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

All in pricing: Taxes and fees included

Save $172

House in Chester, MD

Nov 16 - 19

$330/night

New

4 bedrooms

10 guests

$1,262$1,089total

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 $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 $205

Preferred host

House in Stevensville, MD

Nov 16 - 19

$467/night

4.9

12

3 bedrooms

6 guests

$1,681$1,476total

Save $138

House in Grasonville, MD

Nov 29 - Dec 2

$484/night

New

4 bedrooms

8 guests

$1,729$1,591total

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 $433

Preferred host

Entire home in Queenstown, MD

Nov 16 - 19

$1,514/night

5.0

3

5 bedrooms

10 guests

$5,411$4,978total

Save $135

House in Annapolis, MD

Dec 20 - 23

$458/night

5.0

10

3 bedrooms

8 guests

$1,686$1,551total

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 $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 $261

Preferred host

Cottage in Annapolis, MD

Nov 16 - 19

$511/night

4.8

18

3 bedrooms

8 guests

$1,991$1,730total

Save $182

Preferred host

House in Annapolis, MD

Dec 8 - 11

$619/night

5.0

19

3 bedrooms

8 guests

$2,278$2,096total

Save $228

Whimstay gem

House in Annapolis, MD

Nov 16 - 19

$276/night

4.9

27

2 bedrooms

4 guests

$1,162$934total

Save $426

Preferred host

House in Annapolis, MD

Dec 31 - Jan 3

$726/night

4.6

19

2 bedrooms

7 guests

$2,882$2,456total

Save $306

Preferred host

House in Annapolis, MD

Nov 18 - 21

$421/night

5.0

9

4 bedrooms

8 guests

$1,729$1,423total

Save $293

Preferred host

House in Annapolis, MD

Nov 16 - 19

$706/night

5.0

6

4 bedrooms

12 guests

$2,680$2,387total

Save $280

Whimstay gem

House in Annapolis, MD

Dec 27 - 30

$951/night

5.0

37

3 bedrooms

8 guests

$3,496$3,217total

Save $306

Preferred host

Apartment in Annapolis, MD

Nov 19 - 22

$532/night

5.0

13

1 bedroom

4 guests

$2,106$1,800total

Save $439

Whimstay gem

House in Annapolis, MD

Nov 20 - 23

$896/night

5.0

33

4 bedrooms

12 guests

$3,469$3,030total

Save $183

Preferred host

Entire home in Annapolis, MD

Nov 21 - 24

$343/night

5.0

3

4 bedrooms

8 guests

$1,336$1,153total

Save $225

Preferred host

House in Annapolis, MD

Nov 16 - 19

$469/night

4.3

3

3 bedrooms

9 guests

$1,812$1,588total

View all properties in Chester

Map shows last minute vacation rentals in Chester