Title: Book The Best Hotels in Chestertown, MD for 2025 from CA $77 - Fully Refundable Options - Expedia.ca

 

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![Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA](https://images.trvl-media.com/place/7215/2810851e-b7cc-4dfb-bf7e-dc0611ab1b49.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Find hotels in Chestertown, MD from CA $77

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## Go beyond your typical stay in Chestertown

Pet friendly

[](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=2025-12-14&d1=2025-12-14&endDate=2025-12-16&d2=2025-12-16&amenities=PETS)

Pool

[](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=2025-12-14&d1=2025-12-14&endDate=2025-12-16&d2=2025-12-16&amenities=POOL)

Hot tub

[](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=2025-12-14&d1=2025-12-14&endDate=2025-12-16&d2=2025-12-16&amenities=HOT_TUB)

House­boat

[](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=2025-12-14&d1=2025-12-14&endDate=2025-12-16&d2=2025-12-16&lodging=HOUSE_BOAT)

Cottage

[](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=2025-12-14&d1=2025-12-14&endDate=2025-12-16&d2=2025-12-16&lodging=COTTAGE)

Family friendly

[](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=2025-12-14&d1=2025-12-14&endDate=2025-12-16&d2=2025-12-16&travelerType=family_friendly)

Apart­ment

[](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=2025-12-14&d1=2025-12-14&endDate=2025-12-16&d2=2025-12-16&lodging=APARTMENT)

Waterpark

[](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=2025-12-14&d1=2025-12-14&endDate=2025-12-16&d2=2025-12-16&amenities=WATER_PARK)

## Check prices for these dates

Tonight

[Nov 30 - Dec 1](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-11-30&endDate=2025-12-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 1 - Dec 2](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-12-01&endDate=2025-12-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-12-05&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Compare 1,086 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

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

![Lobby](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/b0d84a77.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/da06d995.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/9a7a154a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Comfort Inn & Suites Chestertown

Chestertown

8.6/10

Excellent

(857)

"The room was a great size and very clean. The staff were very accommodating and friendly. The amenities were very good. We would definitely recommend this hotel. "

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

Santa

CA $143

CA $158 total

includes taxes & fees

Dec 4 - Dec 5

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

![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)

![Lobby lounge](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/799945fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/cbce9d0c.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)

### Red Roof Inn & Suites Chestertown

Chestertown

7.2/10

Good

(417)

"This property was clean but dated. The carpet was stained, the furniture and fixtures were worn and broken, towels were washed but old and in need of replacement."

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

Derek

CA $101

CA $112 total

includes taxes & fees

Dec 7 - Dec 8

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

![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)

![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)

![Point of interest](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/01b06110.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/72a73d25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Lodge at Great Oak Landing

Chestertown

8.0/10

Very good

(76)

"Very nice rooms, "

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

Stephania

CA $138

CA $158 total

includes taxes & fees

Dec 2 - Dec 3

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

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

![Exterior](https://images.trvl-media.com/lodging/5000000/4870000/4862400/4862316/50bc617c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/5000000/4870000/4862400/4862316/5800905c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Driftwood Inn

Chestertown

5.2/10

(175)

"Rooms are clean, staf was helpful "

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

Daryl

CA $89

CA $99 total

includes taxes & fees

Dec 24 - Dec 25

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

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/10000/3900/3897/8051c714.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/3900/3897/5b523daa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/3900/3897/dfe0704f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/3900/3897/b1fff75b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Rossville

7.0/10

Good

(1077)

"Easy check in and out. "

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

Andrew

CA $89

CA $103 total

includes taxes & fees

Dec 9 - Dec 10

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

![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/a8fad934.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/5139c564.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/8e62a1db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/6b94b388.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

9.2/10

Wonderful

(927)

"nice, clean, up to date, budget friendly hotel"

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

mike

CA $111

CA $123 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.Hotel-Information)

![Desk, free WiFi, bed sheets, alarm clocks](https://images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/95fafc76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/abecbdac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/8f6f9db7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/0c88ebfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quality Inn & Suites Bel Air I-95 Exit 77A

Edgewood

7.4/10

Good

(1028)

"Staff was very friendly. "

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

Ashlee

CA $88

CA $99 total

includes taxes & fees

Dec 1 - Dec 2

[](https://www.expedia.ca/Edgewood-Hotels-Quality-Inn-Suites-Bel-Air-I-95-Exit-77A.h4862298.Hotel-Information)

![Restaurant](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/264f48e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/19cae57c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Two queen studio suite](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/4152f194.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/05b80e5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampton Inn & Suites Edgewood/Aberdeen-South

Edgewood

9.4/10

Exceptional

(1013)

"Would stay again"

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

Dena

CA $114

CA $128 total

includes taxes & fees

Dec 21 - Dec 22

[](https://www.expedia.ca/Edgewood-Hotels-Hampton-Inn-Suites-EdgewoodAberdeen-South.h4617887.Hotel-Information)

![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1400000/1395600/1395595/0fca1b7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily full breakfast](https://images.trvl-media.com/lodging/2000000/1400000/1395600/1395595/9f4cdea7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1400000/1395600/1395595/c6592633.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/2000000/1400000/1395600/1395595/4e480368.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Comfort Inn & Suites Aberdeen near APG

Aberdeen

7.8/10

Good

(802)

"The front desk staff were friendly and welcoming!"

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

Bonnie

CA $108

CA $121 total

includes taxes & fees

Dec 21 - Dec 22

[](https://www.expedia.ca/Aberdeen-Hotels-Comfort-Inn-Suites-Aberdeen-Near-APG.h1395595.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/3000000/2410000/2410000/2410000/7de3cb16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/3000000/2410000/2410000/2410000/12e4e2d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/3000000/2410000/2410000/2410000/5c9fbfa2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/3000000/2410000/2410000/2410000/0c8b9f64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Rossville

7.2/10

Good

(1004)

"The reason I booked this hotel was because it had a hot tub and pool. These were both closed for "the season" without notification. If I knew that, I would have booked elsewhere. Everything else was just ok."

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Brian

CA $116

CA $134 total

includes taxes & fees

Dec 22 - Dec 23

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

![Lobby](https://images.trvl-media.com/lodging/1000000/20000/10300/10260/314defe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/20000/10300/10260/58057ff7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Junior Suite (2 Queen Beds with Sofa bed)](https://images.trvl-media.com/lodging/1000000/20000/10300/10260/65534781.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/1000000/20000/10300/10260/a9a9ef59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Best Western Plus Hotel & Conference Center

Medford

7.8/10

Good

(1003)

"Yes I love how the room was, I had an amazing stay, the staff was nice and easy to manage I loved it thank you "

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

Carmen

CA $124

CA $146 total

includes taxes & fees

Dec 14 - Dec 15

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

![Restaurant](https://images.trvl-media.com/lodging/16000000/16000000/15990300/15990289/47756559.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/16000000/16000000/15990300/15990289/0ab02da4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, in-room safe, individually furnished, desk](https://images.trvl-media.com/lodging/16000000/16000000/15990300/15990289/6d549ff2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/16000000/16000000/15990300/15990289/8dff74ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampton Inn & Suites Baltimore/Aberdeen

Aberdeen

9.0/10

Wonderful

(595)

"Wonderful room and location "

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

Caren

CA $126

CA $142 total

includes taxes & fees

Dec 8 - Dec 9

[](https://www.expedia.ca/Aberdeen-Hotels-Hampton-Inn-Suites-BaltimoreAberdeen.h15990289.Hotel-Information)

![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/30000/20100/20063/b1bb9d9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/30000/20100/20063/1c55f3cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/30000/20100/20063/c1cd1534.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lounge](https://images.trvl-media.com/lodging/1000000/30000/20100/20063/ee9bd670.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Americas Best Value Inn Edgewood

Edgewood

5.6/10

(1006)

"I love staying here. The prices are always reasonable, the staff are always so nice & helpful. The area is kept clean there's stores close to this hotel all around so convient! "

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

Christeena

CA $71

CA $80 total

includes taxes & fees

Dec 1 - Dec 2

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

![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/367a733a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/66a1e121.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/e17d8d11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/6468097d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilton Garden Inn Kent Island Marina

Grasonville

9.0/10

Wonderful

(1007)

"Easy parking and check in. Conveniently located within walking distance of some great seafood restaurants. Always an enjoyable stay"

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

Roberta

CA $167

CA $185 total

includes taxes & fees

Dec 7 - Dec 8

[](https://www.expedia.ca/Grasonville-Hotels-Hilton-Garden-Inn-Kent-Island.h1222176.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/60000/50200/50106/180b8972.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 King Bed, Non Smoking (One-Bedroom)](https://images.trvl-media.com/lodging/1000000/60000/50200/50106/fb66f5b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/60000/50200/50106/5177cf8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/60000/50200/50106/a1cb4d24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Super 8 by Wyndham Aberdeen MD

Aberdeen

7.0/10

Good

(857)

"Nice and clean. Staff was friendly. I had no problems whatsoever, and I would stay here again."

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

Shelly

CA $69

CA $77 total

includes taxes & fees

Dec 2 - Dec 3

[](https://www.expedia.ca/Aberdeen-Hotels-Super-8-By-Wyndham-Aberdeen-MD.h50106.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/35e0cb86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/8890e17f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/e60ed5ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/9e72db94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hyatt Place Kent Narrows & Marina

Grasonville

9.4/10

Exceptional

(668)

"My favorite hotel "

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

Jen

CA $162

CA $180 total

includes taxes & fees

Dec 2 - Dec 3

[](https://www.expedia.ca/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/600/507/ef21026e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/10000/600/507/0de2177e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/600/507/250ceaaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/600/507/e2e5d244.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Express Aberdeen by IHG

Aberdeen

8.6/10

Excellent

(426)

"Kid friendly for sure! The room and hotel is clean and comfy, no complaints! Chlorine smell a bit strong in pool area but it didn’t bother me. We missed breakfast so not sure about that but everything else was great!"

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

Gabrielle

CA $180

CA $202 total

includes taxes & fees

Dec 1 - Dec 2

[](https://www.expedia.ca/Aberdeen-Hotels-Holiday-Inn-Express-Aberdeen.h507.Hotel-Information)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/2000000/1890000/1888500/1888500/8434bf12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1890000/1888500/1888500/ad2aa516.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Business centre](https://images.trvl-media.com/lodging/2000000/1890000/1888500/1888500/7c3be532.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1890000/1888500/1888500/0dd46a2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Fairfield Inn & Suites by Marriott White Marsh

Nottingham

8.6/10

Excellent

(1007)

"Great place to stay"

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

brian

CA $127

CA $147 total

includes taxes & fees

Dec 7 - Dec 8

[](https://www.expedia.ca/Baltimore-Hotels-Fairfield-Inn-Suites-By-Marriott-White-Marsh.h1888500.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/50000/49900/49889/dd2808c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Combined shower/tub, hair dryer, towels](https://images.trvl-media.com/lodging/1000000/50000/49900/49889/304c53d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/1000000/50000/49900/49889/2b727b85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/50000/49900/49889/61b9d981.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Super 8 by Wyndham Baltimore/Essex Area

Essex

5.4/10

(409)

"The hotel was great the staff was great very clean "

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

Sean

CA $105

CA $121 total

includes taxes & fees

Dec 1 - Dec 2

[](https://www.expedia.ca/Baltimore-Hotels-Super-8-By-Wyndham-BaltimoreEssex-Area.h49889.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/60000/57100/57004/932b25b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/60000/57100/57004/748fa5a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![One queen bed suite non smoking](https://images.trvl-media.com/lodging/1000000/60000/57100/57004/d9f316c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/60000/57100/57004/b83d6711.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampton Inn Baltimore/White Marsh

Nottingham

7.8/10

Good

(1009)

"Breakfast lady fabulous Staff very friendly "

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

Alan

CA $122

CA $141 total

includes taxes & fees

Dec 9 - Dec 10

[](https://www.expedia.ca/Baltimore-Hotels-Hampton-Inn-BaltimoreWhite-Marsh.h57004.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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-14&endDate=2025-12-15&regionId=7215&adults=2&sort=RECOMMENDED&openPlayBack=true)

![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg)

Save an average of 15% on thousands of hotels when you're signed in

[Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChestertown-Hotels.d7215.Travel-Guide-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChestertown-Hotels.d7215.Travel-Guide-Hotels)

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## 

Black Friday Sale

Limited-time deals: save up to 50% on select hotels

[Book now](https://expedia.ca/deals?rfrr=HTG_BF_PROMO_7215)

## 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 harbour.

[See all hotels in Chestertown](https://www.expedia.ca/Hotel-Search?startDate=2025-12-14&endDate=2025-12-15&adults=2&regionId=7215)

![Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA](https://images.trvl-media.com/place/7215/2810851e-b7cc-4dfb-bf7e-dc0611ab1b49.jpg?impolicy=fcrop&w=900&h=314&p=1&q=high)

### Stay near popular Chestertown attractions

[](https://expedia.ca/Washington-College-Hotels.0-l553248621561000403-0.Travel-Guide-Filter-Hotels)

#### Washington College

Take a campus tour or just explore the area of Washington College, during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.

[See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=553248621561000403)

[](https://expedia.ca/Rolphs-Wharf-Marina-Hotels.0-l553248621561879605-0.Travel-Guide-Filter-Hotels)

#### Rolphs Wharf Marina

Explore the waterfront in Chestertown with a trip to Rolphs Wharf Marina. Take in the festivals in this family-friendly area.

[See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=553248621561879605)

[](https://expedia.ca/Crumpton-Auction-Hotels.0-l553248621532662415-0.Travel-Guide-Filter-Hotels)

#### Crumpton Auction

Take the family on an outing to Crumpton Auction during your trip to Chestertown. Take in the festivals while you're in the area.

[See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=553248621532662415)

[](https://expedia.ca/Historical-Society-Of-Kent-County-Maryland-Hotels.0-l553248621561000400-0.Travel-Guide-Filter-Hotels)

#### Historical Society of Kent County Maryland

You can spend an afternoon exploring the galleries in Historical Society of Kent County Maryland during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.

[See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=553248621561000400)

[](https://expedia.ca/River-Arts-Chestertown-Hotels.0-l553248621532662298-0.Travel-Guide-Filter-Hotels)

#### River Arts Chestertown

Explore the campus of River Arts Chestertown, during your travels in Chestertown. Take in the festivals in this family-friendly area.

[See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=553248621532662298)

[](https://expedia.ca/Wilmer-Park-Hotels.0-l553248621561000402-0.Travel-Guide-Filter-Hotels)

#### Wilmer Park

Wilmer Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Amble around this family-friendly area's riverfront or experience its festivals.

[See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=553248621561000402)

## More cheap stays in Chestertown

![Best Western Plus Hotel & Conference Center](https://images.trvl-media.com/lodging/1000000/20000/10300/10260/314defe9_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Best Western Plus Hotel & Conference Center

5625 O'Donnell Street Baltimore MD

CA $124

CA $146 total

Dec 14 - Dec 15

includes taxes & fees

7.8/10 Good! (1,001 reviews)

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

![Quality Inn & Suites Bel Air I-95 Exit 77A](https://images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/95fafc76_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Quality Inn & Suites Bel Air I-95 Exit 77A

2112a Emmorton Park Road Edgewood MD

CA $88

CA $99 total

Dec 1 - Dec 2

includes taxes & fees

7.2/10 Good! (1,024 reviews)

[](https://expedia.ca/Edgewood-Hotels-Quality-Inn-Suites-Bel-Air-I-95-Exit-77A.h4862298.Hotel-Information)

![Fairfield Inn & Suites by Marriott White Marsh](https://images.trvl-media.com/lodging/2000000/1890000/1888500/1888500/8434bf12_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Fairfield Inn & Suites by Marriott White Marsh

8477 Cordon Way Baltimore MD

CA $127

CA $147 total

Dec 7 - Dec 8

includes taxes & fees

8.4/10 Very Good! (1,005 reviews)

[](https://expedia.ca/Baltimore-Hotels-Fairfield-Inn-Suites-By-Marriott-White-Marsh.h1888500.Hotel-Information)

![Americas Best Value Inn Edgewood](https://images.trvl-media.com/lodging/1000000/30000/20100/20063/b1bb9d9d_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Americas Best Value Inn Edgewood

1709 Edgewood Road Edgewood MD

CA $71

CA $80 total

Dec 1 - Dec 2

includes taxes & fees

5.6/10 (1,004 reviews)

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

![Hampton Inn & Suites Edgewood/Aberdeen-South](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/264f48e5_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Hampton Inn & Suites Edgewood/Aberdeen-South

2110 Emmorton Park Rd Edgewood MD

CA $114

CA $128 total

Dec 21 - Dec 22

includes taxes & fees

9.2/10 Wonderful! (1,009 reviews)

[](https://expedia.ca/Edgewood-Hotels-Hampton-Inn-Suites-EdgewoodAberdeen-South.h4617887.Hotel-Information)

![Comfort Inn & Suites Aberdeen near APG](https://images.trvl-media.com/lodging/2000000/1400000/1395600/1395595/0fca1b7b_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Comfort Inn & Suites Aberdeen near APG

980 Hospitality Way Aberdeen MD

CA $108

CA $121 total

Dec 21 - Dec 22

includes taxes & fees

7.8/10 Good! (799 reviews)

[](https://expedia.ca/Aberdeen-Hotels-Comfort-Inn-Suites-Aberdeen-Near-APG.h1395595.Hotel-Information)

## Hotels in Chestertown with star-rating

![5 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/25600/25559/c6e0103a_z.jpg)

5 Star Hotels

1 properties

[](https://expedia.ca/5Star-Chestertown-Hotels.s50-0-d7215.Travel-Guide-Filter-Hotels)

![4 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/23700/23677/6ae928dd_z.jpg)

4 Star Hotels

2 properties

[](https://expedia.ca/4Star-Chestertown-Hotels.s40-0-d7215.Travel-Guide-Filter-Hotels)

![3 Star Hotels](https://images.trvl-media.com/lodging/20000000/19690000/19681400/19681371/84fffc75_z.jpg)

3 Star Hotels

74 properties

[](https://expedia.ca/3Star-Chestertown-Hotels.s30-0-d7215.Travel-Guide-Filter-Hotels)

![2 Star Hotels](https://images.trvl-media.com/lodging/92000000/91830000/91828000/91827910/6717a2ac_z.jpg)

2 Star Hotels

165 properties

[](https://expedia.ca/2Star-Chestertown-Hotels.s20-0-d7215.Travel-Guide-Filter-Hotels)

## Find out more about Chestertown

### Top reasons to visit Chestertown

-   **Scenic Outdoor Adventures:** Experience beautiful landscapes and recreational activities along the picturesque Chester River.
-   **Charming Downtown:** Stroll along Main Street to discover delightful shops and local attractions.
-   **Rich Historical Experience:** Explore the town's rich heritage through house tours and historic sites.
-   **Festive Community Events:** Enjoy lively holiday activities and festivals that showcase the warmth of the community.
-   **Diverse Accommodation Options:** Find a range of pet-friendly and welcoming stays for all types of travellers.

### Find great hotels near Chestertown

Explore a variety of accommodation options in Chestertown, Maryland, where you can find pet-friendly hotels and motels, perfect for business travellers and those seeking an LGBTQIA welcoming environment. Whether you're looking for vacation rentals, suites, or house rentals, Chestertown offers a range of choices to ensure a comfortable and enjoyable stay in this charming riverside town.

-   **[Quality Inn & Suites Bel Air I-95 Exit 77A:](https://www.expedia.ca/Edgewood-Hotels-Quality-Inn-Suites-Bel-Air-I-95-Exit-77A.h4862298.Hotel-Information)** A prime choice for business travellers, Quality Inn & Suites Bel Air I-95 Exit 77A combines convenience and professionalism. Located 33.8km from Chestertown, this hotel offers an array of amenities designed to cater to business needs, such as meeting rooms, free Wi-Fi, and a business centre. Guests have praised the comfortable rooms, ideal for unwinding after a busy day of meetings, along with complimentary breakfast options to kickstart their mornings. Its strategic location near major highways makes it an excellent stop for those on the go.
-   **[La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A:](https://www.expedia.ca/Edgewood-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Bel-AirI-95-Exit-77A.h1916020.Hotel-Information)** This welcoming hotel, situated 33.8km from Chestertown, is a haven for pet owners and travellers seeking relaxation. La Quinta Inn & Suites features a pet-friendly policy, allowing dogs and cats to stay with their owners, making it perfect for those travelling with furry friends. Guests appreciate the spacious rooms and complimentary breakfast, which provides a delightful start to their day. The hotel also boasts a convenient location near local attractions and dining options, ensuring an enjoyable and hassle-free stay for all.
-   **[Red Roof Inn Aberdeen:](https://www.expedia.ca/Aberdeen-Hotels-Red-Roof-Inn-Aberdeen.h12576.Hotel-Information)** Located 35.4km from Chestertown, Red Roof Inn Aberdeen is a vibrant option for pet-lovers and LGBTQIA-friendly travellers. This hotel not only welcomes pets but also supports an inclusive environment, making it a comfortable choice for all guests. With amenities that allow pets in rooms and a waived fee for service animals, it’s designed with comfort in mind. Guests have highlighted the affordable rates, clean accommodations, and friendly staff, making it a popular choice for those looking for a welcoming getaway.

### Where to stay in and around Chestertown

Chestertown, Maryland, offers a delightful blend of outdoor adventures and rich history, perfect for a family-friendly getaway. Explore charming neighbourhoods and discover friendly resorts that capture the essence of hometown holidays. Enjoy the scenic beauty while soaking in the historical atmosphere, making it an ideal destination for a relaxing weekend escape. Experience the warmth of the community during the holiday season and uncover the hidden gems that make Chestertown a must-visit spot.

-   **[Worton:](https://www.expedia.ca/Worton-Hotels.d3000440948.Travel-Guide-Hotels)** Located a mere 6.4km from Chestertown, Worton offers a charming escape for those seeking outdoor adventures and stunning scenery. While the number of visitors fluctuates throughout the year, the peak seasons in April to May and July draw in nature enthusiasts eager to explore its recreational areas and nearby national parks. With attractions such as beautiful beaches and marinas, Worton is perfect for a leisurely day of exploration or fun-filled activities on the water.
-   **[Georgetown:](https://www.expedia.ca/Georgetown-Hotels.d553248635975874069.Travel-Guide-Hotels)** Nestled in the vicinity of Chestertown, Georgetown is a quaint village that captivates visitors with its romantic outdoor settings and adventurous spirit. The peak tourist months from June to August offer a lively atmosphere, where you can engage in various recreational activities or relax at local recreation centres. Notable landmarks like sports facilities and a stadium enhance the area’s appeal, making it an excellent spot for those looking to combine relaxation with a dash of excitement.
-   **[Tolchester Beach:](https://www.expedia.ca/Tolchester-Beach-Hotels.d553248635975848245.Travel-Guide-Hotels)** As a delightful village close to Chestertown, Tolchester Beach is an ideal destination for beach lovers and those yearning for natural beauty. While it experiences consistent visitor numbers throughout the year, summer months from June to August are particularly popular. Enjoy leisurely strolls along the boardwalk or take advantage of the recreational areas and nearby marinas. With its proximity to national parks and serene beaches, Tolchester Beach promises a refreshing getaway filled with outdoor enjoyment.

### Things to do in and around Chestertown

Chestertown, Maryland, is perfect for an outdoor getaway, offering beautiful scenery and a range of activities. Visitors can enjoy house tours, explore recreational areas, stroll along the boardwalk, and participate in festival events. The downtown area hosts festive holiday activities, making it an ideal spot for a weekend escape or day trip, ensuring a delightful experience for all who visit.

**Shopping**

In Chestertown, you can enjoy local shops and boutiques for unique gifts. If you're up for a drive, visit the [Queenstown Premium Outlets](https://www.expedia.ca/Queenstown-Premium-Outlets-Hotels.0-l553248621532662352-0.Travel-Guide-Filter-Hotels), located 27.4km away, for brand-name bargains. [Paul Reed Smith Guitars](https://www.expedia.ca/Paul-Reed-Smith-Guitars-Hotels.0-l747757786500468736-0.Travel-Guide-Filter-Hotels), 33.8km away, offers a unique shopping experience for music enthusiasts.

**Recreation**

At [Ripken Stadium](https://www.expedia.ca/Ripken-Stadium-Hotels.0-l6145161-0.Travel-Guide-Filter-Hotels), you can immerse yourself in the vibrant sports atmosphere while enjoying various recreational events. Meanwhile, the [Queenstown Harbor Golf Club](https://www.expedia.ca/Queenstown-Harbor-Golf-Club-Hotels.0-l6091731-0.Travel-Guide-Filter-Hotels) and [Queenstown Harbor Golf Links](https://www.expedia.ca/Queenstown-Harbor-Golf-Links-Hotels.0-l553248621532662350-0.Travel-Guide-Filter-Hotels) offer beautiful outdoor settings for a relaxing yet active day on the greens, surrounded by nature's beauty.

**Adventure**

At the [Annapolis Sailing School](https://www.expedia.ca/Annapolis-Sailing-School-Hotels.0-l553248621532662324-0.Travel-Guide-Filter-Hotels), located 45.1km from Chestertown, you can immerse yourself in thrilling sailing experiences on the beautiful Chesapeake Bay. Alternatively, the Emmorton Recreation & Tennis Center, 38.6km away, offers various engaging recreational activities, while the Tose Family Tennis Center, also 45.1km away, boasts fantastic tennis facilities.

**Nightlife**

In Chestertown, the [Garfield Center for the Arts at the Prince Theater](https://www.expedia.ca/Garfield-Center-For-The-Arts-At-The-Prince-Theater-Hotels.0-l553248621561000401-0.Travel-Guide-Filter-Hotels) offers vibrant performances in a charming atmosphere. Just a short drive away, [Church Hill Theatre](https://www.expedia.ca/Church-Hill-Theatre-Hotels.0-l844528418122231808-0.Travel-Guide-Filter-Hotels) and [Avalon Theatre](https://www.expedia.ca/Avalon-Theatre-Hotels.0-l6286426-0.Travel-Guide-Filter-Hotels) also provide engaging shows, each with a touch of culture and romance, perfect for a delightful evening out.

*\*Distances are measured in a straight line; actual driving distances may vary depending on the route.*

### Booking tips and Expedia advantages for Chestertown

For a budget-friendly trip to Chestertown, consider visiting between January to February or November for lower accommodation rates. Tuesdays are the cheapest days to stay, while Saturdays tend to be pricier. Use Expedia’s search tool to find budget options, including eco-friendly hotels, and filter by price to uncover the best deals. Additionally, you can save money by bundling your hotel, flights, and activities into an Expedia package. Don’t forget to explore free local attractions to enhance your experience while keeping costs down.

-   **The most and least expensive months on average to stay in a hotel:** The cheapest months to stay in Chestertown are January to February and November, where the prices are slightly lower. This is in comparison to June to July and October, where prices are slightly higher.
-   **The most and least expensive days on average to stay in a hotel:** The least expensive day to stay in Chestertown is Tuesday. The most expensive day to stay in Chestertown is Saturday.
-   **Find cheap hotels on Expedia:** Utilize Expedia’s search tool to customize your travel preferences, such as your budget, desired location, and preferred type of accommodation. For instance, selecting the Eco-certified option will showcase sustainable and environmentally-friendly hotels that are currently available. To find the best prices and deals, simply sort the price filter from lowest to highest.
-   **Consider bundling your trip:** You can save some money by combining your Chestertown hotel reservation with your flights and activities through an Expedia package.

### Find the best attractions in Chestertown

Chestertown, Maryland, offers a delightful mix of outdoor adventures and scenic beauty, perfect for a family beach vacation. Visitors can explore urban parks, marinas, and the picturesque Chester River. A stroll down Main Street Chestertown reveals charming shops and local attractions, making it an ideal destination for those seeking a relaxing getaway in nature.

-   **[Washington College:](https://www.expedia.ca/Washington-College-Hotels.0-l553248621561000403-0.Travel-Guide-Filter-Hotels)** Experience the charm of this historic institution, renowned for its picturesque campus and rich cultural heritage. Engage in various events, art exhibitions, and lectures that showcase the vibrant academic community.
-   **[Rolphs Wharf Marina:](https://www.expedia.ca/Rolphs-Wharf-Marina-Hotels.0-l553248621561879605-0.Travel-Guide-Filter-Hotels)** Dive into outdoor adventures at this scenic marina. Enjoy kayaking, paddleboarding, or simply relaxing by the water's edge, surrounded by beautiful beach vibes and stunning views of the Chester River.
-   **[Historical Society of Kent County Maryland:](https://www.expedia.ca/Historical-Society-Of-Kent-County-Maryland-Hotels.0-l553248621561000400-0.Travel-Guide-Filter-Hotels)** Discover the local history at this engaging museum. Explore fascinating exhibits that highlight the region's past, offering insight into the culture and traditions of Kent County.

### Best time to go to Chestertown

The best time to visit Chestertown is dependant on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with light rain.

| **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** |
| --- | --- | --- | --- | --- | --- |
| January | 34.2°F (1.2°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low |
| February | 36.9°F (2.7°C) | Light Rain | Mostly Sunny | Average | Slightly Low |
| March | 43.7°F (6.5°C) | Light Rain | Mostly Sunny | Average | Average |
| April | 54.3°F (12.4°C) | Light Rain | Mostly Sunny | Slightly High | Average |
| May | 63.7°F (17.6°C) | Light Rain | Mostly Sunny | Average | Average |
| June | 72.1°F (22.3°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High |
| July | 77.4°F (25.2°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High |
| August | 75.6°F (24.2°C) | Light Rain | Mostly Sunny | Average | Average |
| September | 69.4°F (20.8°C) | Light Rain | Mostly Sunny | Average | Average |
| October | 59.2°F (15.1°C) | Light Rain | Mostly Sunny | Average | Slightly High |
| November | 47.3°F (8.5°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low |
| December | 40.1°F (4.5°C) | Light Rain | Mostly Sunny | Slightly Low | Average |

### The nearest major airports for your trip to Chestertown

Chestertown, Maryland, can be conveniently accessed via three major airports. Washington, DC ([DCA](https://www.expedia.ca/Ronald-Reagan-Washington-National-Airport-Hotels.0-aDCA-0.Travel-Guide-Filter-Hotels)\-Ronald Reagan Washington National) is located 93.3km away, with notable hotels like the 5-star InterContinental Washington D.C. - The Wharf and [Riggs Washington DC](https://www.expedia.ca/Washington-Hotels-Riggs-Washington-DC.h37192042.Hotel-Information), both within 4.8km. Baltimore, MD ([BWI](https://www.expedia.ca/Baltimore-Washington-Intl-Thurgood-Marshall-Airport-Hotels.0-aBWI-0.Travel-Guide-Filter-Hotels)\-Baltimore Washington Intl. Thurgood Marshall) is closer at 51.5km, featuring luxurious options such as the [Sagamore Pendry Baltimore](https://www.expedia.ca/Baltimore-Hotels-Sagamore-Pendry-Baltimore.h17395897.Hotel-Information) and [Four Seasons Hotel Baltimore](https://www.expedia.ca/Baltimore-Hotels-Four-Seasons-Hotel-Baltimore.h4603198.Hotel-Information), both 12.9km from the airport, offering shuttle services. Lastly, Baltimore, MD ([MTN](https://www.expedia.ca/Martin-State-Airport-Hotels.0-aMTN-0.Travel-Guide-Filter-Hotels)\-Martin State) lies 32.2km away, with hotels like [Canopy by Hilton Baltimore Harbor Point](https://www.expedia.ca/Baltimore-Hotels-Canopy-By-Hilton-Baltimore-Harbor-Point.h45976006.Hotel-Information) and [Hyatt Place Baltimore Inner Harbor](https://www.expedia.ca/Baltimore-Hotels-Hyatt-Place-Baltimore-Inner-Harbor.h8842065.Hotel-Information), both around 16.1km from the airport.

## Recent reviews of Chestertown hotels

![Courtyard by Marriott Baltimore Downtown/McHenry Row](https://images.trvl-media.com/lodging/43000000/42120000/42119100/42119031/fba8c798_y.jpg)

### Courtyard by Marriott Baltimore Downtown/McHenry Row

5/5 Excellent

"The staff was wonderful."

A verified traveller stayed at Courtyard by Marriott Baltimore Downtown/McHenry Row

Posted 2 days ago

[](https://expedia.ca/Holabird-Industrial-Park-Hotels-Courtyard-By-Marriott-Baltimore-DowntownMcHenry-Row.h42119031.Hotel-Information)

![Comfort Inn & Suites Chestertown](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/a1387f46_y.jpg)

### Comfort Inn & Suites Chestertown

5/5 Excellent

"Excellent hotel. Will stay there anytime I travel to the area."

A verified traveller stayed at Comfort Inn & Suites Chestertown

Posted 4 days ago

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

5/5 Excellent

"Amazing hotel, staff was great. It was clean and I will be returning "

A verified traveller stayed at Best Western Plus Hotel & Conference Center

Posted 4 days ago

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

![La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A](https://images.trvl-media.com/lodging/2000000/1920000/1916100/1916020/f387b1aa_y.jpg)

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

5/5 Excellent

"Convenient, clean and friendly courteous staff."

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

Posted 5 days ago

[](https://expedia.ca/Edgewood-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Bel-AirI-95-Exit-77A.h1916020.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

5/5 Excellent

"Convenient location to John Hopkins Bayview campus "

A verified traveller stayed at Hampton Inn Baltimore Bayview Campus

Posted 5 days ago

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

![SpringHill Suites Baltimore White Marsh/Middle River](https://images.trvl-media.com/lodging/24000000/23690000/23686900/23686806/ac399738_y.jpg)

### SpringHill Suites Baltimore White Marsh/Middle River

5/5 Excellent

"Excellent stay and service "

A verified traveller stayed at SpringHill Suites Baltimore White Marsh/Middle River

Posted 5 days ago

[](https://expedia.ca/Baltimore-Hotels-SpringHill-Suites-Baltimore-White-MarshMiddle-River.h23686806.Hotel-Information)

![Quality Inn & Suites Bel Air I-95 Exit 77A](https://images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/95fafc76_y.jpg)

### Quality Inn & Suites Bel Air I-95 Exit 77A

5/5 Excellent

"Yes "

A verified traveller stayed at Quality Inn & Suites Bel Air I-95 Exit 77A

Posted 6 days ago

[](https://expedia.ca/Edgewood-Hotels-Quality-Inn-Suites-Bel-Air-I-95-Exit-77A.h4862298.Hotel-Information)

![Americas Best Value Inn Edgewood](https://images.trvl-media.com/lodging/1000000/30000/20100/20063/b1bb9d9d_y.jpg)

### Americas Best Value Inn Edgewood

5/5 Excellent

"Great "

A verified traveller from Baltimore stayed at Americas Best Value Inn Edgewood

Posted 6 days ago

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

![Hampton Inn & Suites Edgewood/Aberdeen-South](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/264f48e5_y.jpg)

### Hampton Inn & Suites Edgewood/Aberdeen-South

5/5 Excellent

"The entire property was clean, and the staff was very courteous. I definitely will be staying here the next time I'm in town!"

A verified traveller stayed at Hampton Inn & Suites Edgewood/Aberdeen-South

Posted 6 days ago

[](https://expedia.ca/Edgewood-Hotels-Hampton-Inn-Suites-EdgewoodAberdeen-South.h4617887.Hotel-Information)

## Frequently asked questions

### What is the best area to stay in Chestertown?

> Great Oak Landing is the premier area to stay in Chestertown, Maryland, highly favoured by our travellers. Nestled along the picturesque Chester River, this serene neighbourhood offers stunning waterfront views and easy access to nature's beauty. Guests can enjoy leisurely strolls along the riverwalk or explore the nearby parks, making it a fantastic spot for outdoor enthusiasts.
> 
>   
> 
> For couples seeking a tranquil escape, Great Oak Landing provides a romantic backdrop for quality time together. Imagine sipping coffee on your private balcony while watching the sunrise over the water or enjoying a sunset picnic on the riverbank. The intimate setting is great for creating cherished memories.
> 
>   
> 
> Families will also appreciate the area, as it combines relaxation with family-friendly activities. The spacious rooms and proximity to local attractions mean there's something for everyone, from exploring the charming town centre to engaging in water sports on the Chester River.

### What are the best hotels in Chestertown that travellers recommend?

> [The Lodge at Great Oak Landing](https://www.expedia.ca/Chestertown-Hotels-The-Lodge-At-Great-Oak-Landing.h96826266.Hotel-Information) is a charming getaway in Chestertown, rated 7.8 by guests. This hotel offers a picturesque setting with an onsite golf course, superb for those looking to enjoy a leisurely game amidst stunning natural surroundings. The attentive staff and friendly setting create a lovely retreat for all visitors.

### What are the best family hotels in Chestertown?

> [The Lodge at Great Oak Landing](https://www.expedia.ca/Chestertown-Hotels-The-Lodge-At-Great-Oak-Landing.h96826266.Hotel-Information) in Chestertown is a delightful option for families seeking a relaxing getaway. This charming property boasts a refreshing pool, great for kids to splash around and enjoy sunny days, along with a playground that guarantees endless fun for the little ones. Find more [child-friendly accommodations in Chestertown](https://www.expedia.ca/Chestertown-Hotels-Family-Hotel.0-0-d7215-tFamilyHotel.Travel-Guide-Filter-Hotels).

### What are the best budget hotels in Chestertown?

> For travellers seeking budget-friendly accommodations in Chestertown, the [Comfort Inn & Suites Chestertown](https://www.expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) stands out with an excellent review score of 8.6. This inviting hotel offers a range of family-friendly amenities, including a seasonal outdoor pool and complimentary breakfast, ensuring a delightful start to your day. Families will appreciate the child-friendly window design and the availability of cribs, making it a great choice for those traveling with little ones. Plus, the convenience of free WiFi and self-parking adds to the overall value.
> 
>   
> 
> Another excellent option is the [Red Roof Inn & Suites Chestertown](https://www.expedia.ca/Chestertown-Hotels-Red-Roof-Inn-Suites-Chestertown.h40352.Hotel-Information), which scores a solid 7.4 in guest reviews. This hotel also provides a inviting space for families, featuring free cribs and a sofa bed that can accommodate larger groups. The free long-distance calls and in-room internet make it easy to stay connected during your travels. Located in the historical district, this property offers unique charm alongside practicality without breaking the bank.
> 
>   
> 
> For those interested in a slightly different experience, [The Lodge at Great Oak Landing](https://www.expedia.ca/Chestertown-Hotels-The-Lodge-At-Great-Oak-Landing.h96826266.Hotel-Information), with a review score of 7.8, caters well to couples and those looking for a scenic getaway. Nestled by the water, it features a shared outdoor pool and beachfront access, great for romantic strolls on the sand. Golf enthusiasts will also find delight in the on-site golf course, adding an adventurous twist to their stay. View all [budget hotels in Chestertown](https://www.expedia.ca/Chestertown-Hotels-Cheap-Hotels.0-0-d7215-tCheapHotels.Travel-Guide-Filter-Hotels).

### When is the best time to go to Chestertown?

> The most popular time to visit Chestertown is during the vibrant summer months, particularly July. With average temperatures reaching around 28°C, this is when the town truly comes alive with outdoor activities, festivals, and events. The warm weather invites visitors to enjoy the scenic waterfront, explore the charming streets filled with historic architecture, and take part in local celebrations.
> 
>   
> 
> As you plan your visit, bear in mind that the peak tourist season runs from June to August. This bustling time offers a plethora of activities, from boating on the Chester River to strolling through the lively farmers' market. The atmosphere is electric, with plenty of opportunities for outdoor dining, allowing you to savour local seafood while soaking up the sun. Engaging with the local community at various events can enhance your experience, making it a memorable adventure.
> 
>   
> 
> For those who prefer a quieter experience, consider visiting Chestertown in the shoulder season of late September or early October. The weather remains pleasant, with temperatures around 22°C, and you can enjoy the stunning autumn foliage without the summer crowds. It's an excellent time for leisurely walks along the river or visiting nearby wineries, where you can indulge in tastings amidst beautiful fall scenery.

### Can I cancel my hotel reservation on Expedia?

> You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Chestertown.

### How can I save on a Chestertown hotel booking with Expedia?

> Before booking your Chestertown hotel, remember to join Expedia's free travel rewards program. Just sign up and sign in to access our lowest Member Prices as well as members-only perks. You could also enjoy savings by bundling together your hotel and flights on Expedia.

### How much is the nightly rate at a Chestertown hotel?

> Prices for hotels in Chestertown often vary, but you can find a great deal from CA $77 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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-   [Aparthotels in White Crystal Beach](https://www.expedia.ca/White-Crystal-Beach-Apart-Hotels.d553248635975865930-aaApartHotels.Travel-Guide-Accommodation)
-   [B&B in White Crystal Beach](https://www.expedia.ca/White-Crystal-Beach-Bed-And-Breakfast.d553248635975865930-aaBedAndBreakfast.Travel-Guide-Accommodation)
-   [Cottages in White Crystal Beach](https://www.expedia.ca/White-Crystal-Beach-Cottages.d553248635975865930-aaCottages.Travel-Guide-Accommodation)
-   [White Crystal Beach Hotels](https://www.expedia.ca/White-Crystal-Beach-Hotels.d553248635975865930.Travel-Guide-Hotels)
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-   [Wye Mills Hotels](https://www.expedia.ca/Wye-Mills-Hotels.d6359185.Travel-Guide-Hotels)

-   [Flights from Gunpowder](https://www.expedia.ca/lp/flights/3000347895/flights-from-gunpowder)
-   [Flights from Kennedyville](https://www.expedia.ca/lp/flights/3000440679/flights-from-kennedyville)
-   [Flights from Massey](https://www.expedia.ca/lp/flights/3000440702/flights-from-massey)
-   [Flights from Barclay](https://www.expedia.ca/lp/flights/553248634998993874/flights-from-barclay)
-   [Flights from Aberdeen Proving Ground](https://www.expedia.ca/lp/flights/553248634999428212/flights-from-aberdeen-proving-ground)
-   [Flights from Centreville](https://www.expedia.ca/lp/flights/88125/flights-from-centreville)

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-   [Wilmer Park](https://www.expedia.ca/Wilmer-Park-Chestertown.d553248621561000402.Vacation-Attraction)

-   [Car rental Centreville](https://www.expedia.ca/Car-Rentals-In-Centreville.d88125.Car-Rental-Guide)
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-   [Centreville Vacation Rentals](https://www.expedia.ca/Centreville-Vacation-Rentals.d88125.Travel-Guide-VacationRentals)

-   [Book Hotels in Chestertown on Expedia.com](https://www.expedia.com/Chestertown-Hotels.d7215.Travel-Guide-Hotels)

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