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 2 - Sep 3
Tomorrow
Sep 3 - Sep 4
This weekend
Sep 4 - Sep 6
Next weekend
Sep 11 - Sep 13

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 hotel room with two beds, a desk, a TV, and a window with curtains.
A modern lounge area with seating, a fireplace, 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.
$105 nightly
$116 total
Sep 27 - Sep 28
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 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.

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 9 - Sep 10
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 house with a swimming pool, surrounded by a fence, and two red umbrellas.

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 3 - Sep 4
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
A bedroom with a bed, a ceiling fan, a door, and a window with blinds.

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

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
$273 nightly
$289 total
Sep 8 - Sep 9
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 boat deck with a white bench and a view of a calm lake and distant trees.
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
Sep 7 - Sep 8
Total with taxes and fees
Inn at Huntingfield Creek
Two Adirondack chairs facing a calm body of water with a clear sky above.
A hotel room with a large bed, a desk with a flat-screen TV, a chair, a small table with a lamp, and a window with curtains.
A Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.
A swimming pool with lounge chairs and umbrellas, surrounded by a white fence.

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.
$127 nightly
$141 total
Sep 7 - Sep 8
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
A swimming pool with a white fence, lounge chairs, and flags.
A spacious living area with a staircase, a fireplace, a sofa, and a dining area.
A Country Inn & Suites hotel with a brick facade, multiple windows, and a sign indicating the entrance.
A hotel room with two beds, a desk with a television, a chair, and a window with curtains.

7. 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.
$90 nightly
$101 total
Sep 9 - Sep 10
Total with taxes and fees
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
An indoor swimming pool with a hot tub, lounge chairs, and a sunset mural on the wall.
A hotel room with a large bed, a desk, a chair, a TV, and a window with curtains.
A restaurant with a counter, seating area, and a clock on the wall.

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.
$116 nightly
$129 total
Sep 28 - Sep 29
Total with taxes and fees
Best Western Kent Narrows Inn
A spacious lobby with a staircase, a reception desk, and a dining area.
A bathroom with a green wall, a white sink, a mirror, and a towel rack.
A hotel room with a bed, a sofa, a desk, and two chairs. There are two lamps on the desk and a picture frame on the wall.
A hotel room with a sofa, armchairs, a desk with a computer, a TV, and a plant.

9. 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
Sep 28 - Sep 29
Total with taxes and fees
Quality Inn Grasonville near Kent Island
An indoor swimming pool with clear depth markers, lounge chairs, and umbrellas.
A modern restaurant with a bar area, seating, and a counter with a menu display.
A multi-story hotel with a modern facade, featuring a prominent 'HOME 2' sign. The entrance is accessible via a covered walkway, and the building is equipped with large windows and a flagpole.
An outdoor patio with a stone fire pit, wicker furniture, and a view of the interior.

10. Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
Aberdeen
  • Indoor pool retreat offers relaxing swims with modern amenities and helpful staff around the clock.
$102 nightly
$114 total
Sep 9 - Sep 10
Total with taxes and fees
Home2 Suites by Hilton Baltimore / Aberdeen, MD
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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

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

10/10 Excellent
"Close to the bay"
Joshua 1-night trip
Posted 15 hours ago
Best Western Kent Narrows Inn
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

8/10 Good
"good stay"
Jose 1-night trip
Posted 22 hours ago
Comfort Inn & Suites Chestertown
Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

10/10 Excellent
"My visit was great I have no complaints also the complimentary breakfast was really good alot of options and great food choices in also liked the fact that check out time was at 12 noon I'll definitely stay next time I visit the area thank you"
Iam 1-night trip
Posted 1 day ago
Best Western Plus Hotel & Conference Center
Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

8/10 Good
"Only one elevator working and it was the slowest elevator ever, especially since there is only 5 floors! The lobby is bright and welcoming, but the room, while clean, had dark furniture and dark carpeting and are generally just not very bright and cheery. We have stayed here before and had no issues either the room but this time the air conditioner seemed to blow bad smelling air. It might have been due to the standing water on the flat roof outside our window."
Leigh 2-night trip
Posted 2 days ago
Hampton Inn Baltimore/Glen Burnie
Hampton Inn Baltimore/White Marsh

Hampton Inn Baltimore/White Marsh

10/10 Excellent
"Room was clean. Max, Netflix, Apple+ available besides some channels."
Urserla 1-night trip
Posted 3 days ago
Hampton 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 $101 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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