Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA

Find Hotels with a Pool in Chestertown, MD

Check availability on Chestertown Hotels with a Pool

Our top choices for Chestertown hotels with a pool

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.0 star property
Chestertown
7.8 out of 10, Good, (88 reviews)
  • cleanliness
    Waterfront lodge's seasonal outdoor pool offers sun-drenched days with loungers and umbrellas.
$151 nightly
The price is $168
Jun 18 - Jun 19
Total with taxes and fees
The Lodge at Great Oak Landing

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (925 reviews)
  • cleanliness
    Dive into the seasonal outdoor pool with comfortable loungers and umbrellas at this refreshing hotel retreat in Chestertown.
$103 nightly
The price is $115
Jul 12 - Jul 13
Total with taxes and fees
Comfort Inn & Suites Chestertown

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (113 reviews)
  • cleanliness
    Serene backyard pool with hot tub and golf course views provides ideal relaxation in historic Chestertown.
$144 nightly
The price is $159
Jun 23 - Jun 24
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.4 out of 10, Exceptional, (144 reviews)
  • cleanliness
    Victorian pool retreat with sun loungers and umbrellas by Chesapeake Bay Bridge.
$182 nightly
The price is $198
Jul 5 - Jul 6
Total with taxes and fees
Kent Island Resort

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (920 reviews)
  • cleanliness
    Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay.
$100 nightly
The price is $111
Jun 24 - Jun 25
Total with taxes and fees
Quality Inn Grasonville near Kent Island

Hilton Garden Inn Aberdeen

Hilton Garden Inn Aberdeen
3.0 star property
Aberdeen
8.6 out of 10, Excellent, (660 reviews)
  • cleanliness
    Plunge into tranquil waters at this hotel's refreshing indoor pool for a serene aquatic escape.
$103 nightly
The price is $115
Jun 28 - Jun 29
Total with taxes and fees
Hilton Garden Inn Aberdeen

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, (1,012 reviews)
  • cleanliness
    Seasonal outdoor pool beckons with umbrella-shaded lounging spots perfect for refreshing dips amid Maryland's summer sun.
$94 nightly
The price is $105
Jun 18 - Jun 19
Total with taxes and fees
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

Courtyard Aberdeen at Ripken Stadium

Courtyard Aberdeen at Ripken Stadium
3.0 star property
Aberdeen
8.6 out of 10, Excellent, (228 reviews)
  • cleanliness
    Dive into relaxation at this city-center hotel, where an inviting indoor pool awaits after exploring Aberdeen's attractions.
$84 nightly
The price is $94
Jul 5 - Jul 6
Total with taxes and fees
Courtyard Aberdeen at Ripken Stadium

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,001 reviews)
  • cleanliness
    Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary.
$110 nightly
The price is $122
Jul 6 - Jul 7
Total with taxes and fees
Best Western Kent Narrows Inn

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (905 reviews)
  • cleanliness
    Splash into serenity at this indoor pool sanctuary with a hot tub and fitness amenities for a complete wellness getaway.
$116 nightly
The price is $129
Jul 2 - Jul 3
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 $94 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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