Chestertown Vacation Rentals | Book Now, Save Up to 30%

All in pricing: Taxes and fees included

Save $281

Whimstay gem

House in Chestertown, MD

Nov 16 - 19

$375/night

5.0

107

3 bedrooms

10 guests

$1,519$1,238total

Save $71

Preferred host

Entire home in Chestertown, MD

Nov 16 - 19

$211/night

4.3

3

3 bedrooms

6 guests

$765$693total

Save $128

Preferred host

Entire home in Chestertown, MD

Nov 16 - 19

$222/night

5.0

17

2 bedrooms

6 guests

$859$731total

Save $220

Preferred host

Entire home in Chestertown, MD

Nov 16 - 19

$770/night

5.0

3

4 bedrooms

14 guests

$2,752$2,532total

Save $326

Preferred host

Entire home in Millington, MD

Nov 16 - 19

$522/night

5.0

1

7 bedrooms

10 guests

$2,042$1,716total

Save $78

Preferred host

Entire home in Rock Hall, MD

Nov 16 - 19

$274/night

5.0

2

3 bedrooms

6 guests

$979$900total

Save $97

Preferred host

Entire home in Queenstown, MD

Dec 16 - 19

$339/night

5.0

1

4 bedrooms

8 guests

$1,211$1,114total

Save $112

Preferred host

Entire home in Edgewood, MD

Jul 1 - 4

$390/night

4.0

1

3 bedrooms

4 guests

Pay only $148 today

$1,406$1,293total

Save $280

House in Warwick, MD

Nov 16 - 19

$629/night

New

6 bedrooms

15 guests

$2,375$2,095total

Save $165

Preferred host

Entire home in Grasonville, MD

Apr 29 - May 2

$575/night

5.0

5

3 bedrooms

8 guests

Pay only $219 today

$2,056$1,892total

Save $92

Preferred host

Entire home in Aberdeen, MD

May 15 - 19

$252/night

4.5

6

3 bedrooms

6 guests

Pay only $128 today

$1,153$1,060total

Save $240

House in Pasadena, MD

Nov 16 - 19

$816/night

4.9

14

4 bedrooms

10 guests

$2,999$2,759total

Save $40

Preferred host

Entire cabin in Hartly, DE

Nov 23 - 26

$150/night

5.0

1

Studio

2 guests

$505$465total

Save $746

Preferred host

Entire townhouse in Abingdon, MD

Nov 16 - Dec 14

$229/night

5.0

1

3 bedrooms

6 guests

$7,820$7,074total

Save $172

House in Chester, MD

Nov 16 - 19

$330/night

New

4 bedrooms

10 guests

$1,262$1,089total

Save $138

House in Grasonville, MD

Nov 29 - Dec 2

$484/night

New

4 bedrooms

8 guests

$1,729$1,591total

Save $324

Preferred host

Entire home in Stevensville, MD

Nov 16 - 19

$970/night

4.9

7

3 bedrooms

11 guests

$3,515$3,191total

Save $130

Preferred host

Entire home in Annapolis, MD

Nov 16 - 19

$443/night

5.0

1

4 bedrooms

8 guests

$1,622$1,492total

Save $135

House in Annapolis, MD

Dec 20 - 23

$458/night

5.0

10

3 bedrooms

8 guests

$1,686$1,551total

Save $84

Preferred host

Entire cottage in Annapolis, MD

Nov 16 - 19

$287/night

4.0

4

3 bedrooms

5 guests

$1,051$967total

Save $144

Preferred host

House in Nottingham, MD

Nov 16 - 19

$315/night

4.4

10

4 bedrooms

7 guests

$1,217$1,073total

View all properties in Chestertown

Map shows last minute vacation rentals in Chestertown