Sleeps 26 | Historic Inn + Barn | Near Ski Hills

Welcome to Old Drovers Inn & Carriage House by AvantStay. Book the full compound and this 1750 Hudson Valley landmark is yours alone, with the restored inn on one side of the street, the Carriage House on the other, and hotel-level service running throughout the stay. 🛏️ 12 guest rooms across 2 buildings, sleeps 26 🍳 Daily farm-fresh breakfast + coffee and tea all day 🌾 Library, Federal Room dining, firepit + an event barn for up to 250 guests The space Welcome to Old Drovers Inn & Carriage House by AvantStay! Book the full compound and this 1750 Hudson Valley landmark becomes yours alone: twelve guest rooms across two buildings, sleeping 26, with the inn's lobby, library, sitting room, dining rooms, and grounds reserved for your group, the Carriage House waiting just across the street, and hotel-level service running throughout. Since 1750, this Dover Plains landmark has been a place to stop, settle in, and stay a while. It opened as the Clear Water Tavern, catering to the cattle drovers who bought herds off New England farms and drove them down the post roads toward the New York City markets. The Preston family held the place for 160 years, and Elizabeth Taylor and Richard Burton took over every room in 1962 when they needed somewhere the world wouldn't find them — the same arrangement you're making now. A two-year, top-to-bottom restoration returned the building to form without sanding away what makes it worth the drive. The common rooms are the reason people linger, and with the house to yourselves, they work like the shared spaces of a grand private home. The sitting room and library invite the kind of afternoon where a book gets started, a board game comes out, and a schedule quietly falls apart. The Federal Room, the inn's formal dining room, is the architectural centerpiece: a grand wood-burning fireplace and murals painted by Edward Paine in 1941, recently restored, depicting the Millerton schoolhouse, Springwood at Hyde Park, the turrets of West Point, and the inn itself. The Colonial Tap Room — dark wood, plastered walls, candlelight and lanterns — serves a classic bill of fare, and in warm weather the seasonal patio takes over, surrounded by open, quiet country. Mornings begin with a breakfast made from local ingredients and changed daily — farm-fresh eggs with chives cut from the garden, homemade home fries, pancakes, pastries, yogurt and fruit parfaits, depending on the season. A concierge is on hand for coffee, tea, and refreshments throughout the day, and every room comes with central air conditioning, a fan for anyone who likes moving air, cable TV, WiFi, 800-thread-count linens, down comforters, and pillow-top mattresses. Every bathroom is stocked with Frette towels, plush robes, and a hair dryer. For celebrations, The Preston Barn stands just to the left of the inn — a wood-frame period structure built with re-purposed beams and stonework, outfitted with every modern amenity, and holding up to 250 people. Paired with a full buyout, it handles the complete arc of a wedding weekend: a Friday rehearsal dinner, the ceremony and reception, an after-party in the Tap Room, a send-off brunch the next morning. Something smaller works just as easily — the Federal Room seats 30, the Tap Room seats 55, and the house's private and semi-private corners suit a gathering of fifty or fewer. THE INN'S SIX ROOMS - The Meeting Room — The largest and most memorable room in the house, and the one with the best story: the Town of Dover formally separated from Pawling within these walls in 1807. An arch-shaped ceiling gives the second-floor space unusual height, and a wood-burning fireplace anchors a separate sitting area with room to spread out. - The Sleigh — A second-floor room named for the antique cherry sleigh bed at its center, a queen and the kind of piece that sets the tone for the whole room. A propane fireplace adds real warmth through the cooler months. - The Cherry Room — A second-floor room built around a queen brass bed, with a propane fireplace that comes into its own once the weather turns. Comfortable proportions, a calm mood, and the common rooms just down the stairs. - The Rose — The most intimate room in the house, with windows over the gardens — the quietest outlook at the inn. An ornate carved walnut bed anchors the room; this is the only room with a full bed, a natural fit for a couple traveling light. - The Gables 1 — At the top of the house on the third level, tucked under the roofline where wide plank wood paneling wraps the walls. A queen brass bed and an intentionally intimate scale, several flights removed from everything — the room for whoever in your group wants quiet above all else. - The Gables 2 — One of the superior rooms, sharing the third floor's wide plank paneling. A queen upholstered floral bed gives it a softer register, and its private bath is noticeably larger than most in the house — the strongest pairing of character and space on the upper floor. THE CARRIAGE HOUSE: SIX MORE, ACROSS THE STREET Directly across from the inn, the Carriage House gives the compound its second act: six additional rooms sharing an open-concept living space with a TV, dining area, and sitting area, plus a firepit just outside. Ideal for the overflow of a wedding weekend or for splitting a big group into houses without splitting the party. - Ali's Suite — The Carriage House's family quarters: two bedrooms, one with a queen and one with two twins, sharing a full bath with a shower. - The Coach Room — A queen bedroom with its own TV and an ensuite bath with a shower. - The Peacock Room — Mirrors the Coach Room's easy setup: a queen bed, in-room TV, and an ensuite bath with a shower. - The Loft — Bright and tucked away, with a queen bed and a private ensuite with a walk-in shower. Made for two people keeping their own schedule. - Cleopatra Room — The best bath in the Carriage House: a standalone tub and a separate walk-in shower off a bright queen bedroom, built for slow mornings and unhurried evenings. - Charlie's Room — A bright queen bedroom with a private ensuite walk-in shower. A simple, quiet base for two. Ninety minutes from midtown Manhattan puts you somewhere that feels considerably further out. The inn sits centrally in the Hudson Valley, long a favorite waypoint for anyone Berkshire-bound, with the region's history within easy reach: Franklin D. Roosevelt's home and presidential library, the Eleanor Roosevelt National Historic Site, and the Vanderbilt Mansion all cluster around Hyde Park, with the Culinary Institute of America alongside them. Dia Beacon draws down toward the river, and Caramoor, the Bardavon 1869 Opera House, and the Hudson Valley Shakespeare Festival fill out a full calendar of summer and shoulder-season programming. Outdoors, the Appalachian Trail crosses nearby, and Innisfree Garden, the Pawling Nature Preserve, the Stone Church, and the Walkway Over the Hudson are all within a comfortable drive. Winter brings skiing at Thunder Ridge and Mohawk Mountain; warmer months bring racing at Lime Rock Park and back-road antiquing through Millbrook, Millerton, and Kent. Two hundred and seventy-five years on, the assignment hasn't changed: good rooms, good meals, and nowhere in particular anyone needs to be — except that this time, both sides of the street are yours. AvantStay provides an upscale experience with services that elevate your stay and save time so you can enjoy every moment. Guests have access to a 24/7 support team and a tech-enabled concierge to book services, such as fridge stocking, mid-stay cleanings, and private chefs. For anything you need (or never knew you needed), we’re at your service! 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. Experience Hudson Valley, AvantStay Style! Other things to note 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. - *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: - Please make sure you park only in the designated property parking locations. [DISCLAIMERS] - No smoking in or outside of this home. Subject to a $300 fine. - Occupancy and noise limits are strongly enforced. Subject to fines that can reach up to $10,000 per violation. - IDs and security deposits when applicable will be requested after booking - We have the right to report and prosecute all Credit Card Fraud All bookings over 30 days require a security deposit to be charged after booking.