Welcome to Lakeside Peninsula Escape, a stunning getaway with sweeping lake views

A perfect lake view on the deck above the dock.

Make new memories while cooking your favorite dish.

Dine in our all-season room with lovely lake views on all sides!

Private dock on the property with picnic tables for eating lakeside.

Bedroom 4: Queen sized bed. Downstairs Mother-in-law suite with private patio

Bedroom #2 on the main floor is perfect room for children or singles

Fill this radiant living room with laughter

Feel the warmth of the sun while chatting with loved ones

Enjoy a game night with family and friends

Eat and be merry in the all-season room.

Bedroom #1: King sized bed on the main floor

Our pristine bathroom on the main floor with jacuzzi jets

Perfect lighting to get ready in the bathroom on the main floor

Bedroom 3 is located downstairs with a TV & Book Nook and has a King sized bed

A quaint downstairs bathroom across from bedroom 3

Bedroom 4: Queen sized bed. Have a peaceful morning in our breakfast nook

Bathroom 3: adjoining bathroom to the Mother in law suite

Welcome to your serene lakeside getaway!

Thoughtful landscaping is a perfect compliment to the natural terrain.

Porch with lake views off the lower bedroom.

The patio complete with grill, down the steps from the all season room with lake views on every side.

Nothing like sitting around a fire along the shore.

Enjoy a Home Sweet Hudson cider by the fire pit

Swing under the trees as you listen to the waves lapping the shore.

The peninsula, surrounded by the cool, blue waters of the lake.

The private dock, looking up toward the house.

Adirondack chairs for lounging on the dock.

Views from the dock, looking out over the water.

Overlooking the lake from your private peninsula.

This long, private driveway is a stunning entry for your peaceful escape.

More Photos

All Properties

Pine Plains
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

Show All

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.

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.

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.

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.

Transit

-New York City is approximately 2 hours 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.

IMPORTANT NOTE:

To ensure community safety and preserve the natural surroundings, please note that the New York State annual outdoor brush burning ban is currently in effect from March 16 through May 14. During this time, New York prohibits all open residential fires to prevent spring wildfires. This includes the use of outdoor firepits, as well as the burning of debris, leaves, or brush

Amazing stay

Megan Harley

October 24, 2025

We had a wonderful stay at Greycliff. The property is absolutely beautiful — thoughtfully designed, incredibly peaceful, and positioned to take full advantage of the stunning views. Every window feels like a postcard, and the outdoor spaces make it…

Greycliff: Mohonk Preserve Getaway

The place was amazing – exceeded expectations

Tiffany

November 8, 2021

We loved the fire pits as well as the well stocked kitchen. The living room couches and beds were so comfortable! 10/10 would recommend

Charming and secluded, couple suggestions

Caroline Mackenzie Kennedy

July 16, 2024

We enjoyed staying in your lovely home. The privacy and seclusion is delightful, the setting lovely and the house comfortable. Just two suggestions: - the pillows on all the beds are sham fillers for decorative purposes and not sleeping pillows…

This is a perfect stay for a weekend away.

Dorothy

September 21, 2021

This is a perfect stay for a weekend away. Its a spacious and beautiful home that has all the amenities you need. The kitchen has vast collection of spices. The hot tub was a nice way to relax after a day of hiking.

Beautiful Home

Francisco Van Marissing

November 3, 2025

The experience of renting this property was great. The home is comfortable and the sauna and hot tub where great. House is well maintained and very comfy. Many things to do in Kingston and great restaurants.

Rondout Retreat: Private Poolside Luxury

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 home away from home on the Rail Trail

April Ricotta

May 21, 2020

Our family spent a month in this home and loved every minute of it. The location couldn’t be better, the hosts incredibly accommodating and helpful, and the house was everything we needed! We couldn’t have been happier with our stay. Walk out the ba…

We had a lovely stay at Jo’s place!

Karen

October 11, 2021

There was even wine and coffee left for us, what a lovely touch! We enjoyed coffee in the sunroom and the hot tub amongst the trees. This is a unique stay, and I hope we can visit again one day.

Quiet/Picturesque Getaway

Allison

September 10, 2022

We thoroughly enjoyed our time at the cabin. It was a great place for our dog to explore and for us to refresh and relax.

Mossybrook Hideout: Private Creek Oasis w Hot Tub

Cozy and Elegant

Deyano Manco

August 29, 2023

Great location and super cozy and well appointed. Really nice decor and bathrooms! Will definitely be back!

Serene weekend spot

Julia

August 12, 2024

This house was logistically convenient for my friends' weekend trip. The kitchen was well-stocked and the size of the house worked so well for our big group. BUT that's not the best part - the best part is the house itself! So so beautiful. Every co…

This house is in impeccable condition and extremely com

Paula

August 26, 2021

This house is in impeccable condition and extremely comfortable. The kitchen is very well stocked, the beds are comfortable and the place feels spacious, clean, and calm in the woods. My kids loved the pool! We loved it. :)

Great house and location

John Morrissey

March 31, 2025

We had a wonderful time at the house and in the area. Everything was just like in the photos and it was very clean and well stocked.

Hilltop House in Kingston is nothing short of wonderful

Jordan

October 3, 2021

Hilltop House in Kingston is nothing short of wonderful. The description and pictures were very accurate - large kitchen and living room with plenty of space for big families and friends to gather, cozy and comfortable bedrooms, all the amenities yo…

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…

We had a fantastic girls weekend away in the woods.

Lauren

January 31, 2022

We had a fantastic girls weekend away in the woods. The house was full of supplies to cook and relax and the hot tub was amazing! The house is spacious and beds were very comfortable. We would definitely stay here again!

Perfect Getaway

Katie Broderick

September 15, 2025

A group of 13 of us spent a weekend at the house and it could not have been more perfect. Plenty of space and accommodations. Super functional space and extremely easy process overall. Would definitely rent again.

Home Sweet Hudson: A Retreat Main House

The house is close to many things to do

Jan

September 20, 2021

We stayed as three families with kids and had a great time. The house is close to many things to do, safe for kids and allowed us to let them sleep in different spots. Very well equipped with essentials and beyond. Outside space very nice. Very well…

Beautiful home with gorgeous views!

Kelly Lynch

November 12, 2025

This home was absolutely beautiful! The views of the mountain and lake, especially with all the fall foliage was breathtaking! The house was really large and spacious especially for a big group. Also, the listing says 4 bedrooms but it actually has…

Sparkling Ridge: Private Lake + Stunning Views

January 4, 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…

Great stay!

Samm

January 27, 2022

Our stay was great, the location can’t be beat.

Charlotte

March 7, 2022

Beautiful space, definitely recommend. Perfect space to

Mark

October 6, 2021

Beautiful space, definitely recommend. Perfect space to relax and enjoy a nice rainy day with some friends. Had a great time

Amazing home in an amazing place. The hosts were very c

Jon

February 28, 2022

Amazing home in an amazing place. The hosts were very communicative and we had a great stay!

Lakeside Escape: Serene Waterfront Getaway

8

4

3

Rooms and Beds

Living Room

Living Room #2

Bedroom #1

Bedroom #2

Bedroom #3

Bedroom #4

Features and Amenities

Rates and Availability

Reviews

Peaceful and Well Appointed Retreat

Dreamy Wedding Weekend

Price Details

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Gardiner, NY

A very clean and spacious place to enjoy the area. Very

Beautiful Home

Wonderful

The house is close to many things to do

perfect fall getaway

we had a nice, relaxing few days.

Beautiful Property!!!

Amazing Home!

Definite in love with this place!

Description

Space

Neighborhood

Access

Transit

Notes

Features and Amenities

Amazing stay

The place was amazing – exceeded expectations

Charming and secluded, couple suggestions

This is a perfect stay for a weekend away.

Beautiful Home

The home was exactly as described

Beautiful home away from home on the Rail Trail

We had a lovely stay at Jo’s place!

Quiet/Picturesque Getaway

Cozy and Elegant

Serene weekend spot

This house is in impeccable condition and extremely com

Great house and location

Hilltop House in Kingston is nothing short of wonderful

Lovely house outside of Kingston!

We had a fantastic girls weekend away in the woods.

Perfect Getaway

The house is close to many things to do

Beautiful home with gorgeous views!

Peaceful and Well Appointed Retreat

Great stay!

Our stay was great, the location can’t be beat.

Beautiful space, definitely recommend. Perfect space to

Amazing home in an amazing place. The hosts were very c