Chestertown Vacation Home Rentals, Treehouses & More


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1
1 / 7

Cozy Apartment in Chestertown

  • 1
  • 2
  • Min stay varies

$88

Details

1
1 / 22

Sunview Cottage on Chesapeake Bay

  • 2
  • 5
  • Min stay varies

$145

Details

7
1 / 10

Charming Apartment in Historic Chestertown, MD

  • 1
  • 2
  • Min stay varies

$99

Details

3
1 / 14

Retreat at a quiet, water front cottage

  • 3
  • 8
  • 2 nights min

$295

Details

2
1 / 11

Chester River House with Views

  • 3
  • 7
  • 2 nights min

$145

Details

3
1 / 28

Bayview by Chesapeake Bay

  • 1
  • 4
  • Min stay varies

$120

Details

1
1 / 16

Gorgeous Home on Chester River

  • 4
  • 8
  • 3 nights min

$650

Details

Great rentals within 30 miles that match your search

2
1 / 15

Waterfront Cottage at Spring Cove

  • 3
  • 6
  • 3 nights min

$250

Details

1
1 / 12

Captain's Quarters, a waterfront couples retreat

  • 1
  • 4
  • 2 nights min

$180

Details

3
1 / 17

* 3 Bedroom Rental House in Historic Rock Hall MD

  • 3
  • 7
  • 2 nights min

$250

Details

21
1 / 34

Waterfront House, Eastern Shore Chesapeake Bay

  • 4
  • 8
  • Min stay varies

$350

Details

11
1 / 19

Love Point Waterfront

  • 3
  • 12
  • Min stay varies

$250

Details

1 / 12

Love Point Bay Luxury Waterfront House

  • 3
  • 10
  • 3 nights min

$900

Details

1 / 39

Love Point Bay Vacation Home

  • 2
  • 6
  • 2 nights min

$299

Details

1 / 11

Love Point Bay Vacation Home

  • 2
  • 6
  • 2 nights min

$209

Details

13
1 / 35

Luxury vacation condominum with private beach

  • 4
  • 10
  • 2 nights min

$440

Details

1 / 26

Finches' Nest

  • 8
  • Min stay varies

$204

Details

1 / 22

Cozy Cabin

  • 6
  • 2 nights min

$146

Details

3
1 / 21

Peaceful, Waterfront Home on 3 Acres (pier + western view w/gorgeous sunsets)

  • 4
  • 8
  • 3 nights min

$180

Details

1
1 / 10

C/ean & Cozy

  • 1
  • 2
  • 1 night min

$59

Details

1 / 19

Clean & Spacious

  • 4
  • 9
  • 1 night min

$350

Details

18
1 / 20

Mahogany Ridge, Elegant comfort,Pool, Ocean Views.

  • 4
  • 8
  • 3 nights min

$234

Details

1 / 22

Luxurious apartment in the center

  • 1
  • 2
  • 1 night min

$236

Details

1
1 / 19

Annapolis Waterfront very near USNA

  • 3
  • 6
  • Min stay varies

$285

Details

3
1 / 17

KI Golf House-A PAR for the Course & Mile to Beach

  • 4
  • 10
  • Min stay varies

$425

Details

1
1 / 24

Waterfront Property close to Annapolis and the the Naval Academy!

  • 4
  • 10
  • Min stay varies

$400

Details

6
1 / 9

DUKES at Silver Sands Resort

  • 6
  • 14
  • 3 nights min

$787

Details

1 / 19

Historic Row House with unique characteristics

  • 2
  • 1 night min

$69

Details

1 / 15

Annapolis Area Waterview--Fully Furnished 4-Bedroom Home

  • 4
  • 6
  • 90 nights min

$134

Details

1 / 23

Canton Rowhome with Amazing View

  • 3
  • 10
  • 2 nights min

$180

Details

1
1 / 12

Beautiful, Spacious Houseboat in Downtown Baltimore

  • 2
  • 6
  • 2 nights min

$225

Details

1 / 27

New! Waterfront 5BR Stevensville House w/ Pier!

  • 5
  • 12
  • Min stay varies

$375

Details

1 / 26

Stunning Home in Historic District Annapolis, Steps to Academy

  • 4
  • 9
  • Min stay varies

$900

Details

1
1 / 7

Charming Townhouse - Steps to City Dock and USNA

  • 3
  • 8
  • 3 nights min

$450

Details

1 / 24

Charming Artists Home in Eastport/Annapolis

  • 3
  • 6
  • 3 nights min

$375

Details

2
1 / 15

Historic Rowhouse Convenient to the Best of Baltimore's Attractions and Hopkins

  • 3
  • 9
  • 2 nights min

$250

Details

1 / 4

LOCATION,LOCATION,,LUXURY,WALK TO CITY ,PARKING. Annapolis, MD

  • 2
  • 5
  • 3 nights min

$250

Details

1 / 15

Location,location,location,walk to city dock,free

  • 2
  • 5
  • Min stay varies

$180

Details

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