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Check prices for these dates

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Sep 5 - Sep 7
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Sep 12 - Sep 14
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Sep 26 - Sep 28
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Oct 24 - Oct 26

Browse Select Chestertown Guest Houses

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Recommended hotels in Chestertown

Motel Edgewood
Basic Single Room

Motel Edgewood

2.0 star property
8.6 out of 10, Excellent, (7)
"Bed was clean and crisply made. Occupants were respectful of sleeping hours. Check-in and check-out were simple. Parking was convenient and had easy access to the highway."
The price is CA $75
CA $85 total
includes taxes & fees
Sep 25 - Sep 26
Motel Edgewood
Holiday Inn Express Annapolis East-Kent Island by IHG
Exterior

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (894)
"Wonderful breakfast and lovely outdoor seating next to the water! My favorite place to stay when I visit!!!"
The price is CA $187
CA $207 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn Express Annapolis East-Kent Island by IHG
Quality Inn
Suite, 1 Queen Bed, Non Smoking

Quality Inn

2.5 star property
7.8 out of 10, Good, (816)
"Conveniently located with overall great value."
The price is CA $135
CA $150 total
includes taxes & fees
Sep 17 - Sep 18
Quality Inn
The Lodge at Great Oak Landing
Private beach nearby, sun loungers, beach volleyball

The Lodge at Great Oak Landing

3.5 star property
8.0 out of 10, Very good, (66)
"Great place to get some quiet rest by the water"
The price is CA $183
CA $203 total
includes taxes & fees
Aug 26 - Aug 27
The Lodge at Great Oak Landing
Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (803)
"staff was friendly, accomodations were fine."
The price is CA $152
CA $168 total
includes taxes & fees
Sep 7 - Sep 8
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (388)
"Good location."
The price is CA $106
CA $117 total
includes taxes & fees
Sep 1 - Sep 2
Red Roof Inn & Suites Chestertown
First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (99)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
The price is CA $137
CA $220 total
includes taxes & fees
Aug 26 - Aug 27
First Floor Studio Apartment in Historic Chestertown
Holiday Inn Express & Suites Middletown by IHG
Exterior

Holiday Inn Express & Suites Middletown by IHG

2.5 star property
9.2 out of 10, Wonderful, (609)
"Very beautiful and clean properly with great staff. "
The price is CA $148
CA $164 total
includes taxes & fees
Sep 7 - Sep 8
Holiday Inn Express & Suites Middletown by IHG
Mariners Motel
Marina

Mariners Motel

2.0 star property
9.4 out of 10, Exceptional, (89)
"Very nice old school motel just about on the water in Rock Hall. Perfect if you’re in town for marina stuff. "
The price is CA $215
CA $238 total
includes taxes & fees
Aug 26 - Aug 27
Mariners Motel
Hampton Inn Middletown
Reception

Hampton Inn Middletown

2.5 star property
8.8 out of 10, Excellent, (826)
"Staff was pleasant…room was clean, comfortable and very quiet. Good choice…nice stay."
The price is CA $152
CA $168 total
includes taxes & fees
Sep 1 - Sep 2
Hampton Inn Middletown
Relax Inn Smyrna
Reception

Relax Inn Smyrna

2.0 star property
7.8 out of 10, Good, (87)
"Owner was very nice. "
The price is CA $123
CA $137 total
includes taxes & fees
Aug 26 - Aug 27
Relax Inn Smyrna
Vandiver Inn
The Stokes (Standard / 2nd Floor Vandiver Mansion) | Terrace/patio

Vandiver Inn

3.5 star property
9.4 out of 10, Exceptional, (509)
"Staff was very friendly. We had a very relaxing stay. "
The price is CA $175
CA $197 total
includes taxes & fees
Aug 26 - Aug 27
Vandiver Inn
Fairfield Inn & Suites by Marriott Middletown
Lobby

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
9.2 out of 10, Wonderful, (265)
"I’ve stayed here a few times now and everyone is so pleasant and helpful. "
The price is CA $142
CA $158 total
includes taxes & fees
Sep 4 - Sep 5
Fairfield Inn & Suites by Marriott Middletown
Holiday Inn Express White Marsh by IHG
Free continental breakfast

Holiday Inn Express White Marsh by IHG

2.5 star property
9.6 out of 10, Exceptional, (916)
"The facility is very clean and quiet. The staff is very polite and accommodating. The complimentary breakfast is very good. My family and I will stay again."
The price is CA $135
CA $156 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn Express White Marsh by IHG
SpringHill Suites Baltimore White Marsh/Middle River
Desk, laptop workspace, blackout drapes, iron/ironing board

SpringHill Suites Baltimore White Marsh/Middle River

2.5 star property
9.0 out of 10, Wonderful, (724)
"Love this place"
The price is CA $169
CA $196 total
includes taxes & fees
Aug 31 - Sep 1
SpringHill Suites Baltimore White Marsh/Middle River
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
Studio Suite, 1 King Bed with Sofa bed, Non Smoking

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

3.0 star property
8.2 out of 10, Very good, (1007)
"Good hotel, good location "
The price is CA $99
CA $110 total
includes taxes & fees
Aug 31 - Sep 1
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
Inn at Haven Harbour
View from property

Inn at Haven Harbour

3.0 star property
8.0 out of 10, Very good, (3)
"Steps to the 3rd floor attic Low headroom every where 4' to 5' headroom in front of the toilet 8 yr old banged his head Everything was good except the very small room Don't rent this room unless you're 4' tall I'm surprised it passed inspection "
The price is CA $268
CA $329 total
includes taxes & fees
Sep 25 - Sep 26
Inn at Haven Harbour
Quality Inn
Free daily self-serve breakfast

Quality Inn

2.5 star property
7.6 out of 10, Good, (1001)
"Wonerful place, all good..Hotel,area, staff."
The price is CA $122
CA $135 total
includes taxes & fees
Sep 24 - Sep 25
Quality Inn
Best Western Kent Narrows Inn
In-room safe, individually decorated, individually furnished, desk

Best Western Kent Narrows Inn

2.5 star property
8.2 out of 10, Very good, (1003)
"Excellent location"
The price is CA $141
CA $156 total
includes taxes & fees
Sep 1 - Sep 2
Best Western Kent Narrows Inn
Hampton Inn & Suites Edgewood/Aberdeen-South
Restaurant

Hampton Inn & Suites Edgewood/Aberdeen-South

2.5 star property
9.4 out of 10, Exceptional, (1007)
"We have stayed here many times as our family lives in the area! Its a great place "
The price is CA $122
CA $137 total
includes taxes & fees
Aug 31 - Sep 1
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

Find out more about Chestertown

Find out more about Chestertown

Chestertown Guest Houses information

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17 Guest Houses
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