We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers: Windows: Internet Explorer, Mozilla Firefox. Mac: Safari.

Chestertown

Free Newsletter

Interested in Chestertown?

We'll send you updates with the latest deals, reviews and articles for Chestertown each week.

Chestertown Hotel Deals

With a colonial history dating back to the 17th century, Chestertown, Maryland is proud of its maritime heritage. Sitting on the banks of the Chester River, sailing ships can still be seen coming into port. The city is the home of the Schooner Sultana, an exact replica of an 18th century ship that served in the British Royal Navy, now operating as an educational vessel. Every Memorial Day, the city hosts The Chestertown Tea Party Festival, proudly tossing the British overboard annually.
Chestertown travellers are raving about
Comfort Suites
160 Scheeler Rd., Chestertown, MD 21620
Great place to stay! 15 Oct 2009
We stayed here for a weekend in order to attend an event at the college. My boyfriend and I are both graduates of WC and thought this hotel was perfect...
Check Rates ABS:HotelCheckRates-d93725?src=SmartDeals&fromServlet=SmartDeals&Action=QC_Button
£90 ($144) Average price*
Holiday Inn Express Hotel & Suites Chestertown
150 Scheeler Road, Chestertown, MD 21620
budget hotel - needs improvement 27 Oct 2009
If this hotel was cleaner it would be a good choice. It seems to have gone downhill lately. The hallway rugs are dirty and bathrooms had mold around...
Check Rates ABS:HotelCheckRates-d672957?src=SmartDeals&fromServlet=SmartDeals&Action=QC_Button
£76 ($121) Average price*
Sleep Inn
101 VFW Avenue, Grasonville, MD 21638
30.1 km from Chestertown
The hotel was conveniently located for my niece's wedding and she had listed it among the area hotels at the Maryland shore where her wedding was to take...
Check Rates ABS:HotelCheckRates-d89439?src=SmartDeals&fromServlet=SmartDeals&Action=QC_Button
£63 ($100) Average price*
Holiday Inn Express Kent Island
1020 Kent Narrows Rd., Grasonville, MD 21638
30.9 km from Chestertown
Nice 22 Dec 2009
Not exceptional but good. A bit dated here and there but perfectly acceptable. We have stopped here several times so we can go to Annie's or Harris Crab...
Check Rates ABS:HotelCheckRates-d93655?src=SmartDeals&fromServlet=SmartDeals&Action=QC_Button
£82 ($130) Average price*
Hilton Garden Inn Kent Island
3206 Main St, Grasonville, MD 12345
31.1 km from Chestertown
Expensive for what you get 1 Nov 2009
This was a very nice, clean hotel with friendly staff, but it should be for almost $250.00 on a Friday night (included breakfast.) However, the view out...
Check Rates ABS:HotelCheckRates-d566438?src=SmartDeals&fromServlet=SmartDeals&Action=QC_Button
£96 ($153) Average price*
Best Western Kent Narrows Inn
3101 Main Street, (formerly Comfort Inn Kent Narrows), Grasonville, MD 21638
31.1 km from Chestertown
$179 a night for this dump, you've got to be kidding me. Do not stay here, I've already made the mistake for you. I swear, I'm not that picky, but this is...
Check Rates ABS:HotelCheckRates-d89438?src=SmartDeals&fromServlet=SmartDeals&Action=QC_Button
£54 ($86) Average price*
Wingate by Wyndham - Aberdeen
1326 Policy Drive, I-95 & Route 543, Belcamp, MD 21017
33.5 km from Chestertown
We stayed at this hotel on the way down to Florida. All aspects of our stay were excellent - from the kindness and helpfulness of the front desk, the...
Check Rates ABS:HotelCheckRates-d259276?src=SmartDeals&fromServlet=SmartDeals&Action=QC_Button
£48 ($76) Average price*
Candlewood Suites Aberdeen - Edgewood - Bel Air
4216 Philadelphia Road, Bel Air, MD 21015
34.0 km from Chestertown
As a clinical pharmacist providing temporary and consulting services to hospitals for weeks at a time, my sense of quality and attention to detail is quite...
Check Rates ABS:HotelCheckRates-d1216724?src=SmartDeals&fromServlet=SmartDeals&Action=QC_Button
£47 ($75) Average price*
SpringHill Suites Edgewood Aberdeen
1420 Handlir Drive, Bel Air, MD 21015
34.0 km from Chestertown
My husband and I stayed at the Spring Hill Suites for a friends wedding along with an extended stay and we thought what a deal for everything that you get...
Check Rates ABS:HotelCheckRates-d224060?src=SmartDeals&fromServlet=SmartDeals&Action=QC_Button
£78 ($124) Average price*
Country Inn & Suites - Bel Air East
1435 Handlir Drive, Bel Air, MD 21015
34.0 km from Chestertown
great value, great experience 24 Dec 2009
My wife and I stopped here on a trip to New York from South Carolina. The room was clean and comfortable. The staff was friendly and helpful and it made our...
Check Rates ABS:HotelCheckRates-d254766?src=SmartDeals&fromServlet=SmartDeals&Action=QC_Button
£57 ($91) Average price*