Chestertown, Maryland

Rovers Retreat

6 Guests | 3 Bedrooms | 5 Beds | 2.5 Baths

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Front view of a three-story house with a yellow front door decorated with a holiday wreath. The house has brick walls with red shutters and six windows on the upper two floors. There are two bushes in front, and a small front yard with a sidewalk and driveway. The sky is overcast.

Welcome to Rover’s Retreat

Charming 1907 house in the historic district of Chestertown, Maryland. The house is just one block from Washington College and four blocks from Fountain Square in the heart of downtown with its  cute shops, unique restaurants, and the Arts & Entertainment district that stretches to the Chester River.

Front view of a three-story beige brick house with red shutters and a yellow front door decorated with a wreath. There are small bushes in front and leafless trees nearby, with neighboring houses visible on both sides. The sky is overcast.
Front view of a two-story house with a beige brick exterior and green front door, flanked by shrubbery, with neighboring houses on either side, in a suburban neighborhood.
A residential street with a two-story brick house in the center, a parked car to the right, neighboring houses on either side, and a small white shed in the background. The front yard has a concrete sidewalk and some bushes.
A two-story beige brick house with green shutters and a green front door decorated with a wreath. The house has a small front porch, two bushes on either side, and a gravel driveway on the right leading to a small white garage. A red car is parked ne
A kitchen with white cabinets, black countertops, a white refrigerator, a wooden dining table with chairs, a ceiling fan, and windows with blue and white striped curtains.
Interior view of a house showing a staircase with green risers and brown treads, a partial view of a room with a bed covered in a blue and white quilt, a TV mounted on the wall, and wooden furniture.
A kitchen with white cabinets, a brown dining table with chairs, a white refrigerator, and a ceiling fan with lights. There are appliances on the countertop, including a microwave, toaster, and coffee maker. The floor is wood, and there's a window wi
Dining room with wooden table and six matching chairs, hardwood floors, wall decor including paintings and hanging pans, window with blue and white striped curtains, ceiling fan with light, poinsettia plant on table, doorway leading to a bright livin
A small laundry room with a washing machine and a dryer side by side, a window with a valance, white walls, and a closet with a brass doorknob.
Small bathroom with a toilet, a white cabinet with a sink, a window with navy blue curtains, and a lighthouse picture above the window.
Living room with a beige sofa, two gray armchairs, wooden coffee table, and built-in bookshelf. Windows with white curtains, wall art, and an air conditioning unit. Decor includes a gold tray and a bowl of fruit.
Living room with beige walls, hardwood floor, white curtains, a colorful area rug, various chairs, a coffee table, bookshelves, artworks, and a ceiling fan.
Bathroom with blue accent wall, white vanity with countertop, mirror, and light fixtures, shower with glass door, towels, and bathroom accessories.
A bedroom with wooden flooring, beige walls, a wooden bed with patterned bedding, three windows with white blinds, a ceiling fan, a bedside table with a blue lamp, a wooden dresser, and a black chair with gold accents.
Small home office with a wooden desk, chair, printer, and computer near a window, featuring a large hand-painted mural of a countryside scene on the right wall.
A bedroom with hardwood flooring, three windows with white shutters, a ceiling fan with a light, two beds with bedding, a nightstand with a lamp, and a luggage rack.
Living room with a green futon, wooden coffee table, desk with a lamp, framed artwork on walls, and a view into a laundry area with baskets.
A small bathroom with a toilet, window, and shelves with rolled towels on the wall. A shower curtain is partially visible, and there is a wicker laundry basket on the floor.
A vintage-style bathroom with a wooden vanity, a white vessel sink, a large mirror, and a small wooden stool in front. There are two green towels hanging on the wall, and a window with white blinds. The floor is tiled with brown tiles, and the walls
A corner of a room with a wooden desk, a table lamp, framed artwork on the wall, an old wooden cabinet, window with blinds, and hardwood flooring.
Backyard with a green lawn, a white picket fence, and tall trees with bare branches, on a cloudy day.
Backyard with trees, a white picket fence, and a brick patio.
Back porch of a brick apartment building with two black chairs, a table, an air conditioning unit, and a small ramp leading to a brick sidewalk.
A two-story brick house with a yellow front door decorated with a holiday wreath, orange shutters, paced steps, and a front yard with grass, bushes, a small tree, and a sidewalk.
Living room with large windows, white curtains, a beige sofa, wooden coffee table, armchairs, a TV on a wooden stand, a framed mirror, and ceiling fan with wooden blades.
A cozy bedroom with light blue walls and green trim, featuring a wooden bed with a patterned blue and white quilt, a large window with white curtains, a ceiling fan, and a small bathroom visible through an open door.
A bedroom with two twin beds with white and blue patterned bedding, a wooden dresser, a nightstand with a lamp, and a ceiling fan. The room has hardwood floors and two windows with white shutters.

House Details

The home features 3 bedrooms and 2.5 bathrooms, including a ground-floor double bedroom with an en suite bath. Upstairs, you’ll find two more bedrooms -one with a queen bed, one with three twin bed, a cozy sitting room with a double futon, comfortably accommodating up to 7 guests.

Enjoy a fully equipped kitchen with a dishwasher, a laundry room with washer and dryer, and a charming porch off the kitchen that opens to a brick patio, perfect for relaxing or entertaining. Parking is convenient with a driveway for a small car and ample on-street parking for larger vehicles.

Bedroom with a wooden bed frame, a blue table lamp, and three windows with white blinds, hardwood floor, and light-colored walls.

The house itself has a few remarkable features. The kitchen has hand-painted tiles for two  backsplashes, and unique drawer pulls in the shape of forks, spoons, and knives. The upstairs hall has a hand-painted mural depicting scenes of the Eastern Shore of Maryland. 

Chestertown

Chestertown is host to many festivals and events including the National Music Festival, the Chestertown Tea Party, the Sultana Downrigging Festival, the Dickens Christmas Festival, and a Jazz Festival each summer, in addition to events at Washington College that are open to the public. Every Saturday morning the Farmers Market takes over blocks of High Street, offering fruits, vegetables, flowers, eggs, various kinds of meats, honey, coffee, bakery items, and much more. There is always something happening in Chestertown!

Not far away is the town of Rock Hall, home to the Mainstay, which hosts musical events throughout the year. Rock Hall is also the place to go for great seafood dining year round.

Illustration of a fish with detailed fins, gills, and scales, drawn with white lines on a black background.
Living room with light-colored walls, hardwood floor, multiple windows with white curtains, a ceiling fan with leaf-shaped blades, a patterned sofa, armchairs, coffee table, area rug, TV on a wooden stand, and decorative framed artwork.

Amenities

  • First floor - Double with en suite bath

    Second floor - 2 bedrooms: one with a queen bed, one with 3 twins, and there is a sitting room with a double futon; the house easily sleeps 7

    • Washer & Dryer with laundry detergent

    • Towels

    • Bed sheets

    • Bed linens

    • Hair dryer

    • Shampoo, Conditioner, & Body Wash

    • Toilet paper

    • Soap

    • Kitchen space where guests can cook their own meals

    • Refrigerator

    • Microwave

    • Cooking basics

    • Pots and pans, oil, salt and pepper

    • Dishes and silverware

    • Freezer

    • Stove & oven

    • Coffee maker: drip coffee maker

    • Baking sheet

    • Dining table

    • Wifi

    • TV with Ruku

    • Dedicated workspace

Nearby Attractions

Rock Hall, MD - 20 minutes

Galena, MD - 20 minutes

Sassafras River/Georgetown, MD - 25 minutes

Middletown, DE - 35 minutes

Chesapeake City, MD - 40 minutes

Kent Island - 45 minutes

Line drawing of three Brussels sprouts on a black background.