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 18 - Oct 19
Tomorrow
Oct 19 - Oct 20
Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1

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 two beds, a desk, a flat-screen TV, and a window with curtains.
A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.
A modern bathroom with a white sink, mirror, and toilet. There is a hand dryer and a towel rack.

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
$108 total
Nov 8 - Nov 9
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 reception area with two reception desks, a cityscape mural, and a clock on the wall.
A hotel room with two beds, a desk, a TV, a lamp, and a window with curtains.
A modern hotel lobby with a seating area, a reception desk, and a dining area.

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

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
Rossville
$73 nightly
$84 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 19 - Oct 20
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 hotel room with a wooden cabinet, a sink, a mirror, a chair, and a table.
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.

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
Oct 25 - Oct 26
Total with taxes and fees
Hampton Inn Baltimore/White Marsh
A swimming pool with lounge chairs and a pergola under a clear sky.
A spacious living room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.
A residential area with a garden, a patio with outdoor furniture, and a house with a chimney.

5. 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
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 patio with outdoor seating, overlooking a marina with boats.
A balcony with a view of a marina and row houses.

6. 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.
$125 nightly
$139 total
Nov 18 - Nov 19
Total with taxes and fees
Hilton Garden Inn Kent Island Marina
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 reception area with a wooden reception desk, a coffee station, and framed pictures on the wall.
A hotel room with a bed, a chair, a bathtub, a framed picture, and a nightstand with a lamp.

7. 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 spacious lobby with a fireplace, comfortable seating, and large windows.
An outdoor patio area with wicker furniture and a small table, surrounded by brick buildings and a well-maintained garden.
A living room with a fireplace, a television mounted above it, and a coffee table with decorative items.

8. 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
Oct 26 - Oct 27
Total with taxes and fees
Hilton Garden Inn Baltimore/White Marsh
A pool area with lounge chairs, a pool, and large windows offering a view of the sunset.
An outdoor event area with round tables and a view of the water.
A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.

9. 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
Oct 25 - Oct 26
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 store interior with shelves stocked with snacks, a refrigerated beverage display, and wicker baskets on a table.
A bar area with a circular seating arrangement, a central bar counter, and a hanging plant decoration.

10. The Westin Annapolis

The Westin Annapolis
Annapolis
  • Aquatic serenity awaits at this urban hotel with a refreshing indoor pool and full-service spa.
$199 nightly
$227 total
Oct 25 - Oct 26
Total with taxes and fees
The Westin Annapolis
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Choose what matters most at hotels with a pool in Chestertown

Breakfast included
Hot tub
4 stars
5 stars
Spa

Top Chestertown Hotel Reviews

Country Inn & Suites by Radisson, Baltimore North, MD

Country Inn & Suites by Radisson, Baltimore North, MD

10/10 Excellent
"I stayed here for a mini staycation and was not disappointed. The parking situation was easy, the room was very nice, and the continental breakfast was great! The staff were very friendly and helpful, which is always a plus in my book. The close proximity to restaurants and some shops was another bonus. I have no complaints whatsoever and would definitely stay here again."
Cara 1-night trip
Posted 2 hours ago
Country Inn & Suites by Radisson, Baltimore North, MD
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

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

10/10 Excellent
"Good."
Dexter 1-night trip
Posted 3 hours ago
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

10/10 Excellent
"Propre et tranquille, déjeuner complet. Stationnement gratuit."
Sophie 1-night trip
Posted 1 day ago
Hampton Inn & Suites Edgewood/Aberdeen-South
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 2 days ago
Red Roof Inn & Suites Chestertown
Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

8/10 Good
"A good location. Many stores and restaurants within walking distance and many more a short drive away."
Justin 2-night trip
Posted 7 days ago
Hampton Inn Baltimore/Glen Burnie

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.
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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