Historic Cottage w Brand New Hot Tub and Game Room | House in Pine Plains

Summary:
Restored 1810 cottage where historic charm meets modern living. Follow and tag us on IG @theupstatecub!
Welcome to The Upstate Cub by Summer, a beautifully designed historic 1810 cottage with modern amenities. Located near Pine Plains, this three-bedroom, two-bathroom home on a 1.2-acre plot features a converted barn game room and a new hot tub. Perfect for a private weekend getaway, it offers easy access to popular Catskills destinations like Rhinebeck, Red Hook, Millerton, and Millbrook.
The Space:
As you step inside, you're greeted by a home where historical elements like exposed beams and wooden floors are elegantly intertwined with modern updates. The den, warmed by a wood stove and equipped with a full bath, provides a cozy retreat after a day of hiking or skiing. With its own separate entrance, this den offers the perfect escape as a quiet work-from-home space.
The heart of the home is the open kitchen and dining area, designed to be both inviting and functional. The kitchen, a dream for any culinary enthusiast, boasts sleek stainless steel appliances, soft-closing cabinets, and chic butcher block countertops. On the upper level, three snug bedrooms await, sharing a well-fitted bathroom. The house comfortably hosts up to 5 guests across 3 bedrooms and can accommodate an extra 2 guests with a pullout couch. Each bedroom features luxurious linens and dream mattresses to ensure a restorative sleep.
Step outside to discover a world of natural beauty and entertainment. The home is surrounded by landscaped gardens and a welcoming front porch – the ideal spot for morning coffee. A bluestone walkway leads to a spacious backyard, complete with multiple patios and a fire pit, set against a stunning mountainous backdrop – perfect for enjoying starry nights with loved ones. Adjacent to this, a newly converted barn now serves as a fun-packed game room, and a brand new hot tub invites relaxation under the stars. The partially fenced property offers both ample space and privacy, crafting it into a serene haven for those in search of tranquil respite.
Key Features:
- Renovated 1810 cottage with original wood doors, wood beam floors, and exposed beams
- Spacious, open floor plan perfect for entertaining
- A full kitchen with stainless steel appliances and butcher block countertops
- Three comfortable bedrooms with dream mattresses and luxury linens
- Two well-maintained bathrooms that include a walk-in shower and standalone tub
- Warm and inviting den, featuring a wood stove
- Dedicated work-from-home space with multiple desks throughout the house and high-speed WiFi for working and streaming
- Game room with Foosball and Ping Pong tables, and a TV
- Brand New Hot Tub (7-person with jets and lights)
- Outdoor entertainment including, outdoor dining area, brand new fire pit, and grill
- Spacious partly fenced backyard with stone patios and an enclosed flower garden
- Ample parking space in front of the game room and overflow on the driveway towards the back
Sleeping Arrangements:
- Bedroom 1: 1 queen bed
- Bedroom 2: 1 twin bed
- Bedroom 3: 1 queen bed
- Pullout couch
Guest Access:
We offer convenient door codes for self-check-in. Portoro Homes uses convenient keyless entry for self check-in, details provided 2 weeks (or less) prior to arrival by email and text message.
• Early check-ins or late check-outs: If the property happens to be ready earlier than the standard 4 pm check-in time on the day of your arrival, in most cases an early arrival option may be available when confirmed with the main office. Late check-outs must be confirmed with main office staff prior to the date of departure.
The Neighborhood:
The Catskills and Hudson Valley are fantastic destinations for anyone looking to escape the city and experience a blend of natural beauty, vibrant culture, and small-town charm. This region is famous for its rolling mountains, lush forests, and scenic river views—perfect for hiking, biking, kayaking, or simply soaking up the outdoors. In autumn, the foliage is truly spectacular, painting the landscape in vibrant colors. Throughout the area, you’ll discover a unique mix of history and creativity, with beautifully preserved architecture, art galleries, boutique shops, and a thriving farm-to-table dining scene featuring fresh local produce and artisanal goods. Weekend markets, cozy cafés, and a welcoming community vibe are found in every corner. The region is rich in culture, with attractions like Olana, Clermont State Historic Site, and regular art shows, music events, and seasonal festivals. Whether you’re after adventure, relaxation, or a foodie experience, the Catskills and Hudson Valley deliver it all—making any of these charming towns a perfect home base for exploring this special corner of New York.
Pine Plains is a classic Hudson Valley town where rolling farmland, sparkling lakes, and a sense of community define daily life. The area is known for its equestrian culture—horse farms and riding trails abound—and for its pastoral scenery, which feels both timeless and welcoming. Stissing Mountain rises above the landscape, and its fire tower offers one of the most inspiring panoramic views in the region. Pine Plains is also home to historic barns, vibrant farmers’ markets, and local festivals that bring neighbors and visitors together. Its blend of rural charm, outdoor recreation, and small-town warmth make Pine Plains a true hidden gem for those seeking a peaceful, authentic upstate experience.
Things to See & Do:
• Things to Do:
- Hike to the top of Stissing Mountain and climb the fire tower.
- Birdwatch and walk at Thompson Pond Preserve.
- Attend a concert or event at Pine Plains Memorial Hall.
- Dine at the historic Stissing House.
- Visit Willowbrook Farm for equestrian events.
- Enjoy fishing or kayaking at Twin Island Lake.
- Browse the Little Nine Partners Historical Society Museum.
• Things to See:
- The sweeping views from Stissing Mountain Fire Tower
- Thompson Pond’s serene nature preserve
- The historic Little Nine Partners Schoolhouse
- Stissing House (historic inn and restaurant)
- Twin Island Lake’s peaceful waters
- Pine Plains Memorial Hall’s classic architecture
- Willowbrook Farm’s rolling pastures
- Antique shops and historic barns dotting the countryside
• Golf Courses: Red Hook Golf Club, Copake Country Club, Dutcher Golf Course
• Museums: Little Nine Partners Historical Society Museum, Stissing House (historic site, local history), Roeliff Jansen Historical Society Museum (Hillsdale, nearby)
• Local Markets: Pine Plains Farmers Market, Thompson Pond Farm Stand (seasonal), Millerton Farmers Market (nearby), Red Hook Farmers Market (nearby)
• Local Restaurants & Shopping
- Restaurants: Stissing House, Champetre, Lia’s Mountain View Restaurant, Pine Plains Platter, Four Brothers Pizza Inn, El Guacamole Mexican Grill, Canoe Hill (Millerton, nearby)
- Shops: Pine Plains Platter (market/café/shop), Hammertown Barn, Willowbrook Farm (farm shop), Lia’s Mountain View (market & deli), Stissing House Shop, Little Nine Partners Antiques, Canoe Hill (Millerton, nearby)
Annual Festivals & Events:
• Pine Plains Community Day
• Stissing House New Year’s Eve Celebration
• Dutchess County Fair (Rhinebeck, nearby)
• Millerton Fall for Art Festival (Millerton, nearby)
• Red Hook Apple Blossom Festival (Red Hook, nearby)
• Pine Plains FFA Agricultural Fair
• Hudson Valley Wine & Food Fest (Rhinebeck, nearby)
• Hudson Valley Hot Air Balloon Festival (Rhinebeck, nearby)
• Copake Hillsdale Farmers Market Summer Fest (Copake, nearby)
• Oldtone Roots Music Festival (Hillsdale, nearby)
Getting Around:
Getting around Pine Plains is relaxed and scenic, with well-maintained country roads leading past lakes, horse farms, and open meadows. Your own car gives you the freedom to visit local markets, historic barns, and the base of Stissing Mountain whenever you like. Parking is easy and free throughout the area.
Drives along Route 199 and the surrounding byways showcase the tranquil charm of the northern Hudson Valley. You’ll pass through rolling farmland and picturesque hamlets, making each trip a chance to enjoy the peaceful landscape and maybe spot a local farm stand or antique shop.
Wildlife is often seen along the roadside, adding to the rural charm—just be cautious at dawn and dusk. Cell service is generally good, but downloading maps is always smart for backroad adventures. Exploring Pine Plains by car means every drive is a scenic escape.
Airports:
• Stewart International Airport (SWF): 1 hour 10 minutes
• Albany International Airport (ALB): 1 hour 20 minutes
• Westchester County Airport (HPN): 1 hour 20 minutes
• New York City Airports (JFK/LGA/EWR): 2–2.5 hours
Popular Landmarks:
• Stissing Mountain Fire Tower (hiking, panoramic views)
• Thompson Pond Preserve (nature, birdwatching)
• Pine Plains Memorial Hall (community events)
• Mashomack Fish & Game Preserve (historic, private)
• Little Nine Partners Historical Society Museum
• Stissing House (historic inn & restaurant)
• Twin Island Lake (recreation)
• Pine Plains Free Library (historic building)
• Willowbrook Farm (equestrian events)
• Pine Plains Central School (historic architecture)
• Silvernails Rail Trail (walking, biking)
Interaction with Guests:
Our goal is that your vacation exceed your expectations. Portoro Homes communicates via email and phone. After a booking is confirmed, rental agreement will be emailed to the guest for e-signature. Check-in instructions are sent by email and text message 14 days (or less) prior to arrival date. We offer convenient keyless entry for self-check in. We do typically check in with guests by text 1-2 times during their stays to ensure a 5-star experience and remain available for any questions. We are available to guests 24/7 for any inquiries.

Historic Cottage w Brand New Hot Tub and Game Room is located in Pine Plains. Historic Cottage w Brand New Hot Tub and Game Room provides accommodation, featuring Fireplace/Heating, Guest Services, Hot Tub, among other amenities. This House features Fireplace/Heating, Guest Services, Hot Tub, to make your stay a comfortable one.

Historic Cottage w Brand New Hot Tub and Game Room has 3 Bedrooms , 2 Bathrooms, and max occupancy of 6 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Pine Plains has interesting places to visit. If you want to learn more about the House in Pine Plains, such as places to visit and things to do nearby, you can check below to learn more.