Chestertown Vacation Homes

Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA

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Our top choices for Chestertown holiday homes

Charming 2-bedroom house in Aberdeen with WiFi and AC

Aberdeen

christine

HK$727 total

includes taxes & fees

25 Jun - 26 Jun

Hidden Fells Point Gem / Private Courtyard Patio

Fells Point

Mark M.

HK$1,720 total

includes taxes & fees

30 Jun - 1 Jul

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Stevensville

HK$2,582 total

includes taxes & fees

29 Jun - 30 Jun

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

Stevensville

Handy M.

HK$2,635 total

includes taxes & fees

29 Jun - 30 Jun

Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC

Aberdeen

HK$1,363 total

includes taxes & fees

1 Jul - 2 Jul

Large 2 bedroom house with private parking in a nice neighborhood

Arnold

Vesta M.

HK$3,127 total

includes taxes & fees

20 Jul - 21 Jul

Gorgeous 3-bedroom townhome with AC in friendly Dundalk

Dundalk

HK$1,652 total

includes taxes & fees

30 Jun - 1 Jul

BAYSIDE BUNGALOW

Rock Hall

Roger

HK$2,376 total

includes taxes & fees

24 Jun - 25 Jun

Bayside Cottage steps from Rock Hall Harbor

Rock Hall

Adam S.

HK$2,849 total

includes taxes & fees

29 Jun - 30 Jun

Family-friendly home in Baltimore with WiFi, AC, Pool table, Washer & dryer

Berea

Patrick S.

HK$1,539 total

includes taxes & fees

30 Jun - 1 Jul

Patterson Park Gem, Walk Everywhere

Patterson Place

Deborah O.

HK$1,742 total

includes taxes & fees

30 Jun - 1 Jul

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

Grasonville

Robin

HK$3,281 total

includes taxes & fees

24 Jun - 25 Jun

Secluded Tiny Pool House -Private Pool -Self Check in

Glen Burnie

Stephen R A.

HK$2,144 total

includes taxes & fees

14 Jul - 15 Jul

Johns Hopkins Historic Renovated home - Location!

Upper Fells Point

Sharon P.

2 Mi to APG: Edgewood Family Home w/ Fenced Yard

Edgewood

"The house was okay. Definitely wasnt cleaned thoroughly as there was still food stains in the fridge and peices of food in the butter tray inside the fridge. The stove would not work until i set the time to the correct time so that was a bit of a question mark as to why that was. There was ants all over inside the house which personally was very disgusting. Both me and my son woke up with ants crawling on us in both the master bedroom and back bedroom. So that is something that should be...

Sean G.

HK$3,452 total

includes taxes & fees

25 Jun - 26 Jun

5 bedrooms, iron/ironing board, travel cot, free WiFi

Upscale Escape with Private Garden-Perfect for Relax & Intimate Moments

Marley

tom d.

HK$6,638 total

includes taxes & fees

7 Jul - 8 Jul

Cute, Cozy 2-bedroom house near Annapolis with water access

Herald Harbor

Katherine P.

HK$1,836 total

includes taxes & fees

28 Jun - 29 Jun

Spacious 4-bedroom retreat house with plenty of parking

Overlea

Jeton E.

HK$4,336 total

includes taxes & fees

24 Jun - 25 Jun

Glen Burnie Escape - Pet friendly with easy access to multiple attractions.

Glen Burnie

Shanice

HK$3,029 total

includes taxes & fees

28 Jun - 29 Jun

Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Cape Saint Claire

KateriK

HK$5,655 total

includes taxes & fees

26 Jun - 27 Jun

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Top Chestertown Hotel Reviews

Historic Inns of Annapolis

10/10 Excellent

"Very beautiful hotel"

Red Roof Inn & Suites Chestertown

8/10 Good

"The property is a little older and could benefit from a good deep cleaning of carpets and upholstery, but the bed and bathroom were clean and the staff were great. Considering the price of other accomodations in the area it's an excellent value for the money if you're just looking for a clean place to sleep."

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

8/10 Good

"We stayed for a tournament… the hotel was very clean and seemed to be very well maintained.. we arrived 1.5 hours before check in time … rooms were available but a 25.00 fee was added .. We paid because we were tired from a long drive.. There was a removal sign advertising an indoor pool outside … however once inside there was another sign stating the pool, gym and laundry room were closed .. We also had early tournaments, so we did not even get the complementary breakfast… it seems like it was served later than most hotels . Overall it was a great deal for the money … but if a laundry room to wash a kids’s uniform after day one of a tournament is a selling point .. I would suggest calling to see if it’s open ."

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

8/10 Good

"The hotel room was very nice and clean. The included breakfast got started late, and we had to skip it as we were on a schedule. Looked like the staff was having a hard time getting things together to open on time. We also could not find any staff to check out in the morning at the front desk, so I had to do it by phone. That being said, those we did interact with were pleasant. Location was good for our purpose."

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