Find Hotels with a Pool in Chestertown, MD

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Nov 8 - Nov 9
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Nov 9 - Nov 10
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Nov 13 - Nov 15
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Nov 20 - Nov 22

Our top choices for Chestertown hotels with a pool

A hotel courtyard with a swimming pool, lounge chairs, and a brick building facade.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (999 reviews)
  • cleanliness
    Dive into the seasonal outdoor pool with comfortable loungers and umbrellas at this refreshing hotel retreat in Chestertown.
$98 nightly
The price is $109
Dec 6 - Dec 7
Total with taxes and fees
Comfort Inn & Suites Chestertown
A living room with a fireplace, a television, and a stone accent wall.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (513 reviews)
  • cleanliness
    Tranquil outdoor pool and inviting lounge chairs offer relaxation after Chestertown exploration.
$72 nightly
The price is $80
Nov 15 - Nov 16
Total with taxes and fees
Red Roof Inn & Suites Chestertown
A modern kitchen with a built-in coffee station, a toaster, and a variety of food items on display.

3. La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
3.0 star property
Rossville
7.0 out of 10, Good, (1,259 reviews)
$69 nightly
The price is $79
Nov 15 - Nov 16
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
An aerial view of a wooden deck with a swimming pool, lounge chairs, and umbrellas.

4. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
8.0 out of 10, Very good, (128 reviews)
  • cleanliness
    Waterfront lodge's seasonal outdoor pool offers sun-drenched days with loungers and umbrellas.
$124 nightly
The price is $137
Nov 9 - Nov 10
Total with taxes and fees
The Lodge at Great Oak Landing
A swimming pool with blue chairs and umbrellas, surrounded by a fence and trees.

5. Hampton Inn Baltimore/White Marsh

Hampton Inn Baltimore/White Marsh
2.5 star property
Nottingham
7.8 out of 10, Good, (1,000 reviews)
  • cleanliness
    Dive into Maryland's inviting seasonal outdoor pool with loungers, umbrellas, and fitness center nearby.
$102 nightly
The price is $117
Nov 15 - Nov 16
Total with taxes and fees
Hampton Inn Baltimore/White Marsh
An indoor swimming pool with clear views of boats and water.

6. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
8.8 out of 10, Excellent, (1,002 reviews)
  • cleanliness
    Dive into ultimate bay views with serene indoor pool sessions at this waterfront hotel.
$120 nightly
The price is $133
Nov 18 - Nov 19
Total with taxes and fees
Hilton Garden Inn Kent Island Marina
A swimming pool with lounge chairs and a pergola under a clear sky.

7. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (512 reviews)
  • cleanliness
    Dive into summer luxury at this Eastern Shore retreat with a seasonal outdoor pool and personalized spa services.
$204 nightly
The price is $226
Dec 9 - Dec 10
Total with taxes and fees
The Inn at Chesapeake Bay Beach Club
A spacious lobby with a high ceiling, a reception desk, seating areas, and a central decorative piece.

8. The Westin Annapolis

The Westin Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,004 reviews)
  • cleanliness
    Aquatic serenity awaits at this urban hotel with a refreshing indoor pool and full-service spa.
$169 nightly
The price is $193
Nov 15 - Nov 16
Total with taxes and fees
The Westin Annapolis
A pool area with lounge chairs, a pool, and large windows offering a view of the sunset.

9. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (857 reviews)
  • cleanliness
    Scenic waters beckon at this island escape with a relaxing indoor pool and waterfront deck for breathtaking sunset views.
$134 nightly
The price is $149
Nov 15 - Nov 16
Total with taxes and fees
Hyatt Place Kent Narrows & Marina
A hotel pool area with a clear pool, lounge chairs, and a seating area with tables and chairs.

10. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1,001 reviews)
  • cleanliness
    Serene indoor pool sanctuary awaits at this hotel, with health club access and round-the-clock amenities for a refreshing stay.
$85 nightly
The price is $96
Nov 23 - Nov 24
Total with taxes and fees
Hampton Inn & Suites Edgewood/Aberdeen-South
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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Choose what matters most at hotels with a pool in Chestertown

Breakfast included
Hot tub

Top Chestertown Hotel Reviews

A hotel courtyard with a swimming pool, lounge chairs, and a brick building facade.
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown

10/10 Excellent

Inside the building it was clean, quiet and nice. In the back parking lot, it was very dirty. The grounds surrounding the lot was littered with trash and debris. One person looked to be sleeping in his car. I did appreciate the very bright lighting in that lot. A small clean up of the back lot would make a big difference in first impressions!!
United States
Laura
Reviewed April 12, 2025
Comfort Inn & Suites Chestertown

Find out more about Chestertown

Discover top Chestertown attractions

Chestertown is a charming destination that offers a delightful blend of history and outdoor adventure, perfect for travelers seeking a unique getaway. Start your exploration at the picturesque waterfront, where you can enjoy scenic views and perhaps take a leisurely stroll along the banks of the Chester River. For history enthusiasts, the historical district is a treasure trove, featuring beautifully preserved colonial architecture and intriguing stories from the town's rich past. Art lovers will appreciate the vibrant local art scene, with galleries showcasing works from talented regional artists. If you're feeling adventurous, consider renting a kayak to paddle through the serene waters, allowing you to connect with nature in a truly immersive way. Finally, foodies will relish the opportunity to sample the farm-to-table offerings at local eateries, where seasonal ingredients shine in every dish. After a day of exploration, unwind in one of the cozy accommodations nearby, where attentive service and comfort await, ensuring that your stay is as enjoyable as your adventures.

Find the best pool hotels in Chestertown

For travelers seeking a refreshing escape in Chestertown, these hotels feature inviting pools perfect for relaxation and recreation. Enjoy a delightful stay with top amenities tailored to your poolside enjoyment.

Comfort Inn & Suites Chestertown

  • Why it's great: For a budget-friendly stay that highlights poolside leisure, the Comfort Inn & Suites Chestertown is an excellent choice. With a strong traveler review rating of 9 out of 10, this hotel boasts a secure and accessible pool area equipped with sun loungers and umbrellas, ensuring travelers can soak up the sun in comfort. It's a welcoming place for all travelers, including families looking for a fun getaway.
  • Other amenities: Beyond the inviting pool, travelers can enjoy a complimentary full breakfast, ensuring a great start to the day. The hotel features designer toiletries and a hydromassage showerhead for added relaxation. Amenities like free Wi-Fi, daily housekeeping, and self-parking enhance convenience, while the historical district location offers a charming backdrop for exploring Chestertown.
  • Nearby attractions: Kings Town Park - 2 miles, Roundtop Park - 5 miles, Urieville Park - 5 miles

The Lodge at Great Oak Landing

  • Why it's great: The Lodge at Great Oak Landing is perfect for travelers who appreciate beautiful waterfront views alongside a shared pool experience. With a solid traveler review rating of 8 out of 10, this 3.5-star hotel features a secure pool area with sun loungers and umbrellas, ideal for sunbathing or enjoying a good book by the water.
  • Other amenities: In addition to the pool, travelers can access a nearby private beach with direct access, perfect for leisurely strolls or beach volleyball. The hotel also offers a mini-refrigerator in rooms for added convenience, as well as self-parking. The scenic marina views and a playground for children add to the family-friendly atmosphere, making it a delightful option for all.
  • Nearby attractions: Chestertown Historic District - 12 miles, Kings Town Park - 12 miles, The Mainstay - 15 miles

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 $79 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.

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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