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Vacation Rentals near Tilghman Island

Tilghman Island Road, St. Michaels, Maryland
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Bedrooms

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5 mi
31 rentals in St. Michaels.
Stay in the HEART of Saint Michaels!, vacation rental in St. Michaels
Stay in the HEART of Saint Michaels!, vacation rental in St. Michaels
Stay in the HEART of Saint Michaels!, vacation rental in St. Michaels

Stay in the HEART of Saint Michaels!

Rental Home
3.0 miles from Tilghman Island
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch, vacation rental in St. Michaels
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch, vacation rental in St. Michaels
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch, vacation rental in St. Michaels

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Rental Home
3.0 miles from Tilghman Island
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!, vacation rental in St. Michaels
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!, vacation rental in St. Michaels
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!, vacation rental in St. Michaels

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Rental Home
3.1 miles from Tilghman Island
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Walk to Everything House, vacation rental in St. Michaels
Walk to Everything House, vacation rental in St. Michaels
Walk to Everything House, vacation rental in St. Michaels

Walk to Everything House

Rental Home
3.0 miles from Tilghman Island
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Premier St. Michaels Cottage - T. Blades House -  Walk to Everything in Town, vacation rental in St. Michaels
Premier St. Michaels Cottage - T. Blades House -  Walk to Everything in Town, vacation rental in St. Michaels
Premier St. Michaels Cottage - T. Blades House -  Walk to Everything in Town, vacation rental in St. Michaels

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

Rental Home
3.1 miles from Tilghman Island
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Dollhouse in Central Historic St Michaels, vacation rental in St. Michaels
Dollhouse in Central Historic St Michaels, vacation rental in St. Michaels
Dollhouse in Central Historic St Michaels, vacation rental in St. Michaels

Dollhouse in Central Historic St Michaels

Rental Home
2.9 miles from Tilghman Island
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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St. Michael's Premier In-Town Rental with heated pool-opens 4/22, vacation rental in St. Michaels
St. Michael's Premier In-Town Rental with heated pool-opens 4/22, vacation rental in St. Michaels
St. Michael's Premier In-Town Rental with heated pool-opens 4/22, vacation rental in St. Michaels

St. Michael's Premier In-Town Rental with heated pool-opens 4/22

Rental Home
3.3 miles from Tilghman Island
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Chase Away the Chill with Our Winter Stay Specials!, vacation rental in St. Michaels
Chase Away the Chill with Our Winter Stay Specials!, vacation rental in St. Michaels
Chase Away the Chill with Our Winter Stay Specials!, vacation rental in St. Michaels

Chase Away the Chill with Our Winter Stay Specials!

Condo/Apartment
3.2 miles from Tilghman Island
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife, vacation rental in St. Michaels
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife, vacation rental in St. Michaels
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife, vacation rental in St. Michaels

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Rental Home
3.0 miles from Tilghman Island
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Chic Flat with King Bed & Fireplace, vacation rental in St. Michaels
Chic Flat with King Bed & Fireplace, vacation rental in St. Michaels
Chic Flat with King Bed & Fireplace, vacation rental in St. Michaels

Chic Flat with King Bed & Fireplace

Condo/Apartment
3.0 miles from Tilghman Island
2 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
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Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels, vacation rental in St. Michaels
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels, vacation rental in St. Michaels
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels, vacation rental in St. Michaels

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Rental Home
3.1 miles from Tilghman Island
3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Harbor View Suite, vacation rental in St. Michaels
Harbor View Suite, vacation rental in St. Michaels
Harbor View Suite, vacation rental in St. Michaels

Harbor View Suite

Condo/Apartment
3.4 miles from Tilghman Island
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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2025 Renovation Beautiful Waterfront Home w/ Pool In St. Michaels, vacation rental in St. Michaels
2025 Renovation Beautiful Waterfront Home w/ Pool In St. Michaels, vacation rental in St. Michaels
2025 Renovation Beautiful Waterfront Home w/ Pool In St. Michaels, vacation rental in St. Michaels

2025 Renovation Beautiful Waterfront Home w/ Pool In St. Michaels

Rental Home
3.8 miles from Tilghman Island
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Downtown St. Michaels | Bikes | Kayaks | Private Pier, vacation rental in St. Michaels
Downtown St. Michaels | Bikes | Kayaks | Private Pier, vacation rental in St. Michaels
Downtown St. Michaels | Bikes | Kayaks | Private Pier, vacation rental in St. Michaels

Downtown St. Michaels | Bikes | Kayaks | Private Pier

Rental Home
3.6 miles from Tilghman Island
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly, vacation rental in St. Michaels
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly, vacation rental in St. Michaels
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly, vacation rental in St. Michaels

Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

Rental Home
2.3 miles from Tilghman Island
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Seasonal Rental: Artisan designed 3 bedroom home., vacation rental in St. Michaels
Seasonal Rental: Artisan designed 3 bedroom home., vacation rental in St. Michaels
Seasonal Rental: Artisan designed 3 bedroom home., vacation rental in St. Michaels

Seasonal Rental: Artisan designed 3 bedroom home.

Rental Home
3.5 miles from Tilghman Island
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Warm Up Here! Your Winter Getaway Awaits, vacation rental in St. Michaels
Warm Up Here! Your Winter Getaway Awaits, vacation rental in St. Michaels
Warm Up Here! Your Winter Getaway Awaits, vacation rental in St. Michaels

Warm Up Here! Your Winter Getaway Awaits

Rental Home
3.8 miles from Tilghman Island
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Grace Cottage, Saint Michaels Walk to everything!, vacation rental in St. Michaels
Grace Cottage, Saint Michaels Walk to everything!, vacation rental in St. Michaels
Grace Cottage, Saint Michaels Walk to everything!, vacation rental in St. Michaels

Grace Cottage, Saint Michaels Walk to everything!

Rental Home
3.1 miles from Tilghman Island
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels, vacation rental in St. Michaels
Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels, vacation rental in St. Michaels
Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels, vacation rental in St. Michaels

Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels

Rental Home
2.6 miles from Tilghman Island
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Minutes from Downtown St. Michaels | Pool | Hot Tub | Pickle Ball Court, vacation rental in St. Michaels
Minutes from Downtown St. Michaels | Pool | Hot Tub | Pickle Ball Court, vacation rental in St. Michaels
Minutes from Downtown St. Michaels | Pool | Hot Tub | Pickle Ball Court, vacation rental in St. Michaels

Minutes from Downtown St. Michaels | Pool | Hot Tub | Pickle Ball Court

Rental Home
2.6 miles from Tilghman Island
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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ST MICHAELS-Private Waterfront, Huge Deck& 19’Swim spa-pool, Kayaks, 2 MBRooms, vacation rental in St. Michaels
ST MICHAELS-Private Waterfront, Huge Deck& 19’Swim spa-pool, Kayaks, 2 MBRooms, vacation rental in St. Michaels
ST MICHAELS-Private Waterfront, Huge Deck& 19’Swim spa-pool, Kayaks, 2 MBRooms, vacation rental in St. Michaels

ST MICHAELS-Private Waterfront, Huge Deck& 19’Swim spa-pool, Kayaks, 2 MBRooms

Rental Home
2.4 miles from Tilghman Island
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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TRUE IN-TOWN ST MICHAELS 6 ACRE WATERFRONT - Heated Pool, vacation rental in St. Michaels
TRUE IN-TOWN ST MICHAELS 6 ACRE WATERFRONT - Heated Pool, vacation rental in St. Michaels
TRUE IN-TOWN ST MICHAELS 6 ACRE WATERFRONT - Heated Pool, vacation rental in St. Michaels

TRUE IN-TOWN ST MICHAELS 6 ACRE WATERFRONT - Heated Pool

Rental Home
4.6 miles from Tilghman Island
6 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!, vacation rental in St. Michaels
Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!, vacation rental in St. Michaels
Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!, vacation rental in St. Michaels

Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!

Rental Home
3.1 miles from Tilghman Island
7 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Minutes from Downtown St. Michael's | Game Room | Pool | Hot Tub | Pickle Ball C, vacation rental in St. Michaels
Minutes from Downtown St. Michael's | Game Room | Pool | Hot Tub | Pickle Ball C, vacation rental in St. Michaels
Minutes from Downtown St. Michael's | Game Room | Pool | Hot Tub | Pickle Ball C, vacation rental in St. Michaels

Minutes from Downtown St. Michael's | Game Room | Pool | Hot Tub | Pickle Ball C

Rental Home
2.5 miles from Tilghman Island
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Minutes from Downtown St. Michaels | Private Dock | Kayaks | 1000 Ft of Shorelin, vacation rental in St. Michaels
Minutes from Downtown St. Michaels | Private Dock | Kayaks | 1000 Ft of Shorelin, vacation rental in St. Michaels
Minutes from Downtown St. Michaels | Private Dock | Kayaks | 1000 Ft of Shorelin, vacation rental in St. Michaels

Minutes from Downtown St. Michaels | Private Dock | Kayaks | 1000 Ft of Shorelin

Rental Home
3.7 miles from Tilghman Island
5 bedrooms
6 bathrooms
Sleeps 9
Match: Sleeps
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Classic Eastern Shore Waterfront Manor House - ST-936, vacation rental in St. Michaels
Classic Eastern Shore Waterfront Manor House - ST-936, vacation rental in St. Michaels
Classic Eastern Shore Waterfront Manor House - ST-936, vacation rental in St. Michaels

Classic Eastern Shore Waterfront Manor House - ST-936

Rental Home
1.3 miles from Tilghman Island
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Minutes from Downtown Easton and St. Michaels | Pool | Private Dock | Golf Cours, vacation rental in St. Michaels
Minutes from Downtown Easton and St. Michaels | Pool | Private Dock | Golf Cours, vacation rental in St. Michaels
Minutes from Downtown Easton and St. Michaels | Pool | Private Dock | Golf Cours, vacation rental in St. Michaels

Minutes from Downtown Easton and St. Michaels | Pool | Private Dock | Golf Cours

Rental Home
3.5 miles from Tilghman Island
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Minutes from Downtown St. Michaels | Pool | Kayaks | 350 Ft of Shoreline | Luxur, vacation rental in St. Michaels
Minutes from Downtown St. Michaels | Pool | Kayaks | 350 Ft of Shoreline | Luxur, vacation rental in St. Michaels
Minutes from Downtown St. Michaels | Pool | Kayaks | 350 Ft of Shoreline | Luxur, vacation rental in St. Michaels

Minutes from Downtown St. Michaels | Pool | Kayaks | 350 Ft of Shoreline | Luxur

Rental Home
2.5 miles from Tilghman Island
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Bateau Cabin one of three Cove Cabins in St Michaels, vacation rental in St. Michaels
Bateau Cabin one of three Cove Cabins in St Michaels, vacation rental in St. Michaels
Bateau Cabin one of three Cove Cabins in St Michaels, vacation rental in St. Michaels

Bateau Cabin one of three Cove Cabins in St Michaels

Rental Home
3.7 miles from Tilghman Island
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Warm their heart with a valentine getaway!, vacation rental in St. Michaels
Warm their heart with a valentine getaway!, vacation rental in St. Michaels
Warm their heart with a valentine getaway!, vacation rental in St. Michaels

Warm their heart with a valentine getaway!

Condo/Apartment
3.0 miles from Tilghman Island
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Lovely Cottage in St.Michael’s.Dock 7‘ Depth,Pet Friendly. A VIP Vacation Rental, vacation rental in St. Michaels
Lovely Cottage in St.Michael’s.Dock 7‘ Depth,Pet Friendly. A VIP Vacation Rental, vacation rental in St. Michaels
Lovely Cottage in St.Michael’s.Dock 7‘ Depth,Pet Friendly. A VIP Vacation Rental, vacation rental in St. Michaels

Lovely Cottage in St.Michael’s.Dock 7‘ Depth,Pet Friendly. A VIP Vacation Rental

Rental Home
2.5 miles from Tilghman Island
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Showing results 1-31 of 31