2 Br Guest House Vacation Rental In Pine Plains, New York

Escape to Stissing Lake Guest Cottage, a newly renovated 2-bed, 2-bath retreat in the Hudson Valley. Nestled on an 11-acre estate by Stissing Lake, just 90 miles from NYC. Immerse in country living, swim, kayak, and explore nearby adventures like antiquing, horseback riding, golfing, skiing, and ziplining. Your gateway to peace and small-town charm!

We’ve just renovated our cozy cottage to offer a fresh and inviting stay! Enjoy a brand-new country kitchen, new appliances, updated bathrooms (photos coming soon), fresh paint, and brand-new beds, mattresses and linens throughout.

Choose from two charming bedrooms: The sunny yellow room features one double and one twin bed, plus a soothing clawfoot tub for ultimate relaxation. The blue bedroom, also with one double and one single bed, offers an en-suite bathroom complete with rain shower and a peaceful, windowless environment—ideal for those who crave privacy and uninterrupted rest.

Located just a short stroll from Stissing Lake, our guest cottage is perfect for year-round stays, whether you’re seeking a peaceful retreat or need temporary housing for employees.

$5.5k/month for the full experience, or reach out for shorter stays. Embrace the cabin life and leave the city hustle behind!

Your stay, your adventure! Enjoy the fire pit, BBQ, kayaking, and swimming from the private dock—all included in the rental. Dive into lake life! #GuestAccess #LakeEscape

We have a caretaker cottage on the property and are available for recommendations and questions as needed.

Stissing Lake offers an ideal place to relax, lots of room to roam and indulge in the magic of nature. Enjoy spring blossoms, summer fun in the water or the gorgeous fall foliage. Hike Stissing Mountain, picnic on the lawn, kayak or paddle boat around Stissing Lake, swim without the distraction of motorized boats, fish for Bass, watch the swans and turtles on the lake or birdwatch at Thomson Nature Preserve. Hudson Valley is home to artisan distillers, breweries, dairies, farmers markets, historic mansion tours, horseback riding, antiquing, and much more!

MetroNorth Train to Wassaic (25 mins), Poughkeepsie (45 mins) or Amtrak Rhinebeck (25 mins). Once here you can get around by bike or walking into town. With a car you can explore the Hudson Valley.

LOCATION
The guest cottage is set on an 11-acre estate, just down the driveway from the main house. It now has its own private entrance to Stissing Lake. The cottage is rustic, equipped with ceiling fans, and has air conditioning in the main living space for your comfort.

SELECTIVE RENTALS
We are very selective about who we rent to in order to maintain the peaceful charm of the property.

MONTHLY GUESTS
Heating is controlled by guests. For monthly stays, electric (summer) and propane (winter) are an additional charge.

LINENS PROVIDED
We provide all bedding, towels, and an initial supply of paper towels and toilet paper.

PET POLICY
We have a strict NO pets policy.

INTERNET
The property is equipped with the fastest WiFi available in the area. Please keep in mind this is the countryside, so speeds may vary.

DISCOUNTS
We currently do not offer senior or military discounts but do offer reduced rates for stays of 4 months or longer.

WEDDINGS AND EVENTS
We do not permit weddings or large events on the property. Only guests included in your reservation are allowed on-site during your stay.

NEAREST STORE
Peck’s Market, located just a mile away in town, offers a small selection of local produce, meats, and dairy. Nearby, you’ll also find a pharmacy, wine shop, and bank. Please note, these businesses operate on “country hours,” so check ahead before visiting.

NEARBY ACTIVITIES
• Dining: Stissing House, one of the Hudson Valley’s top restaurants, led by chef Clare de Boer.
• Hiking: Explore Thompson Pond Nature Conservancy, Stissing Mountain, or the Appalachian Trail.
• Horseback Riding: Available at Millbrook Stables.
• Historic Tours: Discover Hudson Valley’s historic homes.
• Wineries & Breweries: Visit local tasting spots.
• Artisan Foods: Irving Coffee Roasters in Millbrook, Coach Farms, and other cheese makers.
• Antiquing: Explore antique shops in neighboring towns.
• Indie Films: Catch a movie at Upstate Films in Rhinebeck.
• Farmers Markets: In Millerton, Rhinebeck, Millbrook, Pawling, and Amenia.
• Woodstock: Take a day trip to this iconic town.
• Golf: Tee off in Amenia.
• Water Adventures: Raft or canoe down the Housatonic River.

And so much more—your perfect Hudson Valley escape awaits!

Located in Pine Plains, this guesthouse is on a lake. Hornets Nest Paintball and Lake Taghkanic State Park are worth checking out if an activity is on the agenda, while those looking for area attractions can visit The Stissing Center and Northern Dutchess Botanical Gardens. Trevor Zoo and Center for Performing Arts at Rhinebeck are also worth visiting. Relax and indulge in the area's winery tours, or seek out an adventure with horse riding nearby.