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Search Guest Houses in Chestertown

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Check prices for these dates

Next weekend
11 Rab. II - 13 Rab. II
In two weeks
18 Rab. II - 20 Rab. II
In one month
2 Jum. I - 4 Jum. I
In two months
30 Jum. I - 1 Jum. II

Compare Guest Houses in Chestertown with updated reviews, rates, and availability.

Island Life! Kent Island Waterfront with Pool-Bring your boat!
3 bedrooms, iron/ironing board, travel crib, free WiFi

Island Life! Kent Island Waterfront with Pool-Bring your boat!

10.0 out of 10, Exceptional, (183)
"Our host Jon was so nice, checked in with us to make sure all was good, and it was. He had the place decorated for Christmas and even had a tree - we appreciated it very much since we were not home for Christmas. Beautiful setting on Cox creek. The guest house was well maintained and fully equipped kitchen. Very Comfortable beds and bedding which we find unique for VRBOs. "
Island Life! Kent Island Waterfront with Pool-Bring your boat!
Calico Cottage Guest House
Terrace/patio

Calico Cottage Guest House

10.0 out of 10, Exceptional, (8)
"This tiny house is tastefully furnished and, coupled with the quiet neighborhood, provides a relaxing, peaceful environment."
Calico Cottage Guest House
Top Floor East Handicap Accessible
Miscellaneous

Top Floor East Handicap Accessible

2.0 star property
The price is SAR 1,316
SAR 1,872 total
includes taxes & fees
9 Apr - 10 Apr
Top Floor East Handicap Accessible
Center Parlor Room at Sandy Cove
Miscellaneous

Center Parlor Room at Sandy Cove

2.5 star property
The price is SAR 1,415
SAR 1,977 total
includes taxes & fees
13 Apr - 14 Apr
Center Parlor Room at Sandy Cove
First Floor Bay View Deluxe Suite
Miscellaneous

First Floor Bay View Deluxe Suite

2.0 star property
The price is SAR 1,564
SAR 2,135 total
includes taxes & fees
9 Apr - 10 Apr
First Floor Bay View Deluxe Suite
Top Floor Deluxe Suite Bay View
Miscellaneous

Top Floor Deluxe Suite Bay View

2.5 star property
The price is SAR 1,564
SAR 2,135 total
includes taxes & fees
9 Apr - 10 Apr
Top Floor Deluxe Suite Bay View
First Floor Family Deluxe Suite
Miscellaneous

First Floor Family Deluxe Suite

2.5 star property
The price is SAR 1,316
SAR 1,872 total
includes taxes & fees
9 Apr - 10 Apr
First Floor Family Deluxe Suite
Second Floor Standard Deluxe Bay View
Miscellaneous

Second Floor Standard Deluxe Bay View

2.0 star property
The price is SAR 1,415
SAR 1,977 total
includes taxes & fees
9 Apr - 10 Apr
Second Floor Standard Deluxe Bay View
Top Floor Standard Deluxe
Miscellaneous

Top Floor Standard Deluxe

2.5 star property
The price is SAR 1,316
SAR 1,872 total
includes taxes & fees
9 Apr - 10 Apr
Top Floor Standard Deluxe
Top Floor Family Deluxe
Miscellaneous

Top Floor Family Deluxe

2.5 star property
The price is SAR 1,316
SAR 1,872 total
includes taxes & fees
9 Apr - 10 Apr
Top Floor Family Deluxe
Second Floor East Standard Deluxe
Miscellaneous

Second Floor East Standard Deluxe

2.0 star property
The price is SAR 1,316
SAR 1,872 total
includes taxes & fees
9 Apr - 10 Apr
Second Floor East Standard Deluxe
Top Floor Family Deluxe Bay View
Miscellaneous

Top Floor Family Deluxe Bay View

2.0 star property
The price is SAR 1,415
SAR 1,977 total
includes taxes & fees
9 Apr - 10 Apr
Top Floor Family Deluxe Bay View
Top Floor Handicap Accessible Bay View
Miscellaneous

Top Floor Handicap Accessible Bay View

2.0 star property
The price is SAR 1,415
SAR 1,977 total
includes taxes & fees
9 Apr - 10 Apr
Top Floor Handicap Accessible Bay View
Second Floor Standard Suite Bay View
Miscellaneous

Second Floor Standard Suite Bay View

2.0 star property
The price is SAR 1,489
SAR 2,056 total
includes taxes & fees
9 Apr - 10 Apr
Second Floor Standard Suite Bay View
Second Floor Family Deluxe
Miscellaneous

Second Floor Family Deluxe

2.0 star property
The price is SAR 1,316
SAR 1,872 total
includes taxes & fees
13 Apr - 14 Apr
Second Floor Family Deluxe
Top Floor Standard Suite
Miscellaneous

Top Floor Standard Suite

2.0 star property
The price is SAR 1,390
SAR 1,951 total
includes taxes & fees
9 Apr - 10 Apr
Top Floor Standard Suite
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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Other property types in Chestertown

Beautiful, spacious waterfront home, an easy walk to historic Chestertown
Exterior

Beautiful, spacious waterfront home, an easy walk to historic Chestertown

9.8 out of 10, Exceptional, (22)
"Perfect spot for our whole family to be together. It has it all. Everything worked. Super comfy. Thank you!!!!"
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Miscellaneous

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (210)
"We loved our visit to Annapolis, and our stay at 10 Randall was all that we’d imagined it would be.We wish the weather has been a tad warmer, but I don’t think John could have fixed that .We highly recommend this charming home."
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Outdoor dining

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

10.0 out of 10, Exceptional, (180)
"This house was so cozy yet spacious! The house was amply stocked with just about everything you would want or need. The owner responded to our inquiries immediately! I hope we go back there again! "
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
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.