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Find hotels in Chestertown, MD from AED70

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Check Chestertown hotel prices

Tonight
May 23 - May 24
Tomorrow night
May 24 - May 25
This weekend
May 24 - May 26
Next weekend
May 31 - Jun 2

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Compare 1,002 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Exterior
Comfort Inn & Suites Chestertown
2.5 star property
8.6 out of 10, Excellent, (674)
"The onsite manager was very helpful. The staff was very nice. "
The price is AED 436
AED 479 total
includes taxes & fees
28 May - 29 May
Comfort Inn & Suites Chestertown
Exterior
Red Roof Inn & Suites Chestertown
2.0 star property
7.4 out of 10, Good, (267)
"Sometimes, you don’t need a fancy place; just a clean place. That’s what this is. Maybe there weren’t the newest finishes, but we really appreciated having the extra pull-out couch and space in the room. It was perfect for traveling with my 3 teenagers."
The price is AED 281
AED 308 total
includes taxes & fees
30 May - 31 May
Red Roof Inn & Suites Chestertown
Beach
The Lodge at Great Oak Landing
3.0 star property
7.6 out of 10, Good, (4)
"The place is beautiful. The rooms are little small and could use updating. When I turned the air on the windows rattled so loud. I had to keep it on low to avoid the noise. No microwave in the room and be prepared for the slamming door at 6am. Other than those things we really enjoyed our time. "
The price is AED 514
AED 580 total
includes taxes & fees
28 May - 29 May
The Lodge at Great Oak Landing
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Front of property - evening/night
Driftwood Inn
2.0 star property
5.0 out of 10, (159)
"It was clean and everything worked--more than I could say for many other more expensive rooms I've stayed in. The shower was exceptionally good. Watch out for the hot water: very hot! The TV had Netflix, Hulu, Roku, & Vudu. And they worked. On the downside, the furnishings and carpet were worn, but not terrible. "
The price is AED 233
AED 259 total
includes taxes & fees
26 May - 27 May
Driftwood Inn
Property grounds
Inn at Huntingfield Creek
3.5 star property
10.0 out of 10, Exceptional, (44)
"Lovely property with wonderful owners and staff, including three very welcoming dogs. We had a perfect weekend getaway."
The price is AED 843
AED 936 total
includes taxes & fees
27 May - 28 May
Inn at Huntingfield Creek
Room
Mariners Motel
2.0 star property
9.4 out of 10, Exceptional, (85)
"Really cute property and rooms. The rooms are small but exceptionally clean and nicely decorated. Pretty grounds with a pool, fire pit, hammocks and yard games available. Easy walking distance to a few restaurants. Staff was very pleasant. "
The price is AED 612
AED 680 total
includes taxes & fees
27 May - 28 May
Mariners Motel
Exterior
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (16)
"We have been coming to Rock Hall for years and have stayed at the cottage the last two times and we have really enjoyed it. We will be back again and we will stay at this cottage again. My husband loves the sauna. Bill and Hannah"
The price is AED 643
AED 981 total
includes taxes & fees
28 May - 29 May
BAYSIDE BUNGALOW
Back Yard
First Floor Studio Apartment in Historic Chestertown
9.8 out of 10, Exceptional, (59)
"This was the perfect place to rest our heads along our trip down the east coast. Very comfortable, clean and quiet. We made time to visit the beautiful town and I’m glad we did!"
The price is AED 404
AED 603 total
includes taxes & fees
27 May - 28 May
First Floor Studio Apartment in Historic Chestertown
Living area
Carriage House Hideaway in Middle of Chestertown
10.0 out of 10, Exceptional, (76)
"Bob and Beth's apartment was absolutely perfect for us. It was the cleanest VRBO that we have ever stayed in. All of the amenities were above and beyond what we expected. The apartment is in a great location and walkable into town and the WC campus. We will definitely stay again when we come back to town."
Carriage House Hideaway in Middle of Chestertown
Cottage style house
200 steps to the beach!
10.0 out of 10, Exceptional, (74)
"Just what we needed! I did a 3 day get-a-way with my husband and 3 year old. It was perfect. The house was very cute, clean, and had everything we needed. You cannot beat the location!"
200 steps to the beach!
Beach
Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
10.0 out of 10, Exceptional, (37)
"This was the perfect landing pad for us and our dog during out 4 night visit. Very clean kitchen and bathrooms, and conveniently located. Well-stocked with all the comforts and conveniences of home. We really loved our meals out at Harbor Shack. We would definitely stay here again!"
Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
Your private dock to swan creek.
Cute waterfront apartment -- 8 min from the beach!
10.0 out of 10, Exceptional, (5)
"I raced the Waterman's tri and this location was perfect, well equipped, comfortable, clean, easy."
Cute waterfront apartment -- 8 min from the beach!
looking down river from the dock
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
9.8 out of 10, Exceptional, (77)
"We had a great stay and the property is well maintained. They had a lot of extras for our convenience such as toothbrushes, snacks, and more. The dock and view was beautiful and relaxing. We plan to come back soon!"
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Interior
Waterfront Oasis w/ Private Dock, 3BR/2BA
9.8 out of 10, Exceptional, (19)
"We really enjoyed our stay. We were in town to celebrate my Dad's 80th birthday and the house was convenient to Parkville and Towson. The view from the sunroom was gorgeous. It was everything we needed for a quick weekend stay. Thank you."
Waterfront Oasis w/ Private Dock, 3BR/2BA
Exterior
Rambling Victorian Beach House on Maryland's Eastern Shore
10.0 out of 10, Exceptional, (13)
"Our group of couples + kids enjoyed our getaway to the Eastern Shore. Betterton was a great home base to visit our alma mater, Washington College, in Chestertown. There, we visited the farmers market and waterfront park & playground with the kids. Back in Betterton, the house fit our group well. Plenty of bedrooms, bathrooms and space for each family. The kids & adults enjoyed spending time lounging in the third floor living room. We were pleased that the house had plenty of games, kids toys,...
Rambling Victorian Beach House on Maryland's Eastern Shore
back deck
This is truly a Baydream!
10.0 out of 10, Exceptional, (27)
"Close to everything. Cute quiet neighborhood. Well equipped kitchen."
This is truly a Baydream!
Exterior
Bayside Cottage steps from Rock Hall Harbor
10.0 out of 10, Exceptional, (1)
"Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!"
The price is AED 739
AED 1,445 total
includes taxes & fees
27 May - 28 May
Bayside Cottage steps from Rock Hall Harbor
From your private pier
Serene Waterfront Cottage with dock and gorgeous views.
9.6 out of 10, Exceptional, (35)
"Nice place with everything I could want. Would stay there again!"
Serene Waterfront Cottage with dock and gorgeous views.
Betterton Beachhouse - historic Buena Vista, overlooking the Chesapeake Bay
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
9.4 out of 10, Exceptional, (26)
"This was our second stay here. The property is well appointed for a relaxing stay with 5-star views! Lots of room for family to spread out and relax, and the kitchen has everything you need to make delicious meals. Betterton is extra relaxing with its beautiful views and quiet stillness. We'll be back!"
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Bulkhead In Backyard
Charming Chestertown Waterfront Cottage
10.0 out of 10, Exceptional, (59)
"This is a great place to relax. The house had everything we needed and was very comfortable."
Charming Chestertown Waterfront Cottage
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See all available properties in Chestertown
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.

More cheap stays in Chestertown

Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A

2112a Emmorton Park Road, Edgewood, MD
The price is AED70 per night from May 26 to May 27
AED70
per night
May 26 - May 27
7.4/10 Good! (971 reviews)

Stay near popular Chestertown attractions

Image for Washington College

Washington College

4/5(13 reviews)

Take a campus tour or just explore the area of Washington College, during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.

See properties
Washington College

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.

Recent reviews of Chestertown hotels
Expedia verified reviews

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

5/5 Excellent
"I’ve stayed here before so it was familiar and consistent with my expectations. However, for a non-Baltimorean it is not the easiest place to find, GPS or not."
A verified traveler stayed at Best Western Plus Hotel & Conference Center
Posted 2 days ago
Best Western Plus Hotel & Conference Center