Find Hotels with a Pool in Chestertown, MD

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Our top choices for Chestertown hotels with a pool

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108 reviews)
  • cleanliness
    Serene backyard pool with hot tub and golf course views provides ideal relaxation in historic Chestertown.
$144 nightly
The price is $159
Mar 25 - Mar 26
Total with taxes and fees
First Floor Studio Apartment in Historic 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)
  • cleanliness
    Waterfront lodge's seasonal outdoor pool offers sun-drenched days with loungers and umbrellas.
$124 nightly
The price is $137
Mar 25 - Mar 26
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, (890 reviews)
  • cleanliness
    Dive into the seasonal outdoor pool with comfortable loungers and umbrellas at this refreshing hotel retreat in Chestertown.
$110 nightly
The price is $122
Apr 12 - Apr 13
Total with taxes and fees
Comfort Inn & Suites Chestertown

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (134 reviews)
  • cleanliness
    Victorian pool retreat with sun loungers and umbrellas by Chesapeake Bay Bridge.
$134 nightly
The price is $145
Mar 25 - Mar 26
Total with taxes and fees
Kent Island Resort

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,007 reviews)
  • cleanliness
    Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary.
$101 nightly
The price is $112
Mar 31 - Apr 1
Total with taxes and fees
Best Western Kent Narrows Inn

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, (356 reviews)
  • cleanliness
    Indoor pool retreat offers relaxing swims with modern amenities and helpful staff around the clock.
$98 nightly
The price is $109
Apr 3 - Apr 4
Total with taxes and fees
Home2 Suites by Hilton Baltimore / Aberdeen, MD

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (62 reviews)
  • cleanliness
    Waterfront escape with a sun-drenched outdoor pool and spa services at this peaceful bed and breakfast retreat.
$156 nightly
The price is $173
Mar 25 - Mar 26
Total with taxes and fees
Inn at Huntingfield Creek

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Dive into ultimate bay views with serene indoor pool sessions at this waterfront hotel.
$139 nightly
The price is $154
Mar 29 - Mar 30
Total with taxes and fees
Hilton Garden Inn Kent Island Marina

Quality Inn Smyrna

Quality Inn Smyrna
2.5 star property
Smyrna
7.6 out of 10, Good, (1,000 reviews)
  • cleanliness
    Dip into poolside bliss at this hotel with a sun-soaked outdoor pool and modern fitness center nearby.
$80 nightly
The price is $89
Mar 25 - Mar 26
Total with taxes and fees
Quality Inn Smyrna

Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (81 reviews)
  • cleanliness
    Waterfront paradise beckons with a heated outdoor pool, private aquatic oasis, and scenic creek views in tranquil Annapolis.
$363 nightly
The price is $414
Mar 25 - Mar 26
Total with taxes and fees
Waterfront Oasis of Annapolis Star
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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