Pine Plains, New York
Historic Cottage w Brand New Hot Tub and Game Room
4.76 • 37 reviews
House
3 bedrooms
4 beds
2 baths
6 guests
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.
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.
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)
Other Things to Note
Please pay close attention to following the house rules. Non compliance could result in sizable fines.
- All guests staying at a Portoro Homes are required to sign (esignature) a rental agreement and complete identity registration.
- Age restrictions apply. Reservation holder must be 25 years of age.
- No Parties or Events. - Quiet Hours observed, 10:00pm - 8:00am.
- Upon arrival, we aim to ensure your safety, proper access to the home, and guest features. Should you have any questions, please don't hesitate to reach out to Portoro Homes directly.
- Known damages incurred during your stay must be reported to the property manager immediately.
- Before check in, we will send you detailed directions to ensure a seamless arrival.
- Check-in time is 4:00 p.m. Check-out time is 11:00 a.m.
- We cannot guarantee early check ins or late checkouts, fee typically applies. When it is possible to check in early or check out late, there will be a fee for anything outside of a one hour window within our standard times. If your need for an early check in or late check out is great, your best option is to book an additional night.
- Some homes have cameras for external monitoring only.
- Some homes have pools and hot tubs. There is no guard around the water features. - Use at your own risk.
- In the State of New York and in Dutchess County, all hotel and vacation rental hosts are required to collect hotel tax. We collect these taxes within the booking transaction.
- This is a No Smoking property. Penalty fees for violations will apply and you may be asked to vacate the premises with no refund at the discretion of the Host.
- Animals/Pets -- Dogs Only, Guidelines and Fee*
Animals/pets must be disclosed prior to reservation arrival date, maximum of 2 per stay. Only dogs are permitted in “Pet-Friendly” Property listings. Allowed number of dogs will be expressly stated in the listing and a $150.00 fee per animal/pet is required. Animals/pets are not permitted anywhere on the premises unless prior approval is obtained. Any unauthorized animals/pets at the property will result in a $150.00 per day / per animal/pet fee, and may result in your reservation being canceled, and you may be required to vacate from the Property.
Amenities
BBQ grill
Garden or backyard
Hot tub
Indoor fireplace
Hair dryer
Hot water
Shampoo
Towels provided
Bed linens
Dryer
Essentials
26 more
Accommodation
Bedroom 1
1 sofa bed
Bedroom 2
1 queen bed
Bedroom 3
1 single bed
Bedroom 4
1 queen bed
Terms & Rules
Quiet hours required between 10:00 PM and 8:00 AM
Pets allowed (charges may apply)
Suitable for Children
Suitable for Infants
Availability
June 2025
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Check-in: After 4pm • Check-out: Before 11am
Reviews
4.76 • 37 reviews
JB
J B.
April 2025
Beautiful and clean
Everything good to say about our stay. Highly recommend!!
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J
John
April 2025
Nice house close to Pine Plains/Millbrook
Good outdoor area, plenty of room for 3 adults.
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M
Mariah
March 2025
Fantastic place. All the amenities were exactly what we were looking for. Would definitely stay again.
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A
Alycelee
February 2025
We had a great time! Loved the dear old house with modern amenities. Host was very responsive. We look forward to going back! ❤️
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Location
Pine Plains, New York. Exact location is provided after booking is confirmed.
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)
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