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Our top choices for Chestertown hotels with a pool
1. Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown2.5 star property
Chestertown
8.6 out of 10, Excellent, (1,000 reviews)
8.6/10
Excellent
(1,000 reviews)
- Dive into the seasonal outdoor pool with comfortable loungers and umbrellas at this refreshing hotel retreat in Chestertown.
$97 nightly
The price is $107
$107 total
Dec 6 - Dec 7
Total with taxes and fees
2. Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown2.0 star property
Chestertown
7.2 out of 10, Good, (513 reviews)
7.2/10
Good
(513 reviews)
- Tranquil outdoor pool and inviting lounge chairs offer relaxation after Chestertown exploration.
$72 nightly
The price is $80
$80 total
Nov 17 - Nov 18
Total with taxes and fees
3. La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh3.0 star property
Rossville
7.0 out of 10, Good, (1,263 reviews)
7.0/10
Good
(1,263 reviews)
$67 nightly
The price is $78
$78 total
Nov 15 - Nov 16
Total with taxes and fees
4. The Lodge at Great Oak Landing
The Lodge at Great Oak Landing3.5 star property
Chestertown
8.0 out of 10, Very good, (129 reviews)
8.0/10
Very good
(129 reviews)
- Waterfront lodge's seasonal outdoor pool offers sun-drenched days with loungers and umbrellas.
$124 nightly
The price is $137
$137 total
Nov 11 - Nov 12
Total with taxes and fees
5. Hampton Inn Baltimore/White Marsh
Hampton Inn Baltimore/White Marsh2.5 star property
Nottingham
7.8 out of 10, Good, (1,001 reviews)
7.8/10
Good
(1,001 reviews)
- Dive into Maryland's inviting seasonal outdoor pool with loungers, umbrellas, and fitness center nearby.
$102 nightly
The price is $117
$117 total
Nov 19 - Nov 20
Total with taxes and fees
6. Hilton Garden Inn Kent Island Marina
Hilton Garden Inn Kent Island Marina3.0 star property
Grasonville
8.8 out of 10, Excellent, (1,005 reviews)
8.8/10
Excellent
(1,005 reviews)
- Dive into ultimate bay views with serene indoor pool sessions at this waterfront hotel.
$120 nightly
The price is $133
$133 total
Nov 18 - Nov 19
Total with taxes and fees
7. The Inn at Chesapeake Bay Beach Club
The Inn at Chesapeake Bay Beach Club4.0 star property
Stevensville
9.4 out of 10, Exceptional, (514 reviews)
9.4/10
Exceptional
(514 reviews)
- Dive into summer luxury at this Eastern Shore retreat with a seasonal outdoor pool and personalized spa services.
$204 nightly
The price is $226
$226 total
Dec 9 - Dec 10
Total with taxes and fees
8. The Westin Annapolis
The Westin Annapolis4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,005 reviews)
8.8/10
Excellent
(1,005 reviews)
- Aquatic serenity awaits at this urban hotel with a refreshing indoor pool and full-service spa.
$164 nightly
The price is $187
$187 total
Nov 15 - Nov 16
Total with taxes and fees
9. Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & Marina3.0 star property
Grasonville
9.4 out of 10, Exceptional, (859 reviews)
9.4/10
Exceptional
(859 reviews)
- 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
$149 total
Nov 15 - Nov 16
Total with taxes and fees
10. Hampton Inn & Suites Edgewood/Aberdeen-South
Hampton Inn & Suites Edgewood/Aberdeen-South2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1,004 reviews)
9.4/10
Exceptional
(1,004 reviews)
- 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
$96 total
Nov 22 - Nov 23
Total with taxes and fees
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.
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.
Top Chestertown Hotel Reviews
Inn at Huntingfield Creek
Inn at Huntingfield CreekRock Hall
10/10 Excellent
Quaint property - very laid-back. Exactly what we were looking for.
Quaint property - very laid-back. Exactly what we were looking for.
George
Comfort Inn & Suites Chestertown
Comfort Inn & Suites ChestertownChestertown
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!!
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!!
Laura
The Lodge at Great Oak Landing
The Lodge at Great Oak LandingChestertown
10/10 Excellent
Great place! Clean, comfortable and in a beautiful area. I won’t stay anywhere else when I’m in that area.
Great place! Clean, comfortable and in a beautiful area. I won’t stay anywhere else when I’m in that area.
William
Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & MarinaGrasonville
10/10 Excellent
Loved it
Loved it
Joe
Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHGGrasonville
10/10 Excellent
The staff is friendly and helpful. The pool is refreshing, and I love the benches overlooking the waters and jetty from which you can view a lot of nature. There is always complimentary coffee and tea and apples available as well as filtered water. The best for me is that the property is on the Cross Island Trail so I can enjoy a walk/run or bike ride (you can rent bikes) to Terrapin Nature Park on the other side of Kent Island. It's also a short walk to a handful of great restaurants. We look...
The staff is friendly and helpful. The pool is refreshing, and I love the benches overlooking the waters and jetty from which you can view a lot of nature. There is always complimentary coffee and tea and apples available as well as filtered water. The best for me is that the property is on the Cross Island Trail so I can enjoy a walk/run or bike ride (you can rent bikes) to Terrapin Nature Park on the other side of Kent Island. It's also a short walk to a handful of great restaurants. We look...
Christina
Hilton Garden Inn Bel Air
Hilton Garden Inn Bel AirBel Air
10/10 Excellent
Everything was excellent! Clean room, comfortable bed, friendly and helpful staff. We also enjoyed the pool and the on-site restaurant. Chef Dave’s cooking was delicious, we would go back for dinner even if we weren’t staying there!
Everything was excellent! Clean room, comfortable bed, friendly and helpful staff. We also enjoyed the pool and the on-site restaurant. Chef Dave’s cooking was delicious, we would go back for dinner even if we weren’t staying there!
Ami
The Inn at Chesapeake Bay Beach Club
The Inn at Chesapeake Bay Beach ClubStevensville
10/10 Excellent
Beautiful place, quiet and clean.
Beautiful place, quiet and clean.
Chuck
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MDBel Air
10/10 Excellent
Nice place to stop on the way down to Florida.
Nice place to stop on the way down to Florida.
Lori
Hilton Garden Inn Kent Island Marina
Hilton Garden Inn Kent Island MarinaGrasonville
10/10 Excellent
I had a very nice stay, the room had a very nice view of the Bay.
I had a very nice stay, the room had a very nice view of the Bay.
Kathie
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHGEdgewood
10/10 Excellent
Stay here with two friends. The room was very clean and the beds comfortable. There is an indoor that looked nice though we did not use it. The Front desk guy on checkin was very friendly and helpful
Stay here with two friends. The room was very clean and the beds comfortable. There is an indoor that looked nice though we did not use it. The Front desk guy on checkin was very friendly and helpful
Heather
Kent Island Resort
Kent Island ResortStevensville
10/10 Excellent
I stayed here for a quick overnight and did not utilize many of the amenities however, the staff was incredibly kind overall and with tips on dinner. This place is historic, which is a nice way of saying old but classic. Don’t expect a huge room, the photos portray the room accurately. Some things were a little rickety, but everything was clean. Overall I recommend this if you’re solo or a couple looking for a place as you enjoy the bay.
I stayed here for a quick overnight and did not utilize many of the amenities however, the staff was incredibly kind overall and with tips on dinner. This place is historic, which is a nice way of saying old but classic. Don’t expect a huge room, the photos portray the room accurately. Some things were a little rickety, but everything was clean. Overall I recommend this if you’re solo or a couple looking for a place as you enjoy the bay.
John
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Home2 Suites by Hilton Baltimore / Aberdeen, MDAberdeen
10/10 Excellent
convenient to APG gate snd facilities for longer stays.
convenient to APG gate snd facilities for longer stays.
Terry
Hampton Inn & Suites Baltimore/Aberdeen
Hampton Inn & Suites Baltimore/AberdeenAberdeen
10/10 Excellent
Very clean, comfortable....and great linens on the beds! YAY! Very good breakfast also!
Very clean, comfortable....and great linens on the beds! YAY! Very good breakfast also!
Anonymous traveler
City Express by Marriott Aberdeen
City Express by Marriott AberdeenAberdeen
10/10 Excellent
Great place to stay. Clean, modern. Nice restaurant across the street that was recommended by front desk. Breakfast a disappointment. Sparce selection of choices. Would definitely stay here again.
Great place to stay. Clean, modern. Nice restaurant across the street that was recommended by front desk. Breakfast a disappointment. Sparce selection of choices. Would definitely stay here again.
Pamela
Fairfield Inn & Suites by Marriott Middletown
Fairfield Inn & Suites by Marriott MiddletownMiddletown
10/10 Excellent
Very nice hotel. One breakfast complaint: As with so many hotels, no sense of what tea-drinkers want. A wide selection of flavored "teas" (which are not actually teas), but no simple, normal tea, such as an English Breakfast Tea. This may seen like nit-picking, but it isn't to tea drinkers. You would never treat coffee drinkers this way.
Very nice hotel. One breakfast complaint: As with so many hotels, no sense of what tea-drinkers want. A wide selection of flavored "teas" (which are not actually teas), but no simple, normal tea, such as an English Breakfast Tea. This may seen like nit-picking, but it isn't to tea drinkers. You would never treat coffee drinkers this way.
Anonymous traveler
Holiday Inn Belcamp - Aberdeen Area by IHG
Holiday Inn Belcamp - Aberdeen Area by IHGBelcamp
10/10 Excellent
Loved it very nice. Great staff! Very clean had a great time. Will go back again when I have another trip to Belcamp!
Loved it very nice. Great staff! Very clean had a great time. Will go back again when I have another trip to Belcamp!
Evelyn
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 $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.