Houses in Chestertown and Apartments – Holiday Lettings - Holiday Rentals Chestertown

Close

Enter dates for more accurate prices

Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

21 Holiday homes

(3) Excellent 

7

Chestertown holiday cottage accommodation

Maryland / Chestertown

1 3 1 night min

  • 1 bedroom
  • sleeps 3
  • 1 night min
  • Air conditioning
  • Private garden

from £174 / night

£1,217 / week

Book View

from £174 / night

(5) Excellent 

Certificate of Excellence

28

Holiday home with swimming pool in Chestertown

Maryland / Chestertown

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Nearest beach 5 km
  • Swimming pool
  • Child friendly

Certificate of Excellence

from £223 / night

£1,247 / week

Book View

Responds fast!
avg. 2 hours 43 minutes

from £223 / night

(3) Very Good 

14

Home rental in Chestertown

Maryland / Chestertown

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Private garden

from £263 / night

£1,778 / week

Book View

Responds fast!
avg. 3 hours 30 minutes

from £263 / night

(3) Excellent 

17

Chestertown holiday home let

Maryland / Chestertown

1 3 1 night min

  • 1 bedroom
  • sleeps 3
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly

from £121 / night

£713 / week

Book View

from £121 / night

(2) Very Good 

16

Chestertown holiday home rental

Maryland / Chestertown

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

from £580 / night

£3,565 / week

Book View

from £580 / night

(4) Very Good 

11

Holiday home in Chestertown

Maryland / Chestertown

3 7 2 nights min

  • 3 bedrooms
  • sleeps 7
  • 2 nights min
  • Child friendly

from £130 / night

£838 - £1,025 / week

Book View

Responds fast!
avg. 1 hour 40 minutes

from £130 / night

(1) Excellent 

22

Holiday home in Chestertown

Maryland / Chestertown

2 5 3 nights min

  • 2 bedrooms
  • sleeps 5
  • 3 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

from £130 / night

£802 / week

Book View

Responds fast!
avg. 2 hours 19 minutes

from £130 / night

(1) Excellent 

7

Holiday apartment in Chestertown

Maryland / Chestertown

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Child friendly
  • Air conditioning

from £79 / night

£549 / week

Book View

Responds fast!
avg. 2 hours 19 minutes

from £79 / night

(7) Excellent 

10

Chestertown holiday apartment rental

Maryland / Chestertown

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Nearest beach 24 km
  • Child friendly
  • Air conditioning

from £89 / night

£611 / week

Book View

Responds fast!
avg. 2 hours 19 minutes

from £89 / night

Great rentals within 20 miles that match your search

Distance approx 18.6 miles from Chestertown

26

Stevensville holiday home rental

Kent Island / Stevensville

3 10 3 nights min

  • 3 bedrooms
  • sleeps 10
  • 3 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

from £1,247 / night

£6,235 / week

Book View

from £1,247 / night

Distance approx 10.9 miles from Chestertown Show on Map

(1) Excellent 

10

Holiday bungalow in Rock Hall

Maryland / Rock Hall

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

from £254 / night

£1,777 / week

Book View

from £254 / night

Distance approx 10.97 miles from Chestertown Show on Map

8

Rock Hall holiday home rental

Maryland / Rock Hall

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

from £223 / night

£1,559 / week

Book View

Responds fast!
avg. 3 hours 15 minutes

from £223 / night

Distance approx 17.67 miles from Chestertown

13

Holiday apartment in Centreville

Maryland / Centreville

1 3 1 night min

  • 1 bedroom
  • sleeps 3
  • 1 night min
  • Air conditioning
  • Private garden

from £105 / night

£730 / week

Book View

from £105 / night

Distance approx 7.52 miles from Chestertown

(2) Very Good 

39

Still Pond holiday home rental

Maryland / Still Pond

1 3 1 night min

  • 1 bedroom
  • sleeps 3
  • 1 night min
  • Nearest beach 5 km
  • Child friendly
  • Air conditioning

from £49 / night

£358 / week

Book View

Responds fast!
avg. 2 hours 9 minutes

from £49 / night

Distance approx 10.7 miles from Chestertown Show on Map

(3) Excellent 

12

Rock Hall holiday home rental

Maryland / Rock Hall

3 10 2 nights min

  • 3 bedrooms
  • sleeps 10
  • 2 nights min
  • Child friendly
  • Pet friendly

from £303 / night

£1,908 / week

Book View

Responds fast!
avg. 3 hours 15 minutes

from £303 / night

Distance approx 7.52 miles from Chestertown

58

Holiday home in Still Pond

Maryland / Still Pond

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Nearest beach 5 km
  • Child friendly
  • Air conditioning

from £49 / night

£343 / week

Book View

Responds fast!
avg. 2 hours 9 minutes

from £49 / night

Distance approx 18.76 miles from Chestertown

11

Holiday apartment in Stevensville

Kent Island / Stevensville

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Child friendly

from £294 / night

£1,743 / week

Book View

from £294 / night

Distance approx 18.02 miles from Chestertown Show on Map

(14) Excellent 

19

Holiday home rental

Maryland / Kent Island

3 12 3 nights min

  • 3 bedrooms
  • sleeps 12
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Child friendly

from £223 / night

£1,248 - £2,228 / week

Book View

from £223 / night

Distance approx 19.14 miles from Chestertown

15

Wye Mills holiday apartment rental

Talbot County / Wye Mills

1 5 1 night min

  • 1 bedroom
  • sleeps 5
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly

from £124 / night

£867 / week

Book View

from £124 / night

Distance approx 10.71 miles from Chestertown Show on Map

88

Holiday home in Rock Hall

Maryland / Rock Hall

4 7 1 night min

  • 4 bedrooms
  • sleeps 7
  • 1 night min
  • Child friendly

from £90 / night

£576 - £2,087 / week

Book View

Responds fast!
avg. 2 hours 9 minutes

from £90 / night

Distance approx 11.02 miles from Chestertown Show on Map

8

Holiday home in Rock Hall

Maryland / Rock Hall

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly

from £205 / night

£1,434 / week

Book View

Responds fast!
avg. 3 hours 15 minutes

from £205 / night

Also consider