Lakeside Escape: Serene Waterfront Getaway
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Pine Plains
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House
Lakeside Peninsula Escape
8
Guests
4
Bedrooms
3
Bathrooms
Lakeside Retreat on a Private Peninsula in Pine Plains
Escape to this charming lakefront guest house nestled on a private peninsula in Pine Plains, NY. Enjoy breathtaking views, cozy amenities, and easy access to outdoor recreation and local attractions.
Rooms and Beds
Living Room
Living Room #2
Bedroom #1
king beds: 1
Bedroom #2
single beds: 2
Bedroom #3
king beds: 1
Bedroom #4
queen beds: 1
Features and Amenities
Boat Slip
Lakefront
Childrens Books And Toys
Pack N Play Travel Crib
Baby High Chair
Baking Sheet
Barbecue
Barbeque Utensils
Blender
Board Games
Body Soap
Carbon Monoxide Detector
Rates and Availability
Taxes and fees are additional
Reviews
Peaceful and Well Appointed Retreat
Natalie Spak
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…
Dreamy Wedding Weekend
Marisa Speranzi
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.
Add-ons
Total
Price Details
When
Comfotable cottage in wooded setting
Joe Fantozzi
September 12, 2022
My wife and I enjoyed our peaceful stay at the Rail Trail Cottage (and so did our dog Roxie). In terms of furniture and decor this is more of a home than a thrown-together rental. We made great use of the screen porch and comfortable living room…
We had a great weekend in the Catskills
Jody
November 16, 2021
Kitchen dishware was well stocked, and the open kitchen layout allowed for a very social experience. Lots of toys and board games there for the kids. Host was super responsive. Location is excellent for all kinds of hiking and exploring. House was a…
This home is stunning.
Ellen
October 17, 2021
This home is stunning. It has everything you could possibly need for a relaxing and accommodating stay. The outdoor spaces are beautiful, and the inside is modern and comfortable. Check-In/check-out process was easy. Would absolutely stay here again!
The home was exactly as described
Michelle
March 16, 2022
The home was exactly as described, great communication all along. The kitchen is well equipped and the bedrooms were comfortable. You can see the attention to detail in the bathroom amenities and throughout the house.
Beautiful Property!!!
Jeffrey Kauffman
January 16, 2024
We had a fantastic time at the cabin. Great space with a wonderful fireplace that led to lots of late night game playing (and a few cocktails)! The property is beautiful with the roaring creek just down the hill. A perfect stay!
Love the home!
Laura Leigh Rogers
September 16, 2025
Great experience at the Todd Hill farmhouse! Thank you for having us. It is well equipped and such a restful and expansive hosting space for a large group. I will note, this is the second year coming and we always struggle with the coffee pot whe…
Magical
Maggie Watson
October 23, 2024
Had a magical weekend with close friends for my 50th celebration. The property is stunning and a great gathering place.
Wonderful
Don
September 16, 2025
Lovely house, and amazing views. Home Sweet Hudson made everything so easy. Thank you!
Really Enjoyed Our Stay!
Allie Goldberg
September 29, 2025
Thank you, team, for a wonderful stay at Hudson Woods. The property and homes were beautiful and fit our needs perfectly.
The only feedback we have is that we wish we had known the pool would be closed for the weekend. Everyone brought swimsuits…
Description
Lakeside Retreat on a Private Peninsula in Pine Plains
Escape to this charming lakefront guest house nestled on a private peninsula in Pine Plains, NY. Enjoy breathtaking views, cozy amenities, and easy access to outdoor recreation and local attractions.
Space
This inviting home offers a comfortable and well-equipped space for your getaway. Relax in the sun-drenched sunroom overlooking the lake, gather around the fireplace in the living room, or prepare delicious meals in the fully stocked kitchen. 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.
Enjoy a soothing soak in the tub with jacuzzi jets after a day of exploring.
Neighborhood
So many great places to see in the area!
3 min to Thompson Pond Preserve – Enjoy walking trails perfect for birdwatching and experiencing diverse wildlife.
3 min to Stissing Mountain Fire Tower for amazing scenic views and hiking.
5 min to Stissing Lake Park and Pine Plains Beach – Enjoy two playgrounds and open park areas for family fun and outdoor activities.
5 min to Stissing House in Pine Plains – Dine at one of The New York Times’ 50 Most Exciting Restaurants in the U.S. 2023 or go to Champetre – A renowned French restaurant run by a famous NYC chef. Just make sure you book a table as soon as possible!
18 min by car to Lake Taghkanic State Park, a great place for lake activities and hiking.
20 minutes by car to the Duchess Wine Trail – Discover exquisite wineries offering tastings and tours amidst stunning vineyard landscapes.
45 min by car to Kingston, a destination for most city-dwellers for great food and shopping.
3 min to Thompson Pond Preserve – Enjoy walking trails perfect for birdwatching and experiencing diverse wildlife.
3 min to Stissing Mountain Fire Tower for amazing scenic views and hiking.
5 min to Stissing Lake Park and Pine Plains Beach – Enjoy two playgrounds and open park areas for family fun and outdoor activities.
5 min to Stissing House in Pine Plains – Dine at one of The New York Times’ 50 Most Exciting Restaurants in the U.S. 2023 or go to Champetre – A renowned French restaurant run by a famous NYC chef. Just make sure you book a table as soon as possible!
18 min by car to Lake Taghkanic State Park, a great place for lake activities and hiking.
20 minutes by car to the Duchess Wine Trail – Discover exquisite wineries offering tastings and tours amidst stunning vineyard landscapes.
45 min by car to Kingston, a destination for most city-dwellers for great food and shopping.
Access
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 for guests and not included in the reservation.
As guests, you will have access to the guest house, backyard, grill, fire pit, and lakeside deck. This is a dog-friendly property and has bowls and throw blankets available for your dog.
Please note, this property does have exterior cameras for safety and security. These are only located on the exterior of the property, never the interior, and will not be monitored during your stay unless an issue arises.
As guests, you will have access to the guest house, backyard, grill, fire pit, and lakeside deck. This is a dog-friendly property and has bowls and throw blankets available for your dog.
Please note, this property does have exterior cameras for safety and security. These are only located on the exterior of the property, never the interior, and will not be monitored during your stay unless an issue arises.
Transit
-New York City is approximately 2 hours away.
-Amtrak: Rhinecliff Station
-Metro-North: Wassaic station
*Both stations are approximately 20 minutes away.
-Amtrak: Rhinecliff Station
-Metro-North: Wassaic station
*Both stations are approximately 20 minutes away.
Notes
Twin Island Lake (formerly, Mud Pond) (TWIL) is an approximately 60-acre lake, nestled at the base of Stissing Mountain in the Town of Pine Plains, Dutchess County, New York. Our peaceful property is nestled on a private peninsula on the beautiful shoreline.
🐾 Pet Policy: We welcome all types of dogs with a fee of $50 per animal/per night. If you plan to bring more than one dog, please obtain prior approval from the host. All fees are due before check-in and we cannot accept other types of animals at this time. Any undisclosed pets will incur a $300 deep-cleaning fee.
Please be advised that every 30 minutes spent on the property past 11am check out time a $50 fee will be initiated and charged to the card on file used to book the listing. We appreciate your cooperation and understanding.
🐾 Pet Policy: We welcome all types of dogs with a fee of $50 per animal/per night. If you plan to bring more than one dog, please obtain prior approval from the host. All fees are due before check-in and we cannot accept other types of animals at this time. Any undisclosed pets will incur a $300 deep-cleaning fee.
Please be advised that every 30 minutes spent on the property past 11am check out time a $50 fee will be initiated and charged to the card on file used to book the listing. We appreciate your cooperation and understanding.
Features and Amenities
Boat Slip
Lakefront
Childrens Books And Toys
Pack N Play Travel Crib
Baby High Chair
Baking Sheet
Barbecue
Barbeque Utensils
Blender
Board Games
Body Soap
Carbon Monoxide Detector
Ceiling Fan
Chef's kitchen
Cleaning Products
Cleaning With Disinfectants
Coffee
Coffee Maker
Conditioner
Contactless Checkin
Cooking Basics
Crockery Cutlery
Deck Patio
Dining Table
Dishwasher
Dryer
Emergency Exit
Enhanced Cleaning
Essentials
Extra Pillows And Blankets
Family-friendly
Fire Extinguisher
Fire Pit
Fireplace Guards
First Aid Kit
Free Parking
Freezer
Fridge
Game Console
Garden
Hair Dryer
Hammock
Hangers
Heating
High Touch Surfaces Cleaning With Disinfectants
Hot Water
Indoor Fireplace
Internet Wifi
Iron
Jacuzzi
Lake
Lake View
Laptop Friendly
Linens
Microwave Oven
Outdoor Lighting
Outdoor Seating
Oven
Pet-friendly
Pots Pans
Private Entrance
Shampoo
Shower Gel
Smoke Detector
Stove
Toaster
Toiletries
Towels
Town
TV
Ventilation Fan
Wardrobe
Washer/dryer
Water Front
Water Kettle
Water View
Wine Glasses