Lakeside Peninsula: Serene Lakefront Getaway
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Pine Plains
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House
Lakeside Peninsula Escape
8
Guests
4
Bedrooms
3
Bathrooms
Wake up to stunning views at this lakefront guest house on a private peninsula in Pine Plains, New York. Enjoy the lake from the sunroom, snuggle by the fireplace, or relax on the dock. Pine Plains offers scenic beauty, rolling farmland, and a welcoming community. Explore nearby hiking trails, beaches, historic sites, and local eateries, or visit Rhinebeck, Millerton, and Red Hook, just 15 miles away. Skiing is less than 40 minutes away.
Rooms and Beds
Bedroom #1
king beds: 1
Bedroom #2
single beds: 2
Bedroom #3
king beds: 1
Bedroom #4
queen beds: 1
Living Room #1
Living Room #2
Features and Amenities
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
Rates and Availability
Taxes and fees are additional
Reviews
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
Lovely house outside of Kingston!
Jodie
October 5, 2021
Lovely house outside of Kingston! The location is fabulous for access to the Wallkill Valley Rail Trail and we enjoyed 2 great days of autumn biking (extra shout-out to Overlook Bicycles near Woodstock, NY for a great bike rental experience!). The h…
Absolutely loved our stay here.
Rebekah
November 1, 2021
Absolutely loved our stay here.
Superb
Adelle Wadsworth
June 17, 2025
We loved this cabin.. the location, the peace and quiet, the ambiance and of course the mod pool. We did have a bit of trouble getting the pool heated up as it was a bitter cold March weekend …problem solved via texting. Also the cabin itself needed…
Great home for a family get together
Priya Hariani
May 22, 2023
We thoroughly enjoyed our stay at Saugerties Manor. The house was large enough for three generations to have their own space. The hot tub was a big hit and the kitchen was well stocked.
Our Favorite Rental House!
Jennifer Chan
July 15, 2025
Hands down the best house I've ever rented. Our yearly tradition involves me planning a getaway trip for my entire extended family and most houses are usually sufficient. This house totally blew me out of the water! Amazing pool, sauna, jacuzzi and…
The house is exactly as promised & a great value.
James
November 8, 2021
The house: New, beautifully designed open floor plan with plenty of common space for the whole group inside & out. There was plenty of patio / outdoor furniture near the firepit, the main floor / fireplace was perfect for a game night & meals / drin…
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…
This house was fantastic in every way
Eli
November 1, 2021
The hot tub on a cold fall night was SUBLIME! Also, being in walking distance from the Hudson walkway was a real treat. Would definitely come back!
The place was awesome. Enjoyed every part of it.
Mendil
February 15, 2022
The place was awesome. Enjoyed every part of it.
Home was picture perfect for us.
Steven
March 26, 2022
Very private location within 10-30 minutes of Woodstock, Kingston and Phoenicia.
Tastefully decorated with comfortable furnishings. Communication was excellent.
Would definitely return.
Description
Wake up to stunning views at this lakefront guest house on a private peninsula in Pine Plains, New York. Enjoy the lake from the sunroom, snuggle by the fireplace, or relax on the dock. Pine Plains offers scenic beauty, rolling farmland, and a welcoming community. Explore nearby hiking trails, beaches, historic sites, and local eateries, or visit Rhinebeck, Millerton, and Red Hook, just 15 miles away. Skiing is less than 40 minutes away.
Space
As you enter the home through the front door, you will be greeted by the spacious living room. Gather around the fireplace for a fun board game or snuggle up on the couch for a movie after a long day of Twin Island adventures.
Through the living room is the fully stocked kitchen, providing you with every essential cooking item to provide was home-cooked meal. Craving 'smores? No fear, we provide all that you would need at the 'smores bar located on the hutch in the kitchen. Enjoy your morning coffee overlooking the lake in the sunroom just down the steps from the kitchen.
Down the hall from the living room, you will find two spacious bedrooms. One bedroom with two twin-sized beds perfect for children or singles. The other is a king bedroom that offers a garden-side view of the property. Just off these two bedrooms, you will find a full bathroom. This bathroom features a tub with jacuzzi jets, perfect for relaxing and soothing your muscles after a day of hiking Stissing Mountain.
Just down the stairs is another level of bedrooms. To the left at the bottom of the stairs, is a king bed with a smart TV for when you're ready to put your feet up. On this level, there is an additional full bath with a tub. Through the garage and down the hall is a fourth bedroom with a private bathroom. This additional bedroom has more of a private almost "mother-in-law suite" feel to it with exterior access and a hidden coffee bar just inside the hutch. This bedroom also has an Xbox provided, so feel free to bring your favorite game for those rainy days!
Through the living room is the fully stocked kitchen, providing you with every essential cooking item to provide was home-cooked meal. Craving 'smores? No fear, we provide all that you would need at the 'smores bar located on the hutch in the kitchen. Enjoy your morning coffee overlooking the lake in the sunroom just down the steps from the kitchen.
Down the hall from the living room, you will find two spacious bedrooms. One bedroom with two twin-sized beds perfect for children or singles. The other is a king bedroom that offers a garden-side view of the property. Just off these two bedrooms, you will find a full bathroom. This bathroom features a tub with jacuzzi jets, perfect for relaxing and soothing your muscles after a day of hiking Stissing Mountain.
Just down the stairs is another level of bedrooms. To the left at the bottom of the stairs, is a king bed with a smart TV for when you're ready to put your feet up. On this level, there is an additional full bath with a tub. Through the garage and down the hall is a fourth bedroom with a private bathroom. This additional bedroom has more of a private almost "mother-in-law suite" feel to it with exterior access and a hidden coffee bar just inside the hutch. This bedroom also has an Xbox provided, so feel free to bring your favorite game for those rainy days!
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 along the beautiful lake.
🐾 Pet Policy: We welcome all types of dogs with a $50 fee per animal. 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 $50 fee per animal. 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
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
Coffee
Coffee Maker
Conditioner
Contactless Checkin
Cooking Basics
Crockery Cutlery
Deck Patio
Dining Table
Dishwasher
Dryer
Emergency Exit
Essentials
Extra Pillows And Blankets
Family-friendly
Fire Extinguisher
Fire Pit
Fireplace Guards
First Aid Kit
Free Parking
Freezer
Fridge
Game Console
Hair Dryer
Hammock
Hangers
Heating
Hot Water
Indoor Fireplace
Internet Wifi
Iron
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 Kettle
Water View
Wine Glasses