Villas in Chestertown

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Dec 12 - Dec 14
In two weeks
Dec 19 - Dec 21
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Jan 2 - Jan 4
In two months
Jan 30 - Feb 1

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
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
$102 nightly
The price is $113
Dec 25 - Dec 26
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

Lodge in Chestertown

3.5 star property
8.0 out of 10, Very Good, (76)
"Very nice rooms, "
United States
Stephania
$113 nightly
The price is $126
Dec 7 - Dec 8
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
7.2 out of 10, Good, (420)
"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

Apartment in 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 8 - Dec 9
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
Front of property - evening/night
Driftwood Inn

Motel in Chestertown

2.0 star property
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
9.2 out of 10, Wonderful, (643)
"This was a great relaxing stay"
United States
Pamela
$79 nightly
The price is $88
Jan 4 - Jan 5, 2026
Total with taxes and fees
Holiday Inn Express & Suites Middletown by IHG
View from property
Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
9.2 out of 10, Wonderful, (312)
"Great overall experience "
United States
Clement
$108 nightly
The price is $120
Dec 14 - Dec 15
Total with taxes and fees
Fairfield Inn & Suites by Marriott Middletown
Exterior
Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

2.5 star property
9.2 out of 10, Wonderful, (1000)
"Would stay again"
United States
Dena
$82 nightly
The price is $91
Dec 11 - Dec 12
Total with taxes and fees
Hampton Inn & Suites Edgewood/Aberdeen-South
Exterior
Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen

2.5 star property
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
Exterior
La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG

3.0 star property
9.0 out of 10, Wonderful, (1000)
"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
$90 nightly
The price is $101
Jan 4 - Jan 5, 2026
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Exterior
Quality Inn

Quality Inn

2.5 star property
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
Aerial view
Kent Island Resort

Kent Island Resort

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

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

3.0 star property
8.8 out of 10, Excellent, (1011)
"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
Restaurant
Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD

3.0 star property
8.8 out of 10, Excellent, (337)
"The breakfast menu was okay but not great. The overall hotel was very nice and the staff were friendly."
United States
Gregory
$80 nightly
The price is $90
Dec 12 - Dec 13
Total with taxes and fees
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Terrace/patio
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (1001)
"Easy parking and check in. Conveniently located within walking distance of some great seafood restaurants. Always an enjoyable stay"
United States
Roberta
$103 nightly
The price is $115
Dec 21 - Dec 22
Total with taxes and fees
Hilton Garden Inn Kent Island Marina
Exterior
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (930)
"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
Exterior
Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen

2.5 star property
9.0 out of 10, Wonderful, (299)
"Great location close to everything we needed"
United States
John
$109 nightly
The price is $122
Dec 10 - Dec 11
Total with taxes and fees
Fairfield Inn & Suites by Marriott Aberdeen
Exterior
Hampton Inn Middletown

Hampton Inn Middletown

2.5 star property
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
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

2.5 star property
8.0 out of 10, Very Good, (1001)
"Our room was clean, smelled great, and the breakfast was good with many options."
United States
Eric
$84 nightly
The price is $93
Dec 10 - Dec 11
Total with taxes and fees
Best Western Kent Narrows Inn
Exterior
Super 8 by Wyndham Aberdeen MD

Motel in Aberdeen

2.0 star property
7.0 out of 10, Good, (857)
"Nice and clean. Staff was friendly. I had no problems whatsoever, and I would stay here again."
United States
Shelly
$50 nightly
The price is $56
Dec 16 - Dec 17
Total with taxes and fees
Super 8 by Wyndham 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 4 days ago
Hilton Garden Inn Baltimore/White Marsh

Find out more about Chestertown

Chestertown Villas information

Number of reviews
12,620
Accommodation
4 Villas
Lowest Price
$56
Highest Price
$159

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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