Escape to Olive Pit, a designer home in Hillsdale, NY. This renovated retreat offers 5 acres of tranquility amidst its beautiful natural surroundings.
Inside, an open floor plan connects an inviting kitchen, dining for 10 and living room with a fireplace. French doors lead to a screened porch and wraparound deck. Outside, the private pool and an additional deck provides endless outdoor fun and relaxation surrounded by nature.
The Space:
Welcome to Olive Pit, an exquisite home tucked away in the serene beauty of Hillsdale, NY. Meticulously revitalized through a recent gut renovation, this exceptional home radiates designer charm and character, offering an idyllic escape to Upstate New York.
Nestled on a private 5-acre property, Olive Pit beckons with its captivating allure. Step inside and immerse yourself in an open floor plan living space that seamlessly weaves together comfort and elegance. The heart of the home is a spacious eat-in kitchen, complete with an inviting island that serves as a gathering point for culinary delights. The adjoining dining area accommodates 10 guests, setting the stage for memorable feasts, while the living room, with its grand fireplace and bespoke built-in benches, provides the perfect backdrop for shared stories and laughter.
A true highlight awaits through the set of French doors that lead to the sprawling screened-in porch. Perched on an expansive wrap-around deck, this outdoor oasis offers stunning views of surrounding verdant landscape. As the gentle breeze rustles through the trees, the porch becomes a sanctuary for relaxation and contemplation. Venture down a set of stairs to discover an additional deck nestled among the trees, a hidden haven for solitude and reflection.
The main floor boasts a sumptuous primary bedroom, complete with a king bed, vaulted ceilings, and sliding doors that open to the deck. An en-suite bathroom with a shower adds a touch of opulence. Two additional bedrooms on this floor each feature queen beds and share a conveniently located bathroom.
Descending a staircase just off the kitchen, the lower level unveils a media room and play space, offering entertainment for all ages. Two bedrooms grace this level as well - one adorned with two bunk beds, the other furnished with two twin beds. A shared bathroom boasting a generous bathtub completes this level's offerings.
Outside, on the south side of the property, a private pool promises refreshment and leisure.
Olive Pit isn't just a vacation rental; it's an invitation to embrace the tranquility of the Hudson Valley. With its captivating pool, thoughtfully designed interiors, and enchanting outdoor spaces, this haven promises an unforgettable escape where cherished memories are waiting to be made.
The Neighborhood:
Experience the best of outdoor charm and adventure in Copake and Hillsdale, New York! Situated near the renowned Catamount Ski Area, our town offers a captivating blend of rustic beauty. Summer beckons with hikes at Bash Bish Falls, Taconic State Park trails, and kayaking on Copake Lake. Indulge in farm-fresh delights and, as winter arrives, hit Catamount's slopes.
Discover our tranquil aesthetic, from rolling hills and quaint farms to vibrant foliage. Explore golf at Copake Country Club, delve into Historic Hillsdale, and easily access Hudson's art scene and Great Barrington's boutiques. Unveil the heart of the Hudson Valley in Copake and Hillsdale!
Getting Around:
Olive Pit is about 2.5 hours from New York City, and you'll definitely want a car to get there and around the area.
In the winter, we recommend a car with four-wheel drive that can handle the snow and gravel roads.
Other Things to Note:
Cooling: There is central AC upstairs and split units downstairs.
*Please note that the pool is available during the summer season only. Please inquire regarding opening and closing dates.
Our prices include all fees. No hidden fees.
Add dates for prices
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AGE REQUIREMENT
Primary guest booking must be 25 years or older. The person booking should also not have any negative reviews.
PETS
Well-behaved d...
Important information
You need to know
Property # 3553077
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
About the neighborhood
Hillsdale
Hillsdale is home to this vacation home. W.E.B. Du Bois Boyhood Homesite and Mahaiwe Performing Arts Center are local landmarks, and the area's natural beauty can be seen at New Forge State Forest and Mount Washington State Forest.
National Shrine of the Divine Mercy - 39 min drive - 60.3 km
Bard College - 45 min drive - 58.4 km
Tanglewood Music Center - 46 min drive - 64.2 km
Omega Institute - 47 min drive - 56.2 km
Getting around
Hudson Station - 28 min drive
Hudson, NY (HCC-Columbia County) - 24 min drive
Restaurants
Stewart's Shops - 10 min drive
Four Brothers Pizza Inn - 10 min drive
Martindale Chief Diner - 10 min drive
Little Cat Lodge - 14 min drive
Fat Cat - 15 min drive
Frequently asked questions
Does Olive Pit: Scenic Designer Retreat +Pool—Sleeps 12 have a pool?
Yes, this property has a pool. Pool types include heated pools.
How much does it cost to stay at Olive Pit: Scenic Designer Retreat +Pool—Sleeps 12?
As of May 14, 2026, prices found for a 1-night stay for 2 adults at Olive Pit: Scenic Designer Retreat +Pool—Sleeps 12 on Oct 21, 2025 start from $643, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
Is Olive Pit: Scenic Designer Retreat +Pool—Sleeps 12 pet-friendly?
Yes, pets are allowed at this property.
How much is parking?
Onsite parking is available at the property.
What time is check-in at Olive Pit: Scenic Designer Retreat +Pool—Sleeps 12?
Check-in begins at 4:00 PM.
What time is check-out at Olive Pit: Scenic Designer Retreat +Pool—Sleeps 12?
Check-out is at 11:00 AM.
Where is Olive Pit: Scenic Designer Retreat +Pool—Sleeps 12 located?
Situated in Hillsdale, this vacation home is 0.2 mi (0.3 km) from Copake Lake and 1.8 mi (2.9 km) from Mosquito Island. Copake Town Hall and Copake Town Park are also within 6 mi (10 km).
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
stayed here with a group of 10 friends and it was the perfect spot to spend a Fall weekend with friends! we especially loved the design and style of every room - they didn’t miss a single detail! an added bonus: the deck in the back yard is the perfect spot for an engagement :) the pathway is all lit up with lights so it was very romantic and the pics came out great. definitely recommend staying here! hoping to come back in the summer!
We stayed here with extended family - grandparents, two couples, and 4 grandkids. The space worked very well for adults and children. We stayed in the winter so could not enjoy the pool, but the property was beautiful. We'd love to return in the summer. The house was exactly as described, had a well-stocked kitchen, and was a great place to stay.