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Find Extended Stay Hotels in Chestertown, MD

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Top Chestertown Extended Stay Hotels | Reserve now, pay later

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 1 - Dec 2
Total with taxes and fees
Inn at Huntingfield Creek

Home2 Suites by Hilton Baltimore / Aberdeen, MD

3.0 star property
Aberdeen
8.8 out of 10, Excellent, (334)
"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
Nov 30 - Dec 1
Total with taxes and fees
Home2 Suites by Hilton Baltimore / Aberdeen, MD

Residence Inn Aberdeen at Ripken Stadium

3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (106)
"The view from our room of the Cal Ripkin complex was amazing. "
United States
Christopher
$110 nightly
The price is $123
Dec 11 - Dec 12
Total with taxes and fees
Residence Inn Aberdeen at Ripken Stadium

Hyatt Place Kent Narrows & Marina

3.0 star property
Grasonville
9.4 out of 10, Exceptional, (655)
"My favorite hotel "
United States
Jen
$159 nightly
The price is $176
Nov 19 - Nov 20
Total with taxes and fees
Hyatt Place Kent Narrows & Marina

Vandiver Inn

3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (529)
"Lovely inn & receptionist was wonderful. "
United States
Deborah
$145 nightly
The price is $163
Dec 18 - Dec 19
Total with taxes and fees
Vandiver Inn

Small House on Gentleman’s Farm

Bel Air
10.0 out of 10, Exceptional, (12)
"Wonderful property located in a peaceful setting. This is our next stay at the Gentlemen’s Farm. Pastoral location that is convenient to Bel Air. House is so clean and well maintained. We had everything available that we needed. Tracey is so responsive in providing information that makes the stay even better. We will stay here again when in the area visiting family."
United States
Jim S.
$297 nightly
The price is $299
Dec 9 - Dec 10
Total with taxes and fees
Small House on Gentleman’s Farm

5 Mi to Downtown Baltimore: Quiet Home w/ Porch

3.0 star property
Rosedale
10.0 out of 10, Exceptional, (1)
$399 nightly
The price is $460
Nov 19 - Nov 20
Total with taxes and fees
5 Mi to Downtown Baltimore: Quiet Home w/ Porch

Candlewood Suites Aberdeen-Bel Air by IHG

2.5 star property
Bel Air
8.0 out of 10, Very Good, (465)
"Good room and service "
United States
Robert
$88 nightly
The price is $99
Nov 23 - Nov 24
Total with taxes and fees
Candlewood Suites Aberdeen-Bel Air by IHG

Charming Coastal/Country Home w/3 Acres & Sauna!

Stevensville
9.6 out of 10, Exceptional, (32)
"Very nice house! We had 3 people in our party and didn't want to rent 2 hotel rooms, this is a great way to save money and enjoy time together. "
United States
Pamela
$227 nightly
The price is $241
Nov 19 - Nov 20
Total with taxes and fees
Charming Coastal/Country Home w/3 Acres & Sauna!

Homewood Suites by Hilton Bel Air

3.0 star property
Bel Air
8.8 out of 10, Excellent, (432)
"We had a great stay here! The room was clean and the beds were very comfortable, even the pull out sofa. The breakfast buffet had a good number of options. All of the staff we encountered were so friendly and helpful. My kids enjoyed the pool, and the hot tub was the cleanest - I even went in! We would stay here again the next time we are in the area! "
United States
Holly
$95 nightly
The price is $107
Nov 30 - Dec 1
Total with taxes and fees
Homewood Suites by Hilton Bel Air
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.

Find out more about Chestertown

Discover top Chestertown attractions

Chestertown, Maryland, offers a delightful blend of historical charm and modern experiences that cater to quality-seeking travelers. Start your exploration at the historic Chestertown waterfront, where you can stroll along the scenic streets lined with 18th-century architecture, quaint shops, and art galleries. Don't miss a visit to the Chester River Yacht & Country Club, where you can indulge in a round of golf or simply enjoy the breathtaking riverside views. For families, the nearby Sultana Education Foundation provides engaging educational programs and eco-tours, perfect for kids eager to learn about the Chesapeake Bay's ecology. Art enthusiasts will appreciate the local art scene showcased at the Kent County Arts Council, featuring rotating exhibitions and community events. After a day of adventures, consider staying in one of Chestertown's charming boutique hotels, such as the Brampton Inn, where you can unwind in elegant rooms and enjoy a delicious gourmet breakfast. This area offers a cozy and inviting atmosphere, making it easy to explore local favorites like the historic downtown district or take leisurely walks along the river, ensuring a memorable and rejuvenating getaway.

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Most booked related extended stays in Chestertown in 2025

Frequently asked questions

What are the best extended stay hotels in Chestertown?
Red Roof Inn & Suites Chestertown is one of the 9 long-term rentals waiting for you in Chestertown. Laundry facilities and free bottled water are the start of the amenities you'll have access to here. Another excellent option is Comfort Inn & Suites Chestertown. It offers a swimming pool and laundry facilities. Whichever getaway you choose, you'll appreciate the convenience of having a kitchen where you can make your own breakfast and save on restaurant visits. Expedia's range of extended hotel stays in Chestertown have an average guest review rating of 9.2.
Why book an extended stay hotel in Chestertown through Expedia?
If you're after a long-term rental for your extended stay in Chestertown, Expedia's got your back. Simply filter your results by rating, price and location to find your ideal long-term stay. Some of these great properties may even offer discounted weekly rates. Want to learn how to snag the best deals? Become an Expedia member for free and save big with special offers — plus you'll earn reward points on every booking. Our extended stay hotels in Chestertown come with conveniences like refrigerators and dining areas, so even though you're far away, you can still enjoy the creature comforts of home.
What can I expect from an extended stay hotel?
With amenities such as kitchens, laundries and dining areas, extended stay hotels in Chestertown can be a convenient and cheaper alternative to a standard hotel room. Make home-cooked meals and wash your own clothes. Sometimes offering discounted weekly rates, extended stay hotels range from studios for one to large and luxurious options with two or more bedrooms. They also offer many of the same amenities you'd expect to find in a standard hotel, like gyms and 24/7 guest services. If you need flexibility, privacy and a comfortable home away from home for a while, an extended stay hotel is a wonderful choice.

Top Chestertown Hotel Reviews

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