Historic luxury townhouse in the heart of downtown Chestertown | House in Chestertown, MD
3 Bedroom House with Bedding, Wellness Facilities and Fireplace
Historic Luxury Townhouse on High Street – Heart of Downtown Chestertown
Welcome to 125 High Street—an exquisitely renovated, sun-filled brick townhouse nestled in the heart of historic downtown Chestertown, Maryland. Steps from the river, surrounded by charming restaurants, cafes, galleries, and boutiques, this home offers a one-of-a-kind blend of modern luxury and timeless Eastern Shore character. Whether you’re here for a romantic getaway, family vacation, or a relaxing solo retreat, this property promises comfort, style, and walkable convenience like no other.
The Space: Where History Meets High-End Living
Originally built in the 1800s, this beautifully restored home retains its historic charm with exposed original brickwork throughout, thoughtfully paired with state-of-the-art upgrades to provide a truly special stay.
-Bedrooms & Comfort: Each bedroom is outfitted with luxury bedding and ultra-comfortable mattresses, curated for restful sleep. Whether you’re traveling with family or friends, you’ll enjoy hotel-quality linens and serene design in each sleeping space.
• Marble Spa Bathroom: Step into elegance in the stunningly upgraded bathroom, featuring high-end marble finishes, a spa-like walk-in shower, and sleek modern fixtures. It’s the perfect way to unwind after a day exploring town or kayaking along the Chester River.
-Chef’s Kitchen: Cook up a storm (or reheat your gourmet leftovers from one of the nearby restaurants) in the chef’s kitchen, complete with top-of-the-line stainless steel appliances, induction cook top, granite countertops, and all the cookware and utensils you need. High-quality appliances ensure every meal prep feels easy and indulgent.
-Living Room: Relax in the stylish and cozy living area, which features a blend of antique touches and modern design. Enjoy streaming your favorite shows, reading a book by the window, or planning your next adventure in town.
-Historic Details: Original exposed brick walls run throughout the house, adding warmth and texture to every room. The hardwood floors and preserved architectural details offer a nod to the past while blending seamlessly with the updated, designer interiors.
Unbeatable Location: Downtown Chestertown at Your Doorstep
You quite literally cannot stay in a better location in Chestertown. Step out the front door and you’re just a block from the water, where the Chester River glistens in the sunlight. Take a morning stroll to the town marina and watch the boats, or sip coffee on a bench by the riverfront.
-Dining & Cafes: Some of the Eastern Shore’s best restaurants, bakeries, and wine bars are just steps away. From fresh local seafood to warm croissants and artisan espresso, you’ll find culinary gems at every turn.
-Shops & Galleries: Explore local boutiques, art galleries, and bookstores—many of which are housed in historic buildings. The town’s walkable charm makes it easy to discover something new every day.
-Marina & Waterfront: The Chestertown Marina is just a block away. Enjoy breathtaking sunsets, rent a kayak, or simply watch the tide roll in. The proximity to the water adds a serene, coastal energy to your stay.
-Cultural Events & Farmers Market: Chestertown is known for its vibrant calendar of events—from the weekly Saturday Farmer’s Market to First Fridays, jazz festivals, and tall ship visits. And you’re right in the middle of it all.
Why You’ll Love Staying Here
• Location, location, location – it doesn’t get better.
• A rare combination of historic charm and modern luxury.
• Comfort-forward design: plush beds, quiet nights, and natural light.
• Easy parking and quick access to nature, water, and culture.
Perfect For:
• Weekend escapes from D.C Baltimore, or Philadelphia
• Wedding weekends, family gatherings, or small group getaways
• Writers, artists, and creatives seeking inspiration in a beautiful place
• Professionals looking for a peaceful and luxurious remote work setting
Historic luxury townhouse in the heart of downtown Chestertown is located in Chestertown. Historic luxury townhouse in the heart of downtown Chestertown provides accommodation, featuring Bedding/Linens, Wellness Facilities, Fireplace/Heating, among other amenities. This House features Bedding/Linens, Wellness Facilities, Fireplace/Heating, to make your stay a comfortable one.
Historic luxury townhouse in the heart of downtown Chestertown has 3 Bedrooms , 2 Bathrooms, and max occupancy of 6 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 House because of the excellent services rendered by the owner or manager of this House, 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. House has a friendly neighborhood, and the Chestertown has interesting places to visit. If you want to learn more about the House in Chestertown, such as places to visit and things to do nearby, you can check below to learn more.
This Property is OneKey Eligible
Earn OneKeyCash for every dollar spent on eligible vacation rentals, villas, cottages, cabins, and more when you book on Vrbo.
Amenities
Facility Overview
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Heating
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Air conditioning
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Towels provided
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Shower
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2 bathrooms
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Soap
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Toilet paper
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Hair dryer
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3 bedrooms
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Bed sheets provided
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Laundry facilities
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Washing machine and dryer
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No pets allowed
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Smoke-free property
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Iron/ironing board
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WiFi available
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Carbon monoxide detector installed (host has indicated there is a carbon monoxide detector on the property)
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Smoke detector installed (host has indicated there is a smoke detector on the property)
Policies
FAQ's
Is this Chestertown house pet-friendly for guests?
No, pets are not allowed at this property. Check the guest reviews to learn what guests had to share.
Does the Chestertown house have a swimming pool?
No, this Chestertown house does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.
How much does it cost per night to stay in Chestertown house?
Best-rates for the Chestertown house starts from $401 per night with includes Internet, Laundry, Air Conditioner, Security/Safety, Bedding/Linens, Wellness Facilities, Fireplace/Heating, Child Friendly with all other facilities. Casai.ca matches every traveler with their perfect accommodation, whether you are traveling with a group, friends, family, or pets.
Is Chestertown house a family-friendly place to stay?
Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house Good or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.
Is the Chestertown house wheelchair accessible or offer services for disabled guests?
Based on the information received from our partner, the Chestertown house has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.
What is the minimum night stay policy for the Chestertown house?
Based on the information reported by the owner or manager, the Chestertown house indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.
What cancellation policy is in place for Chestertown house?
Based on the information reported by the owner or manager, details for the cancellation policy for the Chestertown house are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.
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