Photo by Patricia Knorr

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Check prices for these dates

Next weekend
9 Jan - 11 Jan
In two weeks
16 Jan - 18 Jan
In one month
30 Jan - 1 Feb
In two months
27 Feb - 1 Mar

Our top choices for Chestertown cottages

House (3 Bedrooms) | Interior
5 Mi to Downtown Baltimore: Quiet Home w/ Porch

Cottage in Rosedale

5 Mi to Downtown Baltimore: Quiet Home w/ Porch
3.0 star property
9.0 out of 10, Wonderful, (2)
"It took a whole day for the house to get warm.No utensils.And last but not least the heat was turned off in the middle of the night.Monday morning was very cold,that’s why we left at nine thirty. "
United States
Cathy
The price is AED 584
AED 1,829 total
includes taxes & fees
5 Jan - 6 Jan
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
Exterior
Grandma’s Cottage will wrap around you like a warm hug

Cottage in Betterton

Grandma’s Cottage will wrap around you like a warm hug
The price is AED 826
AED 1,549 total
includes taxes & fees
5 Jan - 6 Jan
Grandma’s Cottage will wrap around you like a warm hug
Terrace/patio
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

Cottage in Stevensville

Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
2.0 star property
10.0 out of 10, Exceptional, (6)
"Beautiful home. Very nice and quiet neighborhood on the water. "
United States
shannan t.
The price is AED 1,465
AED 3,251 total
includes taxes & fees
7 Jan - 8 Jan
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Outdoor dining
Chesapeake Cottages- 2 Quaint Waterfront Retreats

Cottage in Pasadena

Chesapeake Cottages- 2 Quaint Waterfront Retreats
9.6 out of 10, Exceptional, (22)
"Excellent Property"
United States
Buu T.
The price is AED 1,322
AED 2,441 total
includes taxes & fees
5 Jan - 6 Jan
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Exterior detail
Secluded Cozy Cottage in Historic Downtown

Cottage in Historic District

Secluded Cozy Cottage in Historic Downtown
9.6 out of 10, Exceptional, (16)
"Lovely, secluded cottage close to downtown Annapolis. Host was very accommodating and communicated lots of great info. Looking forward to coming back when we can stay longer."
United States
Michael C.
The price is AED 1,061
AED 1,967 total
includes taxes & fees
5 Jan - 6 Jan
Secluded Cozy Cottage in Historic Downtown
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

Holiday Inn Express White Marsh by IHG

Holiday Inn Express White Marsh by IHG

10/10 Excellent
"Super clean, spacious rooms, great location on the highway. "
Jessica 1-night trip
Posted 2 days ago
Holiday Inn Express White Marsh by IHG

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