Chestertown Vacation Homes

An aerial view of a town with a river, buildings, and surrounding greenery.

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Our top choices for Chestertown holiday homes

A living room with a brown leather sofa, a wooden coffee table, and a ceiling fan.

1. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Chestertown

HK$2,170 total

includes taxes & fees

5 Oct - 6 Oct

A park with a curved wooden bridge, a tree with purple blossoms, and a grassy area.

2. Wren Retweet- Country Estate in Center of C’Town

Chestertown

Mandy D.

HK$3,774 total

includes taxes & fees

30 Sept - 1 Oct

A building with a gabled roof and a circular vent on the roof.

3. BAYSIDE BUNGALOW

Rock Hall

Diane V.

HK$2,476 total

includes taxes & fees

14 Sept - 15 Sept

A spacious living room with a leather sofa, a wooden coffee table, and a fireplace.

4. Bayside Cottage steps from Rock Hall Harbor

Rock Hall

Adam S.

HK$3,342 total

includes taxes & fees

28 Sept - 29 Sept

A living room with teal walls, a black sofa, a patterned rug, a flat-screen TV on a wooden stand, and a painting on the wall.

5. Charming 2-bedroom house in Aberdeen with WiFi and AC

Aberdeen

christine

HK$847 total

includes taxes & fees

22 Sept - 23 Sept

A kitchen with wooden cabinets, a dining table, and a refrigerator.

6. Family Retreat at Lansdowne Manor

Centreville

Emily C.

HK$3,181 total

includes taxes & fees

30 Sept - 1 Oct

A lighthouse with a white exterior, a balcony, and a metal roof.

7. Charming Coastal/Country Home w/3 Acres & Sauna!

Stevensville

Michelle P.

HK$2,528 total

includes taxes & fees

17 Sept - 18 Sept

A dining area with a wooden table and chairs, beige curtains, and a ceiling light fixture.

8. Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Grasonville

Robin

HK$3,982 total

includes taxes & fees

14 Sept - 15 Sept

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Top Chestertown Hotel Reviews

The Lodge at Great Oak Landing

10/10 Excellent

"I booked this stay last minute being undecisive and missed other bookings. The best stay in my state short trip ever. The pictures don't do the place justice."

Quality Inn & Suites Bel Air I-95 Exit 77A

8/10 Good

"Everything else was great except, i was placed in a room with an in-between door i didn't appreciate or felt safe. On opening the door, the room smells like construction work was just completed, very dissatisfied. Had 2 stains in the tub. Morning was great, except for the individual cleaning up at breakfast, she did not respect others as the were making their waffles, counter top was clean but she continues to disturb others buy wiping counter & other had to wait on her while their food was getting cold"

Hyatt Place Kent Narrows & Marina

10/10 Excellent

"Would gladly book again. Upgrading to a room with a balcony overlooking the Bay was too expensive but it was a special occasion, so I paid it. The upgrade would be a lot cheaper, most likely, it I had done in it advance. The desk clerk allowed us to check in early because the room was clean and ready. This was very kind and not usually offer in any case at hotels and motels. It made it easier when we came back later in the afternoon and went directly to the room. Thanks!"

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