Find Hotels with a Pool in Chestertown, MD

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Our top choices for Chestertown hotels with a pool

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

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

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

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

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

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

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

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

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 9 - Feb 10
Total with taxes and fees
Candlewood Suites Aberdeen-Bel Air by IHG

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (875 reviews)
"Amazing stay"
United States
Katiana
$95 nightly
The price is $106
Feb 24 - Feb 25
Total with taxes and fees
Hampton Inn Middletown
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.

Choose what matters most at hotels with a pool in Chestertown

Top Chestertown Hotel Reviews

Frequently asked questions

How much does a hotel with outdoor pool in Chestertown cost?
Enjoy staying in a hotel in Chestertown with an outdoor pool. You can find a great deal from $89 on Expedia. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.
What are some of the best Chestertown hotels with outdoor pools and scenic views?
The Lodge at Great Oak Landing is a delightful 3.5-star hotel that perfectly combines comfort and scenic beauty. With a traveller rating of 8.0, guests rave about the friendly and helpful staff, ensuring an inviting space for travellers.

This charming hotel features a shared outdoor pool that offers stunning views of the marina and surrounding water, making it an ideal spot for relaxation after a day of exploration. Guests appreciate the comfortable sun loungers and pool umbrellas, which enhance the outdoor experience, allowing families to soak up the sun in a secure and inviting environment.

The Lodge at Great Oak Landing not only provides a fantastic pool area but also boasts a restaurant where families can enjoy delicious meals, contributing to its reputation as a great value destination.
Are there hotels in Chestertown with outdoor pool cabanas or loungers?
The Lodge at Great Oak Landing is a charming 3.5-star hotel in Chestertown that offers a delightful outdoor pool area great for families and travellers seeking relaxation. With a review rating of 8.0, guests consistently praise the friendly and helpful staff, making every stay a pleasant experience.

This hotel features inviting pool sun loungers, allowing you to soak up the sun while enjoying picturesque views of the water. Guests appreciate the shared, secured pool area, which adds an extra layer of comfort and safety. With amenities like pool umbrellas and a dedicated pool gate, you can unwind without worries, making it ideal for families with children looking for a convenient and enjoyable escape.

Additionally, The Lodge at Great Oak Landing is located near a marina, enhancing the outdoor experience with opportunities for boating and water activities.
Is it cheaper to book flights and a Chestertown hotel with a pool as a package?
Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect vacation package.
How can I save on a Chestertown hotel with a pool with Expedia?
Before booking your Chestertown hotel, remember to join One Key™, Expedia's free travel rewards program. Just sign up and sign in to access our lowest Member Prices as well as members-only perks. Booking your hotel in advance will typically help you save, but there are last-minute deals to explore too.
Can I cancel my hotel reservation on Expedia?
Expedia has plenty of refundable hotels. In many cases, you need to cancel your booking 24-48 hours ahead of your arrival date. Remember to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel in Chestertown for you.

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