Family friendly Hotels in Chestertown, Maryland
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Aug 15 - Aug 16Tomorrow
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Aug 21 - Aug 23In two weeks
Aug 28 - Aug 30Our top choices for Chestertown family-friendly hotels
1. Comfort Inn & Suites Chestertown
Comfort Inn & Suites ChestertownChestertown
- Splash into seasonal fun with the family near Washington College, where kids love the outdoor pool and premium entertainment options.
P6,378
P7,080 total
includes taxes & fees
Sep 13 - Sep 14
2. Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites ChestertownChestertown
- Cozy family retreat with free Wi-Fi, cribs, and premium TV entertainment for memorable stays in the heart of Chestertown.
P3,871
P4,297 total
includes taxes & fees
Aug 23 - Aug 24
3. Driftwood Inn
Driftwood InnChestertown
- Clean, comfortable rooms at Driftwood Inn offer free Wi-Fi, premium TV, refrigerators, and microwaves for families.
P3,902
P4,332 total
includes taxes & fees
Aug 17 - Aug 18
P6,145
P6,821 total
includes taxes & fees
Sep 7 - Sep 8
5. Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHGGrasonville
- Family-friendly fun on the Kent Island escape—enjoy the seasonal outdoor pool, hiking trails, and beautiful views of Chesapeake Bay.
P7,743
P8,594 total
includes taxes & fees
Sep 14 - Sep 15
P7,406
P8,221 total
includes taxes & fees
Aug 23 - Aug 24
P10,262
P11,391 total
includes taxes & fees
Sep 8 - Sep 9
8. La Quinta Inn & Suites by Wyndham Aberdeen-APG
La Quinta Inn & Suites by Wyndham Aberdeen-APGAberdeen
- Splash into family fun at Aberdeen's seasonal outdoor pool where comfortable rooms await after sun-filled adventures in the park.
P5,432
P6,084 total
includes taxes & fees
Aug 23 - Aug 24
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Top Chestertown Hotel Reviews
Annapolis Waterfront Hotel, Autograph Collection
10/10 Excellent
"Wonderful view of the water and bay. Convenient walk to downtown Annapolis and area. Room was impeccable."
Holiday Inn Express Annapolis East-Kent Island by IHG
10/10 Excellent
"The room was clean, comfortable and staff were courteous , knowledgeable and professional. I would recommend this Holiday Inn and will definitely return."
Historic Inns of Annapolis
10/10 Excellent
"Really a great experience. The location was amazing the vibe of the hotel was fantastic."
Hampton Inn Baltimore/White Marsh
10/10 Excellent
"The stay was wonderful"
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
10/10 Excellent
"The room was clean. I bit noisy, but not the fault of the hotel."
Best Western Plus Hotel & Conference Center
8/10 Good
"Todo estuvo muy bien. Gracias"
Comfort Inn & Suites Chestertown
8/10 Good
"The door into the building from the parking lot is always locked, which is great, because it cannot be seen from the front desk, but it is difficult to enter with the room key. The key is a typical credit card-like key, but the electronic reader was wonky. Sometimes it worked and sometimes it didn’t. The cards worked well on the room doors but not on the entrance door. It was an inconvenience to walk around the building to get it the main entrance if the card did not work."
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."
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!!"