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Search Guest Houses in Chestertown

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Check prices for these dates

Next weekend
2 Jum. I - 4 Jum. I
In two weeks
9 Jum. I - 11 Jum. I
In one month
23 Jum. I - 25 Jum. I
In two months
20 Jum. II - 22 Jum. II

Compare 16 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, (184)
"Great location, clean and everything was just like it posted. Would 100% stay here again"
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
Outdoor pool

Top Floor East Handicap Accessible

2.0 star property
The price is SAR 1,315
SAR 1,871 total
includes taxes & fees
30 Apr - 1 May
Top Floor East Handicap Accessible
Center Parlor Room at Sandy Cove
Outdoor pool

Center Parlor Room at Sandy Cove

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

First Floor Bay View Deluxe Suite

2.0 star property
The price is SAR 1,564
SAR 2,134 total
includes taxes & fees
30 Apr - 1 May
First Floor Bay View Deluxe Suite
Top Floor Deluxe Suite Bay View
Outdoor pool

Top Floor Deluxe Suite Bay View

2.5 star property
The price is SAR 1,564
SAR 2,134 total
includes taxes & fees
1 May - 2 May
Top Floor Deluxe Suite Bay View
Top Floor Handicap Accessible Bay View
Outdoor pool

Top Floor Handicap Accessible Bay View

2.0 star property
The price is SAR 1,415
SAR 1,977 total
includes taxes & fees
8 May - 9 May
Top Floor Handicap Accessible Bay View
First Floor Family Deluxe Suite
Outdoor pool

First Floor Family Deluxe Suite

2.5 star property
The price is SAR 1,315
SAR 1,871 total
includes taxes & fees
30 Apr - 1 May
First Floor Family Deluxe Suite
Top Floor Standard Deluxe
Outdoor pool

Top Floor Standard Deluxe

2.5 star property
The price is SAR 1,315
SAR 1,871 total
includes taxes & fees
30 Apr - 1 May
Top Floor Standard Deluxe
Second Floor Standard Deluxe Bay View
Outdoor pool

Second Floor Standard Deluxe Bay View

2.0 star property
The price is SAR 1,415
SAR 1,977 total
includes taxes & fees
30 Apr - 1 May
Second Floor Standard Deluxe Bay View
Second Floor East Standard Deluxe
Outdoor pool

Second Floor East Standard Deluxe

2.0 star property
The price is SAR 1,315
SAR 1,871 total
includes taxes & fees
26 Apr - 27 Apr
Second Floor East Standard Deluxe
Top Floor Family Deluxe Bay View
Outdoor pool

Top Floor Family Deluxe Bay View

2.0 star property
The price is SAR 1,415
SAR 1,977 total
includes taxes & fees
1 May - 2 May
Top Floor Family Deluxe Bay View
Top Floor Family Deluxe
Outdoor pool

Top Floor Family Deluxe

2.5 star property
The price is SAR 1,315
SAR 1,871 total
includes taxes & fees
30 Apr - 1 May
Top Floor Family Deluxe
Second Floor Standard Suite Bay View
Outdoor pool

Second Floor Standard Suite Bay View

2.0 star property
The price is SAR 1,489
SAR 2,056 total
includes taxes & fees
25 Apr - 26 Apr
Second Floor Standard Suite Bay View
Top Floor Standard Suite
Outdoor pool

Top Floor Standard Suite

2.0 star property
The price is SAR 1,390
SAR 1,950 total
includes taxes & fees
30 Apr - 1 May
Top Floor Standard Suite
Second Floor Family Deluxe
Outdoor pool

Second Floor Family Deluxe

2.0 star property
The price is SAR 1,315
SAR 1,871 total
includes taxes & fees
30 Apr - 1 May
Second Floor Family Deluxe
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

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Exterior

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (212)
"The house was absolutely perfect for our USNA Reunion. About 10 steps to Gate 1 and just a few more to the heart of downtown made it a weekend we will remember. The host was responsive and accommodated our requests and was very kind. I would definitely stay here again."
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Exterior

Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

9.4 out of 10, Exceptional, (23)
"Decided to try something different, and luckily found the Dockside Doghouse. Very comfortable, incredibly relaxing."
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
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.