Lakeside Peninsula Escape

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.

This property is managed by Home Sweet Hudson, a trusted & local management company. Our team is passionate about connecting with each guest and providing unique stay places for your Hudson Valley vacation! We’re here to help answer any questions and provide thoughtful support throughout your trip.

Home Sweet Hudson has partnered with local third-party vendors who offer amazing add-on features to your stay. The Hudson Valley is a beautiful area to relax and rejuvenate, and now you can do it from the comfort of your ‘home’!

Mobile Sauna Rental: Take wellness and relaxation to the next level with a mobile cedar wood sauna! Enjoy this luxurious experience during your stay with us.

Private Yoga Classes: Bring the studio vibes to you, and enjoy a tailored private yoga class.

In-Home Private Chefs: Skip the shopping and experience fine dining with locally sourced ingredients, seasonal menus and delicious wine pairings.

Private Massage Session: Whether you’ve been hiking, skiing, or just taking in the views, an in-home massage is a perfect way to unwind on your vacation.

Interested in learning more? Be sure to message us with what services you’d like to explore so we can check availability and help coordinate your experience!

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.


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 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!

-New York City is approximately 2 hours away.
-Amtrak: Rhinecliff Station
-Metro-North: Wassaic station
*Both stations are approximately 20 minutes away.

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.