Entire home
Secluded and Spectacular Views
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Reviews
10 out of 10, Loved by Guests
Top 10% based on
5 bedrooms1+ bathroomSleeps 123500 sq ft
Popular amenities
Explore the area

Pine Plains, NY
- Place, Pine Plains Library5 min drive
- Place, The Stissing Center5 min drive
- Place, Stissing Lake Park7 min drive
- Airport, Hudson, NY (HCC-Columbia County)36 min drive
Rooms & beds
5 bedrooms (sleeps 12)
Bedroom 1
1 King Bed
Bedroom 2
4 Single Beds
Bedroom 3
1 Queen Bed
Bedroom 4
1 King Bed
Bedroom 5
2 Single Beds
1 bathroom, 2 half bathrooms
Bathroom 1
Toilet
Bathroom 2
Toilet · Shower only
Bathroom 3
Bathtub · Toilet · Shower only
Spaces
Deck or patio
Porch or lanai
Kitchen
Garden
Dining area
About this property
Secluded and Spectacular Views
The Silo
Set on 700 acres of wooded Hudson Valley real estate, The Silo is reached by crossing a bridge over a flowing stream (part of the intricate Hudson River watershed system). Though the home and property feel secluded, they are within easy driving distance to some of the region’s most chic, lively towns, such as Rhinebeck and Hudson.
Though The Silo has the feel of a converted antique barn, it is entirely new construction, steeped with delicious touches, from the rounded walls of the “silo” to the warm, wide-board flooring. The spacious rooms of this country home are flooded with light from soaring windows that face in all directions.
A big, family-style eat-in kitchen promises lively gatherings for meal preparation, casual dining, conversation, and games as you enjoy the views and the cozy warmth of the antique wood burning stove on winter days. Also on the entrance floor is a majestic great room—living and dining space perfect for holidays, lazy afternoons, or formal entertaining.
Bedrooms both upstairs and downstairs comfortably sleep 12. The downstairs bedroom has outdoor access through French doors, a sitting area and queen bed. This space offers maximum privacy to a young family. Upstairs, three bedrooms—one a cozy kids’ room full of twin beds, and two more large bedrooms with magical sunrise views.
The Hudson Valley boasts one of the longest fall foliage seasons in the country. The autumn colors paint the entire valley with rich warmth from September deep into October. When the winter snows fall across the landscape, take out your snowshoes and experience the drifting silence of the woods under its white mantle. In summer, enjoy long days in nature and leisurely evenings around the giant firepit, or watch a summer storm sweep in across the rural landscape.
The property and the entire region feature majestic scenery and hiking, bike trains, local farms, shopping, museums, historic homes and sites, golf, lakes and hidden swimming holes, theater and music festivals and venues, and opportunities to ski, downhill or cross country.
**Available wedding venues. Cost provided upon request.
Please note that the garage has an efficiency apartment (The Nook) that can be rented with The Silo for additional guests at a discounted price. It is also available for private rental of 1-2people. If rented, they do not have usage of the rear slate patio or firepit/grill area. We do provide a table for two on the porch of the Nook and private parking around the back with separate picnic table and grill.
Set on 700 acres of wooded Hudson Valley real estate, The Silo is reached by crossing a bridge over a flowing stream (part of the intricate Hudson River watershed system). Though the home and property feel secluded, they are within easy driving distance to some of the region’s most chic, lively towns, such as Rhinebeck and Hudson.
Though The Silo has the feel of a converted antique barn, it is entirely new construction, steeped with delicious touches, from the rounded walls of the “silo” to the warm, wide-board flooring. The spacious rooms of this country home are flooded with light from soaring windows that face in all directions.
A big, family-style eat-in kitchen promises lively gatherings for meal preparation, casual dining, conversation, and games as you enjoy the views and the cozy warmth of the antique wood burning stove on winter days. Also on the entrance floor is a majestic great room—living and dining space perfect for holidays, lazy afternoons, or formal entertaining.
Bedrooms both upstairs and downstairs comfortably sleep 12. The downstairs bedroom has outdoor access through French doors, a sitting area and queen bed. This space offers maximum privacy to a young family. Upstairs, three bedrooms—one a cozy kids’ room full of twin beds, and two more large bedrooms with magical sunrise views.
The Hudson Valley boasts one of the longest fall foliage seasons in the country. The autumn colors paint the entire valley with rich warmth from September deep into October. When the winter snows fall across the landscape, take out your snowshoes and experience the drifting silence of the woods under its white mantle. In summer, enjoy long days in nature and leisurely evenings around the giant firepit, or watch a summer storm sweep in across the rural landscape.
The property and the entire region feature majestic scenery and hiking, bike trains, local farms, shopping, museums, historic homes and sites, golf, lakes and hidden swimming holes, theater and music festivals and venues, and opportunities to ski, downhill or cross country.
**Available wedding venues. Cost provided upon request.
Please note that the garage has an efficiency apartment (The Nook) that can be rented with The Silo for additional guests at a discounted price. It is also available for private rental of 1-2people. If rented, they do not have usage of the rear slate patio or firepit/grill area. We do provide a table for two on the porch of the Nook and private parking around the back with separate picnic table and grill.
Add dates for prices
Amenities
Kitchen
Washing machine
Dryer
Pet-friendly
Air conditioning
Outdoor space
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- Kitchen
- Washing machine
- Dryer
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10.0 out of 10, Exceptional, (13 reviews)
House Rules
Check in after 3:00 PM
Minimum age to rent: 19
Check out before 11:00 AM
Children
Children allowed: ages 0–17
Events
Events allowed: family gatherings, birthday parties, weddings
Inquire for price
Pets
Pets allowed: dogs (limit 2 total)
$50 per pet per night
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
Parties and events (including family gatherings, birthday parties and weddings) are allowed on site. Maximum attendees: 99
Note from host: Inquire for price
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 and a deadlock
About the area
Pine Plains
Located in Pine Plains, this holiday home is in a rural area and on a river. Wing's Castle and Scoville Memorial Library are local landmarks, and some of the area's attractions include The Stissing Center and Northern Dutchess Botanical Gardens. Center for Performing Arts at Rhinebeck and Harney and Sons Tea Tasting Room are also worth visiting. Enjoy the area's slopes with cross-country skiing and skiing, and don't miss out on the ice skating and sledging.

Pine Plains, NY
What's nearby
- Pine Plains Library - 5 min drive - 6.1 km
- The Stissing Center - 5 min drive - 6.1 km
- Stissing Lake Park - 7 min drive - 7.1 km
- Thompson Pond - 7 min drive - 7.1 km
- Ancram Opera House - 9 min drive - 13.1 km
Getting around
Restaurants
- Stissing House - 6 min drive
- Dutch's Spirits - 10 min drive
- The Back Yard Garden - 6 min drive
- Champêtre - 6 min drive
- Hillrock Estate Distillery - 10 min drive
Frequently asked questions
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window10/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
10/10
Listing accuracy
Reviews
19 Jan, 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 2 nights in Jan 2026
10/10 Excellent
Randi C.
26 Oct, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy

Randi C.
Stayed 2 nights in Oct 2025
10/10 Excellent
Katharine M.
20 Apr, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful spot
Katharine M.
Stayed 2 nights in Apr 2025
10/10 Excellent
Nathan B.
22 Jun, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Family reunion



Nathan B.
Stayed 2 nights in Jun 2025
10/10 Excellent
Stacy B., Bryn Mawr, USA
24 Jun, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful second stay
Stacy B.
Stayed 2 nights in Jun 2023
10/10 Excellent
Will K.
10 Oct, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful Property
Will K.
Stayed 2 nights in Sep 2024
10/10 Excellent
Steven S.
26 Aug, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful property, great host, can't wait to return!
Steven S.
Stayed 3 nights in Aug 2023
10/10 Excellent
Anthony (Chip) S.
30 Jan, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
70th Birthday Weekend
Anthony (Chip) S.
Stayed 2 nights in Jan 2023
10/10 Excellent
Ptarmigan T.
30 Sept, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect, Beautiful!
Ptarmigan T.
Stayed 2 nights in Sep 2023
10/10 Excellent
Emily S.
16 Jul, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Gorgeous house, perfect weekend!
Emily S.
Stayed 3 nights in Jul 2022
8/10 Good
Stacy B.
15 Jul, 2019
Liked: Cleanliness, check-in, communication, location, listing accuracy
Paradise in Pine Plains
Stacy B.
Stayed 2 nights in Jul 2019
10/10 Excellent
Amanda Z.
30 May, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect for a family weekend!
Amanda Z.
Stayed 3 nights in May 2025
10/10 Excellent
Sava M.
16 Nov, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Silo and Nook
Sava M.
Stayed 2 nights in Nov 2022
10/10 Excellent
lisa A.
16 Sept, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
The setting is even better than the pictures show
lisa A.
Stayed 3 nights in Sep 2022
10/10 Excellent
Brian E.
22 Jun, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
We enjoyed our stay at this beautiful property.
Brian E.
Stayed 2 nights in Jun 2022
10/10 Excellent
Jenifer S.
2 Jun, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
The Silo House
Jenifer S.
Stayed 2 nights in May 2022
10/10 Excellent
Kathy o.
5 Sept, 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful location, private, and comfortable!
Kathy o.
Stayed 3 nights in Aug 2021
10/10 Excellent
Deirdre T.
26 Aug, 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful oasis !
Deirdre T.
Stayed 2 nights in Aug 2021
10/10 Excellent
Rachel C.
12 Aug, 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stunning property and home
Rachel C.
Stayed 2 nights in Jul 2021
10/10 Excellent
Jonathan A.
13 Jul, 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Charming
Jonathan A.
Stayed 3 nights in Jul 2021
10/10 Excellent
Abigail L.
5 Jul, 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stunning views
Abigail L.
Stayed 3 nights in Jul 2021
10/10 Excellent
Jimmy H.
29 Jun, 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great update New York getaway
Jimmy H.
Stayed 3 nights in Jun 2021
10/10 Excellent
Subramani S.
30 May, 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place, beautiful location.
Subramani S.
Stayed 2 nights in May 2021
10/10 Excellent
Amra G., New York
3 Feb, 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely home for a getaway!
Amra G.
Stayed 2 nights in Jan 2021
10/10 Excellent
Sanjeev A.
18 Jan, 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent house with plenty of room
Sanjeev A.
About the host
Hosted by Mary Boyles
Languages:
English
Premier Host
They consistently provide great experiences for their guests
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