Title: Top Chestertown Cabin Rentals | Expedia.ca

[Hotels in Chestertown](https://expedia.ca/Chestertown-Hotels.d7215.Travel-Guide-Hotels)[Vacation Rentals in Chestertown](https://expedia.ca/Chestertown-Vacation-Rentals.d7215.Travel-Guide-VacationRentals)[Flights to Chestertown](https://expedia.ca/Cheap-Flights-To-Chestertown.d7215.Travel-Guide-Flights)[Chestertown Car Rentals](https://expedia.ca/Car-Rentals-In-Chestertown.d7215.Car-Rental-Guide)[Chestertown Vacation Packages](https://expedia.ca/Chestertown.d7215.Destination-Travel-Guides)

![Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA](https://images.trvl-media.com/place/7215/2127ed08-151b-4865-9870-3d0463a3d88b.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/7215/2127ed08-151b-4865-9870-3d0463a3d88b.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 26 - Jun 28](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

No exact matches found, but these alternatives could be just right

## Recommended hotels in Chestertown

![Outdoor banquet area](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/e502e1d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private beach nearby, sun loungers, beach volleyball](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/2b5c3ec1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/c765d8e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private beach nearby, sun loungers, beach volleyball](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/b3c72334.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lodge in Chestertown

[](https://www.expedia.ca/Chestertown-Hotels-The-Lodge-At-Great-Oak-Landing.h96826266.Hotel-Information)

7.8/10

Good

(77 reviews)

"Very nice rooms, "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Stephania

CA $148

CA $169 total

includes taxes & fees

Mar 16 - Mar 17

[](https://www.expedia.ca/Chestertown-Hotels-The-Lodge-At-Great-Oak-Landing.h96826266.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/92366292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, in-room safe, free WiFi, bed sheets](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/44ce5b3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/5cb9165d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/c04c0cce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Chestertown

[](https://www.expedia.ca/Chestertown-Hotels-First-Floor-Studio-Apartment-In-Historic-Chestertown.h75854900.Hotel-Information)

9.6/10

Exceptional

(108 reviews)

"Everything was clean and neat and welcoming "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Iriana J.

CA $135

CA $217 total

includes taxes & fees

Mar 5 - Mar 6

[](https://www.expedia.ca/Chestertown-Hotels-First-Floor-Studio-Apartment-In-Historic-Chestertown.h75854900.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/5b16fcee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily full breakfast](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/f2092e85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/3c69f06e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/a1387f46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel in Chestertown

[](https://www.expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information)

8.6/10

Excellent

(879 reviews)

"Polite and kind hotel manager"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Richard

CA $138

CA $154 total

includes taxes & fees

Mar 15 - Mar 16

[](https://www.expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/cbce9d0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, Multiple Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/9028be2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/25360cf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, Multiple Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/17533737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel in Chestertown

[](https://www.expedia.ca/Chestertown-Hotels-Red-Roof-Inn-Suites-Chestertown.h40352.Hotel-Information)

7.2/10

Good

(429 reviews)

"Arrived earlier than expected and the staff was very accommodating and friendly which made for an excellent stay from start to finish. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Linette

CA $111

CA $123 total

includes taxes & fees

Mar 11 - Mar 12

[](https://www.expedia.ca/Chestertown-Hotels-Red-Roof-Inn-Suites-Chestertown.h40352.Hotel-Information)

![Front of property - evening/night](https://images.trvl-media.com/lodging/5000000/4870000/4862400/4862316/4ed42fd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/5000000/4870000/4862400/4862316/w353h265x3y3-b7952ce4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/5000000/4870000/4862400/4862316/7bc031db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/5000000/4870000/4862400/4862316/1af5cb1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Motel in Chestertown

[](https://www.expedia.ca/Chestertown-Hotels-Driftwood-Inn.h4862316.Hotel-Information)

5.2/10

(175 reviews)

"Rooms are clean, staf was helpful "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Daryl

CA $87

CA $96 total

includes taxes & fees

Mar 6 - Mar 7

[](https://www.expedia.ca/Chestertown-Hotels-Driftwood-Inn.h4862316.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/1d7c16b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Business centre](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/c77ff2d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/3217cd56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/758b9b05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel in Grasonville

[](https://www.expedia.ca/Grasonville-Hotels-Best-Western-Kent-Narrows-Inn.h11278.Hotel-Information)

8.0/10

Very good

(1,004 reviews)

"Nice breakfast, cleanroom. Great location."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Wayne

CA $129

CA $143 total

includes taxes & fees

Mar 8 - Mar 9

[](https://www.expedia.ca/Grasonville-Hotels-Best-Western-Kent-Narrows-Inn.h11278.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96440000/96436800/96436702/3140fc7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/97000000/96440000/96436800/96436702/5727e3f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/97000000/96440000/96436800/96436702/17a596d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/97000000/96440000/96436800/96436702/w1242h853x23y0-9531067a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Houseboat in Baltimore

[](https://www.expedia.ca/Baltimore-Hotels-Urban-Water-Escape-Luxe-Houseboat-With-Scenic-Waterfront-Views.h96436702.Hotel-Information)

10/10

Exceptional

(12 reviews)

"Very clean first off I would’ve ate off the floor. Honestly these people have to love what they do to deliver such a 5 star experience "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Anonymous traveller

CA $330

CA $780 total

includes taxes & fees

Mar 10 - Mar 11

[](https://www.expedia.ca/Baltimore-Hotels-Urban-Water-Escape-Luxe-Houseboat-With-Scenic-Waterfront-Views.h96436702.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/cc957ab5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/ab8d2ac9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Chesapeake Suite](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/49daa5e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/76e5fee9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bed & Breakfast in Historic District

[](https://www.expedia.ca/Annapolis-Hotels-Flag-House-Inn.h27530544.Hotel-Information)

9.4/10

Exceptional

(87 reviews)

"The Inn is beautiful and the staff very welcoming. My room was spotless, cozy, and tastefully decorated. The location is directly across the street from the USNA. I skipped breakfast, but the offerings looked lovely. Will definitely stay here again. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Elizabeth

CA $248

CA $283 total

includes taxes & fees

Mar 8 - Mar 9

[](https://www.expedia.ca/Annapolis-Hotels-Flag-House-Inn.h27530544.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/762da084.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/86c425c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/3a482076.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/e5c30638.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Arnold

[](https://www.expedia.ca/Arnold-Hotels-Large-2-Bedroom-House-Private-Parking-Nice-Neighborhood.h89057630.Hotel-Information)

9.4/10

Exceptional

(36 reviews)

"Super clean place, great communication from the host, and home is exactly as described and shown in pictures. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Traci L.

CA $172

CA $436 total

includes taxes & fees

Mar 10 - Mar 11

[](https://www.expedia.ca/Arnold-Hotels-Large-2-Bedroom-House-Private-Parking-Nice-Neighborhood.h89057630.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/a71c8e39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/w1024h678x0y5-f3e384c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/c53ddff2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/e9f923a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Stevensville

[](https://www.expedia.ca/Stevensville-Hotels-Charming-CoastalCountry-Home-W3-Acres-Sauna.h84063895.Hotel-Information)

9.6/10

Exceptional

(34 reviews)

"Great stay, would do it again."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Brandon D.

CA $127

CA $382 total

includes taxes & fees

Mar 8 - Mar 9

[](https://www.expedia.ca/Stevensville-Hotels-Charming-CoastalCountry-Home-W3-Acres-Sauna.h84063895.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/104000000/103190000/103180100/103180013/7109c6c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/104000000/103190000/103180100/103180013/2fa15be2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/104000000/103190000/103180100/103180013/e8d235bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/104000000/103190000/103180100/103180013/e831c339.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Worton

[](https://www.expedia.ca/Worton-Hotels-Cozy-Waterfront-Retreat-With-Private-Dock-And-BeachSleeps-4-Studio-1-Bath.h103180013.Hotel-Information)

10/10

Exceptional

(25 reviews)

"The apartment, including kitchen and bathroom, was very clean. Plenty of linens available for use. Perfect spot for fishing off of their dock. Very pleased with our reservation. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Debbie S.

CA $239

CA $430 total

includes taxes & fees

Mar 5 - Mar 6

[](https://www.expedia.ca/Worton-Hotels-Cozy-Waterfront-Retreat-With-Private-Dock-And-BeachSleeps-4-Studio-1-Bath.h103180013.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/114000000/113300000/113298400/113298347/5b6a5afe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/114000000/113300000/113298400/113298347/01162ab4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113300000/113298400/113298347/e26e59da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/114000000/113300000/113298400/113298347/3d8089a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Havre de Grace

[](https://www.expedia.ca/Havre-De-Grace-Hotels-Cozy-2-Bedroom-Apartment-With-WiFi.h113298347.Hotel-Information)

10/10

Exceptional

(5 reviews)

"It is a warm and welcoming little home away from home. We will be back!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Brittany C.

CA $207

CA $289 total

includes taxes & fees

Mar 9 - Mar 10

[](https://www.expedia.ca/Havre-De-Grace-Hotels-Cozy-2-Bedroom-Apartment-With-WiFi.h113298347.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1790000/1781300/1781239/e1ce6cf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/2000000/1790000/1781300/1781239/735621f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1790000/1781300/1781239/8628f41a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, laptop workspace, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/2000000/1790000/1781300/1781239/b90292fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel in Smyrna

[](https://www.expedia.ca/Dover-Hotels-Quality-Inn.h1781239.Hotel-Information)

7.6/10

Good

(1,004 reviews)

"Great stay"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Edward

CA $110

CA $123 total

includes taxes & fees

Apr 2 - Apr 3

[](https://www.expedia.ca/Dover-Hotels-Quality-Inn.h1781239.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/20000000/19010000/19008100/19008016/1f4387ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/20000000/19010000/19008100/19008016/6a6e65f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/20000000/19010000/19008100/19008016/b0ad5d56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player, offices](https://images.trvl-media.com/lodging/20000000/19010000/19008100/19008016/7fa2b473.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Fells Point

[](https://www.expedia.ca/Baltimore-Hotels-At-Fells-Point-Courtyard-Your-Historically-Restored-Apartment.h19008016.Hotel-Information)

9.6/10

Exceptional

(94 reviews)

"Lenny & his housekeeper Elviea were exceptionally helpful, funny and a delight to be with! I spent two weeks here & it was the best place I've ever stayed compared to my stays in Korea, Ireland & several other US cities. Highly recommend!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Edward J.

CA $94

CA $294 total

includes taxes & fees

Mar 10 - Mar 11

[](https://www.expedia.ca/Baltimore-Hotels-At-Fells-Point-Courtyard-Your-Historically-Restored-Apartment.h19008016.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/57f188cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/80cf0fdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/99582f9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/c77382da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Stevensville

[](https://www.expedia.ca/Stevensville-Hotels-Relax-On-Kent-Island-In-3-Bedroom-Home-WWaterview.h84063656.Hotel-Information)

9.8/10

Exceptional

(43 reviews)

"We had a great stay! The property has everything we needed and host was easy to communicate with "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Stephanie S.

CA $127

CA $382 total

includes taxes & fees

Mar 10 - Mar 11

[](https://www.expedia.ca/Stevensville-Hotels-Relax-On-Kent-Island-In-3-Bedroom-Home-WWaterview.h84063656.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/35000000/34020000/34013500/34013405/269a9c3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player, books, video library](https://images.trvl-media.com/lodging/35000000/34020000/34013500/34013405/03e12ed5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/35000000/34020000/34013500/34013405/e058846a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/35000000/34020000/34013500/34013405/c3a4247f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Perryville

[](https://www.expedia.ca/Perryville-Hotels-Top-Of-The-Chesapeake-Minutes-From-Historic-Charlestown.h34013405.Hotel-Information)

9.8/10

Exceptional

(148 reviews)

"Magical and made tons of family wedding memories. What a perfect house on the river!! We will be booking again"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Mary D.

CA $353

CA $724 total

includes taxes & fees

Mar 5 - Mar 6

[](https://www.expedia.ca/Perryville-Hotels-Top-Of-The-Chesapeake-Minutes-From-Historic-Charlestown.h34013405.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/102000000/102000000/101992200/101992106/w1024h677x0y0-664bab42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/102000000/102000000/101992200/101992106/w423h683x305y0-6862acf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/102000000/102000000/101992200/101992106/w876h683x74y0-d9537acd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/102000000/102000000/101992200/101992106/w509h683x257y0-37962ab6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Millington

[](https://www.expedia.ca/Millington-Hotels-Guest-Suite-For-Up-To-2-In-A-Victorian-On-The-Chester-River.h101992106.Hotel-Information)

9.6/10

Exceptional

(20 reviews)

"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Cynthia C.

CA $93

CA $171 total

includes taxes & fees

Mar 24 - Mar 25

[](https://www.expedia.ca/Millington-Hotels-Guest-Suite-For-Up-To-2-In-A-Victorian-On-The-Chester-River.h101992106.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/081c863e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/c9b926ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/7e2b4765.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/fc34c762.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Historic District

[](https://www.expedia.ca/Annapolis-Hotels-Cozy-2br-Home-W-Parking-In-Downtown-Annapolis.h42019059.Hotel-Information)

10/10

Exceptional

(75 reviews)

"Welcoming host, great location and easy parking "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Chris B.

CA $183

CA $451 total

includes taxes & fees

Mar 24 - Mar 25

[](https://www.expedia.ca/Annapolis-Hotels-Cozy-2br-Home-W-Parking-In-Downtown-Annapolis.h42019059.Hotel-Information)

![View from property](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/53ee3fe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/fd2dd5eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/879c8a94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/a0c80d79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel in Middletown

[](https://www.expedia.ca/Middletown-Hotels-Fairfield-Inn-Suites-By-Marriott-Middletown.h81261283.Hotel-Information)

9.2/10

Wonderful

(351 reviews)

"Consistently a good stay here with helpful staff and comfortable rooms. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Mary

CA $135

CA $150 total

includes taxes & fees

Mar 15 - Mar 16

[](https://www.expedia.ca/Middletown-Hotels-Fairfield-Inn-Suites-By-Marriott-Middletown.h81261283.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/7000000/6710000/6708100/6708043/w3837h2547x3y4-94e4330e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 Queen Bed, Accessible (Hearing)](https://images.trvl-media.com/lodging/7000000/6710000/6708100/6708043/w3837h2561x3y0-b0885367.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 Queen Bed | Living area](https://images.trvl-media.com/lodging/7000000/6710000/6708100/6708043/f0086565.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/7000000/6710000/6708100/6708043/7074520f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel in Aberdeen

[](https://www.expedia.ca/Aberdeen-Hotels-Home2-Suites-By-Hilton-BaltimoreAberdeen.h6708043.Hotel-Information)

8.8/10

Excellent

(350 reviews)

"Awesome staff, very clean, great pool Awesome breakfast!!! All good things"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Patty

CA $133

CA $149 total

includes taxes & fees

Mar 15 - Mar 16

[](https://www.expedia.ca/Aberdeen-Hotels-Home2-Suites-By-Hilton-BaltimoreAberdeen.h6708043.Hotel-Information)

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.

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## Find vacation rentals that suit your style

Private vacation homes

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Cottages

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Condos

[](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America&regionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=CONDO)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America&regionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=APARTMENT)

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America&regionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=CABIN)

Houseboats

[](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America&regionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=HOUSE_BOAT)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America&regionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=VILLA)

Residences

[](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America&regionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=RESIDENCE)

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## Top Chestertown Hotel Reviews

![Hampton Inn Baltimore/Glen Burnie](https://images.trvl-media.com/lodging/1000000/10000/2800/2759/2b57d3ba_y.jpg)

### Hampton Inn Baltimore/Glen Burnie

10/10 Excellent

" Cl"

[](https://expedia.ca/Baltimore-Hotels-Hampton-Inn-BaltimoreGlen-Burnie.h2759.Hotel-Information)

![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg)

### Historic Inns of Annapolis

10/10 Excellent

"Was at Governor Calvert House. Beautiful historic building that is well maintained. Room was clean and comfortable. Parking is minimal, and valet parking is quite expensive, with "dynamic pricing". Hotel is walking distance to many shops and restaurants. Staff was pleasant and accommodating. "

[](https://expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information)

![Holiday Inn Express White Marsh by IHG](https://images.trvl-media.com/lodging/72000000/71540000/71532200/71532135/9b37b4b6_y.jpg)

### Holiday Inn Express White Marsh by IHG

8/10 Good

"Upon arrival, we were greeted with friendly staff with a quick check in. The hotel is very clean, the linens were so comfortable and the beds were too. The room was spacious and the bathroom was very nice. I love that there are Dove products in the bathroom so you don’t have to worry about bringing those things. "

[](https://expedia.ca/Baltimore-Hotels-Holiday-Inn-Express-White-Marsh.h71532135.Hotel-Information)

![La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh](https://images.trvl-media.com/lodging/1000000/10000/3900/3897/40d24dc0_y.jpg)

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

2/10 Terrible

"I had a one night stay at this property, and I came home with bedbugs and bedbug bites all over my body… I actually had to seek medical attention. The condition of the hotel is very poor and disgusting. I believe it serves as a hotel and a homeless shelter in One. Please be aware of this property."

[](https://expedia.ca/Baltimore-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Baltimore-N-White-Marsh.h3897.Hotel-Information)

![Hampton Inn Baltimore Bayview Campus](https://images.trvl-media.com/lodging/24000000/23840000/23830900/23830804/e92cee9e_y.jpg)

### Hampton Inn Baltimore Bayview Campus

2/10 Terrible

"The bed was extremely uncomfortable and the maid came busting in my room no knock or anything."

[](https://expedia.ca/Baltimore-Hotels-Hampton-Inn-Baltimore-Bayview-Campus.h23830804.Hotel-Information)

![Country Inn & Suites by Radisson, Baltimore North, MD](https://images.trvl-media.com/lodging/3000000/2410000/2410000/2410000/7de3cb16_y.jpg)

### Country Inn & Suites by Radisson, Baltimore North, MD

8/10 Good

"The room was nice and clean and the staff was nice and very helpful "

[](https://expedia.ca/Baltimore-Hotels-Country-Inn-Suites-By-Radisson.h2410000.Hotel-Information)

![Best Western Plus Hotel & Conference Center](https://images.trvl-media.com/lodging/1000000/20000/10300/10260/314defe9_y.jpg)

### Best Western Plus Hotel & Conference Center

6/10 Okay

"great price for my CIAA weekend stay"

[](https://expedia.ca/Baltimore-Hotels-Best-Western-Plus-Hotel-Conference-Center.h10260.Hotel-Information)

![Americas Best Value Inn Edgewood](https://images.trvl-media.com/lodging/1000000/30000/20100/20063/ee9bd670_y.jpg)

### Americas Best Value Inn Edgewood

10/10 Excellent

"Super comfortable and quiet "

[](https://expedia.ca/Edgewood-Hotels-Hilltop-Motel.h20063.Hotel-Information)

![Annapolis Waterfront Hotel, Autograph Collection](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/2011e31d_y.jpg)

### Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent

"We liked it"

[](https://expedia.ca/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information)

## Find out more about Chestertown

## Chestertown Cabin Rentals information

| Number of reviews | 4,920           |
| ----------------- | --------------- |
| Accommodation     | 2 Cabin Rentals |
| Lowest Price      | CA $96          |
| Highest Price     | CA $780         |

## Frequently asked questions

### What are the best cabins near Chestertown?

### Are there cheap cabins in Chestertown?

### What are the best family cabins near Chestertown?

### What are the best river cabins near Chestertown?

### What are the best cabins with pools near Chestertown?

### What are some great Chestertown cabins?

### What are the best weekend cabin rentals in Chestertown?

### What are the best cabin prices in Chestertown?

### Can I find log cabins in Chestertown?

### What are the highest-rated cabins in Chestertown?

### What are the top things to see and do in Chestertown?

### Why should I book a cabin in Chestertown?

### What are the top nature cabins in Chestertown?

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