House in Olive, NY
10 guests · 5 bedrooms · 4 baths
Reasons to book
Top-tier experienceA high end property in this area
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Includes essentials and more
About this house rental
A Retreat @ Hudson Woods is a luxury oasis nestled in the private woods of Kerhonkson. Nearby breweries, farms, and fine dining restaurants make Kerhonkson a true destination, but the privacy and relaxing nature of A Retreat has a uniquely peaceful draw. Featured in Architectural Digest for its exceptional design: https://www.architecturaldigest.com/story/inside-a-creative-couples-sustainable-catskills-getaway
So many great places to see in the Hudson Valley!
18 min by car from Arrowood Farms & Brewpub.
18 min by car from Westwind Orchard, a popular hang out spot for food and drink.
30 min by car to the infamous town of Woodstock with a great dining and bar scene.
40 min by car to New Paltz, a great college town with lots of restaurants and bars.
40 min by car to Kingston, a destination for most city-dwellers for great food and shopping.
Renting this property means that you have access to all 3 buildings on the property:
MAIN HOUSE: 3 bedrooms, 2.5 bathrooms.
GUEST HOUSE: 2 bedrooms, 2 bathrooms.
POOL: Main House Guest Access ONLY (Memorial Day to Labor Day weekend only)
Main House
Bedroom 1: Primary: King size bed, Ensuite bathroom with stand-alone shower
Bedroom 2: Queen size bed w/ access to shared bathroom
Bedroom 3: Queen size bed w/ access to shared bathroom
Guest House
Bedroom 4: King size bed, Ensuite bathroom with stand-alone shower
Bedroom 5: King size bed, Ensuite bathroom with stand-alone shower
This listing is for renting both the main house and guest house together, which accommodates a total of 10 people. Please note that during winter months, access to this property can be challenging. We highly recommend that you have a 4WD vehicle with snow tires for safe travel. If you do not have the proper equipment, we kindly ask that you reconsider booking during this season.
Commercial vehicles are not allowed on the property besides for approved service providers, a maximum of 6 guest vehicles are permitted (strictly limited to 2 at the guest house, 4 at the main house)
**Noise ordinance after 10pm, strictly monitored. All outdoor spaces must be vacated at 10pm and indoor noise kept to a minimum.**
There are two native grass and wildflower meadows, one on the north side of the guest house and another on the south side of the main house. We are working to re-establish these areas by hand weeding and reseeding until the meadow is restored. Note - these areas will not be mowed. The outdoor herb/ vegetable garden is near the guest house and will have bi-weekly visits on Wednesdays to check the garden.
Please be aware that the outdoor kitchen in the pool house is currently not usable, we are in the process of getting it up and running again. We appreciate your understanding!
Please be advised that every 30 minutes spent on the property past 11am check out time a $50 fee will be initiated and charged to the card on file used to book the listing. We appreciate your cooperation and understanding.
So many great places to see in the Hudson Valley!
18 min by car from Arrowood Farms & Brewpub.
18 min by car from Westwind Orchard, a popular hang out spot for food and drink.
30 min by car to the infamous town of Woodstock with a great dining and bar scene.
40 min by car to New Paltz, a great college town with lots of restaurants and bars.
40 min by car to Kingston, a destination for most city-dwellers for great food and shopping.
Renting this property means that you have access to all 3 buildings on the property:
MAIN HOUSE: 3 bedrooms, 2.5 bathrooms.
GUEST HOUSE: 2 bedrooms, 2 bathrooms.
POOL: Main House Guest Access ONLY (Memorial Day to Labor Day weekend only)
Main House
Bedroom 1: Primary: King size bed, Ensuite bathroom with stand-alone shower
Bedroom 2: Queen size bed w/ access to shared bathroom
Bedroom 3: Queen size bed w/ access to shared bathroom
Guest House
Bedroom 4: King size bed, Ensuite bathroom with stand-alone shower
Bedroom 5: King size bed, Ensuite bathroom with stand-alone shower
This listing is for renting both the main house and guest house together, which accommodates a total of 10 people. Please note that during winter months, access to this property can be challenging. We highly recommend that you have a 4WD vehicle with snow tires for safe travel. If you do not have the proper equipment, we kindly ask that you reconsider booking during this season.
Commercial vehicles are not allowed on the property besides for approved service providers, a maximum of 6 guest vehicles are permitted (strictly limited to 2 at the guest house, 4 at the main house)
**Noise ordinance after 10pm, strictly monitored. All outdoor spaces must be vacated at 10pm and indoor noise kept to a minimum.**
There are two native grass and wildflower meadows, one on the north side of the guest house and another on the south side of the main house. We are working to re-establish these areas by hand weeding and reseeding until the meadow is restored. Note - these areas will not be mowed. The outdoor herb/ vegetable garden is near the guest house and will have bi-weekly visits on Wednesdays to check the garden.
Please be aware that the outdoor kitchen in the pool house is currently not usable, we are in the process of getting it up and running again. We appreciate your understanding!
Please be advised that every 30 minutes spent on the property past 11am check out time a $50 fee will be initiated and charged to the card on file used to book the listing. We appreciate your cooperation and understanding.
Amenities at A Retreat @ Hudson Woods With Main & Guest House
Non-smoking
No pets allowed
Family friendly
Map of Olive, NY
Ratings and reviews
10 / 10Outstanding·Sep 2025
Thank you, team, for a wonderful stay at Hudson Woods. The property and homes were beautiful and fit our needs perfectly.
The only feedback we have is that we wish we had known the pool would be closed for the weekend. Everyone brought swimsuits and we had planned an afternoon around it, but had to pivot once we arrived. I later found the note about the closure that was briefly on the Breezeway platform, but it wasn’t clear without searching.
We were also notified that a noise sensor went off one night. We had checked from outside before playing music and couldn’t hear anything, so it was surprising that the sensor flagged us. It may be overly sensitive, as we were confused about why it was triggered.
Otherwise, everything was great, and we truly enjoyed our stay!
$$$$
7Good
(2 Ratings)
"Thank you, team, for a wonderful stay at Hudson Woods. The property and homes were beautiful and fit our needs perfectly.
The only feedback we have is that we wish we had known the pool would be cl..."
Allie G.Don't miss out! Price and availability may change
