Entire home
The Library Retreat Charming Estate w/Pool+Pond
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Reviews
8.0 out of 10
Very good
4 bedrooms5+ bathroomsSleeps 10371.6 sq m
Popular amenities
Rooms & beds
4 bedrooms (sleeps 10)
Bedroom 1
2 Queen Beds
Bedroom 2
1 Queen Bed
Bedroom 3
1 Double Bed
Bedroom 4
1 Double Bed
5 bathrooms, 1 half bathroom
Bathroom 1
Bathtub · Toilet · Shower only
Bathroom 2
Bathtub · Toilet · Shower only
Bathroom 3
Bathtub · Toilet · Shower only
Bathroom 4
Bathtub · Toilet · Shower only
Bathroom 5
Bathtub · Toilet · Shower only
Bathroom 6
Toilet
Spaces
Kitchen
Office
Balcony
Garden
About this property
The Library Retreat Charming Estate w/Pool+Pond
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.
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.
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.
Interaction with Guests:
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.
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.
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.
Interaction with Guests:
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.
Add dates for prices
Amenities
Pool
Kitchen
Washing machine
Dryer
Pet-friendly
Air conditioning
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House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
Pets allowed: dogs less than 23 kg per pet (limit 2 pets total)
Charge may apply
Smoking
Smoking is not permitted
Important information
You need to know
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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Pine Plains
Located in Pine Plains, this holiday home is in a rural area. Scoville Memorial Library and Wing's Castle are local landmarks, and some of the area's attractions include The Stissing Center and Trevor Zoo. Harney and Sons Tea Tasting Room and Northern Dutchess Botanical Gardens are also worth visiting.

Pine Plains, NY
What's nearby
- The Stissing Center - 12 min drive - 9.8 km
- Pine Plains Library - 12 min drive - 9.8 km
- Taconic State Park - 13 min drive - 14.0 km
- Harlem Valley Rail Trail - 13 min drive - 13.7 km
- Stissing Lake Park - 13 min drive - 10.9 km
Getting around
Restaurants
- Cumberland Farms - 12 min drive
- Round Tuit - 11 min drive
- Stissing House - 10 min drive
- Harney & Sons - 11 min drive
- Dutch's Spirits - 15 min drive
Frequently asked questions
Reviews
8.0
Very good
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window8.0/10
Cleanliness
10/10
Check-in
8.8/10
Communication
10/10
Location
6.0/10
Listing accuracy
Reviews
Verified
8 October 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 2 nights in Oct 2025
Verified
6/10 Okay
Verified traveller
31 August 2025
Liked: Check-in, location
Disliked: Cleanliness, listing accuracy
Verified traveller
Stayed 7 nights in Aug 2025
Verified
8/10 Good
Carillon S.
11 August 2025
Liked: Cleanliness, check-in, communication, location
Carillon S.
Stayed 7 nights in Aug 2025
About the host
Hosted by Red Cottage
Red Cottage is redefining what you get from a short-term rental. Our team is dedicated to helping you create the perfect getaway and is here to assist you from the moment you book through the course of your stay.
Our guest services team is available around the clock to assist you with whatever you might need and are passionate and knowledgeable about all that there is to do around the region.
Let us help you build your perfect weekend away.
Our guest services team is available around the clock to assist you with whatever you might need and are passionate and knowledgeable about all that there is to do around the region.
Let us help you build your perfect weekend away.
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