Search Cottages in Chestertown

"It's a beautiful location and we enjoyed our visit."

"Our eighth stay at this property was just as good as ever. It is our home-away-from-home when visiting family in Annapolis. Highly recommended!"

"We had one of the best vacations ever. Our 9 and 7 year old grandchildren wanted to live there forever! We had a beautiful house and access to the outdoor spaces including a dock for gishing, crabbing and swimming. We were able to make smores over a great fire pit and enjoyed phenominal sunsets from a sitting area overlooking the river. Gene and Suzie, the hosts were on-site and so warm and welcoming. Our every need was met immediately. We will definitely be vacationing at Gregg Neck Cottage...

"This VRBO was very clean. Since it is a fairly new addition to VRBO, we thought it could use a little more info, like a portfolio with the combination to the bike locks, where to go to eat and visit, etc. Also, the only coffeemaker was a Keurig and we didn’t bring any K-cups. The 4 of us had a nice 50th Anniversary long weekend."

"This weekend, we had the pleasure of staying at Mark and Karen's place, and it was truly immaculate and thoughtfully designed. They’ve considered every detail, providing everything you could possibly need for a fantastic stay.One of the main reasons we chose this house was to have a gathering with our brother, who uses a wheelchair. This house checks all the boxes for accessibility. The doors throughout the home are wide enough to easily accommodate a larger wheelchair, including the doorways to...

"Very well-maintained property in a quiet neighborhood. Although we didn't need anything, host was always available."

"We booked this property, along with the other property at the marina for our wedding weekend and WOW - we LOVED our stay. The views from this cute little cottage are phenomenal. We woke up each morning to watch the sunrise. The hosts were extremely accommodating and even helped secure our cake topper that we accidentally left behind in the whirlwind of check-out. This was the perfect spot for our first look as well. I would highly recommend booking this place for a cute romantic stay!"

"The place has a wonderful view of the bay & a cabin-like look. The exterior (deck) is fantastic with lots of lawn chairs, bbq grills, & tables and the view of the bay. The main kitchen in the 1st house (you enter into from parking) is good with 2 ovens, 1 big stove, and 1 big refrigerator. Kuerig machines in the main & small kitchen are a nice bonus. The small kitchen in the 2nd house is also nice & functional. The 2 bedrooms & 1 bathroom in the 2nd house are in good condition (except the...

"We were not on vacation we had been displaced from our do to a pipe bursting while we were on a two week vacation.We needed a place that felt like home. It was a lovely home and very comfortable. Its open space is great for family’s. I recommend this property.!"

"We really enjoyed our long weekend at The Oyster Cottage. We needed some rest and relaxation and this cottage was perfect. Very well maintained and stocked! "

"Lovely home with everything you need."