Villas in Chestertown

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Villas in Chestertown

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

Recommended hotels in Chestertown

Exterior
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 star property
Chestertown
8.6 out of 10, Excellent, (858)
"The room was a great size and very clean. The staff were very accommodating and friendly. The amenities were very good. We would definitely recommend this hotel. "
United States
Santa
$101 nightly
The price is $112
Dec 21 - Dec 22
Total with taxes and fees
Comfort Inn & Suites Chestertown
Room, 1 King Bed with Sofa bed, Marina View | 1 bedroom, free WiFi, bed sheets
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3.5 star property
Chestertown
8.0 out of 10, Very Good, (76)
"Very nice rooms, "
United States
Stephania
$113 nightly
The price is $126
Dec 4 - Dec 5
Total with taxes and fees
The Lodge at Great Oak Landing
Exterior
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2.0 star property
Chestertown
7.2 out of 10, Good, (419)
"Professional staff, warm greetings clean room "
United States
Dr. Nicholas and Mrs. Karen
$72 nightly
The price is $80
Dec 10 - Dec 11
Total with taxes and fees
Red Roof Inn & Suites Chestertown
Exterior
First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown

Chestertown
9.6 out of 10, Exceptional, (107)
"Amazing and neat and very private "
United States
Alexander M.
$144 nightly
The price is $159
Dec 4 - Dec 5
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
Front of property - evening/night
Driftwood Inn

Driftwood Inn

2.0 star property
Chestertown
5.2 out of 10, (175)
"Rooms are clean, staf was helpful "
United States
Daryl
$64 nightly
The price is $70
Dec 24 - Dec 25
Total with taxes and fees
Driftwood Inn
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, (643)
"This was a great relaxing stay"
United States
Pamela
$83 nightly
The price is $92
Dec 28 - Dec 29
Total with taxes and fees
Holiday Inn Express & Suites Middletown by IHG
Point of interest
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, (1028)
"Staff was very friendly. "
United States
Ashlee
$62 nightly
The price is $69
Jan 1 - Jan 2, 2026
Total with taxes and fees
Quality Inn & Suites Bel Air I-95 Exit 77A
Exterior
Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen

2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (597)
"very pet friendly!!"
United States
larry
$90 nightly
The price is $101
Dec 13 - Dec 14
Total with taxes and fees
Hampton Inn & Suites Baltimore/Aberdeen
View from property
Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
Middletown
9.2 out of 10, Wonderful, (312)
"Great overall experience "
United States
Clement
$105 nightly
The price is $117
Dec 14 - Dec 15
Total with taxes and fees
Fairfield Inn & Suites by Marriott Middletown
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, (1018)
"I have stayed at this hotel at least 3 times and every time I get to the front entrance, I am always pleased with my choice! The hotel is always clean, well maintained and the front desk assistant very pleasant! La Quinta is our favorite hotel!"
United States
Theresa
$91 nightly
The price is $102
Dec 30 - Dec 31
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Aerial view
Kent Island Resort

Kent Island Resort

3.5 star property
Stevensville
9.2 out of 10, Wonderful, (127)
"The property is very charming and the staff was extremely attentive and friendly. It's a beautiful area. Close to Annapolis and a lot of fun things to do."
United States
Michael
$142 nightly
The price is $154
Dec 7 - Dec 8
Total with taxes and fees
Kent Island Resort
Exterior
Quality Inn

Quality Inn

2.5 star property
Smyrna
7.6 out of 10, Good, (1000)
"Everything was great!! Checked in with ease and staff was great!!"
United States
Tonya
$63 nightly
The price is $70
Dec 14 - Dec 15
Total with taxes and fees
Quality Inn
Exterior
Hampton Inn Middletown

Hampton Inn Middletown

2.5 star property
Middletown
8.8 out of 10, Excellent, (856)
"Enjoyed the amenities and great location for shops nearby "
United States
Erica
$103 nightly
The price is $115
Dec 10 - Dec 11
Total with taxes and fees
Hampton Inn Middletown
Exterior
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, (1010)
"The room was very nice as well as the staff. The guy at the desk let us check in early which was super helpful for us! Would definitely recommend and come back to again! "
United States
Sara
$83 nightly
The price is $93
Dec 26 - Dec 27
Total with taxes and fees
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Front of property
Hudson house

Hudson house

3.5 star property
Canton
$283 nightly
The price is $333
Dec 4 - Dec 5
Total with taxes and fees
Hudson house
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, (929)
"nice, clean, up to date, budget friendly hotel"
United States
mike
$79 nightly
The price is $88
Dec 7 - Dec 8
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
Restaurant
Courtyard Aberdeen at Ripken Stadium

Courtyard Aberdeen at Ripken Stadium

3.0 star property
Aberdeen
8.6 out of 10, Excellent, (215)
"Excellent place to stay. A wonderful maid helped us. Room great and food excellent evening and morning."
United States
Bartley
$84 nightly
The price is $94
Dec 21 - Dec 22
Total with taxes and fees
Courtyard Aberdeen at Ripken Stadium
Property grounds
Inn at Huntingfield Creek

Inn at Huntingfield Creek

3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (56)
"We stayed one night for our Anniversary, and the stay was so peaceful. The grounds are beautiful, the staff so nice, and the main house is amazing. We definitely plan on making this an annual thing!"
United States
Aaron
$144 nightly
The price is $160
Dec 7 - Dec 8
Total with taxes and fees
Inn at Huntingfield Creek
Exterior
Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen

2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (298)
"Great location close to everything we needed"
United States
John
$101 nightly
The price is $113
Dec 15 - Dec 16
Total with taxes and fees
Fairfield Inn & Suites by Marriott Aberdeen
Restaurant
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, (336)
"The breakfast menu was okay but not great. The overall hotel was very nice and the staff were friendly."
United States
Gregory
$95 nightly
The price is $107
Dec 10 - Dec 11
Total with taxes and fees
Home2 Suites by Hilton Baltimore / 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

Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

10/10 Excellent
"Amazing "
Breonah 2-night trip
Posted 3 days ago
Hilton Garden Inn Baltimore/White Marsh

Find out more about Chestertown

Chestertown Villas information

Number of reviews
10,049
Accommodation
4 Villas
Lowest Price
$69
Highest Price
$333

Frequently asked questions

Why book your villa in Chestertown with Expedia?
Booking a villa in Chestertown is as easy as entering your travel dates and picking an option that meets your requirements. On the lookout for something upscale or budget friendly, or a stay that also has WiFi and a hot tub? Use Expedia's search filters to narrow your results and find your perfect match.
How can I find cheap villas in Chestertown?
Expedia is here to help you search for cheap villas in Chestertown. Use our handy filter tool to choose star rating, budget and amenities to refine your search and find a fantastic place to stay in just a few clicks.
What is there to do near my villa in Chestertown?
If you want to discover the sights of Chestertown, make your way to Rolphs Wharf Marina. It's a winner with travelers and locals alike.

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