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Jul 4 - Jul 6
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Jul 11 - Jul 13
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Jul 25 - Jul 27
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Aug 22 - Aug 24

Inns in Chestertown

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Recommended hotels in Chestertown

The Lodge at Great Oak Landing
Private beach nearby, sun loungers, beach volleyball

The Lodge at Great Oak Landing

3.5 star property
7.8 out of 10, Good, (52)
"not super fancy but really well done. comfy beds and a first rate chef. plus great for the boating crowd"
$147 nightly
The price is $163
Jun 29 - Jun 30
Total includes 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, (773)
"Comfortable room, friendly staff. "
$114 nightly
The price is $126
Jul 24 - Jul 25
Total includes 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
7.4 out of 10, Good, (368)
"Was a decent place to stay for the price. "
$68 nightly
The price is $76
Jul 8 - Jul 9
Total includes 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, (88)
"Very pretty location. Few minutes drive to town center."
$144 nightly
The price is $159
Jul 1 - Jul 2
Total includes taxes and fees
First Floor Studio Apartment in Historic Chestertown
Driftwood Inn
Lobby

Driftwood Inn

2.0 star property
5.2 out of 10, (171)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"
$64 nightly
The price is $70
Jul 28 - Jul 29
Total includes taxes and fees
Driftwood Inn
Quality Inn
Free daily self-serve breakfast

Quality Inn

2.5 star property
7.6 out of 10, Good, (1001)
"2nd time staying here no major issues "
$100 nightly
The price is $111
Jun 29 - Jun 30
Total includes taxes and fees
Quality Inn
Relax Inn Smyrna
Reception

Relax Inn Smyrna

2.0 star property
7.8 out of 10, Good, (81)
"The owner/staff were so sweet and helpful "
$91 nightly
The price is $99
Jun 29 - Jun 30
Total includes taxes and fees
Relax Inn Smyrna
Hampton Inn Middletown
Reception

Hampton Inn Middletown

2.5 star property
8.8 out of 10, Excellent, (806)
"Good location. Breakfast was great and plenty of parking. "
$131 nightly
The price is $145
Jun 30 - Jul 1
Total includes taxes and fees
Hampton Inn Middletown
Holiday Inn Express And Suites Middletown by IHG
Exterior

Holiday Inn Express And Suites Middletown by IHG

2.5 star property
9.2 out of 10, Wonderful, (586)
"I would like to share, the staff at the hotel was very pleasant, it felt like a home away from home, and I also enjoyed the breakfast that was offered. "
$143 nightly
The price is $159
Jul 2 - Jul 3
Total includes taxes and fees
Holiday Inn Express And Suites Middletown by IHG
Fairfield Inn & Suites by Marriott Middletown
Lobby

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
9.2 out of 10, Wonderful, (245)
"Clean, friendly staff on checkin and checkout. "
$133 nightly
The price is $148
Jul 27 - Jul 28
Total includes taxes and fees
Fairfield Inn & Suites by Marriott Middletown
Guest Suite for up to 2 in a Victorian on the Chester River
Exterior

Guest Suite for up to 2 in a Victorian on the Chester River

10.0 out of 10, Exceptional, (14)
"Fantastic accommodations! Many amenities! Friendly hostess! "
$113 nightly
The price is $120
Jul 11 - Jul 12
Total includes taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
5-bedroom vacation home 5 minutes from historic Charlestown
Exterior

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (138)
"Can’t wait to come back during warmer weather. It was a perfect over night stay. "
$575 nightly
The price is $610
Jul 1 - Jul 2
Total includes taxes and fees
5-bedroom vacation home 5 minutes from historic Charlestown
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, (780)
"full breakfast, comfortable bed and nice pillows"
$96 nightly
The price is $107
Jul 6 - Jul 7
Total includes taxes and fees
Quality Inn
Vandiver Inn
The Stokes (Standard / 2nd Floor Vandiver Mansion) | Terrace/patio

Vandiver Inn

3.5 star property
9.4 out of 10, Exceptional, (499)
"We alway enjoy our stays at the Vandiver"
$144 nightly
The price is $162
Jul 27 - Jul 28
Total includes taxes and fees
Vandiver Inn
Super 8 by Wyndham Havre De Grace Aberdeen Area
Standard Room, 2 Queen Beds | In-room safe, desk, soundproofing, rollaway beds

Super 8 by Wyndham Havre De Grace Aberdeen Area

2.0 star property
6.8 out of 10, (913)
"Nice, clean, friendly "
$53 nightly
The price is $59
Jul 7 - Jul 8
Total includes taxes and fees
Super 8 by Wyndham Havre De Grace Aberdeen Area
Hilton Garden Inn Kent Island Marina
Terrace/patio

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (945)
"Very nice place to stay. Will definitely stay there again!"
$152 nightly
The price is $169
Jul 6 - Jul 7
Total includes taxes and fees
Hilton Garden Inn Kent Island Marina
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, (858)
"Good location - clean hotel."
$111 nightly
The price is $123
Jul 13 - Jul 14
Total includes taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
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, (1000)
"Second time staying, it’s priced right, great staff, and amazing restaurants right across the street, quiet area right by the bay bridge. "
$109 nightly
The price is $122
Jun 29 - Jun 30
Total includes taxes and fees
Best Western Kent Narrows Inn
Hyatt Place Kent Narrows & Marina
Terrace/patio

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (566)
"Great place to stay. "
$173 nightly
The price is $192
Jul 7 - Jul 8
Total includes taxes and fees
Hyatt Place Kent Narrows & Marina
Cass-N-Reel Luxury Houseboat
Smart TV

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (30)
"We really enjoyed our stay. Looking forward to staying again!"
$290 nightly
The price is $307
Jul 8 - Jul 9
Total includes taxes and fees
Cass-N-Reel Luxury Houseboat
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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