Home Vacation Rentals By Owner In Chestertown, MD

Showing 20 Of 36 Vacation Rentals
Slider Thumb
Exceptional(2)

$354.73

/ Nightly
Private Vacation Home

River Cottage, Chestertown

Chestertown, Maryland, United States

Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps
Slider Thumb
Exceptional(17)

$621.51

/ Nightly
Private Vacation Home

The Lazy River House

Chestertown, Maryland, United States

Bed 3

Bed

Bath 3

Bath

Sleep 10

Sleeps
Slider Thumb
Exceptional(9)

$265.77

/ Nightly
Private Vacation Home

Walk to Historic Chestertown: Dog-Friendly Retreat

Chestertown, Maryland, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
Slider Thumb
Exceptional(1)

$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
Slider Thumb
Exceptional(33)

$353.2

/ Nightly
Apartment

Newly restored apartment in the heart of Chestertown

Chestertown, Maryland, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
Slider Thumb
Exceptional(2)

$273.98

/ Nightly
Apartment

Secluded Cottage in Middle of Chestertown

Chestertown, Maryland, United States

Bed 2

Bed

Bath 1

Bath

Sleep 2

Sleeps
Slider Thumb
Exceptional(31)

$1437.12

/ Nightly
Private Vacation Home

Historic Manor House on Beautiful Eastern Shore Estate

Chestertown, Maryland, United States

Bed 6

Bed

Bath 4

Bath

Sleep 13

Sleeps
Slider Thumb
Exceptional(75)

$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
Slider Thumb
Exceptional(3)

$318.44

/ Nightly
Private Vacation Home

3 Mi to Washington College! Updated Home w/ Patio

Chestertown, Maryland, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps
Slider Thumb
Exceptional(91)

$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
Slider Thumb
Exceptional(3)

$413.4

/ Nightly
Private Vacation Home

Blue Heron Farm Waterfront Chalet

Chestertown, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
Slider Thumb
Exceptional(44)

$882.47

/ Nightly
Private Vacation Home

Breathtaking waterfront home on the Chester River

Chestertown, Maryland, United States

Bed 4

Bed

Bath 4

Bath

Sleep 10

Sleeps
Slider Thumb
Exceptional(96)

$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
Slider Thumb
Exceptional(31)

$859.66

/ Nightly
Private Vacation Home

Escape to Goose Landing: Your Waterfront Retreat in Chestertown!

Chestertown, Maryland, United States

Bed 4

Bed

Bath 2

Bath

Sleep 10

Sleeps
Slider Thumb
Exceptional(27)

$294.15

/ Nightly
Cabin

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Chestertown, Maryland, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
Slider Thumb
Exceptional(1)

$309.52

/ Nightly
Private Vacation Home

Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Chestertown, Maryland, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
Slider Thumb
Exceptional(116)

$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
Slider Thumb

$577.15

/ Nightly
Private Vacation Home

Welcome to the magic of Langford Creek Farm

Chestertown, Maryland, United States

Bed 5

Bed

Bath 3

Bath

Sleep 10

Sleeps
Slider Thumb
Exceptional(6)

$1191.52

/ Nightly
Private Vacation Home

A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown.

Chestertown, Maryland, United States

Bed 5

Bed

Bath 2

Bath

Sleep 7

Sleeps
Slider Thumb
Exceptional(9)

$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
map-loader

Home Most popular vacation rentals in Chestertown

Slider Thumb
Exceptional(9)

$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
Slider Thumb
Exceptional(9)

$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
Slider Thumb
Exceptional(9)

$413.40

/ Nightly
Private vacation home

Blue Heron Farm Waterfront Chalet

Chestertown, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
Slider Thumb
Exceptional(9)

$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
Slider Thumb
Exceptional(9)

$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
Slider Thumb
Exceptional(9)

$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
Slider Thumb
Exceptional(9)

$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
Slider Thumb
Exceptional(9)

$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
Slider Thumb
Exceptional(9)

$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
Slider Thumb
Exceptional(9)

$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