Holiday Homes in Chestertown

Change your mind

Book hotels with free cancellation

Treat yourself

Be picky

Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Featured Holiday Homes in Chestertown

Our top choices for Chestertown holiday homes

"We had 14 family members join us to celebrate my son’s graduation from the Naval Academy. The house is clean, the rooms were great, the property was beautiful, and it was close to USNA. Our family loved the open concept. "

"Loved the location and the pristine condition of the house. "

"Was a good time. Great location Beautiful sunset across the water. Thanks Jeremy "

"Loved everything! Parking garage included, close to everything, very comfortable. Would stay there again!"

"House was in a great location and very well appointed. We had everything we needed. Would highly recommend."

"This place was perfect place to stay while visiting the area. Everything was clean and the location was great for visiting Annapolis. Will stay again when we are back out this way."

includes taxes & fees

1 Sept - 2 Sept

"It was represented very well. I would definitely recommend for getting away from crowds. NEAT place,yes you are at the water! Would give it a 4.7 overall.! "

"It was great!"

"Host was very helpful and accommodating. Place was adorable with beautiful views, just as depicted. Had everything we needed and more! "

"Exactly what we expected. What wasn’t expected is how quiet and serene that entire town is. "

"Great location for our team to stay during Annapolis sail show. "

"The host was amazing. The property was as described and was perfect for our group. "

"Nice property with amazing views. Celebrated college graduation with family. Young ones had fun looking at ducks. Plenty of room for a large group."

includes taxes & fees

1 Sept - 2 Sept

"Very beautiful, uniquely designed home on the water. There were 2 bedrooms on the first floor making in it easy for our elderly quests. The main suite was great for our young adults to stay in together with 2 kings, sectional and multiple love sacs. Plenty of seating throughout the home both inside and out. "

"Excellent property, great communication with the hosts. Quite and relaxing"

"Great location"

Fridge, microwave, dishwasher, coffee/tea maker

"Nice place with everything I could want. Would stay there again!"

"The property is everything it claims to be & more. Awesome location on the bay. Great accommodations. So peaceful. We had a wonderful time. Would highly recommend! "