Library + Sunroom + Dining for 8 | Ensuite Baths + Gardens | Preston House (74)

Set back from the road behind clipped hedges and a stand of old shade trees, Preston House is a deep-green colonial with white trim and the settled, well-proportioned look of a house that's been standing a long time and fully intends to keep standing. There's a fountain on the front lawn, a great deal of birdsong, and no particular reason to hurry.

Inside, the rooms unfold one into the next the way they do in old country houses. A formal living room runs long and bright, with seating pulled in close for conversation. A second sitting room picks up where it leaves off, with more windows and a TV for the nights the weather turns. The best room might be the library — floor-to-ceiling built-ins packed with books, a sofa positioned exactly where the afternoon light lands, and enough quiet that people tend to disappear into it and stay considerably longer than they planned.

The dining room seats eight under a chandelier, which is the right number for a house this size: everyone at one table, nobody eating standing up at the counter. The kitchen runs long and practical, with full-size appliances, real counter space, and windows over the work area. Coffee happens early here and lingers.

Then there's the sunroom, which is the room people remember. Windows and glass doors on nearly every side, wicker and painted chairs, a rug underfoot, and light that changes character hour by hour — grey-blue at dawn, full and warm by eleven, gold across the floorboards by five. It's the room for the crossword, the second cup, the phone call you keep putting off.

Four bedrooms sleep nine, and every one of them has its own full bath — genuinely rare in a house of this vintage, and the detail that makes a group trip here run smoothly. The first-floor bedroom has a queen and an ensuite, useful for anyone who'd rather skip the stairs. Upstairs, three more queens sit under sloped ceilings and painted walls, one with an extra twin daybed tucked in. There's a half bath on the main floor for guests, and a washer and dryer you're free to use whenever you like.

Out back, a bistro table for two sits on the patio under the tree canopy — the spot for the first cup of the morning or the last of the evening. Past the lawn, the ridgelines of the Harlem Valley run north to south, and the sunsets over them tend to empty the house out onto the grass.

The setting is the quiet half of the Hudson Valley: the Harlem Valley, up along the Connecticut line, where the farms are still working farms and the towns are small on purpose. This exact stretch of countryside was painted by Asher Durand in 1848 and now hangs in the Smithsonian, which tells you how long people have been stopping to look at it. Dover Stone Church — an easy trail leading to a cave and waterfall — is minutes north. The Appalachian Trail crosses nearby, the Harlem Valley Rail Trail picks up in Wassaic, and Kent, Bulls Bridge, and the waterfalls of northwest Connecticut are a short drive east. Millerton and Amenia are north for antiquing and farm stands, Thunder Ridge handles winter, and the Wassaic Project's seven-story mill of contemporary art is worth the twenty minutes. There's a very good country-inn dinner to be had just up the road. Manhattan is roughly 90 minutes by car, with Metro-North's Harlem Line running out of Dover Plains if you'd rather let someone else drive.

AvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips!

Comprised of quaint towns, each with their own charming main street, upstate New York’s Hudson Valley is famed for its natural beauty and seasonal produce. After all, it was here that inspired an entire artistic movement of Romantic painters who captured the area’s rolling hills, colorful foliage, and pastoral setting. View the landscapes in person by hiking the Catskill Mountains. Then, visit local farms where there’s a lot to pick: apples in the fall, strawberries in the summer, and vegetables in between.

Local Attraction: Hunter Mountain Ski Resort, Windham Ski Mountain and Resort, Hunter Mountain Ski Resort, Rip Van Winkle Lake Park (just a 1–2 minute walk and literally around the corner from the home), Windham Path, Windham High Peak, North Lake/South Lake hiking and kayaking area, Kaaterskill Falls, Hensonville’s farm-to-table market, Maplecrest trailheads, and the nearby towns of Windham, Tannersville, Hudson, and Catskill.

Home Truths:
- This home allows up to 2 pets for a fee; undisclosed pets brought without AvantStay’s approval may result in a $500 fine per pet.
- Preston House has two lovely original fireplaces, but they are not operational and are not available for guest use. Please do not attempt to light a fire in the home.
- *Complimentary Refreshments:* Bottled water is provided for your stay, and a Keurig coffee machine is available in the sitting room — perfect for a quick cup of coffee whenever you need it.

Parking Details:
- Enjoy ample on-site parking for up to 10 vehicles. Street parking is not permitted.

This is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.

As part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation.

Events or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees.

There is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.

As a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.

IDs will be requested for verification after booking. All bookings over 28 days require a security deposit.

We report and prosecute all Credit Card Fraud.