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

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb
No exact matches found, but these alternatives could be just right

Recommended hotels in Chestertown

A hotel with a two-story building, multiple windows, and a lawn area.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (989 reviews)
"This was a very well maintained place and the breakfast was really good."
United States
Amy
The price is ₹9,356
₹10,385 total
includes taxes & fees
8 Nov - 9 Nov
Comfort Inn & Suites Chestertown
A row of motel rooms with stone walls and red doors.

2. Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.4 out of 10, (183 reviews)
"It was a nice, clean place to stay the night."
United States
Kathy
The price is ₹6,082
₹6,752 total
includes taxes & fees
15 Oct - 16 Oct
Driftwood Inn
A hotel entrance with a clear sky, a parking lot, and a brick building with a covered entrance.

3. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (509 reviews)
"Easy check-in & out. Convenient parking. Room was clean, though there were stains on loveseat, sheets, comforter (look like they’d been there for awhile; washed & put back on)."
United States
Kate
The price is ₹6,895
₹7,654 total
includes taxes & fees
20 Oct - 21 Oct
Red Roof Inn & Suites Chestertown
A swimming pool with a wooden deck and lounge chairs, surrounded by trees and a building with a white roof.

4. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
8.0 out of 10, Very good, (120 reviews)
"This is a wonderful facility for a couple or family. The restaurant is just "ok"."
United States
Sandra
The price is ₹10,291
₹11,765 total
includes taxes & fees
21 Oct - 22 Oct
The Lodge at Great Oak Landing
A two-story house with a covered porch, a staircase, and a garden area.

5. Haven Point Inn and Gallery

Haven Point Inn and Gallery
2.0 star property
Rock Hall
9.6 out of 10, Exceptional, (16 reviews)
"Host is fantastic. Great room with garden view. Breakfast made to order. Beautiful art gallery."
United States
Joe
The price is ₹12,735
₹14,135 total
includes taxes & fees
21 Oct - 22 Oct
Haven Point Inn and Gallery
A large white barn with a star on the side, surrounded by a field of sunflowers, and a large house with a green roof in the background.

6. Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (74 reviews)
"The property was stunning. The rooms were very comfortable and the bathroom had all you need. We also really appreciated the drinks and free salted chocolate chip cookies. They were delicious. The inn keepers were and their dogs were a highlight for us. The breakfast was also absolutely delicious. Definitely would recommend this I"
United States
Christine
The price is ₹15,351
₹17,040 total
includes taxes & fees
1 Nov - 2 Nov
Inn at Huntingfield Creek
A gazebo with a view of a lake at dusk.

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

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (1,001 reviews)
"Good hotel for the money and location."
United States
Marc
The price is ₹10,536
₹11,695 total
includes taxes & fees
25 Oct - 26 Oct
Holiday Inn Express Annapolis East-Kent Island by IHG
A hotel with a modern facade, a covered entrance, and a red car parked outside.

8. SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River
2.5 star property
Middle River
9.0 out of 10, Wonderful, (956 reviews)
"Breakfast was basic nothing fancy.close to store and restaurant."
United States
Juanita
The price is ₹10,205
₹11,787 total
includes taxes & fees
22 Oct - 23 Oct
SpringHill Suites Baltimore White Marsh/Middle River
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.

9. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (844 reviews)
"Awesome place"
United States
Joseph
The price is ₹14,483
₹16,076 total
includes taxes & fees
28 Oct - 29 Oct
Hyatt Place Kent Narrows & Marina
A Country Inn & Suites hotel with a brick facade, multiple windows, and a sign indicating the entrance.

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

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
3.0 star property
Bel Air
8.8 out of 10, Excellent, (1,005 reviews)
"Very big room, everything clean. Great location, friendly staff. Would definitely stay here again."
United States
Vanessa
The price is ₹8,490
₹9,508 total
includes taxes & fees
9 Nov - 10 Nov
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
A modern hotel with a stone facade, a clear entrance canopy, and a prominent Hilton Inn sign.

11. Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
3.0 star property
Bel Air
9.2 out of 10, Wonderful, (311 reviews)
"Lovely place! Friendly staff"
United States
Jaccilynne
The price is ₹10,095
₹11,307 total
includes taxes & fees
1 Nov - 2 Nov
Hilton Garden Inn Bel Air
A Hampton Inn hotel with a modern brick facade, large windows, and a clear blue sky.

12. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1,004 reviews)
"Nice breakfast very pet safe and friendly, Big mini fridge and comfy bed 2 chairs and a bench."
United States
Regina
The price is ₹8,168
₹9,149 total
includes taxes & fees
2 Nov - 3 Nov
Hampton Inn & Suites Edgewood/Aberdeen-South
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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Top Chestertown Hotel Reviews

Pendry Baltimore

Pendry Baltimore

10/10 Excellent
"Great service teams and beautiful property! Also had a large group family style dinner in the Rec Pier Chop House and the food and service was superb! I’d definitely stay here again!"
Lori 2-night trip
Posted 2 hours ago
Pendry Baltimore

Find out more about Chestertown

Chestertown Villas information

Number of reviews
4,808
Accommodation
0 Villas
Lowest Price
₹6,752
Highest Price
₹17,040

Frequently asked questions

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How can I find cheap villas in Chestertown?
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What is there to do near my villa in Chestertown?
If you want to discover the sights of Chestertown, make your way to Rolphs Wharf Marina. It's a winner with travellers and locals alike.

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