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Our top choices for Chestertown cottages
1. Chesapeake Cottages- 2 Quaint Waterfront Retreats
Chesapeake Cottages- 2 Quaint Waterfront RetreatsPasadena
9.6 out of 10, Exceptional, (24 reviews)
9.6/10
Exceptional
(24 reviews)
"Excellent Property"
"Excellent Property"
Buu T.
$554 nightly
The price is $632
$632 total
Nov 11 - Nov 12
Total with taxes and fees
2. Secluded Cozy Cottage in Historic Downtown
Secluded Cozy Cottage in Historic DowntownHistoric District
9.6 out of 10, Exceptional, (24 reviews)
9.6/10
Exceptional
(24 reviews)
"The cottage was perfectly located in the heart of Annapolis. It has many eclectic decorations throughout out it. We enjoyed our stay."
"The cottage was perfectly located in the heart of Annapolis. It has many eclectic decorations throughout out it. We enjoyed our stay."Bridget C.
$624 nightly
The price is $711
$711 total
Nov 11 - Nov 12
Total with taxes and fees
3. Lakefront Home Firepit BWI Marleycreek River
Lakefront Home Firepit BWI Marleycreek River3.0 star property
Marley
$284 nightly
The price is $324
$324 total
Nov 11 - Nov 12
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.
Learn more about Chestertown
Colonial charm meets Chesapeake Bay beauty in this historic waterfront town where 18th-century buildings house art galleries and boutiques. Rent kayaks to explore the Chester River or time your visit for the Downrigging Weekend Festival when tall ships transform the harbor.
Top reviews in Chestertown
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
Driftwood Inn
Driftwood InnChestertown
10/10 Excellent
Nice spot....you can walk to wherever you want....
Nice spot....you can walk to wherever you want....
Anonymous traveler
Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & MarinaGrasonville
10/10 Excellent
Loved it
Loved it
Joe
Hampton Inn & Suites Edgewood/Aberdeen-South
Hampton Inn & Suites Edgewood/Aberdeen-SouthEdgewood
10/10 Excellent
Lovely clean hotel with nice breakfast options. Clean & comfortable accommodations and polite and welcoming staff.
Lovely clean hotel with nice breakfast options. Clean & comfortable accommodations and polite and welcoming staff.
John
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
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
Holiday Inn Express White Marsh by IHG
Holiday Inn Express White Marsh by IHGNottingham
10/10 Excellent
EVERYTHING WAS PERFECT, I love housekeeping come by even during the stay and clean the property WAS AMAZINGLY CLEAN and quiet.
EVERYTHING WAS PERFECT, I love housekeeping come by even during the stay and clean the property WAS AMAZINGLY CLEAN and quiet.
Francis
134 Prince - Luxury Boutique Hotel
134 Prince - Luxury Boutique HotelAnnapolis
10/10 Excellent
Lovely room, comfy bed, great bathroom! Only complaint was that it was SO hot in the room and it was challenging to adjust that even after receiving instructions. Breakfast and coffee was excellent!
Lovely room, comfy bed, great bathroom! Only complaint was that it was SO hot in the room and it was challenging to adjust that even after receiving instructions. Breakfast and coffee was excellent!
Reyna
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
86 State Circle - Luxury Boutique Hotel
86 State Circle - Luxury Boutique HotelHistoric District
10/10 Excellent
The property was immaculate! The room we stayed (Chase suite) was gorgeous!!
The staff were so wonderful and helpful and the location was perfect. Loved everything about this property
The property was immaculate! The room we stayed (Chase suite) was gorgeous!!
The staff were so wonderful and helpful and the location was perfect. Loved everything about this property
MARA
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
SpringHill Suites Baltimore White Marsh/Middle River
SpringHill Suites Baltimore White Marsh/Middle RiverMiddle River
10/10 Excellent
We like how close it is to the shopping center, but that it's in a quieter area. This was our second time there and the cleanliness of the bathroom was a little disappointing but otherwise it was good.
We like how close it is to the shopping center, but that it's in a quieter area. This was our second time there and the cleanliness of the bathroom was a little disappointing but otherwise it was good.
Rachael
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
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 Express & Suites Middletown by IHG
Holiday Inn Express & Suites Middletown by IHGMiddletown
10/10 Excellent
Clean room, and a breakfast. No issues at all.
Clean room, and a breakfast. No issues at all.
Paula
Frequently Asked Questions
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What is there to do in Chestertown near my cottage?
If you'd like to fill up your itinerary in Chestertown, find your way to Rolphs Wharf Marina. It's a winner with locals and tourists alike.