Lakeside Peninsula Escape

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.

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 stays 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.

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.

-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 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.