Chestertown Rentals

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23 Houses

(5) Excellent 

Certificate of Excellence

28

Cozy & Spacious Chestertown Home

Maryland / Chestertown

Chestertown house

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Nearest beach 5 mi
  • Swimming pool
  • Child Friendly

Certificate of Excellence

Price per night from

$287

Responds fast!
avg. 2 hours 43 minutes

Price per night from

$287

(3) Excellent 

7

Cottage On Kent

Maryland / Chestertown

Chestertown cottage

1 3 1 night min

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

Price per night from

$225

Price per night from

$225

(3) Very Good 

14

Retreat at a quiet, water front cottage

Maryland / Chestertown

Chestertown house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden
“A best kept secret!” I have had the pleasure of staying at Cliff Point many times. The view cannot be matched, water views more than 180 degrees, sunsets are stunning. But on top of that the house is so comfortable and charming, spacious and cozy. Ch
…see more

Price per night from

$340

Responds fast!
avg. 3 hours 30 minutes

Price per night from

$340

(4) Very Good 

11

Chester River House with Views

Maryland / Chestertown

Chestertown house

3 7 2 nights min

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

Price per night from

$179

Responds fast!
avg. 1 hour 40 minutes

Price per night from

$179

(3) Excellent 

17

Belle Rose Cottage at Victory Farm (Pet Friendly!)

Maryland / Chestertown

Chestertown house

1 3 1 night min

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

Price per night from

$156

Price per night from

$156

(2) Very Good 

16

Gorgeous Home on Chester River

Maryland / Chestertown

Chestertown house

4 8 2 nights min

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

Price per night from

$745

Price per night from

$745

(1) Excellent 

22

Sunview Cottage on Chesapeake Bay

Maryland / Chestertown

Chestertown house

2 5 3 nights min

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

Price per night from

$167

Responds fast!
avg. 2 hours 19 minutes

Price per night from

$167

(1) Excellent 

7

Cozy Apartment in Chestertown

Maryland / Chestertown

Chestertown apartment

1 2 1 night min

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

Price per night from

$102

Responds fast!
avg. 2 hours 19 minutes

Price per night from

$102

(7) Excellent 

10

Charming Apartment in Historic Chestertown, MD

Maryland / Chestertown

Chestertown apartment

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Nearest beach 24 mi
  • Child Friendly
  • Air conditioning

Price per night from

$114

Responds fast!
avg. 2 hours 19 minutes

Price per night from

$114

Great rentals within 20 miles that match your search

Distance approx 18.6 km from Chestertown

26

Love Point Luxury Waterfront in Stevensville

Kent Island / Stevensville

Stevensville house

3 10 3 nights min

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

Price per night from

$1,608

Price per night from

$1,608

Distance approx 10.9 km from Chestertown Show on Map

(1) Excellent 

10

Summer House

Maryland / Rock Hall

Rock Hall bungalow

3 8 2 nights min

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

Price per night from

$328

Price per night from

$328

Distance approx 17.67 km from Chestertown

13

Luxury Apartment with Private Entrance

Maryland / Centreville

Centreville apartment

1 3 1 night min

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

Price per night from

$135

Price per night from

$135

Distance approx 7.52 km from Chestertown

(2) Very Good 

39

Big BD in Civil War House starting at 55$/night

Maryland / Still Pond

Still Pond house

1 3 1 night min

  • 1 bedroom
  • sleeps 3
  • 1 night min
  • Nearest beach 5 mi
  • Child Friendly
  • Air conditioning

Price per night from

$63

Responds fast!
avg. 2 hours 9 minutes

Price per night from

$63

Distance approx 10.97 km from Chestertown Show on Map

8

Bay Cottage

Maryland / Rock Hall

Rock Hall house

2 5 2 nights min

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

Price per night from

$288

Responds fast!
avg. 3 hours 15 minutes

Price per night from

$288

Distance approx 10.7 km from Chestertown Show on Map

(3) Excellent 

12

Sailors Crossing

Maryland / Rock Hall

Rock Hall house

3 10 2 nights min

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

Price per night from

$391

Responds fast!
avg. 3 hours 15 minutes

Price per night from

$391

Distance approx 7.52 km from Chestertown

58

Great BD in Civil War House starting at 55$/night

Maryland / Still Pond

Still Pond house

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Nearest beach 5 mi
  • Child Friendly
  • Air conditioning

Price per night from

$63

Responds fast!
avg. 2 hours 9 minutes

Price per night from

$63

Distance approx 18.76 km from Chestertown

11

Love Point Bay Vacation Home

Kent Island / Stevensville

Stevensville apartment

2 6 2 nights min

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

Price per night from

$377

Price per night from

$377

Distance approx 18.02 km from Chestertown Show on Map

(14) Excellent 

19

Love Point Waterfront

Maryland / Kent Island

Kent Island house

3 12 3 nights min

  • 3 bedrooms
  • sleeps 12
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 5 mi
  • Child Friendly
“Love Point Retreat” I stayed at Paula's property 3 times so far. We stayed once in October 2014 and twice in April 2015. Here is how I would break it up: Owner: Paula is very nice, accommodating and extremely responsive. She was easy to deal with, ans
…see more

Price per night from

$288

Price per night from

$288

Distance approx 19.14 km from Chestertown

15

Lakeside Private Apartment

Talbot County / Wye Mills

Wye Mills apartment

1 5 1 night min

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

Price per night from

$160

Price per night from

$160

Distance approx 11.02 km from Chestertown Show on Map

8

Bayside Retreat

Maryland / Rock Hall

Rock Hall house

3 6 min stay varies

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

Price per night from

$265

Responds fast!
avg. 3 hours 15 minutes

Price per night from

$265

Distance approx 10.71 km from Chestertown Show on Map

88

Great vacation rental located in the waterfront town of Rock Hall

Maryland / Rock Hall

Rock Hall house

4 7 1 night min

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

Price per night from

$115

Responds fast!
avg. 2 hours 9 minutes

Price per night from

$115

Distance approx 19.48 km from Chestertown

(15) Excellent 

35

Luxury vacation condominum with private beach

Kent Island / Chester

Chester house

4 10 2 nights min

  • 4 bedrooms
  • sleeps 10
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 mi
  • Child Friendly

Price per night from

$440

Price per night from

$440

Distance approx 11.95 km from Chestertown Show on Map

(22) Excellent 

34

Waterfront House, Eastern Shore Chesapeake Bay

Maryland / Centreville

Centreville house

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$458

Price per night from

$458