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

Close

View larger map

Also consider

North America Holidays
207674 properties
United States Holidays
162788 properties

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

19 Holiday homes

(4) Very Good 

11

Ideal house in Chestertown from £110/night | 3 bedrooms, sleeps 7

Maryland / Chestertown

3 7 2 nights min

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

from £111 / night

£715 - £875 / week

Book View

Responds fast!
avg. 2 hours 6 minutes

from £111 / night

(5) Excellent 

28

House with 4 bedrooms in Chestertown, Maryland | wi-fi, air conditioning & garden

Maryland / Chestertown

4 8 2 nights min

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

from £190 / night

£913 - £1,065 / week

Book View

Responds fast!
avg. 1 hour 19 minutes

from £190 / night

(3) Excellent 

17

Self-catering house in Chestertown with wi-fi & garden - Great for tennis in town

Maryland / Chestertown

1 3 1 night min

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

from £103 / night

£609 / week

Book View

from £103 / night

(1) Excellent 

22

Private house with 2 bedrooms in Chestertown | walking holidays, garden and more

Maryland / Chestertown

2 5 3 nights min

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

from £88 / night

£381 - £685 / week

Book View

Responds fast!
avg. 2 hours 10 minutes

from £88 / night

(1) Excellent 

7

Affordable apartment rental in Maryland – 1 bedroom from £67/night

Maryland / Chestertown

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Child friendly
  • Air conditioning

from £67 / night

£343 / week

Book View

Responds fast!
avg. 2 hours 10 minutes

from £67 / night

(3) Very Good 

14

Holiday accommodation in Chestertown with great reviews | garden, bbq | fishing

Maryland / Chestertown

3 8 2 nights min

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

from £225 / night

£1,518 / week

Book View

from £225 / night

(2) Very Good 

16

Chestertown - house with a very good review rating | bicycles available & garden | water sports

Maryland / Chestertown

4 8 2 nights min

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

from £495 / night

£3,041 / week

Book View

from £495 / night

(7) Excellent 

10

Fantastic rental in Chestertown, Maryland - Great for tennis in town and cycling holidays | pet friendly

Maryland / Chestertown

1 2 3 nights min

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

from £76 / night

£521 / week

Book View

Responds fast!
avg. 2 hours 10 minutes

from £76 / night

7

Comfortable cottage in Maryland. Sleeps 3 in Chestertown

Maryland / Chestertown

1 3 1 night min

  • 1 bedroom
  • sleeps 3
  • 1 night min

from £149 / night

£1,038 / week

Book View

from £149 / night