Title: Chestertown Vacation Rentals from $159: Search Short-Term Rentals | Expedia.com

[Chestertown Travel Guide](https://expedia.com/Chestertown.dx7215)[Hotels in Chestertown](https://expedia.com/Chestertown-Hotels.d7215.Travel-Guide-Hotels)[Flights to Chestertown](https://expedia.com/Cheap-Flights-To-Chestertown.d7215.Travel-Guide-Flights)[Car Rentals in Chestertown](https://expedia.com/Car-Rentals-In-Chestertown.d7215.Car-Rental-Guide)[Chestertown Vacation Packages](https://expedia.com/Chestertown.d7215.Destination-Travel-Guides)

![Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA](https://images.trvl-media.com/place/7215/2127ed08-151b-4865-9870-3d0463a3d88b.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/7215/2127ed08-151b-4865-9870-3d0463a3d88b.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

## Check prices for these dates

In two weeks

[Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=7215&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 8 - May 10](https://www.expedia.com/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)

In three months

[Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=7215&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 3 - Jul 5](https://www.expedia.com/Hotel-Search?regionId=7215&startDate=2026-07-03&endDate=2026-07-05&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

![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)

![Exterior](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/92366292.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

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

Chestertown

9.6/10

Exceptional

(108 reviews)

"Every thing was great"

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

lesia k.

$144 nightly

$159 total

Mar 16 - Mar 17

Total with taxes and fees

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

![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)

![Exterior](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/737f2153.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.com/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.

$397 nightly

$421 total

Mar 16 - Mar 17

Total with taxes and fees

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

![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)

![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)

### Hidden Fells Point Gem / Private Courtyard Patio

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

Fells Point

9.6/10

Exceptional

(94 reviews)

"Awesome place, great location"

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

Mark M.

$174 nightly

$201 total

Mar 15 - Mar 16

Total with taxes and fees

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92570000/92564900/92564827/w1014h600x10y12-4e8a8c16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/93000000/92570000/92564900/92564827/598d88e9_edited_b6ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/93000000/92570000/92564900/92564827/86090f06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/93000000/92570000/92564900/92564827/819180d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 18th Cent. Charm in Historic Downtown Annapolis

[](https://www.expedia.com/Annapolis-Hotels-18th-Cent-Charm-In-Historic-Downtown-Annapolis.h92564827.Hotel-Information)

Historic District

9.0/10

Wonderful

(13 reviews)

"Great experience"

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

David P.

$304 nightly

$347 total

Mar 16 - Mar 17

Total with taxes and fees

[](https://www.expedia.com/Annapolis-Hotels-18th-Cent-Charm-In-Historic-Downtown-Annapolis.h92564827.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)

![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)

![2 bedrooms, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/112000000/111820000/111819700/111819612/dbf4caf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Aberdeen

7.6/10

Good

(13 reviews)

"Met our needs. Great stay."

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

Robert C.

$88 nightly

$93 total

Mar 15 - Mar 16

Total with taxes and fees

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

![Smart TV, printers](https://images.trvl-media.com/lodging/125000000/124570000/124564400/124564327/4e1114bf.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/be38f55e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/125000000/124570000/124564400/124564327/9a6a354d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, printers](https://images.trvl-media.com/lodging/125000000/124570000/124564400/124564327/604e090e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Boho Oasis 2 Bed 1 Bath home in Baltimore City!

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

Berea

10/10

Exceptional

(4 reviews)

"Host was very friendly and the space was large and clean! "

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

Mia H.

$229 nightly

$265 total

Mar 16 - Mar 17

Total with taxes and fees

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

![Living area](https://images.trvl-media.com/lodging/114000000/113300000/113298400/113298347/01162ab4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/114000000/113300000/113298400/113298347/3d8089a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113300000/113298400/113298347/e26e59da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113300000/113298400/113298347/0cd3925a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace

[](https://www.expedia.com/Havre-De-Grace-Hotels-Cozy-2-Bedroom-Apartment-With-WiFi.h113298347.Hotel-Information)

Havre de Grace

10/10

Exceptional

(5 reviews)

"It is a warm and welcoming little home away from home. We will be back!"

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

Brittany C.

$211 nightly

$223 total

Mar 16 - Mar 17

Total with taxes and fees

[](https://www.expedia.com/Havre-De-Grace-Hotels-Cozy-2-Bedroom-Apartment-With-WiFi.h113298347.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)

![Interior](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/3a482076.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)

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

### Large 2 bedroom house with private parking in a nice neighborhood

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

Arnold

9.4/10

Exceptional

(36 reviews)

"Super clean place, great communication from the host, and home is exactly as described and shown in pictures. "

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

Traci L.

$278 nightly

$317 total

Mar 15 - Mar 16

Total with taxes and fees

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

![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)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/102000000/101992200/101992106/w584h683x220y0-d805a755.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.com/Millington-Hotels-Guest-Suite-For-Up-To-2-In-A-Victorian-On-The-Chester-River.h101992106.Hotel-Information)

Millington

9.6/10

Exceptional

(20 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.

$118 nightly

$125 total

Mar 24 - Mar 25

Total with taxes and fees

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

![Interior](https://images.trvl-media.com/lodging/102000000/101540000/101539300/101539294/1afdcb86.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)

![Dining](https://images.trvl-media.com/lodging/102000000/101540000/101539300/101539294/cf034cb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.com/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.

$292 nightly

$298 total

Mar 22 - Mar 23

Total with taxes and fees

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

![Marina](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/fc34c762.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/7e2b4765.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/081c863e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/4de85be2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy 2br home w/ parking in downtown Annapolis

[](https://www.expedia.com/Annapolis-Hotels-Cozy-2br-Home-W-Parking-In-Downtown-Annapolis.h42019059.Hotel-Information)

Historic District

10/10

Exceptional

(75 reviews)

"Welcoming host, great location and easy parking "

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

Chris B.

$290 nightly

$331 total

Mar 30 - Mar 31

Total with taxes and fees

[](https://www.expedia.com/Annapolis-Hotels-Cozy-2br-Home-W-Parking-In-Downtown-Annapolis.h42019059.Hotel-Information)

![Marina](https://images.trvl-media.com/lodging/93000000/92570000/92565900/92565863/w1024h447x0y118-8b5ab4ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/93000000/92570000/92565900/92565863/w951h680x36y3-968871c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/93000000/92570000/92565900/92565863/w950h680x38y3-96439ab6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92570000/92565900/92565863/w1024h640x0y22-f248bc40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Secluded Cozy Cottage in Historic Downtown

[](https://www.expedia.com/Annapolis-Hotels-Secluded-Cozy-Cottage-In-Historic-Downtown.h92565863.Hotel-Information)

Historic District

9.6/10

Exceptional

(17 reviews)

"This cottage is a hidden gem. Beautiful decor, perfect for our family of 4 & right in the center of all the main attractions. Jennifer was an amazing host!"

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

Linda Q.

$506 nightly

$577 total

Mar 16 - Mar 17

Total with taxes and fees

[](https://www.expedia.com/Annapolis-Hotels-Secluded-Cozy-Cottage-In-Historic-Downtown.h92565863.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/117000000/116070000/116070000/116069925/56f6cf22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116070000/116070000/116069925/c0f204f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116070000/116070000/116069925/8b45f44e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/117000000/116070000/116070000/116069925/a32de752.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC

[](https://www.expedia.com/Baltimore-Hotels-Cozy-2-Bedroom-Apartment-In-Welcoming-Baltimore-With-WiFi.h116069925.Hotel-Information)

Greektown

9.6/10

Exceptional

(10 reviews)

"The house was clean and the beds were comfortable. "

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

Karen B.

$182 nightly

$210 total

Mar 15 - Mar 16

Total with taxes and fees

[](https://www.expedia.com/Baltimore-Hotels-Cozy-2-Bedroom-Apartment-In-Welcoming-Baltimore-With-WiFi.h116069925.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)

![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)

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

[](https://www.expedia.com/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.

$229 nightly

$242 total

Mar 16 - Mar 17

Total with taxes and fees

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

![Interior](https://images.trvl-media.com/lodging/118000000/117590000/117588800/117588789/1aa587de_edited_b1ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117590000/117588800/117588789/w1359h908x3y0-283a58db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/118000000/117590000/117588800/117588789/w1514h908x8y2-08d635bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117590000/117588800/117588789/w1359h906x3y0-7a94439d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Historic Row Home | Hot Tub - 1 Block from Gate 1!

[](https://www.expedia.com/Annapolis-Hotels-Historic-Row-Home-Hot-Tub-1-Block-From-Gate-1.h117588789.Hotel-Information)

Historic District

10/10

Exceptional

(5 reviews)

"Perfect location. Very clean. Had everything we needed and front porch swing was a nice bonus. Would stay here every visit! "

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

Tracie B.

$638 nightly

$727 total

Mar 16 - Mar 17

Total with taxes and fees

[](https://www.expedia.com/Annapolis-Hotels-Historic-Row-Home-Hot-Tub-1-Block-From-Gate-1.h117588789.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)

![Smart TV](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/e9f923a1.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)

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

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

Stevensville

9.6/10

Exceptional

(34 reviews)

"Great stay, would do it again."

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

Brandon D.

$227 nightly

$240 total

Mar 16 - Mar 17

Total with taxes and fees

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

![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)

![Dining](https://images.trvl-media.com/lodging/97000000/96540000/96533100/96533021/7f3f4259.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.com/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.

$385 nightly

$439 total

Mar 16 - Mar 17

Total with taxes and fees

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

![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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/20000000/19010000/19008000/19007969/2c031a65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Fells Point

9.8/10

Exceptional

(202 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

$177 nightly

$204 total

Mar 18 - Mar 19

Total with taxes and fees

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

![Smart TV](https://images.trvl-media.com/lodging/84000000/83930000/83922000/83921931/a2c7c68e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83930000/83922000/83921931/ce9b7709.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/84000000/83930000/83922000/83921931/21befbf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/84000000/83930000/83922000/83921931/4cfce214.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bayside Cottage steps from Rock Hall Harbor

[](https://www.expedia.com/Rock-Hall-Hotels-Bayside-Cottage-Steps-From-Rock-Hall-Harbor.h83921931.Hotel-Information)

Rock Hall

10/10

Exceptional

(2 reviews)

"Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!"

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

Dorothy R.

$341 nightly

$361 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Rock-Hall-Hotels-Bayside-Cottage-Steps-From-Rock-Hall-Harbor.h83921931.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/103000000/102200000/102191700/102191646/3304b939.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102200000/102191700/102191646/f7aa03df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/103000000/102200000/102191700/102191646/b81cd077.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102200000/102191700/102191646/146254a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Glen Burnie Escape - Pet friendly with easy access to multiple attractions.

[](https://www.expedia.com/Glen-Burnie-Hotels-Glen-Burnie-Escape-Pet-Friendly-With-Easy-Access-To-Multiple-Attractions.h102191646.Hotel-Information)

Glen Burnie

10/10

Exceptional

(23 reviews)

"We enjoyed this property so much that we stayed here again just 4 months later."

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

Kim C.

$338 nightly

$385 total

Mar 15 - Mar 16

Total with taxes and fees

[](https://www.expedia.com/Glen-Burnie-Hotels-Glen-Burnie-Escape-Pet-Friendly-With-Easy-Access-To-Multiple-Attractions.h102191646.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.com/Hotel-Search?startDate=2026-03-28&endDate=2026-03-29&regionId=7215&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.

[Book now](https://expedia.com/deals?rfrr=VR_SPRING_PROMO_7215)

## Find vacation rentals that suit your style

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America&regionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-06-12&d1=2026-06-12&endDate=2026-06-15&d2=2026-06-15&lodging=VACATION_HOME)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America&regionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-06-12&d1=2026-06-12&endDate=2026-06-15&d2=2026-06-15&lodging=COTTAGE)

Cabins

[](https://www.expedia.com/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America&regionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-06-12&d1=2026-06-12&endDate=2026-06-15&d2=2026-06-15&lodging=CABIN)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America&regionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-06-12&d1=2026-06-12&endDate=2026-06-15&d2=2026-06-15&lodging=APARTMENT)

Houseboats

[](https://www.expedia.com/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America&regionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-06-12&d1=2026-06-12&endDate=2026-06-15&d2=2026-06-15&lodging=HOUSE_BOAT)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America&regionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-06-12&d1=2026-06-12&endDate=2026-06-15&d2=2026-06-15&lodging=CONDO)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America&regionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-06-12&d1=2026-06-12&endDate=2026-06-15&d2=2026-06-15&lodging=VILLA)

Residences

[](https://www.expedia.com/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America&regionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-06-12&d1=2026-06-12&endDate=2026-06-15&d2=2026-06-15&lodging=RESIDENCE)

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## Top Chestertown Hotel Reviews

![Hampton Inn Baltimore/Glen Burnie](https://images.trvl-media.com/lodging/1000000/10000/2800/2759/2b57d3ba_y.jpg)

### Hampton Inn Baltimore/Glen Burnie

10/10 Excellent

"Room and all surrounding areas were very clean. The staff was so kind and so friendly. It is in an amazing location and some very good choices for food right in the shopping plaza. "

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

![Fairfield Inn & Suites by Marriott Middletown](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/879c8a94_y.jpg)

### Fairfield Inn & Suites by Marriott Middletown

6/10 Okay

"Wasn’t pleased."

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

![Country Inn & Suites by Radisson, Baltimore North, MD](https://images.trvl-media.com/lodging/3000000/2410000/2410000/2410000/7de3cb16_y.jpg)

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

10/10 Excellent

"Clean quiet "

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

![La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh](https://images.trvl-media.com/lodging/1000000/10000/3900/3897/40d24dc0_y.jpg)

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

10/10 Excellent

"Everything was clean and near"

[](https://expedia.com/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/e84869d1_y.jpg)

### Historic Inns of Annapolis

8/10 Good

"The elevator was not working the entire time."

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

![Hilton Garden Inn Baltimore/White Marsh](https://images.trvl-media.com/lodging/1000000/440000/433700/433663/6e9faa08_y.jpg)

### Hilton Garden Inn Baltimore/White Marsh

10/10 Excellent

" Clean, comfortable, good location."

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

![Holiday Inn Express White Marsh by IHG](https://images.trvl-media.com/lodging/72000000/71540000/71532200/71532135/9b37b4b6_y.jpg)

### Holiday Inn Express White Marsh by IHG

8/10 Good

"The food was better than continental "

[](https://expedia.com/Baltimore-Hotels-Holiday-Inn-Express-White-Marsh.h71532135.Hotel-Information)

![Courtyard by Marriott Baltimore Downtown/McHenry Row](https://images.trvl-media.com/lodging/43000000/42120000/42119100/42119031/c35aa4df_y.jpg)

### Courtyard by Marriott Baltimore Downtown/McHenry Row

8/10 Good

"The hotel has almost everything that we needed. No airport transport. There is a service to get to the cruise port, but a high price to go a very short distance. "

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

![Hyatt Place Kent Narrows & Marina](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/d7f9ddda_y.jpg)

### Hyatt Place Kent Narrows & Marina

10/10 Excellent

"Very nice"

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

## Find out more about Chestertown

**Everything you need to know about Chestertown vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chestertown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chestertown vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Chestertown vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Chestertown. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chestertown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $159 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

**How to find incredible deals on Chestertown rentals**

At Expedia, we put the best Chestertown vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chestertown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chestertown vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chestertown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

## Explore a world of travel with Expedia

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- [Hawaii Vacation Rentals ](https://www.expedia.com/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations)
- [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations)

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

### What can I see and do in Chestertown?

### What are vacation rentals like in Chestertown?

### Expedia's Latest Trends

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- [Hotel Rooms in Silver Spring](https://expedia.com/Silver-Spring-Hotels.d6891.Travel-Guide-Hotels)
- [Hotel Rooms in Ocean City](https://expedia.com/Ocean-City-Hotels.d9151.Travel-Guide-Hotels)
- [Ocean City Oceanfront Hotels](https://expedia.com/Ocean-City-Hotels-Oceanfront-Hotels.0-0-d9151-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
- [Ocean City Cheap Hotels](https://expedia.com/Ocean-City-Hotels-Cheap-Hotels.0-0-d9151-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Hotel Rooms in Bowie](https://expedia.com/Bowie-Hotels.d6278.Travel-Guide-Hotels)
- [Hotel Rooms in Rockville](https://expedia.com/Rockville-Hotels.d6353.Travel-Guide-Hotels)
- [Hotel Rooms in Salisbury](https://expedia.com/Salisbury-Hotels.d6057491.Travel-Guide-Hotels)
- [Hotel Rooms in Aberdeen](https://expedia.com/Aberdeen-Hotels.d6044.Travel-Guide-Hotels)
- [Hotel Rooms in Annapolis](https://expedia.com/Annapolis-Hotels.d6034082.Travel-Guide-Hotels)
- [Hotel Rooms in St. Michaels](https://expedia.com/St-Michaels-Hotels.d5940.Travel-Guide-Hotels)
- [Hotel Rooms in Cumberland](https://expedia.com/Cumberland-Hotels.d6057474.Travel-Guide-Hotels)
- [Hotel Rooms in College Park](https://expedia.com/College-Park-Hotels.d6057494.Travel-Guide-Hotels)
- [Hotel Rooms in Frederick](https://expedia.com/Frederick-Hotels.d6057476.Travel-Guide-Hotels)
- [Annapolis Oceanfront Hotels](https://expedia.com/Annapolis-Hotels-Oceanfront-Hotels.0-0-d6034082-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
- [Hotel Rooms in Bel Air](https://expedia.com/Bel-Air-Hotels.d6023736.Travel-Guide-Hotels)
- [Ocean City Luxury Hotels](https://expedia.com/Ocean-City-Hotels-Luxury-Hotel.0-0-d9151-tLuxuryHotel.Travel-Guide-Filter-Hotels)
- [Hotel Rooms in Gaithersburg](https://expedia.com/Gaithersburg-Hotels.d7427.Travel-Guide-Hotels)

Flights

- [Flights to SBY](https://expedia.com/Cheap-Flights-To-Ocean-City.d9151.Travel-Guide-Flights)

Cars

- [Car rentals in Rockville](https://expedia.com/Car-Rentals-In-Rockville.d6353.Car-Rental-Guide)
- [Car rentals in Silver Spring](https://expedia.com/Car-Rentals-In-Silver-Spring.d6891.Car-Rental-Guide)
- [Car rentals in Frederick](https://expedia.com/Car-Rentals-In-Frederick.d6057476.Car-Rental-Guide)

Activities

- [Things to do in Annapolis](https://expedia.com/Things-To-Do-In-Annapolis.d6034082.Travel-Guide-Activities)
- [Things to do in Ocean City](https://expedia.com/Things-To-Do-In-Ocean-City.d9151.Travel-Guide-Activities)

Packages

- [Holiday in Ocean City](https://expedia.com/Ocean-City.d9151.Destination-Travel-Guides)

Vacation Rentals

- [Ocean City Vacation Rental](https://expedia.com/Ocean-City-Vacation-Rentals.d9151.Travel-Guide-VacationRentals)

General

- [Visit Ocean City](https://expedia.com/Ocean-City.dx9151)
- [Visit Chesapeake City](https://expedia.com/Chesapeake-City.dx177517)