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
Sep 25 - Sep 26
Tomorrow
Sep 26 - Sep 27
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

Our top choices for Chestertown hotels with a pool

A rectangular swimming pool with a tiled edge, surrounded by lounge chairs and a brick building with multiple windows.
A modern dining area with a central island, multiple tables, and chairs. There are signs for 'RISP' and 'SILVER' on the wall, and an 'EXIT' sign above a door.
A modern lounge area with seating, a fireplace, and a television.
A hotel room with two beds, a desk, a TV, and a window with curtains.

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.
$105 nightly
$116 total
Oct 25 - Oct 26
Total with taxes and fees
Comfort Inn & Suites Chestertown
An aerial view of a wooden deck with a swimming pool, lounge chairs, and umbrellas.
A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.
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.

2. 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
Sep 27 - Sep 28
Total with taxes and fees
The Lodge at Great Oak Landing
A swimming pool with a curved edge, surrounded by a brick patio and a hedge.
A closet with a wooden floor, a white door, and a blue bag on top.
A building with a balcony and large windows, surrounded by trees and a fence.
A bedroom with a bed, a ceiling fan, a painting, and a door leading to another room.

3. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
  • Serene backyard pool with hot tub and golf course views provides ideal relaxation in historic Chestertown.
$144 nightly
$159 total
Sep 29 - Sep 30
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
A deck with outdoor furniture, a potted plant, and a house in the background.
A bedroom with a bed, a ceiling fan, a door, and a view of the outdoors.
A compact kitchen with a built-in microwave, oven, and sink. There's a dining area with a wooden table and chairs.
A modern living room with a sofa, a coffee table, and a ceiling fan.

4. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
$290 nightly
$307 total
Oct 5 - Oct 6
Total with taxes and fees
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A poolside area with lounge chairs, a white picket fence, and a stack of towels.
A buffet with various food items including fruits, pastries, and salads.
A large white barn with a star on the side, surrounded by a field of sunflowers, and a large house with a green roof in the background.
A sunflower field with a white barn and a large house in the background.

5. Inn at Huntingfield Creek

Inn at Huntingfield Creek
Rock Hall
  • Waterfront escape with a sun-drenched outdoor pool and spa services at this peaceful bed and breakfast retreat.
$200 nightly
$223 total
Oct 4 - Oct 5
Total with taxes and fees
Inn at Huntingfield Creek
A swimming pool with a white fence, lounge chairs, and umbrellas.
A modern food court with a central island, various food stations, and a yogurt display.
Two Adirondack chairs facing a calm body of water with a clear sky above.
A Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.

6. Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
  • Splashy pool escapes by the bay; seasonal swimming paradise with sun-soaked loungers.
$103 nightly
$114 total
Oct 25 - Oct 26
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
A spacious lobby with a staircase, a reception desk, and a dining area.
A breakfast bar with waffle and juice dispensers, a refrigerator, and a trash bin.
A hotel room with a sofa, armchairs, a desk with a computer, a TV, and a plant.
A bathroom with a green wall, a white sink, a mirror, and a towel rack.

7. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
Grasonville
  • Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay.
$100 nightly
$111 total
Oct 18 - Oct 19
Total with taxes and fees
Quality Inn Grasonville near Kent Island
An indoor swimming pool with a hot tub, lounge chairs, and a sunset mural on the wall.
A hotel room with two beds, a desk, a chair, and a television.
A kitchenette with a coffee machine, a framed picture, and a potted plant.
A bathroom with a bathtub, toilet, and shower.

8. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
  • Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary.
$127 nightly
$141 total
Oct 4 - Oct 5
Total with taxes and fees
Best Western Kent Narrows Inn
A swimming pool with a white fence, lounge chairs, and flags.
A dual-monitor workstation with two chairs, a desktop computer, and framed artwork on the wall.
A hotel room with two beds, a desk with a television, a chair, and a window with curtains.
A spacious living area with a staircase, a fireplace, a sofa, and a dining area.

9. Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Bel Air
  • Seasonal outdoor pool beckons with umbrella-shaded lounging spots perfect for refreshing dips amid Maryland's summer sun.
$94 nightly
$105 total
Oct 25 - Oct 26
Total with taxes and fees
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
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.

10. 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.
$147 nightly
$163 total
Oct 5 - Oct 6
Total with taxes and fees
Hilton Garden Inn Kent Island Marina
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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

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"Overall the job couldn’t have been done better…"
Ahmed 2-night trip
Posted 1 hour ago
Comfort Inn & Suites Chestertown
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

8/10 Good
"room was clean, and the breakfast was as expected. The only bad thing was that treadmill in the gym was out of service, which I found disappointing."
Steven 1-night trip
Posted 2 days ago
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

10/10 Excellent
"Perfectly adequate room for a visit to Chestertown. Good furnishings and amenities. Walkable to stores and restaurants."
John 2-night trip
Posted 2 days ago
Red Roof Inn & Suites Chestertown
Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

10/10 Excellent
"I arrived early for check in and the desk clerk worked hard to get me in my room early before I had to leave for an event. She was very on top of things and friendly. I waited in the lobby while the room was being prepared and it was clean and comfortable. Later when I returned, we had a drink at the bar and the service was once again, great, with a friendly bartender (who remembered me from another stay). I looks as if the rooms have been refreshed since my last stay - clean and well designed. I slept like a log on the very comfortable bed! Basically, it was the least problematic hotel stay I may have ever had."
Barbara 1-night trip
Posted 5 days ago
Hilton Garden Inn Baltimore/White Marsh

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 $77 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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