Title: Chestertown Villas from CA $78 | Expedia.ca

  

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# Search Chestertown Villa Rentals from CA $78

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## Check prices for these dates

In two weeks

[Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-10-31&endDate=2025-11-02&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-11-14&endDate=2025-11-16&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

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

In three months

[Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select Chestertown Villas

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## Recommended hotels in Chestertown

![Room, 1 King Bed with Sofa bed, Marina View](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/3449c94b.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)

![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)

![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)

### The Lodge at Great Oak Landing

Chestertown

7.8/10

Good

(70)

"Everything was perfect. The staff is super friendly, the room was clean and fresh. The beds were super comfy, the food is amazing and the chef was super nice!! Great friendly atmosphere. I’m definitely going back!!"

CA $185

CA $212 total

includes taxes & fees

Oct 14 - Oct 15

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

![Lobby](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/b0d84a77.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)

![1 bedroom, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/959c2292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Comfort Inn & Suites Chestertown

Chestertown

8.6/10

Excellent

(828)

"Friendly staff, clean room, convenient location. "

CA $143

CA $159 total

includes taxes & fees

Oct 19 - Oct 20

[](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)

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

![1 bedroom, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/8b9992bd.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

Chestertown

7.2/10

Good

(402)

"We had a great stay with our two Pups.. The room was very nice and comfortable and very clean."

CA $113

CA $126 total

includes taxes & fees

Oct 19 - Oct 20

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

![Property grounds](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/04bd524d.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)

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

### First Floor Studio Apartment in Historic Chestertown

Chestertown

9.6/10

Exceptional

(103)

"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "

CA $139

CA $222 total

includes taxes & fees

Oct 14 - Oct 15

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

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

![Desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/fe97576e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/52c8cc19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Fairfield Inn & Suites by Marriott Middletown

Middletown

9.2/10

Wonderful

(293)

"One of the best hotels I have ever stayed "

CA $147

CA $163 total

includes taxes & fees

Oct 19 - Oct 20

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

![Exterior](https://images.trvl-media.com/lodging/35000000/34800000/34796100/34796045/1feae509.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)

![Exterior](https://images.trvl-media.com/lodging/35000000/34800000/34796100/34796045/dc410dcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/35000000/34800000/34796100/34796045/0669e46a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Express & Suites Middletown by IHG

Middletown

9.2/10

Wonderful

(627)

"Check in staff was awesome!"

CA $145

CA $160 total

includes taxes & fees

Oct 19 - Oct 20

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

![Exterior](https://images.trvl-media.com/lodging/16000000/16000000/15990300/15990289/8dff74ac.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)

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

![Indoor pool](https://images.trvl-media.com/lodging/16000000/16000000/15990300/15990289/b2e70f95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampton Inn & Suites Baltimore/Aberdeen

Aberdeen

9.0/10

Wonderful

(583)

"This Hotel was excellent in all ways. "

CA $137

CA $153 total

includes taxes & fees

Oct 21 - Oct 22

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

![Exterior](https://images.trvl-media.com/lodging/2000000/1920000/1916100/1916020/326b1394.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/2000000/1920000/1916100/1916020/5673e9db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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)

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

Edgewood

8.2/10

Very good

(1014)

"Our stay was very good enjoyed the continental breakfast and how close the hotel was to other amenities "

CA $118

CA $132 total

includes taxes & fees

Oct 14 - Oct 15

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

![Exterior](https://images.trvl-media.com/lodging/1000000/290000/281700/281612/256d3c46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/290000/281700/281612/742476e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/290000/281700/281612/75e8b664.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/290000/281700/281612/d24d6107.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Edgewood

9.0/10

Wonderful

(527)

"Super clean, a great place to stay"

CA $117

CA $131 total

includes taxes & fees

Oct 19 - Oct 20

[](https://www.expedia.ca/Edgewood-Hotels-Holiday-Inn-Express-Edgewood-Aberdeen-Bel-Air.h281612.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/72000000/71540000/71532200/71532135/b5449a64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/72000000/71540000/71532200/71532135/cfe3570f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/72000000/71540000/71532200/71532135/b93b2e09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room safe, soundproofing, free WiFi, bed sheets](https://images.trvl-media.com/lodging/72000000/71540000/71532200/71532135/ffece2c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Express White Marsh by IHG

Nottingham

9.6/10

Exceptional

(947)

"Excellent place "

CA $133

CA $154 total

includes taxes & fees

Nov 2 - Nov 3

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

![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)

![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)

### Quality Inn

Smyrna

7.6/10

Good

(1006)

"Wonerful place, all good..Hotel,area, staff."

CA $123

CA $136 total

includes taxes & fees

Nov 12 - Nov 13

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

![Lobby](https://images.trvl-media.com/lodging/1000000/50000/40500/40450/a7c447e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/1000000/50000/40500/40450/a5912d87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hypo-allergenic bedding, pillowtop beds, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/50000/40500/40450/a8370cf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Aberdeen

9.0/10

Wonderful

(1008)

"Loved our stay! Will visit again soon!!! "

CA $124

CA $139 total

includes taxes & fees

Oct 20 - Oct 21

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

![Exterior](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/25ad1d72.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)

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

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

Edgewood

9.4/10

Exceptional

(1005)

"Love love love this hotel they provided me with excellent care. Also helped me out with late checkout as needed. Great stay booking again very soon "

CA $117

CA $131 total

includes taxes & fees

Nov 11 - Nov 12

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

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

![In-room safe, blackout drapes, iron/ironing board, cribs/infant beds](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/c38ba9d1.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)

![Indoor pool](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/726148e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampton Inn Middletown

Middletown

8.8/10

Excellent

(841)

"Enjoyed the amenities and great location for shops nearby "

CA $148

CA $165 total

includes taxes & fees

Nov 13 - Nov 14

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

![Exterior](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/7b97c3b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/028c45ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 Queen Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/ead5e21d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/76d50f6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quality Inn

Grasonville

7.8/10

Good

(841)

"Great place and great staff"

CA $137

CA $152 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Grasonville-Hotels-Quality-Inn.h190683.Hotel-Information)

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

![Studio Suite, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/900000/891500/891451/b5f07127.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

![Fitness facility](https://images.trvl-media.com/lodging/1000000/900000/891500/891451/e8c3ab14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Bel Air

8.8/10

Excellent

(1004)

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

CA $118

CA $132 total

includes taxes & fees

Nov 3 - Nov 4

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

![Aerial view](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/5b1966a6.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)

![Restaurant](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/29901fa0.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

Stevensville

9.2/10

Wonderful

(114)

"Great INN super nice staff"

CA $265

CA $346 total

includes taxes & fees

Oct 21 - Oct 22

[](https://www.expedia.ca/Annapolis-Hotels-The-Waterfront-Historic-Kent-Manor-Inn.h194102.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/1000000/120000/117000/116919/2c8e8566.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)

![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

Grasonville

9.2/10

Wonderful

(906)

"Nice Holiday Inn Express with great water views."

CA $167

CA $185 total

includes taxes & fees

Nov 10 - Nov 11

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

![Basic Single Room](https://images.trvl-media.com/lodging/113000000/112790000/112785800/112785783/1965813e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Basic Double or Twin Room](https://images.trvl-media.com/lodging/113000000/112790000/112785800/112785783/45566cc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Basic Double or Twin Room](https://images.trvl-media.com/lodging/113000000/112790000/112785800/112785783/bc3a3100.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112790000/112785800/112785783/793857b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Motel Edgewood

Edgewood

7.6/10

Good

(9)

"Bed was clean and crisply made. Occupants were respectful of sleeping hours. Check-in and check-out were simple. Parking was convenient and had easy access to the highway."

CA $69

CA $78 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Edgewood-Hotels-Motel-Edgewood.h112785783.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/90000000/89680000/89677400/89677382/w1290h969x0y4-ceff4309.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Double or Twin Room](https://images.trvl-media.com/lodging/90000000/89680000/89677400/89677382/db980bf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Basic Single Room | Interior detail](https://images.trvl-media.com/lodging/90000000/89680000/89677400/89677382/1a5dc7d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bathtub, towels](https://images.trvl-media.com/lodging/90000000/89680000/89677400/89677382/w1290h1713x0y0-d518f5f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Relax Inn Smyrna

Smyrna

7.8/10

Good

(90)

"Owner was very nice. "

CA $112

CA $125 total

includes taxes & fees

Oct 31 - Nov 1

[](https://www.expedia.ca/Smyrna-Hotels-Relax-Inn-Smyrna.h89677382.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

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

### Historic Inns of Annapolis

10/10 Excellent

"The hotel was absolutely clean and close to the shops and restaurants. "

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

![La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh](//images.trvl-media.com/lodging/1000000/10000/3900/3897/8051c714_y.jpg)

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

10/10 Excellent

"Very nice and clean"

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

![Red Roof Inn & Suites Chestertown](//images.trvl-media.com/lodging/1000000/50000/40400/40352/17533737_y.jpg)

### Red Roof Inn & Suites Chestertown

10/10 Excellent

"Well received by front desk attendant. Clean room! "

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

![The Inn at Henderson's Wharf, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/890000/890000/889993/38664fff_y.jpg)

### The Inn at Henderson's Wharf, an Ascend Collection Hotel

10/10 Excellent

"Beautiful location and a great stay. Eric at the front desk was great!"

[](https://expedia.ca/Baltimore-Hotels-The-Inn-At-Hendersons-Wharf.h889993.Hotel-Information)

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

### Courtyard by Marriott Baltimore Downtown/McHenry Row

10/10 Excellent

"Great location "

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

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

### Hilton Garden Inn Baltimore/White Marsh

10/10 Excellent

"Loved it"

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

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

### Hampton Inn Baltimore Bayview Campus

10/10 Excellent

"Staff was very friendly and room was clean. The bathroom had some corner shelves that were falling off a bit. Other then that our stay was very pleasant. "

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

![Garner Hotel Glen Burnie BWI Airport Area by IHG](//images.trvl-media.com/lodging/1000000/30000/21100/21017/70fc99c2_y.jpg)

### Garner Hotel Glen Burnie BWI Airport Area by IHG

10/10 Excellent

"everything was very professional."

[](https://expedia.ca/Baltimore-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Baltimore-S-Glen-Burnie.h21017.Hotel-Information)

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

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

10/10 Excellent

"Quiet and clean. Not a LOT of parking but enough if you get there before midnight. "

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

## Find out more about Chestertown

## Chestertown Villas information

| Number of reviews | 12,188 |
| --- | --- |
| Accommodation | 4 Villas |
| Lowest Price | CA $78 |
| Highest Price | CA $346 |

## Frequently asked questions

### Why book your villa in Chestertown with Expedia?

> Booking a villa in Chestertown is as easy as entering your travel dates and picking an option that meets your requirements. On the lookout for something upscale or budget friendly, or a stay that also has WiFi and a hot tub? Use Expedia's search filters to narrow your results and find your perfect match.

### How can I find cheap villas in Chestertown?

> Expedia is here to help you search for cheap villas in Chestertown. Use our handy filter tool to choose star rating, budget and amenities to refine your search and find a fantastic place to stay in just a few clicks.

### What is there to do near my villa in Chestertown?

> If you want to discover the sights of Chestertown, make your way to [Rolphs Wharf Marina](https://www.expedia.ca/Rolphs-Wharf-Marina-Chestertown.d553248621561879605.Vacation-Attraction). It's a winner with travelers and locals alike.

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