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Search Hotels with Pool in Chestertown

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Check availability on Chestertown Hotels with Pool

Tonight
6 Nov - 7 Nov
Tomorrow
7 Nov - 8 Nov
This weekend
7 Nov - 9 Nov
Next weekend
14 Nov - 16 Nov

Top Chestertown Hotels with Pool

Room, 1 King Bed with Sofa bed, Marina View | 1 bedroom, free WiFi, bed sheets
The Lodge at Great Oak Landing
The Lodge at Great Oak Landing
3.5 star property
  • Pool loungers
  • Private beach access
8.0 out of 10, Very good, (74)
Splash into summer fun at the seasonal outdoor pool, complete with loungers and umbrellas for all-day relaxation. Beyond the water, this lodge offers a private beach, 9-hole golf course, and delicious dining at Fairlee's restaurant.
The price is ฿3,217
฿3,678 total
includes taxes & fees
10 Nov - 11 Nov
The Lodge at Great Oak Landing
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
2.5 star property
  • Pool loungers
8.6 out of 10, Excellent, (838)
Poolside relaxation awaits with sun loungers and umbrellas surrounding the seasonal outdoor oasis. After swimming, guests can enjoy the fitness centre, savour a free full breakfast, or explore nearby Washington College and River Arts.
The price is ฿3,314
฿3,679 total
includes taxes & fees
11 Nov - 12 Nov
Comfort Inn & Suites Chestertown
Indoor pool
Fairfield Inn & Suites by Marriott Middletown
Fairfield Inn & Suites by Marriott Middletown
2.5 star property
  • Indoor pool
9.2 out of 10, Wonderful, (300)
Swimming enthusiasts cherish the pristine indoor pool, a centrepiece amenity complemented by exceptional staff service and continental breakfast. Situated near restaurants and attractions, this well-maintained Fairfield Inn & Suites delivers comfort in a convenient location.
The price is ฿3,509
฿3,895 total
includes taxes & fees
20 Nov - 21 Nov
Fairfield Inn & Suites by Marriott Middletown
Indoor pool
Hampton Inn & Suites Edgewood/Aberdeen-South
Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
  • Indoor pool
9.4 out of 10, Exceptional, (1000)
Swimmers splash into the warmth of a pristine indoor pool, accessible from early morning until evening. Beyond aquatic pleasures, guests enjoy a comprehensive health club, 24-hour service, and peaceful accommodation praised for exceptional cleanliness.
The price is ฿2,652
฿2,970 total
includes taxes & fees
20 Nov - 21 Nov
Hampton Inn & Suites Edgewood/Aberdeen-South
Seasonal outdoor pool, open 9 AM to 9 PM, pool umbrellas, pool loungers
Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
  • Pool loungers
9.2 out of 10, Wonderful, (914)
Splashing in the seasonal outdoor pool reveals stunning Chesapeake Bay vistas, creating a waterfront oasis complete with sun loungers and umbrellas. Nearby adventures include hiking trails, kayaking, and sailing for the perfect coastal getaway.
The price is ฿3,087
฿3,426 total
includes taxes & fees
23 Nov - 24 Nov
Holiday Inn Express Annapolis East-Kent Island by IHG
Free daily self-service breakfast
Quality Inn
Quality Inn
2.5 star property
  • Outdoor pool
7.6 out of 10, Good, (1001)
Swimming enthusiasts splash into the inviting outdoor pool, a refreshing centrepiece after workouts in the fitness centre. Friendly staff ensure exceptional service throughout the hotel, complemented by comfortable, clean accommodation just steps from local dining options.
The price is ฿2,253
฿2,500 total
includes taxes & fees
7 Dec - 8 Dec
Quality Inn
Indoor pool
Hampton Inn & Suites Baltimore/Aberdeen
Hampton Inn & Suites Baltimore/Aberdeen
2.5 star property
  • Indoor pool
9.0 out of 10, Wonderful, (588)
Splash into holiday mode at the pristine indoor swimming pool after enjoying the complimentary breakfast buffet. Clean, comfortable accommodation and exceptionally friendly staff create a peaceful retreat complete with fitness centre and tennis courts.
The price is ฿2,937
฿3,290 total
includes taxes & fees
25 Nov - 26 Nov
Hampton Inn & Suites Baltimore/Aberdeen
Indoor pool
Best Western Kent Narrows Inn
Best Western Kent Narrows Inn
2.5 star property
  • Indoor pool
  • Hot tub
8.0 out of 10, Very good, (1000)
Sparkling waters await in the pristine indoor swimming pool, complemented by a rejuvenating hot tub and sauna. Active travellers appreciate the nearby hiking trails while enjoying spotless accommodation with 49-inch TVs and refrigerators.
The price is ฿2,990
฿3,319 total
includes taxes & fees
16 Nov - 17 Nov
Best Western Kent Narrows Inn
Exterior
The Inn at Chesapeake Bay Beach Club
The Inn at Chesapeake Bay Beach Club
4.0 star property
  • Full-service spa
9.4 out of 10, Exceptional, (425)
Seasonal outdoor pool beckons from May to September amid upscale amenities at this Chesapeake Bay hotel. Professional staff complement the experience with nearby dining options, complimentary bicycles, and rejuvenating spa treatments.
The price is ฿6,011
฿7,499 total
includes taxes & fees
1 Dec - 2 Dec
The Inn at Chesapeake Bay Beach Club
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chestertown Hotel Reviews

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

10/10 Excellent
"Super friendly and patient staff, very accomodating in all aspects, front desk, cleaning, and maintenance all with upstanding character and service. "
Monalisa 1-night trip
Posted 5 days ago
Best Western Plus Hotel & Conference Center
Americas Best Value Inn Edgewood

Americas Best Value Inn Edgewood

10/10 Excellent
"It’s great"
Racquel 1-night trip
Posted 6 days ago
Americas Best Value Inn Edgewood

Frequently asked questions

What are some accommodation options with pools in Chestertown?
Red Roof Inn & Suites Chestertown: Offers full, a seasonal outdoor pool and free self parking. Comfort Inn & Suites Chestertown: Provides 3 bars, a seasonal outdoor pool and free self parking. The Lodge at Great Oak Landing: Offers complimentary high-speed (wired) Internet access, an indoor pool and free self parking. Historic Inns of Annapolis: Hotel located near Baltimore Cruise Terminal. Features buffet, an indoor pool and free self parking. Hilton Garden Inn Baltimore/White Marsh: Hotel located near Baltimore Inner Harbor Marina. Offers 2 bars, a seasonal outdoor pool and spa services.
What is there to see and do in Chestertown?
Surround yourself with nature at Chesapeake Bay and Chestertown Dog Park. Discover sights such as Historical Society of Kent County Maryland, Rolphs Wharf Marina 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.