Title: Chestertown Guest Houses from CA $81 | 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)

# Search Guest Houses in Chestertown from CA $81

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## Check prices for these dates

Next weekend

[Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-01-16&endDate=2026-01-18&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-01-23&endDate=2026-01-25&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-02-06&endDate=2026-02-08&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-03-06&endDate=2026-03-08&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

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

## Recommended hotels in Chestertown

![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)

![Lobby](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/a1387f46.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/b0d84a77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Comfort Inn & Suites Chestertown

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

Chestertown

8.6/10

Excellent

(864)

"Everything was well!"

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

Ahmed

CA $141

CA $156 total

includes taxes & fees

Feb 1 - Feb 2

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

![Lobby lounge](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/799945fa.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)

![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/1000000/50000/40400/40352/17533737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Red Roof Inn & Suites Chestertown

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

Chestertown

7.2/10

Good

(426)

"Clean and friendly staff. Good location."

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

Robert

CA $99

CA $110 total

includes taxes & fees

Jan 16 - Jan 17

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

![Property grounds](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/w1322h734x2y1-d973a563.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)

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

### First Floor Studio Apartment in Historic Chestertown

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

Chestertown

9.6/10

Exceptional

(108)

"We had a lovely visit. It was nice and quiet and parking was perfect."

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

Anne D.

CA $137

CA $219 total

includes taxes & fees

Jan 20 - Jan 21

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

![Exterior](https://images.trvl-media.com/lodging/1000000/50000/40500/40450/6adbaac3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 1 King Bed, Accessible, Non Smoking (Roll-In Shower)](https://images.trvl-media.com/lodging/1000000/50000/40500/40450/b92b6259.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/50000/40500/40450/678460fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/50000/40500/40450/d850b13a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### La Quinta Inn & Suites by Wyndham Aberdeen-APG

[](https://www.expedia.ca/Aberdeen-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Aberdeen-APG.h40450.Hotel-Information)

Aberdeen

9.0/10

Wonderful

(1000)

"Room was great and staff excellent. "

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

Robert

CA $119

CA $133 total

includes taxes & fees

Jan 10 - Jan 11

[](https://www.expedia.ca/Aberdeen-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Aberdeen-APG.h40450.Hotel-Information)

![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)

![Indoor pool](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/791afcca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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)

### Fairfield Inn & Suites by Marriott Middletown

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

Middletown

9.2/10

Wonderful

(331)

"Clean room, great staff, recommended. "

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

Tom

CA $149

CA $166 total

includes taxes & fees

Jan 25 - Jan 26

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

![Reception](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/38012dd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/b059c3d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![King suite whirlpool | Bathroom](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/4e0f43cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Two queen studio suite | Bathroom](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/1c15dbb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Edgewood

9.4/10

Exceptional

(1000)

"Great stay as always"

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

Linda

CA $112

CA $126 total

includes taxes & fees

Jan 13 - Jan 14

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

![Exterior](https://images.trvl-media.com/lodging/35000000/34800000/34796100/34796045/82e4e131.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/35000000/34800000/34796100/34796045/3cc8ea80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/35000000/34800000/34796100/34796045/6af27243.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room safe, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/35000000/34800000/34796100/34796045/b95d3d92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Express & Suites Middletown by IHG

[](https://www.expedia.ca/Wilmington-Hotels-Holiday-Inn-Express-And-Suites-Middletown.h34796045.Hotel-Information)

Middletown

9.2/10

Wonderful

(653)

"Room was great the staff is so friendly every visit !!!!!"

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

Dennis

CA $124

CA $138 total

includes taxes & fees

Jan 25 - Jan 26

[](https://www.expedia.ca/Wilmington-Hotels-Holiday-Inn-Express-And-Suites-Middletown.h34796045.Hotel-Information)

![Reception](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/f2cc9e28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aerial view](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/a0732bf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Single Room, 1 King Bed](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/a98cfc15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Single Room, Balcony | Terrace/patio](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/2f6490c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Kent Island Resort

[](https://www.expedia.ca/Annapolis-Hotels-The-Waterfront-Historic-Kent-Manor-Inn.h194102.Hotel-Information)

Stevensville

9.2/10

Wonderful

(130)

"Beautiful and peaceful property!"

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

Jerry

CA $175

CA $243 total

includes taxes & fees

Jan 11 - Jan 12

[](https://www.expedia.ca/Annapolis-Hotels-The-Waterfront-Historic-Kent-Manor-Inn.h194102.Hotel-Information)

![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)

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

![Free daily self-serve breakfast](https://images.trvl-media.com/lodging/2000000/1790000/1781300/1781239/817be2e3.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)

### Quality Inn Smyrna

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

Smyrna

7.6/10

Good

(1000)

"Great stay"

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

Edward

CA $94

CA $105 total

includes taxes & fees

Feb 8 - Feb 9

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

![Free daily continental breakfast](https://images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/55af0030.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, free WiFi, bed sheets, alarm clocks](https://images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/f02c23ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/63592edd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/22f9fe46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 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)

Edgewood

7.4/10

Good

(1021)

"Decent place not loud quiet and out of the way."

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

Tarrell

CA $72

CA $81 total

includes taxes & fees

Jan 22 - Jan 23

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

![Lobby](https://images.trvl-media.com/lodging/1000000/900000/891500/891451/1c3a6583.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/900000/891500/891451/96c882ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Business centre](https://images.trvl-media.com/lodging/1000000/900000/891500/891451/fa561265.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Yoga](https://images.trvl-media.com/lodging/1000000/900000/891500/891451/cfd029ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

[](https://www.expedia.ca/Bel-Air-Hotels-Country-Inn-Suites-By-Radisson.h891451.Hotel-Information)

Bel Air

8.8/10

Excellent

(1006)

"We found the overall hotel and surrounding area very nice. "

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

Jacquelyn

CA $109

CA $123 total

includes taxes & fees

Jan 28 - Jan 29

[](https://www.expedia.ca/Bel-Air-Hotels-Country-Inn-Suites-By-Radisson.h891451.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/16000000/16000000/15990300/15990289/164fd394.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/16000000/16000000/15990300/15990289/6f728b82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/16000000/16000000/15990300/15990289/61b7e8fc.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

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

Aberdeen

9.0/10

Wonderful

(609)

"Excellent customer service at the front desk "

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

Mary

CA $113

CA $126 total

includes taxes & fees

Jan 14 - Jan 15

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

![Reception](https://images.trvl-media.com/lodging/3000000/2810000/2804400/2804384/fafda427.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/3000000/2810000/2804400/2804384/1c5b9984.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/3000000/2810000/2804400/2804384/3c250b1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/3000000/2810000/2804400/2804384/18e3859d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilton Garden Inn Aberdeen

[](https://www.expedia.ca/Aberdeen-Hotels-Hilton-Garden-Inn-Aberdeen.h2804384.Hotel-Information)

Aberdeen

8.6/10

Excellent

(635)

"High quality pillows Comfortable bed Clean room Kuerig Big room Strong WiFi Clean shower Good shampoo Excellent towels Plenty of drawers and closet space Comfy chair Great desk space"

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

John

CA $109

CA $122 total

includes taxes & fees

Feb 6 - Feb 7

[](https://www.expedia.ca/Aberdeen-Hotels-Hilton-Garden-Inn-Aberdeen.h2804384.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/7000000/6710000/6708100/6708043/48ed0abe.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)

![Exterior](https://images.trvl-media.com/lodging/7000000/6710000/6708100/6708043/w3837h2547x3y4-94e4330e.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)

### Home2 Suites by Hilton Baltimore / Aberdeen, MD

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

Aberdeen

8.8/10

Excellent

(341)

"Clean room, friendly staff"

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

Julie

CA $123

CA $138 total

includes taxes & fees

Jan 30 - Jan 31

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

![Studio Suite, 1 King Bed with Sofa bed, Non Smoking](https://images.trvl-media.com/lodging/2000000/1920000/1916100/1916020/f387b1aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/2000000/1920000/1916100/1916020/076885b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1920000/1916100/1916020/ab03e0fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1920000/1916100/1916020/5673e9db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 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)

Edgewood

8.2/10

Very good

(1001)

"Delicious breakfast and very spacious rooms. "

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

Jen

CA $93

CA $104 total

includes taxes & fees

Jan 11 - Jan 12

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

![Indoor pool](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/b66763a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/6a6a4995.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/50463ffe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/6cc4a825.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampton Inn Middletown

[](https://www.expedia.ca/Wilmington-Hotels-Hampton-Inn-Middletown.h1485615.Hotel-Information)

Middletown

8.8/10

Excellent

(870)

"Amazing stay"

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

Katiana

CA $131

CA $146 total

includes taxes & fees

Jan 26 - Jan 27

[](https://www.expedia.ca/Wilmington-Hotels-Hampton-Inn-Middletown.h1485615.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/2c8e8566.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/24fa7509.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 1 King Bed, River View](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/4eefada8.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)

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

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

Grasonville

9.2/10

Wonderful

(947)

"It was very comfortable and clean"

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

Maria

CA $131

CA $146 total

includes taxes & fees

Jan 20 - Jan 21

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

![Exterior](https://images.trvl-media.com/lodging/3000000/2360000/2355900/2355869/951120d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room safe, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/3000000/2360000/2355900/2355869/f9e9188e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room safe, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/3000000/2360000/2355900/2355869/355fffa0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room safe, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/3000000/2360000/2355900/2355869/3bc97cb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Candlewood Suites Aberdeen-Bel Air by IHG

[](https://www.expedia.ca/Bel-Air-Hotels-Candlewood-Suites-Aberdeen-Edgewood-Bel-Air.h2355869.Hotel-Information)

Bel Air

8.0/10

Very good

(477)

"The staff is great, roon clean & spacious"

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

Thomas

CA $115

CA $128 total

includes taxes & fees

Jan 10 - Jan 11

[](https://www.expedia.ca/Bel-Air-Hotels-Candlewood-Suites-Aberdeen-Edgewood-Bel-Air.h2355869.Hotel-Information)

![Bar (on property)](https://images.trvl-media.com/lodging/66000000/65330000/65328000/65327947/ff957644.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/66000000/65330000/65328000/65327947/ca9c2666.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/66000000/65330000/65328000/65327947/61316540.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/66000000/65330000/65328000/65327947/1bbd1ca0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilton Garden Inn Bel Air

[](https://www.expedia.ca/Bel-Air-Hotels-Hilton-Garden-Inn-Bel-Air.h65327947.Hotel-Information)

Bel Air

9.2/10

Wonderful

(237)

"Kind staff, very clean. Lovely stay!"

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

Michelle

CA $135

CA $151 total

includes taxes & fees

Jan 23 - Jan 24

[](https://www.expedia.ca/Bel-Air-Hotels-Hilton-Garden-Inn-Bel-Air.h65327947.Hotel-Information)

![Front of property - evening/night](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/986ce82e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/0fbfe277.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/49680cdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/462e7c63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Inn at Chesapeake Bay Beach Club

[](https://www.expedia.ca/Annapolis-Hotels-The-Inn-At-Chesapeake-Bay-Beach-Club.h12402244.Hotel-Information)

Stevensville

9.4/10

Exceptional

(433)

"Beautiful hotel with friendly staff and great food! Comfortable bed, stayed at the Barn. "

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

Rery

CA $215

CA $274 total

includes taxes & fees

Feb 1 - Feb 2

[](https://www.expedia.ca/Annapolis-Hotels-The-Inn-At-Chesapeake-Bay-Beach-Club.h12402244.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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## Top Chestertown Hotel Reviews

![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

10/10 Excellent

"Everything was clea"

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

10/10 Excellent

"Delicious breakfast and very spacious rooms. "

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

![Fairfield Inn & Suites by Marriott Middletown](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/52c8cc19_y.jpg)

### Fairfield Inn & Suites by Marriott Middletown

10/10 Excellent

"Everything at the hotel was excellent. We had a small dog with us and they were very accommodating. And the breakfast over several days was varied and excellent."

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

![Pendry Baltimore](https://images.trvl-media.com/lodging/18000000/17400000/17395900/17395897/45fde7f6_y.jpg)

### Pendry Baltimore

10/10 Excellent

"The hotel was beautiful, and the staff was courteous and friendly. "

[](https://expedia.ca/Baltimore-Hotels-Pendry-Baltimore.h17395897.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

"Very welcoming and room very clean."

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

"Valet parking was excellent. The men doing it were friendly and professional. The room was just the right temperature. "

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

![Home2 Suites by Hilton Baltimore/White Marsh](https://images.trvl-media.com/lodging/6000000/6000000/5992000/5991951/e611db61_y.jpg)

### Home2 Suites by Hilton Baltimore/White Marsh

10/10 Excellent

"Cleanliness, friendly staff. Spacious room. Great breakfast."

[](https://expedia.ca/Baltimore-Hotels-Home2-Suites-By-Hilton-BaltimoreWhite-Marsh.h5991951.Hotel-Information)

![Hilton Garden Inn Baltimore/White Marsh](https://images.trvl-media.com/lodging/1000000/440000/433700/433663/09307c3d_y.jpg)

### Hilton Garden Inn Baltimore/White Marsh

10/10 Excellent

"Room was very clean...staff was nice..."

[](https://expedia.ca/Baltimore-Hotels-Hilton-Garden-Inn-BaltimoreWhite-Marsh.h433663.Hotel-Information)

![Hampton Inn Baltimore/Glen Burnie](https://images.trvl-media.com/lodging/1000000/10000/2800/2759/526c2bf4_y.jpg)

### Hampton Inn Baltimore/Glen Burnie

10/10 Excellent

"Breakfast could have been better. Would have been nice to have fresher options. The suite was great, except one remote wasn’t working."

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

## Find out more about Chestertown

## Chestertown Guest Houses information

| Number of reviews | 13,093          |
| ----------------- | --------------- |
| Accommodation     | 16 Guest Houses |
| Lowest Price      | CA $81          |
| Highest Price     | CA $274         |

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