Title: Chestertown Vacation Rentals from CA $217: Short-Term Rentals for 2026 | 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

[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

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

In four months

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

## Our top choices for Chestertown vacation rentals

![Pool](https://images.trvl-media.com/lodging/119000000/118140000/118131300/118131300/8266855e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/119000000/118140000/118131300/118131300/6f891835.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/119000000/118140000/118131300/118131300/afbe5ced.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/119000000/118140000/118131300/118131300/w1075h1080x5y0-d2ed6db8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access

[](https://www.expedia.ca/Chestertown-Hotels-Historic-2-Bed2-Bath-Downtown-Loft-WPark-View-Spa-Access.h118131300.Hotel-Information)

Chestertown

10/10

Exceptional

(3 reviews)

"We had a great stay. Property was updated, clean and in a nice part of town walkable to everything. We would definitely stay here again and are looking forward to it."

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

Jason

CA $343

CA $577 total

includes taxes & fees

Feb 21 - Feb 22

[](https://www.expedia.ca/Chestertown-Hotels-Historic-2-Bed2-Bath-Downtown-Loft-WPark-View-Spa-Access.h118131300.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)

![Property grounds](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/c04c0cce.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)

![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)

### 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 reviews)

"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 $135

CA $217 total

includes taxes & fees

Feb 9 - Feb 10

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

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

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

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

![Pool](https://images.trvl-media.com/lodging/97000000/96440000/96436800/96436702/c47b2aa8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxe Houseboat with Epic 360 Views of Baltimore Harbor

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

Baltimore

10/10

Exceptional

(12 reviews)

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

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

Anonymous traveller

CA $323

CA $770 total

includes taxes & fees

Feb 8 - Feb 9

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

![Dining](https://images.trvl-media.com/lodging/102000000/101540000/101539300/101539294/cf034cb3.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)

![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)

### Amazing Modern house with a full kitchen and parking 

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

Smyrna

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 $148

CA $369 total

includes taxes & fees

Feb 8 - Feb 9

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

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

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

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

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

### Guest Suite for up to 2 in a Victorian on the Chester River

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

Millington

9.6/10

Exceptional

(19 reviews)

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

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

Cynthia C.

CA $93

CA $171 total

includes taxes & fees

Feb 11 - Feb 12

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

![Dining](https://images.trvl-media.com/lodging/114000000/113590000/113586700/113586648/w1536h2048x598y0-479799f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113590000/113586700/113586648/w1536h2048x598y0-e0efb6c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113590000/113586700/113586648/w1536h2048x598y0-f666fabb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/114000000/113590000/113586700/113586648/673d3dea_edited_40cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Grandma’s Cottage will wrap around you like a warm hug

[](https://www.expedia.ca/Betterton-Hotels-Grandmas-Cottage-Will-Wrap-Around-You-Like-A-Warm-Hug.h113586648.Hotel-Information)

Betterton

CA $308

CA $577 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Betterton-Hotels-Grandmas-Cottage-Will-Wrap-Around-You-Like-A-Warm-Hug.h113586648.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/120000000/119080000/119071400/119071307/b3e8d5f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119080000/119071400/119071307/a373d2a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/120000000/119080000/119071400/119071307/4d8cbe20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119080000/119071400/119071307/242b2346.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### JVA LUXURY HOUSING

[](https://www.expedia.ca/Smyrna-Hotels-JVA-LUXURY-HOUSING.h119071307.Hotel-Information)

Smyrna

10/10

Exceptional

(1 review)

"The house was clean and wonderful. I highly recommend!"

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

Daryl C.

CA $547

CA $803 total

includes taxes & fees

Feb 14 - Feb 15

[](https://www.expedia.ca/Smyrna-Hotels-JVA-LUXURY-HOUSING.h119071307.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)

![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)

![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)

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

### Charming 2-bedroom house in Aberdeen with WiFi and AC

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

Aberdeen

8.0/10

Very good

(12 reviews)

"Pleasant stay"

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

Yommali G.

CA $92

CA $127 total

includes taxes & fees

Feb 8 - Feb 9

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

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/111000000/110560000/110553100/110553066/aa5cdca7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/111000000/110560000/110553100/110553066/a6ee7c11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/111000000/110560000/110553100/110553066/138fd4f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/111000000/110560000/110553100/110553066/5c7724f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 5 Mi to Downtown Baltimore: Quiet Home w/ Porch

[](https://www.expedia.ca/Baltimore-Hotels-5-Mi-To-Downtown-Baltimore-Quiet-Home-W-Porch.h110553066.Hotel-Information)

Rosedale

9.0/10

Wonderful

(2 reviews)

"It took a whole day for the house to get warm.No utensils.And last but not least the heat was turned off in the middle of the night.Monday morning was very cold,that’s why we left at nine thirty. "

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

Cathy

CA $217

CA $681 total

includes taxes & fees

Feb 15 - Feb 16

[](https://www.expedia.ca/Baltimore-Hotels-5-Mi-To-Downtown-Baltimore-Quiet-Home-W-Porch.h110553066.Hotel-Information)

![Marina](https://images.trvl-media.com/lodging/20000000/19010000/19008000/19007969/65ec141b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/20000000/19010000/19008000/19007969/25648c0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/20000000/19010000/19008000/19007969/w799h599x1y1-de620c30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player](https://images.trvl-media.com/lodging/20000000/19010000/19008000/19007969/085e86e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Fells Point Gem / In The Heart of Fells Point

[](https://www.expedia.ca/Baltimore-Hotels-At-Fells-Point-CitySide-Tons-Better-Than-A-Hotel.h19007969.Hotel-Information)

Fells Point

9.8/10

Exceptional

(201 reviews)

"Amazing all around! Owner didn't miss a beat with communication, great location, cozy and quiet stay "

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

Leanne

CA $79

CA $276 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Baltimore-Hotels-At-Fells-Point-CitySide-Tons-Better-Than-A-Hotel.h19007969.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)

![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)

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

### Charming Coastal/Country Home w/3 Acres & Sauna!

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

Stevensville

9.6/10

Exceptional

(32 reviews)

"Great stay, would do it again."

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

Brandon D.

CA $140

CA $400 total

includes taxes & fees

Feb 17 - Feb 18

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

![Property grounds](https://images.trvl-media.com/lodging/58000000/57720000/57720000/57719943/5f5b0904.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/58000000/57720000/57720000/57719943/a2c5e148.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/58000000/57720000/57720000/57719943/2f9f691d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/58000000/57720000/57720000/57719943/w1474h1242x2y0-82b785fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chesapeake Cottages- 2 Quaint Waterfront Retreats

[](https://www.expedia.ca/Pasadena-Hotels-Chesapeake-Cottages-2-Quaint-Waterfront-Retreats.h57719943.Hotel-Information)

Pasadena

9.6/10

Exceptional

(22 reviews)

"Excellent Property"

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

Buu T.

CA $547

CA $967 total

includes taxes & fees

Mar 2 - Mar 3

[](https://www.expedia.ca/Pasadena-Hotels-Chesapeake-Cottages-2-Quaint-Waterfront-Retreats.h57719943.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/b2a36b22.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/69000000/68990000/68986300/68986275/d5668d89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/8c6112e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/8e1aa433.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Waterfront Oasis of Annapolis Star

[](https://www.expedia.ca/Annapolis-Hotels-Waterfront-Oasis-Sleep-4-Close-To-Downtown.h68986275.Hotel-Information)

Annapolis

10/10

Exceptional

(81 reviews)

"Owners were great hosts. Loved this property!"

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

Thomas

CA $283

CA $563 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Annapolis-Hotels-Waterfront-Oasis-Sleep-4-Close-To-Downtown.h68986275.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/117000000/116310000/116303200/116303188/e0c43571.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/117000000/116310000/116303200/116303188/07d865e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![6 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/117000000/116310000/116303200/116303188/d7dcdb89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/117000000/116310000/116303200/116303188/530190ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury Waterfront Home Built for Entertaining!

[](https://www.expedia.ca/Abingdon-Hotels-Luxury-Waterfront-Home-Built-For-Entertaining.h116303188.Hotel-Information)

Abingdon

8.8/10

Excellent

(8 reviews)

"We had such a wonderful stay! The house was spotless, comfortable, and beautifully maintained. The surrounding area was peaceful and welcoming, and perfect for a relaxing weekend. Highly recommend!"

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

Oluwaseyi E.

CA $752

CA $1,242 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Abingdon-Hotels-Luxury-Waterfront-Home-Built-For-Entertaining.h116303188.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)

![Marina](https://images.trvl-media.com/lodging/20000000/19010000/19008100/19008016/226d6f82.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)

### Hidden Fells Point Gem / Private Courtyard Patio

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

Fells Point

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 $79

CA $273 total

includes taxes & fees

Feb 8 - Feb 9

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

![Dining](https://images.trvl-media.com/lodging/121000000/120700000/120694000/120693945/45d09f56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120700000/120694000/120693945/efa1b184.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120700000/120694000/120693945/5cb185a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/121000000/120700000/120694000/120693945/9e61f018.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious 4-bedroom retreat house with plenty of parking

[](https://www.expedia.ca/Baltimore-Hotels-Spacious-4-Bedroom-Retreat-House-With-Plenty-Of-Parking.h120693945.Hotel-Information)

Overlea

10/10

Exceptional

(1 review)

"Property was comfortable. TV streaming isnt a preferred way to watch, "

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

Joseph M. G.

CA $397

CA $768 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/Baltimore-Hotels-Spacious-4-Bedroom-Retreat-House-With-Plenty-Of-Parking.h120693945.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)

![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)

![Interior](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/30ebd57e.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)

### Spacious 2 bedroom duplex located conveniently near Route 50 East and West. 

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

Grasonville

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 $342

CA $577 total

includes taxes & fees

Feb 9 - Feb 10

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

![Marina](https://images.trvl-media.com/lodging/101000000/100560000/100556100/100556061/83e5c5cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/101000000/100560000/100556100/100556061/173025fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/101000000/100560000/100556100/100556061/1cd38316.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/101000000/100560000/100556100/100556061/6352c6da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Fisher House: Steps From USNA + Covered Parking!

[](https://www.expedia.ca/Annapolis-Hotels-Fisher-House-Downtown-Annapolis.h100556061.Hotel-Information)

Historic District

10/10

Exceptional

(14 reviews)

"Great house and location. Great communication. We had a great time there!"

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

Barbara S.

CA $372

CA $1,020 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/Annapolis-Hotels-Fisher-House-Downtown-Annapolis.h100556061.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/97000000/96540000/96533100/96533021/791810e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/97000000/96540000/96533100/96533021/2cbde7cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, foosball](https://images.trvl-media.com/lodging/97000000/96540000/96533100/96533021/0664f10c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96540000/96533100/96533021/1858d72e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Private Family Palace near BWI, Pet-Friendly

[](https://www.expedia.ca/Baltimore-Hotels-Cozy-Private-Family-Palace-Near-BWI.h96533021.Hotel-Information)

Glen Burnie

9.8/10

Exceptional

(23 reviews)

"Nice place and good location "

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

FRANKLIN S.

CA $271

CA $627 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Baltimore-Hotels-Cozy-Private-Family-Palace-Near-BWI.h96533021.Hotel-Information)

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

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

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

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

### Relax on Kent Island in a 4 Bedroom Home w/Waterview!

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

Stevensville

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 $131

CA $389 total

includes taxes & fees

Feb 17 - Feb 18

[](https://www.expedia.ca/Stevensville-Hotels-Relax-On-Kent-Island-In-3-Bedroom-Home-WWaterview.h84063656.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=2026-02-21&endDate=2026-02-22&regionId=7215&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Cottages

[](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=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=COTTAGE)

Private vacation homes

[](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=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=VACATION_HOME)

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=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=APARTMENT)

Condos

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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=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&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=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&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=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=RESIDENCE)

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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

"It was a comfortable stay. "

[](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

"Rooms were great, but they were FREEZING. had the heater on all night and didn’t help at all. other than that the room was great!"

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

10/10 Excellent

"The service was good and the room was was clean "

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

"The room layout was very good. Like it was done by someone who actually traveled a lot. Nice small kitchen. Lots of counter space. Several hooks in bathroom. Counter space in bathroom. "

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

![La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh](https://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

"Everything was good the staff and room are always nice. "

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

"Everything about this beautiful historic hotel was beautiful and perfect—I can’t wait to come back!"

[](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

"Room was nice, quiet, clean. Great for a stay-cation on the wateefront"

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

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

### Pendry Baltimore

10/10 Excellent

"My favorite baltimore hotel hands down!"

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

10/10 Excellent

"Room was very nice and clean. Spacious "

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

## Find out more about Chestertown

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chestertown. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Québec Vacation Rentals ](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals)

- [Vacation Homes in Chestertown ](https://expedia.ca/Chestertown-Private-Vacation-Homes.d7215-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Apartments in Chestertown ](https://expedia.ca/Chestertown-Apartments.d7215-aaApartments.Travel-Guide-Accommodation)
- [Cottages in Chestertown ](https://expedia.ca/Chestertown-Cottages.d7215-aaCottages.Travel-Guide-Accommodation)
- [Guest Houses in Chestertown ](https://expedia.ca/Chestertown-Guest-Houses.d7215-aaGuestHouses.Travel-Guide-Accommodation)
- [Houseboats in Chestertown ](https://expedia.ca/Chestertown-Houseboats.d7215-aaHouseboats.Travel-Guide-Accommodation)
- [Motels in Chestertown ](https://expedia.ca/Chestertown-Motels.d7215-aaMotels.Travel-Guide-Accommodation)
- [RV Parks in Chestertown ](https://expedia.ca/Chestertown-RV-Parks.d7215-aaRVParks.Travel-Guide-Accommodation)
- [B&B in Chestertown ](https://expedia.ca/Chestertown-Bed-And-Breakfast.d7215-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Farmstay in Chestertown ](https://expedia.ca/Chestertown-Agritourism.d7215-aaAgritourism.Travel-Guide-Accommodation)
- [Villas in Chestertown ](https://expedia.ca/Chestertown-Villas.d7215-aaVillas.Travel-Guide-Accommodation)
- [Condo Rentals in Chestertown ](https://expedia.ca/Chestertown-Condos.d7215-aaCondos.Travel-Guide-Accommodation)
- [Cabin Rentals in Chestertown ](https://expedia.ca/Chestertown-Cabins.d7215-aaCabins.Travel-Guide-Accommodation)
- [Lodges in Chestertown ](https://expedia.ca/Chestertown-Lodges.d7215-aaLodges.Travel-Guide-Accommodation)

## Frequently asked questions

### Are there vacation rentals in Chestertown?

### What are some of the best vacation home rentals that Chestertown has to offer?

### How many vacation rentals are there in Chestertown?

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### What are vacation rentals like in Chestertown?

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