House in Pine Plains, NY
8 guests · 4 bedrooms · 3 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Top-tier experienceA high end property in this area
About this house rental
Escape to this cozy lakefront guest house on a private peninsula in Pine Plains, NY. Enjoy snowy lake views, a fireplace, a sun-drenched sunroom and a jacuzzi tub, with trails, wineries and dining nearby.
YOUR LOCAL HOSTS
This property is managed by Home Sweet Hudson, a trusted and local management company deeply passionate about crafting unforgettable Hudson Valley getaways. From sharing insider recommendations to ensuring every detail of your stay is seamless, we are here to provide attentive, personalized support from the moment you book until the day you depart.
LOCAL EXPERIENCES & ADD-ONS
Home Sweet Hudson has partnered with trusted local vendors who offer wonderful add-ons to your stay. Please message us with the services you would like to explore so we can check availability and help coordinate your experience.
- Mobile Sauna Rental: Enjoy a mobile cedar wood sauna during your stay.
- Private Yoga Classes: Bring the studio vibes to you with a tailored private class.
- In-Home Private Chefs: Skip the shopping and enjoy fine dining with locally sourced ingredients, seasonal menus, and delicious wine pairings.
- Private Massage Sessions: Whether you have been hiking, skiing, or simply taking in the views, an in-home massage is the perfect way to unwind.
So many great places to see in the area!
NEARBY NATURE & RECREATION
- Thompson Pond Preserve (3 min): Walking trails perfect for birdwatching and wildlife.
- Stissing Mountain Fire Tower (3 min): Scenic views and hiking.
- Stissing Lake Park and Pine Plains Beach (5 min): Two playgrounds and open park areas for family fun.
- Lake Taghkanic State Park (18 min by car): A great place for lake activities and hiking.
DINING & WINERIES
- Stissing House (5 min): Dine at one of The New York Times' 50 Most Exciting Restaurants in the U.S. 2023.
- Champetre (5 min): A renowned French restaurant run by a famous NYC chef. Book a table as soon as possible!
- Dutchess Wine Trail (20 min by car): Exquisite wineries offering tastings and tours amid vineyard landscapes.
DAY TRIPS
- Kingston (45 min by car): A destination for great food and shopping.st city-dwellers for great food and shopping.
PROPERTY ACCESS & OUTDOOR LIVING
On this property you will find two mirrored homes. The home on the left is the guest house, for guest use ONLY. The home on the right is not available to guests and is not included in the reservation.
Step outside to discover a private outdoor oasis equipped with fantastic amenities for your winter getaway:
BACKYARD & FIRE PIT: Enjoy the backyard, and the fire pit on a crisp winter evening.
LAKESIDE DECK: Relax on the lakeside deck overlooking the water.
DOG-FRIENDLY: Bowls and throw blankets are available for your dog.
BEDROOM & BATHROOM DISTRIBUTION
The house features multiple bedrooms on both the upper and lower levels with various bed configurations, including a king bedroom with a smart TV and a separate suite with exterior access. Enjoy a soothing soak in the tub with jacuzzi jets after a day of exploring in the snow.
KITCHEN
A fully stocked kitchen for preparing delicious meals.
LIVING SPACE
Gather around the fireplace in the living room, or relax in the sun-drenched sunroom overlooking the snowy lake.
PARKING & VEHICLES
To ensure smooth circulation and preserve our natural grounds, please park only in the designated parking spaces on the property. Additionally, please note that commercial vehicles are reserved exclusively for approved service providers.
TRAVEL INFORMATION
- New York City is approximately 2 hours away.
- Amtrak: Rhinecliff Station (approximately 20 minutes away).
- Metro-North: Wassaic Station (approximately 20 minutes away).
WELCOME TO YOUR STAY!
This rental includes the guest house. Our peaceful property is nestled on a private peninsula on the shoreline of Twin Island Lake (formerly Mud Pond), an approximately 60-acre lake at the base of Stissing Mountain in the Town of Pine Plains, Dutchess County, New York. For winter travel, we recommend a 4WD vehicle with snow tires to ensure a safe and seamless journey through the scenic seasonal landscape.
DEPARTURE & CHECK-OUT
To ensure our team can prepare the home flawlessly for our next guests, check-out is at 11:00 AM. Please note that an overtime fee of $50 per half-hour will apply for departures past this time. We deeply appreciate your cooperation and hope you have an unforgettable stay!
YOUR LOCAL HOSTS
This property is managed by Home Sweet Hudson, a trusted and local management company deeply passionate about crafting unforgettable Hudson Valley getaways. From sharing insider recommendations to ensuring every detail of your stay is seamless, we are here to provide attentive, personalized support from the moment you book until the day you depart.
LOCAL EXPERIENCES & ADD-ONS
Home Sweet Hudson has partnered with trusted local vendors who offer wonderful add-ons to your stay. Please message us with the services you would like to explore so we can check availability and help coordinate your experience.
- Mobile Sauna Rental: Enjoy a mobile cedar wood sauna during your stay.
- Private Yoga Classes: Bring the studio vibes to you with a tailored private class.
- In-Home Private Chefs: Skip the shopping and enjoy fine dining with locally sourced ingredients, seasonal menus, and delicious wine pairings.
- Private Massage Sessions: Whether you have been hiking, skiing, or simply taking in the views, an in-home massage is the perfect way to unwind.
So many great places to see in the area!
NEARBY NATURE & RECREATION
- Thompson Pond Preserve (3 min): Walking trails perfect for birdwatching and wildlife.
- Stissing Mountain Fire Tower (3 min): Scenic views and hiking.
- Stissing Lake Park and Pine Plains Beach (5 min): Two playgrounds and open park areas for family fun.
- Lake Taghkanic State Park (18 min by car): A great place for lake activities and hiking.
DINING & WINERIES
- Stissing House (5 min): Dine at one of The New York Times' 50 Most Exciting Restaurants in the U.S. 2023.
- Champetre (5 min): A renowned French restaurant run by a famous NYC chef. Book a table as soon as possible!
- Dutchess Wine Trail (20 min by car): Exquisite wineries offering tastings and tours amid vineyard landscapes.
DAY TRIPS
- Kingston (45 min by car): A destination for great food and shopping.st city-dwellers for great food and shopping.
PROPERTY ACCESS & OUTDOOR LIVING
On this property you will find two mirrored homes. The home on the left is the guest house, for guest use ONLY. The home on the right is not available to guests and is not included in the reservation.
Step outside to discover a private outdoor oasis equipped with fantastic amenities for your winter getaway:
BACKYARD & FIRE PIT: Enjoy the backyard, and the fire pit on a crisp winter evening.
LAKESIDE DECK: Relax on the lakeside deck overlooking the water.
DOG-FRIENDLY: Bowls and throw blankets are available for your dog.
BEDROOM & BATHROOM DISTRIBUTION
The house features multiple bedrooms on both the upper and lower levels with various bed configurations, including a king bedroom with a smart TV and a separate suite with exterior access. Enjoy a soothing soak in the tub with jacuzzi jets after a day of exploring in the snow.
KITCHEN
A fully stocked kitchen for preparing delicious meals.
LIVING SPACE
Gather around the fireplace in the living room, or relax in the sun-drenched sunroom overlooking the snowy lake.
PARKING & VEHICLES
To ensure smooth circulation and preserve our natural grounds, please park only in the designated parking spaces on the property. Additionally, please note that commercial vehicles are reserved exclusively for approved service providers.
TRAVEL INFORMATION
- New York City is approximately 2 hours away.
- Amtrak: Rhinecliff Station (approximately 20 minutes away).
- Metro-North: Wassaic Station (approximately 20 minutes away).
WELCOME TO YOUR STAY!
This rental includes the guest house. Our peaceful property is nestled on a private peninsula on the shoreline of Twin Island Lake (formerly Mud Pond), an approximately 60-acre lake at the base of Stissing Mountain in the Town of Pine Plains, Dutchess County, New York. For winter travel, we recommend a 4WD vehicle with snow tires to ensure a safe and seamless journey through the scenic seasonal landscape.
DEPARTURE & CHECK-OUT
To ensure our team can prepare the home flawlessly for our next guests, check-out is at 11:00 AM. Please note that an overtime fee of $50 per half-hour will apply for departures past this time. We deeply appreciate your cooperation and hope you have an unforgettable stay!
Amenities
Free WiFi/internet
Free Parking
Non-smoking
Pets allowed
TV
Heating
Coffee/tea maker
Refrigerator
Kitchen
WiFi/Internet
Parking Available
Microwave
Dishwasher
Washing machine
Dryer
Washer/dryer
Patio
Kitchenware
Garden
Oven
Stove
Laundry services
Fireplace
Waterfront
Outdoor Cooking
Family friendly
Children's high chair
Cribs or cots available
Ironing facilities
Towels
Linens
Dining table
Hairdryer
Fire extinguisher
Map of Pine Plains, NY
Ratings and reviews
10 / 10Outstanding·Apr 2026
Great! Exactly what we needed for our stay. Was able to give us valuable family time while celebrating a family wedding. Steps on the side are not very friendly for elderly, but other than that it was great!
10 / 10Outstanding·Jan 2026
Our family of four, plus two friends, had a wonderful stay at this property over New Year's Eve week. It was spacious, clean & comfortable. We cooked 3 meals a day and found everything we needed in the kitchen, plus more. There were two cabinets stocked with lots of games (and even an Xbox for the kids!), and thoughtful amenities like cloth napkins, place mats and candles which made our dinners that much more special. The lakefront location was beautiful in the winter, and morning coffee in the sun room was such a peaceful way to start the day. We also really appreciated the wood burning fireplace, hard to find in a rental property! Beds were comfortable and rooms were quiet.
We had an issue w/ the Smartlock not working at check-in, but our phone call was quickly answered and the issue resolved. There were a couple of small maintenance issues that could be checked over a bit more carefully before check in, including the hood lights and one overhead light in the kitchen which had bulbs out, making the stove corner area vary dark. We did not have access to change them, but management was prompt in replying with a maintenance person to take a look. He did not have the right bulbs, so took notes as to what was needed for the fix for the next renters. There was also no outlet cover on an exposed outlet in the sun room- a potential hazard for young children. These were minor, but we did have kids with us so hoping it's addressed for the next guests.
Overall an excellent stay- we will definitely visit again the next time we are in town!
10 / 10Outstanding·Oct 2025
The team was so kind and accommodating, and communication was seamless from start to finish. The property couldn’t have been more perfect, an absolutely stunning setting for our fall wedding, both inside and out.
10 / 10Outstanding·Jun 2025
Everything was wonderful! Only complaint, no regular coffee pods downstairs, only decaf
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Top rated by guests
9.6Outstanding
(7 Ratings)
"Great! Exactly what we needed for our stay. Was able to give us valuable family time while celebrating a family wedding. Steps on the side are not very friendly for elderly, but other than that it was..."
Ashlee B.Don't miss out! Price and availability may change
