An aerial view of a town with a river, buildings, and surrounding greenery.

Find Hotels with a Pool in Chestertown, MD

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Check availability on Chestertown Hotels with a Pool

Tonight
Oct 24 - Oct 25
Tomorrow
Oct 25 - Oct 26
Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8

Our top choices for Chestertown hotels with a pool

A rectangular swimming pool with a 3 FT depth marker, surrounded by lounge chairs and a small table.
A hotel room with a bed, a sofa, a dining table, and a small round table.
A spacious dining area with multiple tables and chairs, a central island, and a kitchen in the background.
A hotel lobby with a fireplace, seating area, and a television.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
  • Dive into the seasonal outdoor pool with comfortable loungers and umbrellas at this refreshing hotel retreat in Chestertown.
$98 nightly
$109 total
Nov 15 - Nov 16
Total with taxes and fees
Comfort Inn & Suites Chestertown
A modern kitchen with a built-in coffee station, a toaster, and a variety of food items on display.
A hotel room with two beds, a desk, a TV, a lamp, and a window with curtains.
A gym with exercise equipment, weight racks, and a large mirror.
A reception area with two reception desks, a cityscape mural, and a clock on the wall.

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

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
Rossville
$71 nightly
$82 total
Nov 2 - Nov 3
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.
A campfire in a stone fire pit by a lakeside at sunset.
A spacious room with a large window, a seating area with a sofa and armchairs, a small table with a plant, and a display of various items including a mannequin and shelves with products.
A large brick building with a symmetrical facade, multiple chimneys, and a central entrance.

3. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
Chestertown
  • Waterfront lodge's seasonal outdoor pool offers sun-drenched days with loungers and umbrellas.
$124 nightly
$137 total
Oct 25 - Oct 26
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.
A patio area with a fire pit, outdoor seating, and umbrellas providing shade.
A hotel dining area with a long wooden table, multiple chairs, and a buffet counter.
A hotel room with a wooden cabinet, a sink, a mirror, a chair, and a table.

4. Hampton Inn Baltimore/White Marsh

Hampton Inn Baltimore/White Marsh
Nottingham
  • Dive into Maryland's inviting seasonal outdoor pool with loungers, umbrellas, and fitness center nearby.
$102 nightly
$117 total
Nov 1 - Nov 2
Total with taxes and fees
Hampton Inn Baltimore/White Marsh
An indoor swimming pool with clear views of boats and water.
A spacious dining area with a large rectangular table, multiple chairs, and a chandelier.
A balcony with a view of a marina and row houses.
A patio with outdoor seating, overlooking a marina with boats.

5. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
Grasonville
  • Dive into ultimate bay views with serene indoor pool sessions at this waterfront hotel.
$129 nightly
$144 total
Nov 22 - Nov 23
Total with taxes and fees
Hilton Garden Inn Kent Island Marina
A swimming pool with lounge chairs and a pergola under a clear sky.
A balcony with a view of a marina, wooden deck, and outdoor seating.
A bar area with multiple seating options, a variety of bottles and glasses on shelves, and a modern chandelier.
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.

6. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
  • Dive into summer luxury at this Eastern Shore retreat with a seasonal outdoor pool and personalized spa services.
$237 nightly
$263 total
Nov 15 - Nov 16
Total with taxes and fees
The Inn at Chesapeake Bay Beach Club
A pool area with lounge chairs, a pool, and large windows offering a view of the sunset.
A modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.
A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.
An outdoor event area with round tables and a view of the water.

7. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
  • Scenic waters beckon at this island escape with a relaxing indoor pool and waterfront deck for breathtaking sunset views.
$152 nightly
$169 total
Nov 1 - Nov 2
Total with taxes and fees
Hyatt Place Kent Narrows & Marina
A spacious lobby with a high ceiling, a reception desk, seating areas, and a central decorative piece.
A modern hotel lobby with a curved seating area, a bar, and a large bookshelf.
A bar area with a circular seating arrangement, a central bar counter, and a hanging plant decoration.
A store interior with shelves stocked with snacks, a refrigerated beverage display, and wicker baskets on a table.

8. The Westin Annapolis

The Westin Annapolis
Annapolis
  • Aquatic serenity awaits at this urban hotel with a refreshing indoor pool and full-service spa.
$169 nightly
$193 total
Nov 22 - Nov 23
Total with taxes and fees
The Westin Annapolis
A hotel pool area with a clear pool, lounge chairs, and a seating area with tables and chairs.
A modern hotel lobby with a long dining table, several chairs, and a bar area.
A hotel room with a bed, a chair, a bathtub, a framed picture, and a nightstand with a lamp.
A hotel reception area with a wooden reception desk, a coffee station, and framed pictures on the wall.

9. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood
  • Serene indoor pool sanctuary awaits at this hotel, with health club access and round-the-clock amenities for a refreshing stay.
$85 nightly
$96 total
Nov 1 - Nov 2
Total with taxes and fees
Hampton Inn & Suites Edgewood/Aberdeen-South
An indoor swimming pool with clear water, a changing room, and exercise equipment.
A hotel entrance with a covered walkway, brick facade, and multiple windows.
A spacious lobby with a fireplace, comfortable seating, and large windows.
A living room with a fireplace, a television mounted above it, and a coffee table with decorative items.

10. Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh
Nottingham
  • Refresh with a swim in the indoor pool after exploring Baltimore, with fitness center access and on-site dining options nearby.
$102 nightly
$117 total
Nov 1 - Nov 2
Total with taxes and fees
Hilton Garden Inn Baltimore/White Marsh
View all properties

Choose what matters most at hotels with a pool in Chestertown

Breakfast included
Hot tub
4 stars
5 stars
Spa

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

Top Chestertown Hotel Reviews

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"Nice staff Helpful"
carol 1-night trip
Posted 1 day ago
Comfort Inn & Suites Chestertown
Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

10/10 Excellent
"Everyone seemed to care and were nice"
james 1-night trip
Posted 1 day ago
Hampton Inn & Suites Edgewood/Aberdeen-South
Pendry Baltimore

Pendry Baltimore

10/10 Excellent
"Best in room dining"
Edgar 4-night trip
Posted 3 days ago
Pendry Baltimore
Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

10/10 Excellent
"Great stay!"
Dianne 2-night trip
Posted 3 days ago
Hampton Inn Baltimore/Glen Burnie
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

8/10 Good
"The place was a little better than average, I'd stay here again. The room smelled musty as if it used to be a smoking room, but not completely unbearable. The desk help was not friendly but not rude either...kind of robotic. Easy parking, roomy room. Decent shower."
Bill 1-night trip
Posted 9 days ago
Red Roof Inn & Suites Chestertown

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 $93 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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