House in Connecticut
10 guests · 4 bedrooms · 5 baths
Reasons to book
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Top-tier experienceA high end property in this area
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About this house rental
Summary:
Discover "The Library Retreat," a captivating multi-farmhouse in Pine Plains, just 2 hours from NYC. Set on a vast 67-acre estate, this rural haven is perfect for families and friend groups
The mid-19th-century farmhouse and guesthouse offer 4 bedrooms plus 1 children's bedroom/ 5.5 bathrooms, a private pool, outdoor shower, fireplaces, multiple kitchens, and outdoor terraces with pond and meadow views.
Explore Hudson Valley towns like Millbrook and Rhinebeck, both under 30 mins away.
The Space:
Discover an unparalleled retreat in the heart of the Hudson Valley, where a sprawling 67-acre estate unfolds to reveal a home accommodation designed for large groups of families and friends. Comprising two separate distinct buildings, each exuding its own charm and character, this property seamlessly blends historic allure with modern amenities amidst expansive natural beauty.
The Grey House, a mid-19th century farmhouse, boasts two inviting living rooms adorned with fireplaces, a cozy reading/library nook, a fully equipped kitchen, and a dining area, all nicely set into the hillside. On the second floor, discover three spacious bedrooms and a delightful children's room, accompanied by two baths. A patio off the kitchen offers guests a perfect spot to savor the fresh outdoors. One of the living rooms has a Roku Smart TV where you can log in to your favorite apps. This is the only TV on the property.
The Red House, a handsome barn-style guesthouse, perches on a knoll offering commanding views of the surroundings. Its 2,400 square feet include a vaulted great room opening to a stone terrace and covered porch. The large country kitchen and indoor dining area, along with a wonderfully large red library-wall, add to the allure. Please note: the bedrooms in the Red House are in the lofted area behind the red book shelf, and are close together, require walking through one to get to the other, and share one bathroom. This sleeping area would be best for multiple kids, or parents and their kids. The main bedroom space has a queen bed, and then the 'bed nook' has a Queen sized bed. Please note that it is a small space and no space on either side of the bed for standing. Great for kids!
Beyond the well-designed interiors, the property beckons with a private pool overlooking a pond and meadows, creating a picturesque setting for outdoor enjoyment. Expansive outdoor decks invite guests to savor the surrounding natural beauty and the property's vast gardens, woodlands, and a pond offer lots of eye catching opportunities on your leisurely strolls.
This retreat is not just a property; it's an experience – a harmonious blend of historic charm, modern amenities, and natural beauty, creating a sanctuary for large groups to reconnect, unwind, and create lasting memories.
The Neighborhood:
Welcome to picturesque Pine Plains, New York! Nestled just 2 hours from NYC, this charming town offers a perfect blend of natural beauty and outdoor adventures. In summer, explore Stissing Mountain for breathtaking hikes and panoramic views. Discover the quaint local shops and farmers' markets, showcasing the town's artistic spirit. Cool off in serene lakes and relish outdoor concerts.
Winter transforms Pine Plains into a snow-covered wonderland. Hit the slopes at Catamount Ski Area. Cross-country ski through rolling hills or cozy up at local cafes with hot cocoa. Capture the town's rustic charm with historic architecture and warm community vibes.
Explore neighboring gems like Millbrook, known for wineries and Millbrook Vineyards. Delight in the charm and shops in Rhinebeck, a mere 30 mins away. Enjoy the Hudson Valley's culinary delights, from farm-to-table restaurants to artisanal bakeries.
Embrace Pine Plains' beauty year-round, where nature's allure meets small-town charm.
Getting Around:
The Library Retreat is just about two 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:
* Please note that the pool is available during the summer season only. Please inquire regarding opening and closing dates.
Air Conditioning Details:
The Red House: Features a mini-split unit in the living area. Please note: the bedrooms are not air-conditioned.
The Grey House: Fully equipped with central air conditioning for whole-home comfort.
The bedrooms in the Red House do not have window coverings.
Please note, a caretaker resides in the loft apartment above the garage (blue building). During rentals, they will make their best effort to vacate the premises or remain completely out of site. Their car could be present on site, do not be alarmed.
Discover "The Library Retreat," a captivating multi-farmhouse in Pine Plains, just 2 hours from NYC. Set on a vast 67-acre estate, this rural haven is perfect for families and friend groups
The mid-19th-century farmhouse and guesthouse offer 4 bedrooms plus 1 children's bedroom/ 5.5 bathrooms, a private pool, outdoor shower, fireplaces, multiple kitchens, and outdoor terraces with pond and meadow views.
Explore Hudson Valley towns like Millbrook and Rhinebeck, both under 30 mins away.
The Space:
Discover an unparalleled retreat in the heart of the Hudson Valley, where a sprawling 67-acre estate unfolds to reveal a home accommodation designed for large groups of families and friends. Comprising two separate distinct buildings, each exuding its own charm and character, this property seamlessly blends historic allure with modern amenities amidst expansive natural beauty.
The Grey House, a mid-19th century farmhouse, boasts two inviting living rooms adorned with fireplaces, a cozy reading/library nook, a fully equipped kitchen, and a dining area, all nicely set into the hillside. On the second floor, discover three spacious bedrooms and a delightful children's room, accompanied by two baths. A patio off the kitchen offers guests a perfect spot to savor the fresh outdoors. One of the living rooms has a Roku Smart TV where you can log in to your favorite apps. This is the only TV on the property.
The Red House, a handsome barn-style guesthouse, perches on a knoll offering commanding views of the surroundings. Its 2,400 square feet include a vaulted great room opening to a stone terrace and covered porch. The large country kitchen and indoor dining area, along with a wonderfully large red library-wall, add to the allure. Please note: the bedrooms in the Red House are in the lofted area behind the red book shelf, and are close together, require walking through one to get to the other, and share one bathroom. This sleeping area would be best for multiple kids, or parents and their kids. The main bedroom space has a queen bed, and then the 'bed nook' has a Queen sized bed. Please note that it is a small space and no space on either side of the bed for standing. Great for kids!
Beyond the well-designed interiors, the property beckons with a private pool overlooking a pond and meadows, creating a picturesque setting for outdoor enjoyment. Expansive outdoor decks invite guests to savor the surrounding natural beauty and the property's vast gardens, woodlands, and a pond offer lots of eye catching opportunities on your leisurely strolls.
This retreat is not just a property; it's an experience – a harmonious blend of historic charm, modern amenities, and natural beauty, creating a sanctuary for large groups to reconnect, unwind, and create lasting memories.
The Neighborhood:
Welcome to picturesque Pine Plains, New York! Nestled just 2 hours from NYC, this charming town offers a perfect blend of natural beauty and outdoor adventures. In summer, explore Stissing Mountain for breathtaking hikes and panoramic views. Discover the quaint local shops and farmers' markets, showcasing the town's artistic spirit. Cool off in serene lakes and relish outdoor concerts.
Winter transforms Pine Plains into a snow-covered wonderland. Hit the slopes at Catamount Ski Area. Cross-country ski through rolling hills or cozy up at local cafes with hot cocoa. Capture the town's rustic charm with historic architecture and warm community vibes.
Explore neighboring gems like Millbrook, known for wineries and Millbrook Vineyards. Delight in the charm and shops in Rhinebeck, a mere 30 mins away. Enjoy the Hudson Valley's culinary delights, from farm-to-table restaurants to artisanal bakeries.
Embrace Pine Plains' beauty year-round, where nature's allure meets small-town charm.
Getting Around:
The Library Retreat is just about two 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:
* Please note that the pool is available during the summer season only. Please inquire regarding opening and closing dates.
Air Conditioning Details:
The Red House: Features a mini-split unit in the living area. Please note: the bedrooms are not air-conditioned.
The Grey House: Fully equipped with central air conditioning for whole-home comfort.
The bedrooms in the Red House do not have window coverings.
Please note, a caretaker resides in the loft apartment above the garage (blue building). During rentals, they will make their best effort to vacate the premises or remain completely out of site. Their car could be present on site, do not be alarmed.
Amenities at The Library Retreat Charming Estate w/Pool+Pond
Non-smoking
Pets allowed
Family friendly
Map of Connecticut
Ratings and reviews
10 / 10Outstanding·Oct 2025
stay was lovely! very peaceful surroundings and very clean lodging!
8 / 10Excellent·Aug 2025
My family and I had a great time at the library retreat in Pine Plains! The property was gorgeous and great for our large family. There were a few things that could be improved -- there were several wasps nests around the property and a few of us got stung! The rental team was very responsive and someone came out the next day to spray them. We also noticed there were some bats living in one of the chimneys! Luckily they didn't get into the house, but it was a bit unsettling. The listing also stated there were 4 queen sized beds and 2 doubles, but we found out there were actually 3 queen sized beds and 3 double sized beds, which was difficult with the number of and height of our fam! Accurate information in that regard is appreciated. Another suggestion is to install curtains/blinds to all the bedrooms. Some bedrooms did not have any kind of coverings. We also wished there was more outdoor furniture to enjoy. The scenery was beautiful but there were no tables or chairs on the patios. Otherwise the houses were all beautifully decorated and maintained. The rental team was very responsive to any questions we had, which was great. Overall it was a great family vacation spot!
6 / 10Average·Aug 2025
Beautiful area. The layout worked well for our families. Kind of rough homes now and sort of run down since the photos were taken. The lack of outdoor furniture was a drag..
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Top rated by guests
8Excellent
(3 Ratings)
"stay was lovely! very peaceful surroundings and very clean lodging! "
Kelsey K.Don't miss out! Price and availability may change
