Photo by Assya A

Search Farmstay in Chestertown

Plan, book, stay with confidence

Be picky

Search almost a million properties worldwide

Treat yourself

Change your mind

Book hotels with free cancellation

Check availability on Farmstay in Chestertown

Compare 4 Farmstay in Chestertown with updated reviews, rates, and availability.

"Adorable farmhouse, great host, and awesome place for a fall girl's weekend. Thank you John for a great stay!"

Welcome to the Colonial Farmhouse. 4 + acres of peace and tranquility

"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."

"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."

SAR 1,316 total

includes taxes & fees

1 Dec - 2 Dec

Save an average of 15% on thousands of hotels when you're signed in

Other property types in Chestertown

"Great!"

"This cozy home was perfect for my coaches & I that were in town for a lacrosse tourney @ the Naval Academy. This home is literally less than 100 steps from the gate of the Naval Base and same distance to dowtown Annapolis city docks, diming, shopping and sight-seeing. We will defintely be back! Thanks John!!"

"Our group had an amazing time staying on this property. There are many areas inside the house as well as outside the house where you can gather with family and friends. It was very quick and easy to order Ubers/lyfts to the downtow Annapolis area whenever we needed. The house is also convientely located near a small shaping center less than a mile away. We would highly recommend this property!"

Recent reviews of Chestertown hotels

5/5 Excellent

"I love staying at this property. It is within walking distance of everything, especially Main Street and the Naval Academy. The valet service is excellent, and the staff is always friendly and helpful. The rooms are always clean and comfortable."

A verified traveler stayed at Historic Inns of Annapolis

Posted 1 day ago