Historic Inn Fireplace + Farm Breakfast | Appalachian Trail | The Cherry Room | Apartment in Dover Plains

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 — a sporty, cash-flush crowd who galloped inn to inn while hired hands kept the animals moving. The Preston family held the place for 160 years. Elizabeth Taylor and Richard Burton took over every room in 1962 when they needed somewhere the world wouldn't find them. A two-year, top-to-bottom restoration returned the building to form without sanding away what makes it worth the drive.
Old Drovers Inn holds six guest rooms, each with a private bath, alongside common rooms built for what the innkeepers call the lost art of lounging around: a lobby, a sitting room, a library, and a formal dining room whose hand-painted murals date to 1941. It is a small house, deliberately so, run with hotel-level service and the ease of a proper country inn.
The Cherry Room is a second-floor room built around a queen brass bed, with a propane fireplace that comes into its own once the weather turns. The proportions are comfortable and the mood is calm, with the inn's common rooms just down the stairs when you want company. It suits guests who want the fireside version of a country inn stay without the scale of a suite.
One bedroom with a Queen bed, dressed in 800-thread-count linens, a down comforter, and a pillow-top mattress. The room has its own private bath with a walk-in shower, stocked with Frette towels and Frette bathrobes.
The common rooms are the reason people linger. The sitting room and library invite the kind of afternoon where a book gets started and a schedule quietly falls apart, and the lobby carries the same unhurried tone. 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.
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 and the morning. Anyone hoping for a continental spread will be disappointed, which is rather the point. Later in the week, the Colonial Tap Room opens for dinner: dark wood and plastered walls lit by candlelight and lanterns, with a classic bill of fare. In warm weather the seasonal patio takes over, one of the few places nearby to eat outdoors surrounded by open, quiet country.
Just to the left of the inn stands The Preston Barn, a wood-frame period structure built with re-purposed beams and stonework and outfitted with every modern amenity underneath the rustic character. It holds up to 250 people and handles the full arc of a celebration weekend — a Friday rehearsal dinner, the ceremony and reception, an after-party in the Tap Room, a send-off brunch the next morning. The inn itself is equally suited to something smaller: the Federal Room seats 30, the Colonial Tap Room seats 55, and the house's private and semi-private corners make an easy setting for a gathering of fifty or fewer. Book the six rooms together and the whole property becomes yours for the weekend.
Every room comes with central air conditioning, cable TV, and WiFi. Beds are made with 800-thread-count linens, down comforters, and pillow-top mattresses; baths are stocked with Frette towels and Frette bathrobes. A complimentary beverage is provided, and a concierge is on hand for coffee, tea, assorted beverages, and refreshments throughout the day. Breakfast is served daily, and the Tap Room restaurant operates on site.
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, and the Culinary Institute of America sits 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: a good room, a good meal, and nowhere in particular you need to be.
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.
Local attractions: Stone Ridge offers easy access to some of the Hudson Valley’s top spots—hike the cliffs and trails of Mohonk Preserve and Minnewaska, explore Woodstock and Kingston’s arts and dining scenes, visit Olana and Opus 40, sip along the Shawangunk Wine Trail, and unwind by the Ashokan and Rondout Reservoirs.
Home Truths:
- Unfortunately, pets are not allowed in this home. If undisclosed pets are brought into the home without AvantStay's approval there is a fine of $500 per pet.
Parking Details:
- Please make sure you park only in the designated property parking locations. If your home offers street parking, please make sure you read all posted signage.
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.
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.

Historic Inn Fireplace + Farm Breakfast | Appalachian Trail | The Cherry Room is located in Town of Dover. Historic Inn Fireplace + Farm Breakfast | Appalachian Trail | The Cherry Room provides accommodation, featuring Air Conditioner, Security/Safety, Bedding/Linens, among other amenities. This Apartment features Air Conditioner, Parking and TV to make your stay a comfortable one.

Historic Inn Fireplace + Farm Breakfast | Appalachian Trail | The Cherry Room has 1 Bedroom , 1 Bathroom, and max occupancy of 2 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 Apartment because of the excellent services rendered by the owner or manager of this Apartment, 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. Apartment has a friendly neighborhood, and the Town of Dover has interesting places to visit. If you want to learn more about the Apartment in Town of Dover, such as places to visit and things to do nearby, you can check below to learn more.