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Sep 5 - Sep 7
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Dec 12 - Dec 14

Cabin Rentals in Chestertown

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Recommended hotels in Chestertown

Quality Inn
Suite, 1 Queen Bed, Non Smoking | In-room safe, iron/ironing board, free WiFi, bed sheets

Quality Inn

2.5 star property
7.8 out of 10, Good, (813)
"Conveniently located with overall great value."
$98 nightly
The price is $108
Sep 14 - Sep 15
Total with taxes and fees
Quality Inn
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. "
$155 nightly
The price is $172
Aug 24 - Aug 25
Total with taxes and fees
Mariners Motel
Motel Edgewood
Basic Single Room | 1 bedroom, desk, free WiFi, bed sheets

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."
$53 nightly
The price is $60
Sep 7 - Sep 8
Total with taxes and fees
Motel Edgewood
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"
$147 nightly
The price is $163
Aug 24 - Aug 25
Total with taxes and fees
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, (798)
"It was a clean comfortable spot to rest for the night. "
$110 nightly
The price is $122
Sep 7 - Sep 8
Total with taxes and fees
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking | 1 bedroom, desk, laptop workspace, blackout drapes

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (387)
"Good location."
$72 nightly
The price is $80
Aug 31 - Sep 1
Total with taxes and fees
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, (98)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
$144 nightly
The price is $159
Aug 25 - Aug 26
Total with taxes and fees
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, (606)
"Very beautiful and clean properly with great staff. "
$107 nightly
The price is $119
Sep 7 - Sep 8
Total with taxes and fees
Holiday Inn Express & Suites Middletown by IHG
Relax Inn Smyrna
Reception

Relax Inn Smyrna

2.0 star property
7.8 out of 10, Good, (86)
"Owner was very nice. "
$101 nightly
The price is $110
Aug 24 - Aug 25
Total with taxes and fees
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, (508)
"Staff was very friendly. We had a very relaxing stay. "
$149 nightly
The price is $167
Aug 24 - Aug 25
Total with taxes and fees
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, (264)
"I’ve stayed here a few times now and everyone is so pleasant and helpful. "
$103 nightly
The price is $114
Sep 4 - Sep 5
Total with taxes and fees
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, (915)
"We had a great stay!"
$98 nightly
The price is $113
Sep 1 - Sep 2
Total with taxes and fees
Holiday Inn Express White Marsh by IHG
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, (890)
"Wonderful breakfast and lovely outdoor seating next to the water! My favorite place to stay when I visit!!!"
$127 nightly
The price is $141
Sep 22 - Sep 23
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
Hampton Inn Middletown
Reception

Hampton Inn Middletown

2.5 star property
8.8 out of 10, Excellent, (823)
"Staff was pleasant…room was clean, comfortable and very quiet. Good choice…nice stay."
$110 nightly
The price is $122
Sep 1 - Sep 2
Total with taxes and fees
Hampton Inn Middletown
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, (723)
"Love this place"
$123 nightly
The price is $142
Aug 24 - Aug 25
Total with taxes and fees
SpringHill Suites Baltimore White Marsh/Middle River
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 "
$200 nightly
The price is $223
Aug 27 - Aug 28
Total with taxes and fees
Inn at Haven Harbour
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, (1001)
"Excellent location"
$102 nightly
The price is $113
Sep 1 - Sep 2
Total with taxes and fees
Best Western Kent Narrows Inn
Quality Inn
Free daily self-serve breakfast

Quality Inn

2.5 star property
7.6 out of 10, Good, (1000)
"Wonerful place, all good..Hotel,area, staff."
$87 nightly
The price is $96
Sep 21 - Sep 22
Total with taxes and fees
Quality Inn
Hampton Inn & Suites Edgewood/Aberdeen-South
Restaurant

Hampton Inn & Suites Edgewood/Aberdeen-South

2.5 star property
9.4 out of 10, Exceptional, (1002)
"Great stay at a great price "
$88 nightly
The price is $99
Aug 31 - Sep 1
Total with taxes and fees
Hampton Inn & Suites Edgewood/Aberdeen-South
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Lobby

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

3.0 star property
8.8 out of 10, Excellent, (1000)
"Front desk staff very helpful"
$87 nightly
The price is $98
Sep 7 - Sep 8
Total with taxes and fees
Country Inn & Suites by Radisson, Bel Air/Aberdeen, 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.
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Top Chestertown Hotel Reviews

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

10/10 Excellent
"Staff was attentive, breakfast staff kept everything filled hot, and cleaned the area all the time"
Sam 4-night trip
Posted 2 days ago
Hampton Inn & Suites Edgewood/Aberdeen-South