Top 10 Hotels with Pool & Accommodation in Chestertown from AU$138

Q: What are some accommodation options with pools in Chestertown?

Comfort Inn & Suites Chestertown : Features full, a seasonal outdoor pool and free self parking. Red Roof Inn & Suites Chestertown : Provides free self parking, a seasonal outdoor pool and sunloungers. The Lodge at Great Oak Landing : Hotel located near Johns Hopkins Hospital. Provides buffet, an indoor pool and free self parking. Blue Heron Farm Waterfront Chalet : Hotel located near Baltimore Inner Harbor Marina. Features 2 bars, a seasonal outdoor pool and spa services. Historic Inns of Annapolis : Offers complimentary high-speed (wired) Internet access, an indoor pool and free self parking.

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

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Our top choices for Chestertown hotels with a pool

The Lodge at Great Oak Landing

Chestertown

Waterfront lodge's seasonal outdoor pool offers sun-drenched days with loungers and umbrellas.

includes taxes & fees

17 June - 18 June

Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas

Comfort Inn & Suites Chestertown

Chestertown

Dive into the seasonal outdoor pool with comfortable loungers and umbrellas at this refreshing hotel retreat in Chestertown.

includes taxes & fees

29 June - 30 June

First Floor Studio Apartment in Historic Chestertown

Chestertown

Serene backyard pool with spa pool and golf course views provides ideal relaxation in historic Chestertown.

includes taxes & fees

8 June - 9 June

Kent Island Resort

Stevensville

Victorian pool retreat with sun loungers and umbrellas by Chesapeake Bay Bridge.

includes taxes & fees

16 June - 17 June

Desk, laptop workspace, iron/ironing board, free WiFi

Quality Inn Smyrna

Smyrna

Dip into poolside bliss at this hotel with a sun-soaked outdoor pool and modern fitness centre nearby.

includes taxes & fees

16 June - 17 June

Inn at Huntingfield Creek

Rock Hall

Waterfront escape with a sun-drenched outdoor pool and spa services at this peaceful bed and breakfast retreat.

includes taxes & fees

14 June - 15 June

Best Western Kent Narrows Inn

Grasonville

Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and spa pool sanctuary.

includes taxes & fees

9 June - 10 June

La Quinta Inn & Suites by Wyndham Aberdeen-APG

Aberdeen

Splash into summer at this hotel with a sparkling seasonal outdoor pool and tranquil landscaped grounds.

includes taxes & fees

17 June - 18 June

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Choose what matters most at hotels with a pool in Chestertown

Breakfast included

Spa pool

Top Chestertown Hotel Reviews

Hilton Garden Inn Baltimore/White Marsh

10/10 Excellent

"Great location. Friendly staff!"

Hampton Inn Baltimore/Glen Burnie

6/10 Okay

"positives: the room was reasonably clean and pretty good size. The breakfast was acceptable. Notwithstanding the below, the reasonable room and breakfast saved this property from a lower rating. Negatives: we received housekeeping service one time out of five nights. A sign stated it would be every other night which would have been fine, but to then miss one of those nights is unacceptable. There was no fitness center (?) and no laundry room (???) available. I noticed multiple bugs on the property, two in our bathroom. most irritatingly, the hotel only provides Wi-Fi if you sign up for an unwanted Hilton account. Unacceptable"

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

6/10 Okay

"The only thing was the smell on the 2nd floor when we stepped off the elevator the smell was a bit overwhelming it was like dog urine and wet dog. When I was walking to my room I seen 2 dogs actually stop and pee on the side of the walls! The owner of said dogs just looked around to see if i was watching i did say something but nothing was done.The overall stay was fine just the smell in the hallway."

Pendry Baltimore

10/10 Excellent

"Staff, especially Terrance, Brittany, and Issa, were exceptional! Their kindness and professionalism were extremely helpful!! Also, a big shout out to the housekeepers-the rooms and other spaces were spectacular!! Sadly it rained most of our trip and we could not enjoy the outdoor pool. The ducks did tho!"

Frequently asked questions

What are some accommodation options with pools in Chestertown?

Comfort Inn & Suites Chestertown: Features full, a seasonal outdoor pool and free self parking. Red Roof Inn & Suites Chestertown: Provides free self parking, a seasonal outdoor pool and sunloungers. The Lodge at Great Oak Landing: Hotel located near Johns Hopkins Hospital. Provides buffet, an indoor pool and free self parking. Blue Heron Farm Waterfront Chalet: Hotel located near Baltimore Inner Harbor Marina. Features 2 bars, a seasonal outdoor pool and spa services. Historic Inns of Annapolis: Offers complimentary high-speed (wired) Internet access, an indoor pool and free self parking.

What is there to see and do in Chestertown?

Surround yourself with nature at Northern Chesapeake Bay and Chesapeake Bay. Discover sights such as Chestertown Historic District, Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater during your stay.

When is the best time to book a hotel with a pool in Chestertown?

You may want to consider a place to stay that has an outdoor pool if you're planning to visit Chestertown in the hottest months of July, August or June, when the average temperature is 23°C. Accommodation with an indoor pool may be the way to go if you come to town during the coldest months of January, February or December, when the average temp is 4°C.

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