Title: Chestertown Vacation Home Rentals from CA $133: Search Top Private Vacation Homes for Rent | 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)

![](https://images.trvl-media.com/place/7215/2810851e-b7cc-4dfb-bf7e-dc0611ab1b49.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Chestertown vacation homes

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

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

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

![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/12356e9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Stevensville

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

9.8/10

Exceptional

(43 reviews)

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

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

Stephanie S.

CA $89

CA $340 total

includes taxes & fees

Jan 19 - Jan 20

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

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

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

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

![Dining](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/7d796cd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Stevensville

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

9.6/10

Exceptional

(32 reviews)

"Very nice house! We had 3 people in our party and didn't want to rent 2 hotel rooms, this is a great way to save money and enjoy time together. "

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

Pamela

CA $113

CA $370 total

includes taxes & fees

Jan 21 - Jan 22

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

![Smart TV, printers](https://images.trvl-media.com/lodging/125000000/124570000/124564400/124564327/ba5973fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, printers](https://images.trvl-media.com/lodging/125000000/124570000/124564400/124564327/1c8f46b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/125000000/124570000/124564400/124564327/50b5c037.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/125000000/124570000/124564400/124564327/8e81f840.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Berea

[](https://www.expedia.ca/Baltimore-Hotels-Boho-Oasis-2-Bed-1-Bath-Home-In-Baltimore-City.h124564327.Hotel-Information)

10/10

Exceptional

(1 review)

"House kept very clean and neighborhood was really quiet at night! Will be staying again."

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

Pai’Syn

CA $143

CA $364 total

includes taxes & fees

Jan 27 - Jan 28

[](https://www.expedia.ca/Baltimore-Hotels-Boho-Oasis-2-Bed-1-Bath-Home-In-Baltimore-City.h124564327.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/112000000/111820000/111819700/111819612/05f7fb5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111820000/111819700/111819612/7f5de9e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111820000/111819700/111819612/f65b9e5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/112000000/111820000/111819700/111819612/a673c6f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Aberdeen

[](https://www.expedia.ca/Aberdeen-Hotels-Charming-2-Bedroom-House-In-Aberdeen-With-WiFi-And-AC.h111819612.Hotel-Information)

7.6/10

Good

(10 reviews)

"Pleasant stay"

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

Yommali G.

CA $98

CA $133 total

includes taxes & fees

Jan 26 - Jan 27

[](https://www.expedia.ca/Aberdeen-Hotels-Charming-2-Bedroom-House-In-Aberdeen-With-WiFi-And-AC.h111819612.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/102000000/101540000/101539300/101539294/86c67d62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101540000/101539300/101539294/02f199f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/102000000/101540000/101539300/101539294/76b495fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/102000000/101540000/101539300/101539294/1afdcb86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Smyrna

[](https://www.expedia.ca/Smyrna-Hotels-Amazing-Modern-House-With-A-Full-Kitchen-And-Parking.h101539294.Hotel-Information)

9.2/10

Wonderful

(9 reviews)

"The house is a beautiful place to stay. The location was ideal for going to attractions and stores. "

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

Laurie S.

CA $250

CA $494 total

includes taxes & fees

Jan 24 - Jan 25

[](https://www.expedia.ca/Smyrna-Hotels-Amazing-Modern-House-With-A-Full-Kitchen-And-Parking.h101539294.Hotel-Information)

![Marina](https://images.trvl-media.com/lodging/101000000/100140000/100139800/100139799/d79202ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/101000000/100140000/100139800/100139799/a7a0e521.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/101000000/100140000/100139800/100139799/aa9f2ec2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/101000000/100140000/100139800/100139799/w1440h958x0y2-a4146525.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Upper Fells Point

[](https://www.expedia.ca/Baltimore-Hotels-Johns-Hopkins-Historic-Renovated-Home-Location.h100139799.Hotel-Information)

9.4/10

Exceptional

(14 reviews)

"Location was perfect and the place was great"

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

Sharon P.

CA $153

CA $484 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Baltimore-Hotels-Johns-Hopkins-Historic-Renovated-Home-Location.h100139799.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/123000000/122670000/122662900/122662848/b280e6e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122670000/122662900/122662848/cd98fea7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122670000/122662900/122662848/f736837f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122670000/122662900/122662848/5881f494.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Bel Air South

[](https://www.expedia.ca/Abingdon-Hotels-Soothing-Townhome-With-AC-In-Charming-Abingdon.h122662848.Hotel-Information)

CA $115

CA $181 total

includes taxes & fees

Feb 1 - Feb 2

[](https://www.expedia.ca/Abingdon-Hotels-Soothing-Townhome-With-AC-In-Charming-Abingdon.h122662848.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/96000000/95980000/95979600/95979564/9d2ec177.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/96000000/95980000/95979600/95979564/8af0ae73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/96000000/95980000/95979600/95979564/b838ef67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/96000000/95980000/95979600/95979564/a4e1c9eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Bel Air

[](https://www.expedia.ca/Bel-Air-Hotels-Hobbit-House-One-Of-A-Kind-Home.h95979564.Hotel-Information)

10/10

Exceptional

(8 reviews)

"We had a great stay! "

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

Courtney H.

CA $148

CA $410 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Bel-Air-Hotels-Hobbit-House-One-Of-A-Kind-Home.h95979564.Hotel-Information)

![Fridge, microwave, dishwasher, coffee/tea maker](https://images.trvl-media.com/lodging/103000000/102640000/102631200/102631144/3bbc0763.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/103000000/102640000/102631200/102631144/3c8498e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/103000000/102640000/102631200/102631144/ee0975c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/103000000/102640000/102631200/102631144/d4ed594e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Centreville

[](https://www.expedia.ca/Centreville-Hotels-Private.h102631144.Hotel-Information)

10/10

Exceptional

(8 reviews)

"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"

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

Renee P.

CA $274

CA $623 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Centreville-Hotels-Private.h102631144.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/93000000/92310000/92309300/92309210/w1100h506x0y137-5f725067.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/93000000/92310000/92309300/92309210/w1100h506x0y137-97b0328a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/93000000/92310000/92309300/92309210/w1100h508x0y136-4ba3382c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/93000000/92310000/92309300/92309210/w1100h574x0y103-120745ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Glen Burnie

[](https://www.expedia.ca/Glen-Burnie-Hotels-The-Hideaway-Spot-Waterfront-W-Dock-On-Long-Cove.h92309210.Hotel-Information)

8.6/10

Excellent

(8 reviews)

"The property is lovely and the home is truly beautiful and comfortable. I highly recommend staying here; beautiful, peaceful--perfect."

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

Jeffrey S.

CA $151

CA $484 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Glen-Burnie-Hotels-The-Hideaway-Spot-Waterfront-W-Dock-On-Long-Cove.h92309210.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/125000000/124830000/124829800/124829757/f552eabe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/125000000/124830000/124829800/124829757/c9619fa9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, internet, bed sheets](https://images.trvl-media.com/lodging/125000000/124830000/124829800/124829757/4d8e2703.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/125000000/124830000/124829800/124829757/28adc57c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Herald Harbor

[](https://www.expedia.ca/Crownsville-Hotels-Cute.h124829757.Hotel-Information)

CA $113

CA $319 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Crownsville-Hotels-Cute.h124829757.Hotel-Information)

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

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

![Interior](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/a5c24734.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/a70d4b32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Arnold

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

9.4/10

Exceptional

(36 reviews)

"Just as advertised. Clean and quiet."

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

Robert B.

CA $163

CA $429 total

includes taxes & fees

Jan 22 - Jan 23

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

![Smart TV](https://images.trvl-media.com/lodging/109000000/108450000/108444200/108444163/7d3ee483.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108450000/108444200/108444163/3751c07c_edited_5953.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/109000000/108450000/108444200/108444163/1837dc6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108450000/108444200/108444163/b71a43f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Berea

[](https://www.expedia.ca/Baltimore-Hotels-Family-Friendly-2-Bedroom-Home-In-Baltimore-With-WiFi.h108444163.Hotel-Information)

9.6/10

Exceptional

(5 reviews)

"Everything was great, easy check in and simple and clean space!!! Amazing thank you"

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

michael t.

CA $250

CA $442 total

includes taxes & fees

Jan 30 - Jan 31

[](https://www.expedia.ca/Baltimore-Hotels-Family-Friendly-2-Bedroom-Home-In-Baltimore-With-WiFi.h108444163.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/2a64ee56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/30ebd57e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, foosball](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/44a64359.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/23f1d475.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Grasonville

[](https://www.expedia.ca/Spacious-2-Bedroom-Duplex-Located-Conveniently-Near-Route-50-East-And-West.h99830322.Hotel-Information)

9.6/10

Exceptional

(12 reviews)

"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "

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

Joe C.

CA $347

CA $583 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Spacious-2-Bedroom-Duplex-Located-Conveniently-Near-Route-50-East-And-West.h99830322.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/123000000/122590000/122582500/122582410/df095a99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122590000/122582500/122582410/9b7a87a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/123000000/122590000/122582500/122582410/07d78dc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/123000000/122590000/122582500/122582410/dc2f3672.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Middletown

[](https://www.expedia.ca/Middletown-Hotels-Heated-Pool-Private-Backyard-Home-Theater.h122582410.Hotel-Information)

CA $132

CA $688 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Middletown-Hotels-Heated-Pool-Private-Backyard-Home-Theater.h122582410.Hotel-Information)

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

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

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

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

### Vacation Home in Fells Point

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

9.6/10

Exceptional

(94 reviews)

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

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

Edward J.

CA $86

CA $287 total

includes taxes & fees

Feb 1 - Feb 2

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

![Terrace/patio](https://images.trvl-media.com/lodging/121000000/120250000/120248200/120248155/7d6d0051.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120250000/120248200/120248155/296e82bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/121000000/120250000/120248200/120248155/7a413e7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120250000/120248200/120248155/4acd2675.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Kent County

[](https://www.expedia.ca/Still-Pond-Hotels-High-Tide-Haven-Suite.h120248155.Hotel-Information)

CA $241

CA $282 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Still-Pond-Hotels-High-Tide-Haven-Suite.h120248155.Hotel-Information)

![Sun loungers, beach towels](https://images.trvl-media.com/lodging/35000000/34020000/34013500/34013405/w800h599x0y1-14614b8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

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

### Vacation Home in Perryville

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

9.8/10

Exceptional

(146 reviews)

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

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

Mary D.

CA $449

CA $847 total

includes taxes & fees

Jan 20 - Jan 21

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

![Interior](https://images.trvl-media.com/lodging/65000000/64660000/64659100/64659016/w1454h935x0y0-82413ec1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/65000000/64660000/64659100/64659016/8899ed60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/65000000/64660000/64659100/64659016/cfd38abb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/65000000/64660000/64659100/64659016/5b157855.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Upper Fells Point

[](https://www.expedia.ca/Baltimore-Hotels-Entire-House-By-The-Fells-Point.h64659016.Hotel-Information)

9.4/10

Exceptional

(32 reviews)

"Nice location, comfy beds"

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

Paul C.

CA $168

CA $405 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Baltimore-Hotels-Entire-House-By-The-Fells-Point.h64659016.Hotel-Information)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/115000000/114590000/114588800/114588703/708da323.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/115000000/114590000/114588800/114588703/e360a10f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/115000000/114590000/114588800/114588703/e33942cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/115000000/114590000/114588800/114588703/97debd4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Glen Burnie

[](https://www.expedia.ca/Cozy-Private-Suite-Gated-Entry.h114588703.Hotel-Information)

8.0/10

Very good

(2 reviews)

"No problems close to everything, only gripe was it being a basement and little feet upstairs tend to be a bit lohd. However, just the bathroom alone made this property worth another stay"

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

James D.

CA $125

CA $174 total

includes taxes & fees

Jan 22 - Jan 23

[](https://www.expedia.ca/Cozy-Private-Suite-Gated-Entry.h114588703.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=2026-01-31&endDate=2026-02-01&regionId=7215&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Private vacation homes

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Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America&regionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-04-17&d1=2026-04-17&endDate=2026-04-20&d2=2026-04-20&lodging=CABIN)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America&regionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-04-17&d1=2026-04-17&endDate=2026-04-20&d2=2026-04-20&lodging=APARTMENT)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America&regionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-04-17&d1=2026-04-17&endDate=2026-04-20&d2=2026-04-20&lodging=CONDO)

Houseboats

[](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America&regionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-04-17&d1=2026-04-17&endDate=2026-04-20&d2=2026-04-20&lodging=HOUSE_BOAT)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America&regionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-04-17&d1=2026-04-17&endDate=2026-04-20&d2=2026-04-20&lodging=VILLA)

Residences

[](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America&regionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-04-17&d1=2026-04-17&endDate=2026-04-20&d2=2026-04-20&lodging=RESIDENCE)

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## Top Chestertown Hotel Reviews

![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

10/10 Excellent

"Newer looking hotel. Very nice lobby. Kind of upscale. I’ll stay here again if we come this way."

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

"Clean rooms"

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

10/10 Excellent

"Room was clean and comfortable. Staff was courteous "

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

"Kind staff, clean room, and nice accommodations!"

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

![Hyatt Place Kent Narrows & Marina](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/35e0cb86_y.jpg)

### Hyatt Place Kent Narrows & Marina

10/10 Excellent

"The room is clean and staff was courteous "

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

![Comfort Inn & Suites Aberdeen near APG](https://images.trvl-media.com/lodging/2000000/1400000/1395600/1395595/0fca1b7b_y.jpg)

### Comfort Inn & Suites Aberdeen near APG

10/10 Excellent

"Peter was great at the front desk"

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

"This property was amazing. Everything you can ask for in a hotel. The staff is very friendly and always willing to help. The room was very clean. The room and hallway had a very fresh smell. "

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

![Holiday Inn Express White Marsh by IHG](https://images.trvl-media.com/lodging/72000000/71540000/71532200/71532135/7b9d83b4_y.jpg)

### Holiday Inn Express White Marsh by IHG

10/10 Excellent

"Yes breakfast was fresh but I would prefer real eggs. I don’t like those eggs. Other than that it was good. Parking is great. You might want to get more lighting on the side of the building. Other than that I LOVE my stay at Holiday Inn Express. "

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

10/10 Excellent

"Everything was clea"

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

## Find out more about Chestertown

## Chestertown Vacation Homes information

| Number of reviews | 380                |
| ----------------- | ------------------ |
| Accommodation     | 485 Vacation Homes |
| Lowest Price      | CA $133            |
| Highest Price     | CA $847            |

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