tab to browse Highland, New York vacation rentals and inquire about your favorites. If you cant find what youre looking for, consider nearby destinations, or come back for a visit - vacation home rentals in Highland are added and updated every week!

Compared to hotels, Highland vacation rentals are much more family-friendly and flexible, offering a lot more space, a lot more savings, and a lot more amenities - like private pools, gourmet kitchens, and pet-friendly accommodations! Tip: Save money by taking advantage of cheap weekly rates.

Highland, New York Vacation Rentals and Tourism

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Highland things to do


Walkway Over the Hudson

You have to do this at least once, I swear. This renovated railroad bridge sits over 200 feet above the waters of the Hudson, in a clear sunny spot more


Franklin D Roosevelt Presidential Library and Museum

I have previously visited the FDR Home and Presidential Library and loved the experience. It is beautifully preserved and designed to recreate more


Big Bear Ziplines

We had a great time today. Bowser and Yoshi, our tour guides, did a great job and kept the whole group laughing the entire trip. Thanks, Mario and Luigiread more


Home of Franklin D. Roosevelt

What a tease-- I would love to sit in that library and at Eleanor's desk and in the veranda overlooking those beautiful acres of chestnut trees and more


Minnewaska State Park Preserve

Great walk around the lake. Parking was $8.00 for the car, which seemed reasonable. We spent a few hours walking around the different paths to the lake, more


Darkside Records and Gallery

one of the best video game stores ive been to though there service coukd be a little better it is still a great place i love the great quality of games more


Minnewaska State Park Preserve

I visited Minnewaske State Park on July 4th. While everyone was at the beach, climbing or barbecuing, I was lucky enough to have the trails all to more


Paintball Sports New York

What I enjoyed of this paintball field are the rugged locations they had, like Delta for instance Plainwoods nothing but shear wits that you need in more


The Falcon

The four star rating is only for the really great music, beautiful space, and amazing view! However, the food REALLY sucked and was VERY expensive. more


Regal Poughkeepsie Cinema

Spacious, clean, comfortable theatre. Compared to the crowded theatres in NYC, this is like a breathe of fresh air! Friendly staff- when my Fandango more


Rocking Horse Ranch

We just finished a 2 night three day stay and had a phenomenal time! I've never visited here before but my two children and I found tons to do to keep more


Bicycle Depot

My friend and I were planning a bike ride in the New Paltz area for a long while. My friend called in advance and asked to book a bike. He was told more


Benmarl Wine Co

My favourite winery in Hudson Valley. I ended up buying a mixed case here because all of their wines were just exceptional.. High quality stuff here! more


Hyde Park Drive-In Theatre

I feel like drive-ins are about as nice as your car is, so given we were borrowing a small, horrendous car, it was surprising that this was still a more


Chance Theatre

This used to be a great venue, until a new batch of security guards came along. On multiple occasions, reports of excessive force, and more than one more

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Nature Lover's Vacation House
Highland House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $110 - $200 /nt
    $700 - $1,050 /wk
    $2,200 - $3,300 /mth

8 reviews write a review

HeartsEase - National Registry, Historic Hudson River Mansion
Highland Estate Rental Picture
  • bedrooms 5
  • rental type Estate
  • owner badgeowner badge
  • sleeps 13
  • baths
  • rates (USD) $1,863 /nt

5 reviews write a review