Hotels with a Pool in Chestertown
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Hotels with a Pool in Chestertown
The Lodge at Great Oak Landing
The Lodge at Great Oak Landing3.0 star property
Chestertown
- Pool loungers
- Private beach access
7.8 out of 10, Good, (87 reviews)
7.8/10
Good
(87 reviews)
Seasonal swimming awaits with pool umbrellas and loungers providing perfect relaxation after golf rounds or beach volleyball matches. Complete days with meals at Fairlee's restaurant and sunset gatherings around the firepit.
Seasonal swimming awaits with pool umbrellas and loungers providing perfect relaxation after golf rounds or beach volleyball matches. Complete days with meals at Fairlee's restaurant and sunset gatherings around the firepit.
The price is $147
$147
$168 total
includes taxes & fees
Jun 14 - Jun 15
Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown2.5 star property
Chestertown
- Pool loungers
8.6 out of 10, Excellent, (922 reviews)
8.6/10
Excellent
(922 reviews)
Pool perfection awaits from June to September at this pristine hotel. Travelers adore the sun-drenched seasonal pool with loungers for lazy afternoons. After swimming, visitors appreciate the fitness center, full breakfast, and spotlessly clean rooms.
Pool perfection awaits from June to September at this pristine hotel. Travelers adore the sun-drenched seasonal pool with loungers for lazy afternoons. After swimming, visitors appreciate the fitness center, full breakfast, and spotlessly clean rooms.
The price is $106
$106
$118 total
includes taxes & fees
Jul 5 - Jul 6
Best Western Kent Narrows Inn
Best Western Kent Narrows Inn2.5 star property
Grasonville
- Indoor pool
- Hot tub
8.0 out of 10, Very Good, (1,005 reviews)
8.0/10
Very Good
(1,005 reviews)
Glide through crystal-clear waters in the refreshing indoor pool before melting away tension in the bubbling hot tub. Fitness enthusiasts appreciate the on-site sauna and gym while hikers enjoy nearby trails. Comfortable rooms complete the perfect getaway.
Glide through crystal-clear waters in the refreshing indoor pool before melting away tension in the bubbling hot tub. Fitness enthusiasts appreciate the on-site sauna and gym while hikers enjoy nearby trails. Comfortable rooms complete the perfect getaway.
The price is $110
$110
$122 total
includes taxes & fees
Jul 6 - Jul 7
Quality Inn Grasonville near Kent Island
Quality Inn Grasonville near Kent Island2.5 star property
Grasonville
- Pool
- Free parking
- Free WiFi
- Air conditioning
- 24/7 front desk
7.8 out of 10, Good, (917 reviews)
7.8/10
Good
(917 reviews)
Crystal-clear waters beckon at the seasonal outdoor pool, available around the clock from May through October. Comfortable rooms await after exploring Queenstown Harbor Golf Links, while helpful staff earn consistent praise for making every stay exceptional.
Crystal-clear waters beckon at the seasonal outdoor pool, available around the clock from May through October. Comfortable rooms await after exploring Queenstown Harbor Golf Links, while helpful staff earn consistent praise for making every stay exceptional.
The price is $100
$100
$111 total
includes taxes & fees
Jun 21 - Jun 22
9.4 out of 10, Exceptional, (143 reviews)
9.4/10
Exceptional
(143 reviews)
Sparkling waters await at the seasonal outdoor pool, surrounded by sun loungers and umbrellas from April through November. Complimentary bicycles invite exploration, while kayaking and fishing offer aquatic adventures beyond the refreshing pool deck.
Sparkling waters await at the seasonal outdoor pool, surrounded by sun loungers and umbrellas from April through November. Complimentary bicycles invite exploration, while kayaking and fishing offer aquatic adventures beyond the refreshing pool deck.
The price is $144
$144
$194 total
includes taxes & fees
Jun 15 - Jun 16
Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHG2.5 star property
Grasonville
- Pool loungers
9.2 out of 10, Wonderful, (1,001 reviews)
9.2/10
Wonderful
(1,001 reviews)
Sparkling pool waters invite lazy afternoons under umbrellas with Chesapeake Bay vistas just beyond. Pristine rooms, delicious breakfast options, and hiking trails complete this waterfront escape where scenic beauty meets comfort.
Sparkling pool waters invite lazy afternoons under umbrellas with Chesapeake Bay vistas just beyond. Pristine rooms, delicious breakfast options, and hiking trails complete this waterfront escape where scenic beauty meets comfort.
The price is $134
$134
$149 total
includes taxes & fees
Jun 16 - Jun 17
Inn at Huntingfield Creek
Inn at Huntingfield Creek3.5 star property
Rock Hall
- Outdoor pool
- Pool loungers
- Full-service spa
10.0 out of 10, Exceptional, (64 reviews)
10/10
Exceptional
(64 reviews)
Poolside paradise unfolds at this waterfront bed & breakfast, where sun loungers invite leisurely days between spa massages. Egyptian cotton sheets and memory foam beds ensure rejuvenation after biking along nearby trails.
Poolside paradise unfolds at this waterfront bed & breakfast, where sun loungers invite leisurely days between spa massages. Egyptian cotton sheets and memory foam beds ensure rejuvenation after biking along nearby trails.
The price is $178
$178
$198 total
includes taxes & fees
Jun 14 - Jun 15
Fairfield Inn & Suites by Marriott Middletown
Fairfield Inn & Suites by Marriott Middletown3.0 star property
Middletown
- Indoor pool
9.2 out of 10, Wonderful, (405 reviews)
9.2/10
Wonderful
(405 reviews)
Swimming enthusiasts cherish the inviting indoor pool, offering a serene escape regardless of weather. Located near numerous restaurants with convenient dining options, this hotel wins praise for its exceptionally friendly staff and spotless facilities.
Swimming enthusiasts cherish the inviting indoor pool, offering a serene escape regardless of weather. Located near numerous restaurants with convenient dining options, this hotel wins praise for its exceptionally friendly staff and spotless facilities.
The price is $104
$104
$115 total
includes taxes & fees
Jun 21 - Jun 22
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Home2 Suites by Hilton Baltimore / Aberdeen, MD3.0 star property
Aberdeen
- Indoor pool
8.8 out of 10, Excellent, (380 reviews)
8.8/10
Excellent
(380 reviews)
Swimmers dive into vacation bliss at the pristine indoor pool, available from morning until night. After invigorating laps, guests enjoy complimentary breakfast buffet before retreating to spacious rooms featuring kitchens and sofa beds.
Swimmers dive into vacation bliss at the pristine indoor pool, available from morning until night. After invigorating laps, guests enjoy complimentary breakfast buffet before retreating to spacious rooms featuring kitchens and sofa beds.
The price is $98
$98
$109 total
includes taxes & fees
Jun 21 - Jun 22
La Quinta Inn & Suites by Wyndham Aberdeen-APG
La Quinta Inn & Suites by Wyndham Aberdeen-APG3.0 star property
Aberdeen
- Pool
- Free breakfast
- Pet friendly
- Free parking
- Free WiFi
- Connecting rooms available
9.0 out of 10, Wonderful, (1,009 reviews)
9.0/10
Wonderful
(1,009 reviews)
Poolside relaxation meets fitness enthusiasts at this immaculate hotel, featuring a seasonal outdoor oasis and fully-equipped gym. Clean rooms with laptop-friendly workspaces complete the experience, creating the perfect base for both leisure and business travelers.
Poolside relaxation meets fitness enthusiasts at this immaculate hotel, featuring a seasonal outdoor oasis and fully-equipped gym. Clean rooms with laptop-friendly workspaces complete the experience, creating the perfect base for both leisure and business travelers.
The price is $88
$88
$99 total
includes taxes & fees
Jun 21 - Jun 22
Hampton Inn & Suites Baltimore/Aberdeen
Hampton Inn & Suites Baltimore/Aberdeen2.5 star property
Aberdeen
- Indoor pool
9.0 out of 10, Wonderful, (662 reviews)
9.0/10
Wonderful
(662 reviews)
Splash into crystal-clear waters at the inviting indoor pool, where families can enjoy supervised swimming. Comfortable rooms, friendly staff, and a complimentary breakfast buffet complete this serene getaway with tennis courts and fitness center access.
Splash into crystal-clear waters at the inviting indoor pool, where families can enjoy supervised swimming. Comfortable rooms, friendly staff, and a complimentary breakfast buffet complete this serene getaway with tennis courts and fitness center access.
The price is $94
$94
$106 total
includes taxes & fees
Jun 21 - Jun 22
8.6 out of 10, Excellent, (658 reviews)
8.6/10
Excellent
(658 reviews)
Sparkling indoor pool welcomes swimmers with crystal-clear waters from 5 AM to 10 PM daily. Kids love the perfect-sized swimming area while adults appreciate the clean whirlpool after visiting the adjacent fitness center.
Sparkling indoor pool welcomes swimmers with crystal-clear waters from 5 AM to 10 PM daily. Kids love the perfect-sized swimming area while adults appreciate the clean whirlpool after visiting the adjacent fitness center.
The price is $103
$103
$115 total
includes taxes & fees
Jun 21 - Jun 22
Comfort Inn & Suites Aberdeen near APG
Comfort Inn & Suites Aberdeen near APG2.5 star property
Aberdeen
- Pool
- Free breakfast
- Pet friendly
- Free parking
- Free WiFi
- Restaurant
8.0 out of 10, Very Good, (916 reviews)
8.0/10
Very Good
(916 reviews)
Poolside relaxation awaits at this comfort-focused hotel with a seasonal outdoor pool open May through September. After swimming laps, guests can savor American cuisine at the on-site IHOP or maintain fitness routines in the well-equipped gym.
Poolside relaxation awaits at this comfort-focused hotel with a seasonal outdoor pool open May through September. After swimming laps, guests can savor American cuisine at the on-site IHOP or maintain fitness routines in the well-equipped gym.
The price is $80
$80
$89 total
includes taxes & fees
Jun 21 - Jun 22
7.6 out of 10, Good, (1,010 reviews)
7.6/10
Good
(1,010 reviews)
Sparkling waters beckon at the outdoor pool, creating a refreshing escape after exploring nearby attractions. Friendly staff deliver exceptional service at this peaceful retreat with comfortable, immaculately clean rooms and complimentary breakfast.
Sparkling waters beckon at the outdoor pool, creating a refreshing escape after exploring nearby attractions. Friendly staff deliver exceptional service at this peaceful retreat with comfortable, immaculately clean rooms and complimentary breakfast.
The price is $85
$85
$94 total
includes taxes & fees
Jul 13 - Jul 14
Ramada Hotel & Conference Center by Wyndham Edgewood
Ramada Hotel & Conference Center by Wyndham Edgewood2.0 star property
Edgewood
- Pool loungers
6.6 out of 10, (532 reviews)
6.6/10
(532 reviews)
Poolside paradise awaits with sun loungers and umbrellas surrounding the seasonal outdoor pool. Friendly staff ensure a carefree experience, while a fitness center, continental breakfast, and business amenities complete this rejuvenating retreat.
Poolside paradise awaits with sun loungers and umbrellas surrounding the seasonal outdoor pool. Friendly staff ensure a carefree experience, while a fitness center, continental breakfast, and business amenities complete this rejuvenating retreat.
The price is $67
$67
$75 total
includes taxes & fees
Jun 14 - Jun 15
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG2.5 star property
Edgewood
- Pool
- Free breakfast
- Free parking
- Free WiFi
- Connecting rooms available
- Air conditioning
9.0 out of 10, Wonderful, (605 reviews)
9.0/10
Wonderful
(605 reviews)
Sparkling waters welcome weary travelers at this spotless hotel's refreshing pool area. Just off I-95 near Cedar Lane Regional Park, guests praise the comfortable beds, exceptional staff service, and complimentary continental breakfast.
Sparkling waters welcome weary travelers at this spotless hotel's refreshing pool area. Just off I-95 near Cedar Lane Regional Park, guests praise the comfortable beds, exceptional staff service, and complimentary continental breakfast.
The price is $94
$94
$105 total
includes taxes & fees
Jun 16 - Jun 17
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD3.0 star property
Bel Air
- Pool umbrellas
8.8 out of 10, Excellent, (1,009 reviews)
8.8/10
Excellent
(1,009 reviews)
Poolside relaxation awaits beneath umbrella-dotted surroundings at the seasonal outdoor oasis. After swimming, guests appreciate the spotlessly clean rooms with premium bedding and the consistently praised complimentary breakfast.
Poolside relaxation awaits beneath umbrella-dotted surroundings at the seasonal outdoor oasis. After swimming, guests appreciate the spotlessly clean rooms with premium bedding and the consistently praised complimentary breakfast.
The price is $95
$95
$106 total
includes taxes & fees
Jul 6 - Jul 7
Fairfield Inn & Suites by Marriott Aberdeen
Fairfield Inn & Suites by Marriott Aberdeen3.0 star property
Aberdeen
- Indoor pool
9.0 out of 10, Wonderful, (344 reviews)
9.0/10
Wonderful
(344 reviews)
Dive into refreshment at the immaculate indoor pool, where spotless facilities and friendly staff create a welcoming atmosphere. The individually furnished rooms and complimentary continental breakfast add comfort to every stay.
Dive into refreshment at the immaculate indoor pool, where spotless facilities and friendly staff create a welcoming atmosphere. The individually furnished rooms and complimentary continental breakfast add comfort to every stay.
The price is $109
$109
$123 total
includes taxes & fees
Jun 14 - Jun 15
8.8 out of 10, Excellent, (905 reviews)
8.8/10
Excellent
(905 reviews)
Aquatic adventures await in the pristine indoor pool, complemented by a rejuvenating hot tub that guests consistently rate as "amazing." Hearty free breakfast buffet fuels days of swimming, with 8 AM to 10 PM pool hours offering flexible splash time for everyone.
Aquatic adventures await in the pristine indoor pool, complemented by a rejuvenating hot tub that guests consistently rate as "amazing." Hearty free breakfast buffet fuels days of swimming, with 8 AM to 10 PM pool hours offering flexible splash time for everyone.
The price is $107
$107
$119 total
includes taxes & fees
Jul 2 - Jul 3
Days Inn by Wyndham Aberdeen
Days Inn by Wyndham Aberdeen2.0 star property
Aberdeen
- Pool
- Free breakfast
- Pet friendly
- Free parking
- Free WiFi
- Connecting rooms available
7.0 out of 10, Good, (975 reviews)
7.0/10
Good
(975 reviews)
Swimming enthusiasts delight in the seasonal outdoor pool, available from May through September with convenient 10 AM to 9 PM access. Located near Harford Memorial Hospital and Havre de Grace Decoy Museum, this clean, well-maintained motel features friendly staff.
Swimming enthusiasts delight in the seasonal outdoor pool, available from May through September with convenient 10 AM to 9 PM access. Located near Harford Memorial Hospital and Havre de Grace Decoy Museum, this clean, well-maintained motel features friendly staff.
The price is $79
$79
$88 total
includes taxes & fees
Jun 30 - Jul 1
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.
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.
Top landmarks in Chestertown
Historical Society of Kent County Maryland
3.7/5 (6 reviews)
Historical Society of Kent County Maryland is 0.7 mi (1.2 km) from central Chestertown, why not stop by during your stay. If you want to experience more of the culture Chestertown has to offer, head to Chestertown Historic District, River Arts Chestertown, and Wilmer Park.
Garfield Center for the Arts at the Prince Theater
3.4/5 (5 reviews)
Why not give yourself a treat with a trip to Garfield Center for the Arts at the Prince Theater, one of the family attractions located 0.7 mi (1.2 km) from central Chestertown. If you have fun at Garfield Center for the Arts at the Prince Theater, you'll love Larrabee Arts Center, located nearby.