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Best Resorts in Chestertown

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Nov 14 - Nov 16
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Nov 21 - Nov 23
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Dec 5 - Dec 7
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Resorts in Chestertown

No exact matches found, but these alternatives could be just right

Recommended hotels in Chestertown

Lobby
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 star property
Chestertown
8.6 out of 10, Excellent, (841)
"This property is clean and welcoming. We were pleasantly surprised. Check in was easy, and the room was great. Breakfast was wonderful! Great place to stay."
United States
Paula
$102 nightly
The price is $113
Nov 11 - Nov 12
Total with taxes and fees
Comfort Inn & Suites Chestertown
Private beach nearby, sun loungers, beach volleyball
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3.5 star property
Chestertown
8.0 out of 10, Very Good, (74)
"Very nice rooms, "
United States
Stephania
$113 nightly
The price is $126
Nov 9 - Nov 10
Total with taxes and fees
The Lodge at Great Oak Landing
Suite, Multiple Beds, Non Smoking | 1 bedroom, desk, laptop workspace, blackout drapes
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2.0 star property
Chestertown
7.2 out of 10, Good, (410)
"Food stains on the carpets, spots throughout the carpets in commons and in rooms."
United States
Allen
$72 nightly
The price is $80
Nov 30 - Dec 1
Total with taxes and fees
Red Roof Inn & Suites Chestertown
Property grounds
First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown

Chestertown
9.6 out of 10, Exceptional, (105)
"Wonderful stay in a beautiful location convenient to everything. Host was outstanding."
United States
Randy B.
$144 nightly
The price is $159
Nov 10 - Nov 11
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
Fridge, microwave, oven, stovetop
Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown

Chestertown
9.8 out of 10, Exceptional, (27)
"Extremely clean, beautifully updated, and very comfortable. Perfect location—easy to walk to shops and restaurants. Would absolutely stay again!""
United States
Maggie D.
$434 nightly
The price is $479
Nov 14 - Nov 15
Total with taxes and fees
Newly restored apartment in the heart of Chestertown
Restaurant
Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1000)
"Very good breakfast options Convenient parking Clean room Friendly staff"
United States
Alexander
$82 nightly
The price is $91
Nov 17 - Nov 18
Total with taxes and fees
Hampton Inn & Suites Edgewood/Aberdeen-South
Exterior
Holiday Inn Express & Suites Middletown by IHG

Holiday Inn Express & Suites Middletown by IHG

2.5 star property
Middletown
9.2 out of 10, Wonderful, (637)
"This was a great relaxing stay"
United States
Pamela
$104 nightly
The price is $115
Dec 5 - Dec 6
Total with taxes and fees
Holiday Inn Express & Suites Middletown by IHG
Lobby
Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
Middletown
9.2 out of 10, Wonderful, (300)
"Friendly staff, comfortable bed and clean room "
United States
DAVID
$108 nightly
The price is $120
Nov 16 - Nov 17
Total with taxes and fees
Fairfield Inn & Suites by Marriott Middletown
Free daily self-serve breakfast
Quality Inn

Quality Inn

2.5 star property
Smyrna
7.6 out of 10, Good, (1001)
"Good property "
United States
Deryahna
$68 nightly
The price is $75
Dec 9 - Dec 10
Total with taxes and fees
Quality Inn
Lobby
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

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

3.0 star property
Bel Air
8.8 out of 10, Excellent, (1016)
"Would stay there again"
United States
Robin
$84 nightly
The price is $94
Nov 29 - Nov 30
Total with taxes and fees
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Restaurant
Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen

2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (588)
"Great stay!"
United States
Barbara
$90 nightly
The price is $101
Nov 25 - Nov 26
Total with taxes and fees
Hampton Inn & Suites Baltimore/Aberdeen
Desk, free WiFi, bed sheets, alarm clocks
Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A

2.5 star property
Edgewood
7.4 out of 10, Good, (1001)
"It was good for the price and a convenient location, for what I needed to do. Staff was friendly and helpful. Room was clean, bed very comfortable."
United States
Clyde
$63 nightly
The price is $71
Nov 9 - Nov 10
Total with taxes and fees
Quality Inn & Suites Bel Air I-95 Exit 77A
Lobby lounge
Courtyard Aberdeen at Ripken Stadium

Courtyard Aberdeen at Ripken Stadium

3.0 star property
Aberdeen
8.6 out of 10, Excellent, (214)
"The staff was very friendly, easy and quick check-in. I would chose thus hotel again, very quiet. "
United States
Donna
$84 nightly
The price is $94
Nov 24 - Nov 25
Total with taxes and fees
Courtyard Aberdeen at Ripken Stadium
Exterior
La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG

3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (1001)
"The room was nice the bed comfy, the staff was friendly "
United States
Kenya
$91 nightly
The price is $102
Nov 16 - Nov 17
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Reception
Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air

3.0 star property
Bel Air
9.4 out of 10, Exceptional, (218)
"The staff was amazing"
United States
Kendra
$95 nightly
The price is $107
Dec 3 - Dec 4
Total with taxes and fees
Hilton Garden Inn Bel Air
Reception
Hampton Inn Middletown

Hampton Inn Middletown

2.5 star property
Middletown
8.8 out of 10, Excellent, (850)
"Enjoyed the amenities and great location for shops nearby "
United States
Erica
$103 nightly
The price is $115
Nov 19 - Nov 20
Total with taxes and fees
Hampton Inn Middletown
Exterior
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
Grasonville
9.2 out of 10, Wonderful, (914)
"Nice clean room, and nice customer service! Beautiful location close to everything!"
United States
Clara
$99 nightly
The price is $110
Nov 16 - Nov 17
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
Basic Single Room | Desk, free WiFi, bed sheets
Motel Edgewood

Motel Edgewood

2.0 star property
Edgewood
7.6 out of 10, Good, (9)
"Ppl I don’t recommend u to go this place is sh!!t. Americas best. is cheap if that’s what u looking for n cleaner."
Mexico
Roger
$58 nightly
The price is $66
Dec 7 - Dec 8
Total with taxes and fees
Motel Edgewood
Suite, 1 Queen Bed, Non Smoking | In-room safe, iron/ironing board, free WiFi, bed sheets
Quality Inn

Quality Inn

2.5 star property
Grasonville
7.8 out of 10, Good, (848)
"Great place and great staff"
United States
Rhonda
$94 nightly
The price is $104
Nov 23 - Nov 24
Total with taxes and fees
Quality Inn
In-room safe, individually decorated, individually furnished, desk
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

2.5 star property
Grasonville
8.0 out of 10, Very Good, (1002)
"Our room was clean, smelled great, and the breakfast was good with many options."
United States
Eric
$92 nightly
The price is $102
Nov 16 - Nov 17
Total with taxes and fees
Best Western Kent Narrows Inn
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
"Beautiful"
LEIGH 1-night trip
Posted 3 days ago
Historic Inns of Annapolis

Find out more about Chestertown

Chestertown Resorts information

Number of reviews
12,090
Accommodation
0 Resorts
Lowest Price
$66
Highest Price
$479

Frequently asked questions

What is Chestertown like for a resort vacation?
Longing for a relaxing escape? Indulge in all the luxuries and comforts of a resort, where you can find everything you need for your stay from convenient food and drink options to entertainment and shopping. Browse the resorts in the area and discover the right one for you, whether you see yourself sitting down to fine dining or heading to the spa for a deep-tissue massage.
What can I do in Chestertown?
Check out the interesting exhibits at Historical Society of Kent County Maryland, or bring the kids to Crumpton Auction for some family fun. For more to see in the area, you can spend time at Rolphs Wharf Marina or Chesapeake Bay.
What's the seasonal weather like in Chestertown?
The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.
What's the best way to get to and around Chestertown?
Fly into Baltimore, MD (MTN-Martin State), which is located 20.3 mi (32.7 km) from the city center. You can also search for flights into Easton, MD (ESN-Easton - Newnam), which is 28.2 mi (45.3 km) away. If you'd like to explore around the area, you may want to rent a car for your trip.

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