Updating...

Enter dates for more accurate prices

Chestertown Rentals

Filter

Bedrooms

  • Any
  • 1+ Bedrooms
  • 2+ Bedrooms
  • 3+ Bedrooms
  • 4+ Bedrooms
  • 5+ Bedrooms
  • 6+ Bedrooms
  • 7+ Bedrooms
  • 8+ Bedrooms
  • 9+ Bedrooms
  • 10+ Bedrooms
  • 11+ Bedrooms
  • 12+ Bedrooms
  • 13+ Bedrooms
  • 14+ Bedrooms
  • 15+ Bedrooms

Price range

Per night

$10 - $500

Chestertown Rentals

22 Houses

Cottage On Kent

Chestertown cottage

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$224

1 / 7

Cozy & Spacious Chestertown Home

Chestertown house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 16 minutes

Price per night from

$287

1 / 28

Chester River House with Views

Chestertown house

3 bedrooms / 1 bathroom / sleeps 7

Responds fast! avg. 2 hours 53 minutes

Price per night from

$178

1 / 11

Retreat at a quiet, water front cottage

Chestertown house

3 bedrooms / 3 bathrooms / sleeps 8

“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

Price per night from

$338

1 / 14

Belle Rose Cottage at Victory Farm (Pet Friendly!)

Chestertown house

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$155

1 / 17

Gorgeous Home on Chester River

Chestertown house

4 bedrooms / 9 bathrooms / sleeps 8

Price per night from

$744

1 / 16

Sunview Cottage on Chesapeake Bay

Chestertown house

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 3 hours 27 minutes

Price per night from

$166

1 / 22

Cozy Apartment in Chestertown

Chestertown apartment

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 27 minutes

Price per night from

$101

1 / 7

Charming Apartment in Historic Chestertown, MD

Chestertown apartment

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 27 minutes

Price per night from

$114

1 / 10

Great rentals within 20 miles that match your search

Bay Cottage

Rock Hall house

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 3 hours 15 minutes

Price per night from

$229

1 / 8

Sailors Crossing

Rock Hall house

3 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 3 hours 15 minutes

Price per night from

$390

1 / 12

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

Still Pond house

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 2 hours 49 minutes

Price per night from

$63

1 / 39

Love Point Luxury Waterfront in Stevensville

Stevensville house

3 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$1,602

1 / 26

Love Point Bay Vacation Home

Stevensville apartment

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$377

1 / 11

Luxury vacation condominum with private beach

Chester house

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$440

1 / 35

Skeet shoot in the back yard of your rental

Rock Hall house

3 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 2 hours 49 minutes

Price per night from

$115

1 / 43

Great vacation rental located in the waterfront town of Rock Hall

Rock Hall house

4 bedrooms / 3 bathrooms / sleeps 7

Responds fast! avg. 2 hours 49 minutes

Price per night from

$115

1 / 88

Bayside Retreat

Rock Hall house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 15 minutes

Price per night from

$229

1 / 9

Summer House in Rock Hall

Rock Hall house

3 bedrooms / 1 bathroom / sleeps 8

Responds fast! avg. 3 hours 15 minutes

Price per night from

$229

1 / 9

Lakeside Private Apartment

Wye Mills apartment

1 bedroom / 1 bathroom / sleeps 5

Price per night from

$160

1 / 15

Luxury Apartment with Private Entrance

Centreville apartment

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$134

1 / 13

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

Still Pond house

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 2 hours 49 minutes

Price per night from

$63

1 / 58
Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more