An aerial view of a town with a river, buildings, and surrounding greenery.

Find Hotels with a Pool in Chestertown, MD

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Check availability on Chestertown Hotels with a Pool

Tonight
15 Aug - 16 Aug
Tomorrow
16 Aug - 17 Aug
Next weekend
21 Aug - 23 Aug
In two weeks
28 Aug - 30 Aug

Our top choices for Chestertown hotels with a pool

Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
Free daily full breakfast
Desk, laptop workspace, blackout drapes, iron/ironing board
Lobby

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
  • Dive into the seasonal outdoor pool with comfortable loungers and umbrellas at this refreshing hotel retreat in Chestertown.
AED 381
AED 423 total
includes taxes & fees
13 Sep - 14 Sep
Comfort Inn & Suites Chestertown
Aerial view
Private beach nearby, sun loungers, beach volleyball
Point of interest
Reception

2. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
Chestertown
  • Waterfront lodge's seasonal outdoor pool offers sun-drenched days with loungers and umbrellas.
AED 397
AED 454 total
includes taxes & fees
16 Aug - 17 Aug
The Lodge at Great Oak Landing
Outdoor pool
1 bedroom, in-room safe, WiFi (free), bed sheets
Property grounds
Exterior

3. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
  • Serene backyard pool with hot tub and golf course views provides ideal relaxation in historic Chestertown.
AED 364
AED 583 total
includes taxes & fees
20 Aug - 21 Aug
First Floor Studio Apartment in Historic Chestertown
Outdoor pool, sun loungers
Property grounds
Lake
Property grounds

4. Inn at Huntingfield Creek

Inn at Huntingfield Creek
Rock Hall
  • Waterfront escape with a sun-drenched outdoor pool and spa services at this peaceful bed and breakfast retreat.
AED 663
AED 736 total
includes taxes & fees
17 Aug - 18 Aug
Inn at Huntingfield Creek
Seasonal outdoor pool, open 9 AM to 9 PM, pool umbrellas, sun loungers
Free daily buffet breakfast
Standard Room, 1 King Bed, River View | Premium bedding, in-room safe, desk, iron/ironing board
Exterior

5. Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
  • Splashy pool escapes by the bay; seasonal swimming paradise with sun-soaked loungers.
AED 463
AED 514 total
includes taxes & fees
14 Sep - 15 Sep
Holiday Inn Express Annapolis East-Kent Island by IHG
Lobby
Lobby
Combined shower/tub, hair dryer, towels
Suite, 1 Queen Bed, Non Smoking | In-room safe, iron/ironing board, WiFi (free), bed sheets

6. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
Grasonville
  • Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay.
AED 367
AED 408 total
includes taxes & fees
7 Sep - 8 Sep
Quality Inn Grasonville near Kent Island
Seasonal outdoor pool, pool umbrellas
Room, 2 Queen Beds, Non Smoking | Premium bedding, down comforters, pillowtop beds, desk
Business center
Exterior

7. Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Bel Air
  • Seasonal outdoor pool beckons with umbrella-shaded lounging spots perfect for refreshing dips amid Maryland's summer sun.
AED 327
AED 367 total
includes taxes & fees
13 Sep - 14 Sep
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Indoor pool
Free daily buffet breakfast
Terrace/patio
Exterior

8. Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
Aberdeen
  • Indoor pool retreat offers relaxing swims with modern amenities and helpful staff around the clock.
AED 358
AED 401 total
includes taxes & fees
30 Aug - 31 Aug
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Indoor pool
In-room safe, desk, laptop workspace, iron/ironing board
In-room safe, desk, laptop workspace, iron/ironing board
Business center

9. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
  • Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary.
AED 443
AED 491 total
includes taxes & fees
23 Aug - 24 Aug
Best Western Kent Narrows Inn
Indoor pool, sun loungers
Lobby
Exterior
Terrace/patio

10. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
  • Scenic waters beckon at this island escape with a relaxing indoor pool and waterfront deck for breathtaking sunset views.
AED 613
AED 681 total
includes taxes & fees
8 Sep - 9 Sep
Hyatt Place Kent Narrows & Marina
View all properties

Choose what matters most at hotels with a pool in Chestertown

Breakfast included
Hot tub
4 stars
5 stars
Spa

Top Chestertown Hotel Reviews

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

8/10 Good
"Todo estuvo muy bien. Gracias"
Bibiana 2-night trip
Posted 5 hours ago
Best Western Plus Hotel & Conference Center
Hampton Inn Baltimore/White Marsh

Hampton Inn Baltimore/White Marsh

10/10 Excellent
"."
Andrew 1-night trip
Posted 6 hours ago
Hampton Inn Baltimore/White Marsh
Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

10/10 Excellent
"The room was very spacious, and clean. The property was quiet. I would definitely stay there again."
Kimberly 1-night trip
Posted 11 hours ago
Hampton Inn & Suites Edgewood/Aberdeen-South
Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

10/10 Excellent
"The room was immaculate. The bed was very comfortable. The staff was on point and very naturally aware of our needs. Plan time for the elevator. It was slow but still it worked. The property was well cared for also and clean. Parking was easy. Well done Hilton!!"
Kathleen 2-night trip
Posted 1 day ago
Hilton Garden Inn Baltimore/White Marsh
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

10/10 Excellent
"Our room was clean and very quiet!"
Darlene 1-night trip
Posted 2 days ago
Best Western Kent Narrows Inn
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

10/10 Excellent
"Very nice hotel. Have stayed here every year for the Pirates and Wenches Festival in Rock Hall."
Linda 2-night trip
Posted 5 days ago
Red Roof Inn & Suites Chestertown

Frequently asked questions

What are some accommodations with pools in Chestertown?
Comfort Inn & Suites Chestertown: Features full, a seasonal outdoor pool, and free self parking. The Lodge at Great Oak Landing: Offers free self parking, a seasonal outdoor pool, and sun loungers. Red Roof Inn & Suites Chestertown: Hotel located near Baltimore Inner Harbor Marina. Features 2 bars, a seasonal outdoor pool, and spa services. Historic Inns of Annapolis: Hotel located near Johns Hopkins Hospital. Offers buffet, an indoor pool, and free self parking. Annapolis Waterfront Hotel, Autograph Collection: Offers a snack bar/deli, 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, Rolphs Wharf Marina, and Historical Society of Kent County Maryland 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 offers an outdoor pool if you're planning to visit Chestertown in the hottest months of July, August, or June when the average temperature is 74°F. Lodging with an indoor pool may be the way to go if you visit during the coldest months of January, February, or December when the average temp is 39°F.