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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov
In four months
12 Dec - 14 Dec

Featured Cabin Rentals in Chestertown

We don't have any properties that match your exact search

Recommended hotels in Chestertown

Quality Inn
Suite, 1 Queen Bed, Non Smoking

Quality Inn

2.5 star property
7.8 out of 10, Good, (813)
"Conveniently located with overall great value."
The price is AU$167
includes taxes & fees
24 Aug - 25 Aug
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. "
The price is AU$268
includes taxes & fees
25 Aug - 26 Aug
Mariners Motel
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 AU$100
includes taxes & fees
26 Aug - 27 Aug
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, (65)
"Great place to get some quiet rest by the water"
The price is AU$228
includes taxes & fees
24 Aug - 25 Aug
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, (797)
"It was a clean comfortable spot to rest for the night. "
The price is AU$189
includes taxes & fees
7 Sept - 8 Sept
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, (387)
"Good location."
The price is AU$124
includes taxes & fees
28 Aug - 29 Aug
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 - "
The price is AU$250
includes taxes & fees
3 Sept - 4 Sept
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. "
The price is AU$185
includes taxes & fees
7 Sept - 8 Sept
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. "
The price is AU$154
includes taxes & fees
2 Sept - 3 Sept
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. "
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. "
The price is AU$178
includes taxes & fees
4 Sept - 5 Sept
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!"
The price is AU$176
includes taxes & fees
1 Sept - 2 Sept
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!!!"
The price is AU$219
includes taxes & fees
22 Sept - 23 Sept
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."
The price is AU$189
includes taxes & fees
4 Sept - 5 Sept
Hampton Inn Middletown
SpringHill Suites Baltimore White Marsh/Middle River
Desk, laptop workspace, blackout curtains, iron/ironing board

SpringHill Suites Baltimore White Marsh/Middle River

2.5 star property
9.0 out of 10, Wonderful, (723)
"Love this place"
The price is AU$220
includes taxes & fees
24 Aug - 25 Aug
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 "
The price is AU$396
includes taxes & fees
24 Aug - 25 Aug
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"
The price is AU$176
includes taxes & fees
1 Sept - 2 Sept
Best Western Kent Narrows Inn
Quality Inn
Free daily self-service breakfast

Quality Inn

2.5 star property
7.6 out of 10, Good, (1000)
"Wonerful place, all good..Hotel,area, staff."
The price is AU$150
includes taxes & fees
21 Sept - 22 Sept
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, (1001)
"Great stay at a great price "
The price is AU$154
includes taxes & fees
1 Sept - 2 Sept
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"
The price is AU$152
includes taxes & fees
7 Sept - 8 Sept
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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"There were no ghosts!"
judith 1-night trip
Posted 3 days ago
Historic Inns of Annapolis

Frequently asked questions

What are the best cabins near Chestertown?
Book one of our 33 cabins in Chestertown and you'll be rewarded with picturesque scenery, outdoor adventure and memories you'll never forget. Cosy Cabin Happiness is the place to go for a relaxing getaway. Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay is also ideal if you'd love some time out in Mother Nature.
Are there cheap cabins in Chestertown?
For a budget-friendly escape in nature, look no further than our cheap cabins in Chestertown. Wake up in the morning to the sweet sound of birds chirping from one of our cosy retreats priced from to per night.These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best family cabins near Chestertown?
If you're seeking a getaway the kids will go wild for, a family cabin rental in or near Chestertown is ideal. Spend time with the gang at Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay. It offers a meal delivery service and a travel crib as well as ample outdoor adventure. Country Coziness - Lancaster County Private Cabin is another top pick for small groups or families and comes with a deck and a toaster.