Home Vacation Rentals By Owner In Chestertown, MD

Showing 36 Of 36 Vacation Rentals
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Exceptional(5)

$630.26

/ Nightly
Private Vacation Home

Private Waterfront Cottage On Langford Creek With Hot Tub & Pier

Chestertown, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(26)

$1659.72

/ Nightly
Private Vacation Home

Beautiful, spacious waterfront home, an easy walk to historic Chestertown

Chestertown, Maryland, United States

Bed 6

Bed

Bath 6

Bath

Sleep 14

Sleeps
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Exceptional(3)

$728.54

/ Nightly
Private Vacation Home

The Waterfront Retreat- With Sauna and Hot Tub!

Chestertown, Maryland, United States

Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Exceptional(7)

$544.84

/ Nightly
Private Vacation Home

The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown

Chestertown, Maryland, United States

Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(32)

$525.36

/ Nightly
Private Vacation Home

Harbor View Haven | Waterfront w/ Hot Tub + Dock!

Chestertown, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 10

Sleeps
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$239.03

/ Nightly
Private Vacation Home

Chesapeake Getaway - Marinas - Woodland Views

Chestertown, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 7

Sleeps
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Exceptional(88)

$759.78

/ Nightly
Private Vacation Home

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

Chestertown, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(4)

$377.89

/ Nightly
Apartment

Lovely 2 bedroom and loft apartment with AC, WiFi overlooking the Chester River

Chestertown, Maryland, United States

Bed 3

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(9)

$597.84

/ Nightly
Private Vacation Home

Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!

Chestertown, Maryland, United States

Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(31)

$289.01

/ Nightly
Private Vacation Home

Lovely Home in Chestertown - Free EV Charging for guests

Chestertown, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 7

Sleeps
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Exceptional(324)

$567.34

/ Nightly
Private Vacation Home

Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities

Chestertown, Maryland, United States

Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(61)

$1293.66

/ Nightly
Private Vacation Home

Eagles Point Landing-Private Pool, Dock, Pickleball

Chestertown, Maryland, United States

Bed 4

Bed

Bath 4

Bath

Sleep 8

Sleeps
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Exceptional(24)

$641.83

/ Nightly
Private Vacation Home

Victorian Hideaway: Beautiful Exterior, Modern interior

Chestertown, Maryland, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(130)

$158.84

/ Nightly
Apartment

First Floor Studio Apartment in Historic Chestertown

Chestertown, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 3

Sleeps
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Exceptional(27)

$1023.6

/ Nightly
Private Vacation Home

Pet-Friendly Home on Chester River w/ Dock!

Chestertown, Maryland, United States

Bed 4

Bed

Bath 4

Bath

Sleep 14

Sleeps
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Exceptional(57)

$212.02

/ Nightly
Apartment

Historic Downtown Garden Oasis with Private Patio

Chestertown, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
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Home Most popular vacation rentals in Chestertown

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Exceptional(57)

$551.62

/ Nightly
Private vacation home

Riverside at Pear Tree Point Private Waterfront Escape with Hot Tub and Fire Pit

Chestertown, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Exceptional(57)

$404.39

/ Nightly
Private vacation home

Circa 1900 Home in the Heart of Historic Downtown Chestertown

Chestertown, Maryland, United States

Bed 4

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(57)

$413.40

/ Nightly
Private vacation home

Blue Heron Farm Waterfront Chalet

Chestertown, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(57)

$481.27

/ Nightly
Private vacation home

Wren Retweet- Country Estate in Center of C’Town

Chestertown, Maryland, United States

Bed 5

Bed

Bath 4

Bath

Sleep 10

Sleeps
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Exceptional(57)

$496.43

/ Nightly
Cottage

Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock.

Chestertown, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(57)

$525.36

/ Nightly
Private vacation home

Harbor View Haven | Waterfront w/ Hot Tub + Dock!

Chestertown, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Exceptional(57)

$535.48

/ Nightly
Private vacation home

Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

Chestertown, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Exceptional(57)

$542.21

/ Nightly
Private vacation home

Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown

Chestertown, Maryland, United States

Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(57)

$544.84

/ Nightly
Private vacation home

The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown

Chestertown, Maryland, United States

Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(57)

$1293.66

/ Nightly
Private vacation home

Eagles Point Landing-Private Pool, Dock, Pickleball

Chestertown, Maryland, United States

Bed 4

Bed

Bath 4

Bath

Sleep 8

Sleeps

Most Popular Cities in Maryland