Home Vacation Rentals By Owner In Tilghman, MD

Showing 18 Of 18 Vacation Rentals
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Exceptional(27)

$532.65

/ Nightly
Cottage

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Tilghman Island, Maryland, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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$262.47

/ Nightly
Private Vacation Home

Vintage Pet-Friendly Cottage | Tilghman Island

Tilghman Island, Maryland, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(31)

$650.98

/ Nightly
Private Vacation Home

Tilghman Island Waterfront Retreat with Brand New Pool – Summer 2026!

Tilghman, Maryland, United States

Bed 4

Bed

Bath 4

Bath

Sleep 8

Sleeps
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Exceptional(27)

$604.45

/ Nightly
Private Vacation Home

Family Friendly Cottage - Waterfront. Spectacular Sunsets over Chesapeake Bay

Tilghman, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 5

Sleeps
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Exceptional(53)

$538.85

/ Nightly
Private Vacation Home

BOOK NOW FOR SPRING & SUMMER DATES.

Tilghman Island, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(20)

$874.46

/ Nightly
Private Vacation Home

Waterfront Home with Pool, Hot Tub, Dock & Sunset Views – Near St. Michaels

Tilghman Island, Maryland, United States

Bed 5

Bed

Bath 4

Bath

Sleep 8

Sleeps
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Exceptional(8)

$349.01

/ Nightly
Private Vacation Home

Tilghman Island Retreat By Knapps Narrows!

Tilghman, Maryland, United States

Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps
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Exceptional(17)

$678.05

/ Nightly
Private Vacation Home

House on the Chesapeake Bay

Tilghman Island, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(19)

$952.5

/ Nightly
Private Vacation Home

Tilghman | Pool | Private Dock | Pet Friendly

Tilghman, Maryland, United States

Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
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Exceptional(2)

Select Dates for Price
Private Vacation Home

Bayview 2.0 | an ESVR property

Wittman, Maryland, United States

Bed 6

Bed

Bath 6

Bath

Sleep 12

Sleeps
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Exceptional(3)

$1008.74

/ Nightly
Private Vacation Home

Tilghman | Pool | Private Dock | Pet Friendly

Tilghman, Maryland, United States

Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(50)

$529.65

/ Nightly
Private Vacation Home

Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

Tilghman Island, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(16)

$462.08

/ Nightly
Private Vacation Home

Cozy 2-Bedroom Cottage on Tilghman Island – Near Restaurants & Water Activities

Tilghman Island, Maryland, United States

Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps
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Exceptional(16)

$391.02

/ Nightly
Private Vacation Home

Pet-Friendly Cottage on Tilghman Island | Minutes to St. Michaels

Tilghman Island, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(35)

$330.57

/ Nightly
Cottage

Point of View Waterfront cottage with panoramic views on Tilghman Island

Tilghman Island, Maryland, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(25)

$650.98

/ Nightly
Private Vacation Home

Bayfront Retreat Near St. Michaels | Private Dock • Sunset Views

Tilghman Island, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(3)

$747.88

/ Nightly
Private Vacation Home

Tilghman | Fenced Yard | Pet Friendly | Charming

Tilghman, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(14)

$427.03

/ Nightly
Private Vacation Home

Pet-Friendly Tilghman Island Coastal Retreat

Tilghman Island, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 5

Sleeps
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Home Most popular vacation rentals in Tilghman

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Exceptional(14)

$996.52

/ Nightly
Private vacation home

Waterfront Home with Pool, Hot Tub, Dock & Sunset Views – Near St. Michaels

Tilghman Island, Maryland, United States

Bed 5

Bed

Bath 4

Bath

Sleep 8

Sleeps
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Exceptional(14)

$813.37

/ Nightly
Private vacation home

Tilghman Island Waterfront Retreat with Brand New Pool – Summer 2026!

Tilghman, Maryland, United States

Bed 4

Bed

Bath 4

Bath

Sleep 8

Sleeps
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Exceptional(14)

$678.05

/ Nightly
Private vacation home

House on the Chesapeake Bay

Tilghman Island, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(14)

$650.98

/ Nightly
Private vacation home

Bayfront Retreat Near St. Michaels | Private Dock • Sunset Views

Tilghman Island, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(14)

$532.48

/ Nightly
Private vacation home

Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

Tilghman Island, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(14)

$465.26

/ Nightly
Private vacation home

Cozy 2-Bedroom Cottage on Tilghman Island – Near Restaurants & Water Activities

Tilghman Island, Maryland, United States

Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps
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Exceptional(14)

$427.03

/ Nightly
Private vacation home

Pet-Friendly Tilghman Island Coastal Retreat

Tilghman Island, Maryland, United States

Bed 3

Bed

Bath 2

Bath

Sleep 5

Sleeps
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Exceptional(14)

$334.10

/ Nightly
Cottage

\"Point of View\" Waterfront cottage with panoramic views on Tilghman Island

Tilghman Island, Maryland, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(14)

$535.83

/ Nightly
Cottage

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Tilghman Island, Maryland, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(14)

$349.01

/ Nightly
Private vacation home

Tilghman Island Retreat By Knapps Narrows!

Tilghman, Maryland, United States

Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps

Most Popular Cities in Maryland