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Find hotels in Chestertown, MD from AED 185

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Check Chestertown hotel prices

Tonight
21 Nov - 22 Nov
Tomorrow night
22 Nov - 23 Nov
This weekend
22 Nov - 24 Nov
Next weekend
29 Nov - 1 Dec

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Compare 1,021 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

The Lodge at Great Oak Landing
Room
The Lodge at Great Oak Landing
3.5 star property
7.6 out of 10, Good, (45)
"Generally okay, Clean but property could use some upgrade"
The price is AED 369
AED 410 total
includes taxes & fees
25 Nov - 26 Nov
The Lodge at Great Oak Landing
Comfort Inn & Suites Chestertown
Exterior
Comfort Inn & Suites Chestertown
2.5 star property
8.6 out of 10, Excellent, (727)
"Was there just one night and didn't eat breakfast, but staff were wonderful and the room seemed newly renovated. Room was large and clean with coffee maker and mini-fridge. "
The price is AED 392
AED 432 total
includes taxes & fees
15 Dec - 16 Dec
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Exterior
Red Roof Inn & Suites Chestertown
2.0 star property
7.2 out of 10, Good, (320)
"Comfortable room and fair price for the room size. Very clean. Bathroom was nice but had a broken wall mounted hair dryer and the bathroom door did not latch closed so it stayed open about an inch. Front desk was businesslike but not the least bit friendly. There is no breakfast or even coffee offered. You have to go out for breakfast. Excuse was not since Covid. That adds another $20 per couple for breakfast to the room price."
The price is AED 291
AED 319 total
includes taxes & fees
2 Dec - 3 Dec
Red Roof Inn & Suites Chestertown
Driftwood Inn
Front of property - evening/night
Driftwood Inn
2.0 star property
5.0 out of 10, (167)
"It was fine. I have no complaint. I stayed one night.The staff was friendly."
The price is AED 233
AED 259 total
includes taxes & fees
22 Nov - 23 Nov
Driftwood Inn
Inn at Huntingfield Creek
Property grounds
Inn at Huntingfield Creek
3.5 star property
10.0 out of 10, Exceptional, (48)
"Wonderful! Quiet and relaxing anniversary! Pool was great, dock is beautiful, room was clean, comfortable and spacious. Water bottles and cookies are such a nice touch. Breakfast was delicious. Amazing property and genuine hosts. Thank you"
The price is AED 720
AED 799 total
includes taxes & fees
24 Nov - 25 Nov
Inn at Huntingfield Creek
Mariners Motel
Room
Mariners Motel
2.0 star property
9.4 out of 10, Exceptional, (88)
"Great location and very well cared for older motel. Updating extremely well done. We enjoyed the complimentary bikes, being so close to the water and the many good restaurants nearby. We will be back!"
The price is AED 528
AED 586 total
includes taxes & fees
24 Nov - 25 Nov
Mariners Motel
First Floor Studio Apartment in Historic Chestertown
Back Yard
First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (75)
"EasyvPeasy place."
The price is AED 360
AED 579 total
includes taxes & fees
22 Nov - 23 Nov
First Floor Studio Apartment in Historic Chestertown
BAYSIDE BUNGALOW
Exterior detail
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (33)
"The bay cottage's porch was a perfect spot to enjoy a bottle of wine and snacks provided by the thoughtful hosts. Clever decor , furnishings, and sauna made our stay special and warm. Had crab dinner viewing sunset over the bay at dockside suggested by hosts. we hope to return. "
The price is AED 643
AED 997 total
includes taxes & fees
22 Nov - 23 Nov
BAYSIDE BUNGALOW
Waterfront Retreat with Private Dock and Beach
Private Dock
Waterfront Retreat with Private Dock and Beach
10.0 out of 10, Exceptional, (17)
"This property was exactly what we needed! The apartment was very clean and well maintained making it such a pleasant experience. Even though the property is shared with the owners, they weren’t constantly around or hovering over us allowing us to enjoy our time together. We loved having the dock and availability of the kayaks so we didn’t have to bring us along for the long trip there. We found some small shops and cute little towns along with a wonderful winery all within a short drive from...
The price is AED 643
AED 1,144 total
includes taxes & fees
24 Nov - 25 Nov
Waterfront Retreat with Private Dock and Beach
Bayside Cottage steps from Rock Hall Harbor
Exterior
Bayside Cottage steps from Rock Hall Harbor
10.0 out of 10, Exceptional, (2)
"Thank you - towels hanging bathroom. Outside trash can was full when we got there. We took our trash with us. thank you - MBVK"
Bayside Cottage steps from Rock Hall Harbor
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Welcome to Mermaid's Getaway!
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
10.0 out of 10, Exceptional, (4)
"A great place to chill out and enjoy what Rock Hall has to offer. It’s always great to come back to my childhood town. Rick is a great host and takes really good care of the property! We will be back."
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Exterior
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
10.0 out of 10, Exceptional, (31)
"We had my daughter's wedding at this beautiful villa. The views were absolutely amazing! The house is very spacious and accommodated our family. The sunsets were spectacular. Everyone enjoyed the pool, hot tub, and all the other activities this house had to offer"
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Circa 1900 Home in the Heart of Historic Downtown Chestertown
Front Porch
Circa 1900 Home in the Heart of Historic Downtown Chestertown
10.0 out of 10, Exceptional, (64)
"We enjoyed everything about the property."
Circa 1900 Home in the Heart of Historic Downtown Chestertown
River Cottage, Chestertown
River Cottage, Chestertown
2.0 star property
River Cottage, Chestertown
Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD
20982 Bayside Ave, across from town dock, close to harbor and restaurants
Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD
9.8 out of 10, Exceptional, (60)
"Great place near the marina. Kitchen was well equipped for cooking our own meals. Nice recent updates to the bathroom and kitchen. Covered porch out back is also quite nice. We enjoyed our stay and would gladly return to this house!"
Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD
Serene Waterfront Cottage with dock and gorgeous views.
From your private pier
Serene Waterfront Cottage with dock and gorgeous views.
9.6 out of 10, Exceptional, (37)
"Love this place. It was perfect for us. Rooms are spacious. "
Serene Waterfront Cottage with dock and gorgeous views.
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Betterton Beachhouse - historic Buena Vista, overlooking the Chesapeake Bay
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
9.6 out of 10, Exceptional, (35)
"This house had the most amazing views and was clean and tidy. It was perfect for us and the dogs. The yard was clean and mowed and provided plenty of room for frisbee play which is part of my german shepherd's job. The kitchen was very adequate for our needs! As expected, the upstairs bedrooms were "historic" and the staircase was steep also "historic". The showers were perfect. We had a great visit and would love to come back here!"
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Peaceful getaway convenient to local amenities including beach, boating & food
Cottage In Town
Peaceful getaway convenient to local amenities including beach, boating & food
9.8 out of 10, Exceptional, (109)
"We were in town for the local triathlon and had a great stay! My kids (3&4) and I were able to walk to the finish line from the location. The house was clean and large enough that we were all comfortable. If you have kids, it’s across the street from a cool boat playground. Diane was very responsive to my questions and provided plenty of towels, blankets, etc. Overall, a great stay! "
Peaceful getaway convenient to local amenities including beach, boating & food
RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING
Living area
RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING
7.4 out of 10, Good, (3)
"About a 10 minute walk to main street, 15-20 to the Marinas. The house is cute, has a nice common room, and the bed was comfy."
RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
Outdoor seating area just off the kitchen.
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
10.0 out of 10, Exceptional, (5)
"My friend and I wanted to meet up part way between our two cities, and when we decided on the Chesapeake Bay, Rock Hall seemed a good option, and we were right! What a great little town, and the house was just perfect for us. She brought her two little ones (6 and 2), and I was on my own. I think with just 1 bathroom, many more than that would really not be ideal. The whole stay was great, we both agreed we'd love to come back again. The only hiccup (and I am sure it will be fixed), was that...
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
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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Frequently asked questions

Where can I learn more about changing or cancelling my trip to Chestertown?

For more details about rescheduling or cancelling your trip to Chestertown, click here.

What's the seasonal weather like in Chestertown?

The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.