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Find Hotels by Independent in Chestertown from CA $75

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Check prices for these dates

Tonight
Aug 17 - Aug 18
Tomorrow
Aug 18 - Aug 19
Next weekend
Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31

Top Chestertown Independent Hotels

The Inn at Chesapeake Bay Beach Club
Front of property - evening/night

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (411)
"Great location and amenities"
The price is CA $311
CA $380 total
includes taxes & fees
Aug 25 - Aug 26
The Inn at Chesapeake Bay Beach Club
The Lodge at Great Oak Landing
Private beach nearby, sun loungers, beach volleyball

The Lodge at Great Oak Landing

3.5 star property
8.2 out of 10, Very good, (61)
"Great place to get some quiet rest by the water"
The price is CA $183
CA $203 total
includes taxes & fees
Aug 19 - Aug 20
The Lodge at Great Oak Landing
Vandiver Inn
The Stokes (Standard / 2nd Floor Vandiver Mansion) | Terrace/patio

Vandiver Inn

3.5 star property
9.4 out of 10, Exceptional, (507)
"Staff was very friendly. We had a very relaxing stay. "
The price is CA $204
CA $229 total
includes taxes & fees
Sep 17 - Sep 18
Vandiver Inn
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 18 - Sep 19
Motel Edgewood
Relax Inn Smyrna
Reception

Relax Inn Smyrna

2.0 star property
7.8 out of 10, Good, (86)
"Owner was very nice. "
The price is CA $123
CA $137 total
includes taxes & fees
Aug 19 - Aug 20
Relax Inn Smyrna
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 $273
CA $362 total
includes taxes & fees
Aug 19 - Aug 20
Inn at Haven Harbour
Driftwood Inn
Front of property - evening/night

Driftwood Inn

2.0 star property
5.2 out of 10, (172)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"
Driftwood Inn
Flag House Inn
Front of property

Flag House Inn

3.5 star property
9.6 out of 10, Exceptional, (75)
"Lovely B&B close to EVERYTHING! The host were so kind and helpful. The common areas were very nice as well as the front porch!"
The price is CA $193
CA $220 total
includes taxes & fees
Aug 19 - Aug 20
Flag House Inn
134 Prince - Luxury Boutique Hotel
Exterior

134 Prince - Luxury Boutique Hotel

2.5 star property
9.8 out of 10, Exceptional, (23)
"Great boutique hotel for an overnight. Terrific location and accommodating staff. Couldn't have been a better stay. "
The price is CA $283
CA $323 total
includes taxes & fees
Aug 19 - Aug 20
134 Prince - Luxury Boutique Hotel
Kent Island Resort
Aerial view

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (109)
"Hotel was great and peaceful. This hotel was water front. Nice surroundings!! I enjoyed to stay here."
The price is CA $227
CA $303 total
includes taxes & fees
Sep 1 - Sep 2
Kent Island Resort
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

Fairfield Inn & Suites by Marriott White Marsh

Fairfield Inn & Suites by Marriott White Marsh

10/10 Excellent
"Close to shopping and eateries!"
Anissa 1-night trip
Posted 1 day ago
Fairfield Inn & Suites by Marriott White Marsh