Vacation Rentals in New York's Upper Hudson Valley

Rene Syler heads to one of New York's premiere getaway destinations, the Upper Hudson Valley, where best friends Libby and Kim are on the hunt for an inspiring long-weekend retreat.
The Upper Hudson Valley is one of New York's best kept secrets! The quiet unexplored pocket is one of the premiere getaway destinations, and not many know about it! That's about to change as best buds Libby and Kim tackle the tremendous terrains.

The Hudson Valley extends from the outskirts of New York City all the way up to Albany, with the Hudson River running right through the center. This scenic space is accessible for visitors of all kinds; from above the Catskills to Albany, it's reachable from Manhattan in just a couple of hours. It's also adjacent to the Massachusetts boarder, granting visitors access to the western side of the state.

The area features small but charming rural towns that are off the tourism radar -- making it a perfect spot for a quiet getaway. This serene location is chock full of nature too! In fact, visitors can hike the gorgeous Taconic mountain range or hop on over to Massachusetts and explore the Berkshires.

For best friends Libby and Kim, this is the ideal quiet escape to rest, relax, but also check some outdoor activities off their to-do list!

As a self-proclaimed hobby hoarder and writer, Libby has tried 52 hobbies in 52 weeks!

"For the last year I have been working on project called 'The Hobby Hoarder' where I try 52 new hobbies in 52 weeks," said Libby. "The ultimate goal is to write a book and I completed the year by doing a road trip around America and Canada with my good friend Kimberly."

And, Kim joined her for the trip of a lifetime.

"I had always wanted to go on a road trip across America, so I decided it was time to take a little hiatus from my job and jump on the road trip with [Libby] and see the United States. We did so many things I don't think I would have ever done, including hot air ballooning in New Mexico," said Kim.

Now the ladies are venturing a few hours from their New York City apartments to explore a part of the state they have never been before.

The Perfect Sweet Retreat would have the following criteria:

  • Two bedrooms
  • Spot to write
  • Inspiring outdoor space
  • Near area attractions
With their budget of $300 per night for their four-day getaway, the ladies are eager to see Rene's choices!

Contemporary Farmhouse for Rent: This three-bedroom, two-bathroom property sits on an incredible 40 acres of land! With the Taconic Mountain Range, the Berkshires, and the resort Jiminy Peak nearby, there are plenty of places to go and sights to see. There are also luxurious conveniences at the home, such as heated floors and a private pool. And, at just $260 a night, the ladies love the under budget price tag. But with no designated space for writer Libby to focus on her work, will she be deterred from the space? For more information on this property visit

Tuscan Inspired Gem for Rent: This three-bedroom, three-bathroom, Italian-influenced retreat is located in the heart of Canaan, New York. Just 15 minutes away from Lennox, Massachusetts, renters can visit the Boston Symphony! There are four decks and an indoor pool and hot tub at the home, which sits on five acres of land. There is also an ideal space for writing, making it easy for Libby and Kim to be inspired. But at the top of their budget at $300 a night, the ladies will have to decide if the pros outweigh the costs. For more information on this property visit

Kinderhook Farmstay for Rent: This incredible renovated barn is smack in the middle of a working farm! Located in Ghent, New York, visitors are close to villages, towns, and a lovely winery. With two-bedrooms, one-bathroom, and an open view of the roaming animals, the ladies are literally able to count sheep! Since the barn doesn't have any interior walls, it is broken up by three bays with curtains that can be closed for privacy. Just under budget at $295 a night, Libby and Kim are excited about this animal house. But without a designated writing space, will this retreat be a hit or a miss? For more information on this property visit

For more information on the Hudson Valley visit

Segment 1
Contemporary Farmhouse for Rent in Upper Hudson Valley, New York
Contemporary Farmhouse for Rent in Upper Hudson Valley, New York
Best friends Libby and Kim are in Upper Hudson Valley, New York searching for the perfect long-weekend retreat. With beautiful sights to see and tons of towns to explore, the ladies hope to find a property that encourages activities. Rene starts their search by showing them a contemporary farmhouse with lots of land.
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Segment 2
Tuscan-Inspired Gem for Rent in Upper Hudson Valley, New York
Tuscan-Inspired Gem for Rent in Upper Hudson Valley, New York
Best buds Libby and Kim are in the upper region of the Hudson Valley looking for a house for a long-weekend retreat. So far they've seen a three-bedroom contemporary farmhouse that sits on 40 acres of land with a private pool and pond. Next, Rene shows them a house inspired by the Italian countryside.
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Segment 3
Kinderhook Farmstay for Rent in Upper Hudson Valley, New York
Kinderhook Farmstay for Rent in Upper Hudson Valley, New York
Hobby enthusiast Libby and her best friend Kim are hoping to find a retreat for their long-weekend stay in New York's Upper Hudson Valley. They have toured two very unique properties. The last one on Rene's list is a very interactive space!
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Photo Gallery
Behind-the-Scenes Photos: Rental Properties in Hudson Valley, New York
Check out three vacation rental properties in Hudson Valley, New York.
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