Best Resorts in Chestertown

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Check prices for these dates

Next weekend
Feb 13 - Feb 15
In two weeks
Feb 20 - Feb 22
In one month
Mar 6 - Mar 8
In two months
Apr 3 - Apr 5
No exact matches found, but these alternatives could be just right

Recommended hotels in Chestertown

Free daily full breakfast

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (872 reviews)
"Polite and kind hotel manager"
United States
Richard
$101 nightly
The price is $112
Mar 1 - Mar 2
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
7.8 out of 10, Good, (77 reviews)
"Very nice rooms, "
United States
Stephania
$124 nightly
The price is $137
Mar 1 - Mar 2
Total with taxes and fees
The Lodge at Great Oak Landing
Lobby lounge

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (427 reviews)
"Arrived earlier than expected and the staff was very accommodating and friendly which made for an excellent stay from start to finish. "
United States
Linette
$72 nightly
The price is $80
Feb 13 - Feb 14
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, (108 reviews)
"We had a lovely visit. It was nice and quiet and parking was perfect."
United States
Anne D.
$144 nightly
The price is $159
Feb 9 - Feb 10
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
Pool

Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access

Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access
Chestertown
10.0 out of 10, Exceptional, (3 reviews)
"We had a great stay. Property was updated, clean and in a nice part of town walkable to everything. We would definitely stay here again and are looking forward to it."
United States
Jason
$427 nightly
The price is $453
Feb 21 - Feb 22
Total with taxes and fees
Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access
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, (1,001 reviews)
"Everything was great"
United States
juan
$86 nightly
The price is $96
Feb 15 - Feb 16
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Terrace/patio

Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen
2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (310 reviews)
"Always consistent and great staff!"
United States
Linda
$109 nightly
The price is $123
Feb 8 - Feb 9
Total with taxes and fees
Fairfield Inn & Suites by Marriott Aberdeen
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, (660 reviews)
"Clean room and hotel. Breakfast was good, the fresh baked cookies at the front desk were delicious!"
United States
Valerie
$109 nightly
The price is $121
Feb 22 - Feb 23
Total with taxes and fees
Holiday Inn Express & Suites Middletown by IHG
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, (1,001 reviews)
"We always enjoy our stay here when visiting our family as the facility is clean, comfortable and quiet. Only exception was on one of the days a fire alarm had gone off and scared us awake but it turned out to be a false alarm. "
United States
Cheryle
$79 nightly
The price is $89
Mar 1 - Mar 2
Total with taxes and fees
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Desk, laptop workspace, iron/ironing board, free WiFi

Quality Inn Smyrna

Quality Inn Smyrna
2.5 star property
Smyrna
7.6 out of 10, Good, (1,000 reviews)
"Great stay"
United States
Edward
$72 nightly
The price is $80
Feb 16 - Feb 17
Total with taxes and fees
Quality Inn Smyrna
Reception

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1,006 reviews)
"Great stay as always"
United States
Linda
$81 nightly
The price is $91
Feb 13 - Feb 14
Total with taxes and fees
Hampton Inn & Suites Edgewood/Aberdeen-South
Reception

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (132 reviews)
"Beautiful hotel, nice staff"
United States
Kim
$155 nightly
The price is $168
Feb 8 - Feb 9
Total with taxes and fees
Kent Island Resort
In-room safe, individually furnished, desk, laptop workspace

Candlewood Suites Aberdeen-Bel Air by IHG

Candlewood Suites Aberdeen-Bel Air by IHG
2.5 star property
Bel Air
8.0 out of 10, Very Good, (481 reviews)
"The staff is great, roon clean & spacious"
United States
Thomas
$84 nightly
The price is $94
Feb 10 - Feb 11
Total with taxes and fees
Candlewood Suites Aberdeen-Bel Air by IHG
Bar (on property)

Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
3.0 star property
Bel Air
9.2 out of 10, Wonderful, (242 reviews)
"Very friendly staff and easy check in."
United States
Kurt
$102 nightly
The price is $114
Feb 20 - Feb 21
Total with taxes and fees
Hilton Garden Inn Bel Air
View from property

TownePlace Suites by Marriott Edgewood Aberdeen

TownePlace Suites by Marriott Edgewood Aberdeen
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (103 reviews)
"Clean room and attentive staff ."
United States
Stephen
$132 nightly
The price is $148
Feb 8 - Feb 9
Total with taxes and fees
TownePlace Suites by Marriott Edgewood Aberdeen
Terrace/patio

Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
3.0 star property
Aberdeen
8.8 out of 10, Excellent, (344 reviews)
"Awesome staff, very clean, great pool Awesome breakfast!!! All good things"
United States
Patty
$93 nightly
The price is $105
Feb 14 - Feb 15
Total with taxes and fees
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Property amenity

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
2.5 star property
Middletown
9.2 out of 10, Wonderful, (342 reviews)
"Clean room, great staff, recommended. "
United States
Tom
$99 nightly
The price is $110
Feb 15 - Feb 16
Total with taxes and fees
Fairfield Inn & Suites by Marriott 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, (958 reviews)
"Lovely location"
United States
Cheryl
$101 nightly
The price is $112
Feb 8 - Feb 9
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
Basic Double or Twin Room | Desk, free WiFi, bed sheets

Motel Edgewood

Motel Edgewood
2.0 star property
Edgewood
7.4 out of 10, Good, (10 reviews)
"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."
United States
Nancy
$49 nightly
The price is $55
Mar 1 - Mar 2
Total with taxes and fees
Motel Edgewood
Lobby

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (869 reviews)
"Nice staff and rooms"
United States
Walter
$85 nightly
The price is $94
Mar 4 - Mar 5
Total with taxes and fees
Quality Inn Grasonville near Kent Island
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 Baltimore Bayview Campus

Hampton Inn Baltimore Bayview Campus

10/10 Excellent
"Yes room was great"
Anthony 1-night trip
Posted 4 days ago
Hampton Inn Baltimore Bayview Campus

Find out more about Chestertown

Chestertown Resorts information

Number of reviews
9,941
Accommodation
0 Resorts
Lowest Price
$55
Highest Price
$453

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 Northern Chesapeake Bay 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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