Photo by Patricia Knorr

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Compare 3 Farmstay in Chester with updated reviews, rates, and availability.

The Colonial Farmhouse

10.0 out of 10, Exceptional, (5)
"We had a terrific family weekend at this lovely, historic home. The house was perfect for our extended family with multiple adult couples, an 11 month old baby, and two dogs. The property is VERY child friendly with a crib, high chair, and lovely library of children's books, and the pool area was perfect for lazy afternoons. Kitchen is well stocked and very functional, and the house is a short drive to Chestertown and lots of great local seafood. Would strongly recommend."
The Colonial Farmhouse

Farm Stay at Lansdowne Manor

9.8 out of 10, Exceptional, (7)
"Spacious, historical home with wonderful decor. It was just what we needed after spending time in the city visiting family. The only drawback for us (70 year olds) was all the stairs. Nice .25 mile driveway to walk down and back a few times for some exercise."
Farm Stay at Lansdowne Manor

Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate

10.0 out of 10, Exceptional, (4)
"The farmhome, setting and our host could not have been better. Our host was very accomodating, hospitable and welcoming. Easy communications. Such peaceful and serene surroundings, just lovely. The home itself was perfect - comfortable for our family (four adults), with modern amenities and old charm galore! Our Thanksgiving was wonderful and the farmhome will be a repeat visit for sure!"
Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Chester

Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!

10.0 out of 10, Exceptional, (8)
"Overall it was a wonderful stay for me and 4 of my friends. Plenty of space for everyone to spread out and enjoy the wonderful view of the water while we were between wedding events. The home was off the beaten path, which added to the relaxing feeling of the house. Also it was never more than a 20 min drive to get to our events accross the island. The host was very responsive and more than accommodating for my group. The only very minor suggestion I'd like to make is that the trash in the...
Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (205)
"A great experience all around"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (23)
"Fifteen ladies from my church stayed at this Vrbo for a weekend conference in Annapolis. We enjoyed the property and the house! We had a beautiful weekend and even got on the water, played pickle ball, and enjoyed the views. The house is beautiful! The kitchen is well stocked and the house is comfortable and there is plenty of parking. Since it was November, the heated sunroom floors were a wonderful bonus. Thank you for the memories and a wonderful stay!"
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.