Historic in-Town House/Historic District of Chestertown MD

• Wonderful place to stay!

  Wonderful place to stay!

  • Guest NCtraveler
  • Date of stay 10/07/12
  • Review Submitted 11/14/12
  We stayed for a week while visiting family in the area. We loved everything about the home. It's wonderfully situated in the historic part of Chestertown, within walking distance of shops, cafes, and a seasonal farmers' market. We had ample room to spread out and enjoy ourselves and entertain guests as well. The kitchen offers all gourmet amenities. All bedrooms are located upstairs and are comfy and well-appointed. Each of the three bedrooms has a bathroom en suite (two for the master bedroom). The master bedroom and dressing area also offers wonderful space for the regular travelers as well as those preparing for a special occasion. We enjoyed the historic ambience of the home as well as the high-tech kitchen, big screen tv and music system, and Wi-Fi for all of our tablets and laptops. Modern day meets history with luxury! The area offers historical sites, boating and other water sports, biking, and antique shopping. Washington, D.C., Annapolis, and Baltimore are all within driving distance for day trips. We highly recommend this lovely home and will stay again when in the area!

  Recommended for: Girls getaway, families with young children, sightseeing, romantic getaway.

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• Wonderful place to stay!

  Wonderful place to stay!

  • Guest NCtraveler
  • Date of stay 10/07/12
  • Review Submitted 11/13/12
  We stayed for a week while visiting family in the area. We loved everything about the home. It's wonderfully situated in the historic part of Chestertown, within walking distance of shops, cafes, and a seasonal farmers' market. We had ample room to spread out and enjoy ourselves and entertain guests as well. The kitchen offers all gourmet ammenities. All bedrooms are located upstairs and are comfy and well-appointed. Each of the three bedrooms has a bathroom en suite (two for the master bedroom). The master bedroom and dressing area also offers wonderful space for the regular travelers as well as those preparing for a special occasion. We enjoyed the historic ambience of the home as well as the high-tech kitchen, big screen tv and music system, and wifi for all of our tablets and laptops. Modern day meets history with luxury! The area offers historical sites, boating and other water sports, biking, and antique shopping. Washington, D.C., Annapolis, and Baltimore are all within driving distance for day trips. We highly recommend this lovely home and will stay again when in the area!

  Recommended for: Girls getaway, families with young children, sightseeing, romantic getaway.

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• Great house in a great location!

  Great house in a great location!

  • Guest Anonymous
  • Date of stay 09/28/12
  • Review Submitted 10/19/12
  We stayed here as three couples for a friend's wedding and would return without hesitation. The location is in the center of Chestertown and within short walking distance to most anything. The house itself is clean and bright, with high quality finishes and a perfect layout for multiple houseguests. Cathie couldn't have been friendlier or easier to work with. No question a more pleasant experience than hotel alternatives. The rest of the wedding crowd envied our digs!

  Recommended for: Families with teenagers.

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• Wonderful home, well kept and excellent location.

  Wonderful home, well kept and excellent location.

  • Guest Jen
  • Date of stay 10/05/12
  • Review Submitted 10/15/12
  Some members of our bridal party stayed in this beautiful home the first weekend in October and it worked out perfectly. I would highly recommend this home on your next visit to Chestertown, the owner (Cathie) is super friendly and accommodating and the house has 3 master suites with 4.5 baths, perfect for three couples for the weekend. It's within walking distance to everything in Chestertown and you can't beat the price. We will be back in the future!

  Recommended for: Girls getaway, families with young children, sightseeing, families with teenagers, tourists without a car, romantic getaway.

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• Gorgeous House and Very Accommodating

  Gorgeous House and Very Accommodating

  • Guest CB25
  • Date of stay 09/21/12
  • Review Submitted 09/26/12
  This was the perfect place to rent. Every Room had similar features with their own bathrooms that lended itself to the privacy each person needed during our stay. The owner was amazing, she left us breakfast and coffee when we arrived and made it clear that we were to make ourselves right at home. The proximity of the house to everything in town was helpful and the neighbors were all super friendly. We didn't have any issues with noise (on our behalf/and the neighbors). The house was very clean and had everything we needed, including towels. I would HIGHLY recommend.

  Recommended for: Girls getaway, people with disabilities, families with young children, sightseeing, age 55+, families with teenagers, adventure seekers, romantic getaway.

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• A place to relax in Chestertown

  A place to relax in Chestertown

  • Guest Laura & Noah
  • Date of stay 07/20/12
  • Review Submitted 08/20/12
  We were a group of 6 women looking for a great weekend get away for a triathlon taking place in Chestertown. This house did not disappoint. The house was clean, had a well stocked kitchen, a lovely family room and patio to relax and enjoy friends. It was convenient to the center of town and several blocks away from the scenic Chester River. We walked to several restaurants and a delicious little local bakery. It is also just a few miles to Washington College. I would recommend this home to anyone who would enjoy soaking up the sights and sounds of this historic MD town.

  Recommended for: Girls getaway, families with young children, sightseeing, age 55+, families with teenagers, adventure seekers, romantic getaway.

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• Son's Wedding

  Son's Wedding

  • Guest Bill
  • Date of stay 04/26/12
  • Review Submitted 06/10/12
  Absolutely fabulous! Clean, well-appointed, well-stocked (even has a bagel slicer),and centrally located. Owner is friendly, knowledgeable and responsive. I'd not only recommend it, so would all our friends and relatives who saw it. Bottom line, if you're going to stay in Chestertown, and the house is available and meets your sleeping requirements, there is no need to look anywhere else. Book it while it's available!

  Recommended for: Girls getaway, families with young children, sightseeing, age 55+, families with teenagers, tourists without a car, romantic getaway.

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• Outstanding in every regard...

  Outstanding in every regard...

  • Guest Jake
  • Date of stay 05/25/12
  • Review Submitted 05/30/12
  My group of middle-aged friends stayed here four nights over Memorial Day weekend to enjoy the Chestertown Tea Party festival and go kayaking and biking. This house is actually much larger and nicer than its VRBO description, and it's fully stocked with everything we needed. Seven of us fit quite comfortably in the three bedrooms that are large enough to fit an extra cot if needed. From the moment we first walked through the house with the owner, we were all completely impressed with the overall design, the bright ambience with many windows, the tasteful quality furnishings, and the full array of utensils, dishes, towels, and everything else we needed. Having 4.5 modern bathrooms with instant heat water made it easy for everyone. The whole house was immaculately clean, and the kitchen has all new top quality appliances. Truly a gourmet kitchen, and very roomy working around the center island. The rear patio with chairs and gas grill was perfect for us to relax. The long driveway was a welcome place to keep our cars and kayaks off the street. There is also a modern media center with big HDTV in the rear den area that faces the patio. The location is just three blocks from the waterfront area where life is centered in Chestertown, so we walked to all the festival events and town restaurants. The owners are very friendly and welcoming. They even arranged for our group to launch kayaks from the yacht club where they are members. We hope to rent this house again soon for another super weekend. Be aware that the good restaurants in Chestertown stop serving food at 9 pm and are closed on Sunday and Monday. So plan accordingly. We did and everything worked out very well for us. Highly recommended for a comfy and relaxing stay in Chestertown.

  Recommended for: Girls getaway, families with young children, sightseeing, age 55+, families with teenagers, tourists without a car, romantic getaway.

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• THE place to stay in Chestertown

  THE place to stay in Chestertown

  • Guest Grotmo
  • Date of stay 05/14/12
  • Review Submitted 05/22/12
  We rented this historic property in the middle of Chestertown for a golf outing. Five of us stayed here and it was awesome. The home is like a new home inside with everything you need to make your stay outstanding. It is furnished like something you would see in a magazine and the owner provided everything you would need to have an enjoyable stay, coffee, juice and muffins in the morning and a 52 inch plasma TV to keep you entertained in the evening. The location is walking distance to restaurants, shops, and everything that Chestertown has to offer. The write up of the property is right on target, what you read is what you get. I would recommend this property to family and friends without any hestitation. We will be back next year. Thanks for allowing us to use you place. J

  Recommended for: Girls getaway, families with young children, sightseeing, romantic getaway.

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• High class Highcroft

  High class Highcroft

  • Guest Anne
  • Date of stay 03/28/11
  • Review Submitted 07/21/11
  Our family of 5 rented this historic house in March. We were looking for a house with plenty of space for our family to relax, an area with local places to eat and shop, and a safe town that our teenagers could navigate on their own and enjoy a little freedom. The house and location exceeded our expectations. The house is even nicer than the photos depict and it's very convenient for day trips. The owners were very helpful in making sure we had everything we needed for a great stay. I would recommend this house to families with children of all ages, extended families, several couples, a girls' weekend or anyone looking for a base to explore the beauty of the Eastern Shore.

  Recommended for: Girls getaway, families with young children, sightseeing, age 55+, families with teenagers.

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Additional information about rental rates

Holiday weekends and graduation have a three night minimum.

Additional Fees and Taxes:

11% Maryland tax

$135.00 cleaning fee