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Holiday Homes near Tilghman Island

Tilghman Island Road, St. Michaels, Maryland
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5 km
31 rentals in St. Michaels.
Stay in the HEART of Saint Michaels!, holiday rental in St. Michaels
Stay in the HEART of Saint Michaels!, holiday rental in St. Michaels
Stay in the HEART of Saint Michaels!, holiday rental in St. Michaels

Stay in the HEART of Saint Michaels!

Holiday Rental House
4.8 kilometres 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, holiday rental in St. Michaels
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch, holiday rental in St. Michaels
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch, holiday rental in St. Michaels

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

Holiday Rental House
4.8 kilometres from Tilghman Island
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Delightful Close to town, holiday rental in St. Michaels
Delightful Close to town, holiday rental in St. Michaels
Delightful Close to town, holiday rental in St. Michaels

Delightful Close to town

Holiday Rental House
4.7 kilometres from Tilghman Island
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!, holiday rental in St. Michaels
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!, holiday rental in St. Michaels
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!, holiday rental in St. Michaels

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

Holiday Rental House
5.0 kilometres from Tilghman Island
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Walk to Everything House, holiday rental in St. Michaels
Walk to Everything House, holiday rental in St. Michaels
Walk to Everything House, holiday rental in St. Michaels

Walk to Everything House

Holiday Rental House
4.8 kilometres 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, holiday rental in St. Michaels
Premier St. Michaels Cottage - T. Blades House -  Walk to Everything in Town, holiday rental in St. Michaels
Premier St. Michaels Cottage - T. Blades House -  Walk to Everything in Town, holiday rental in St. Michaels

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

Holiday Rental House
5.0 kilometres from Tilghman Island
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Dollhouse in Central Historic St Michaels, holiday rental in St. Michaels
Dollhouse in Central Historic St Michaels, holiday rental in St. Michaels
Dollhouse in Central Historic St Michaels, holiday rental in St. Michaels

Dollhouse in Central Historic St Michaels

Holiday Rental House
4.7 kilometres 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 - Pool is open!, holiday rental in St. Michaels
St. Michael's Premier In-Town Rental with heated pool - Pool is open!, holiday rental in St. Michaels
St. Michael's Premier In-Town Rental with heated pool - Pool is open!, holiday rental in St. Michaels

St. Michael's Premier In-Town Rental with heated pool - Pool is open!

Holiday Rental House
5.3 kilometres from Tilghman Island
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Chase Away the Chill with Our Winter Stay Specials!, holiday rental in St. Michaels
Chase Away the Chill with Our Winter Stay Specials!, holiday rental in St. Michaels
Chase Away the Chill with Our Winter Stay Specials!, holiday rental in St. Michaels

Chase Away the Chill with Our Winter Stay Specials!

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

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

Holiday Rental House
4.8 kilometres from Tilghman Island
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Chic Flat with King Bed & Fireplace, holiday rental in St. Michaels
Chic Flat with King Bed & Fireplace, holiday rental in St. Michaels
Chic Flat with King Bed & Fireplace, holiday rental in St. Michaels

Chic Flat with King Bed & Fireplace

Condo/Apartment
4.8 kilometres 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, holiday rental in St. Michaels
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels, holiday rental in St. Michaels
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels, holiday rental in St. Michaels

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

Holiday Rental House
5.0 kilometres from Tilghman Island
3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Harbor View Suite, holiday rental in St. Michaels
Harbor View Suite, holiday rental in St. Michaels
Harbor View Suite, holiday rental in St. Michaels

Harbor View Suite

Condo/Apartment
5.5 kilometres from Tilghman Island
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Beautiful Waterfront Home w/ Pool In St. Michaels, holiday rental in St. Michaels
Beautiful Waterfront Home w/ Pool In St. Michaels, holiday rental in St. Michaels
Beautiful Waterfront Home w/ Pool In St. Michaels, holiday rental in St. Michaels

Beautiful Waterfront Home w/ Pool In St. Michaels

Holiday Rental House
6.1 kilometres from Tilghman Island
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Downtown St. Michaels | Bikes | Kayaks | Private Pier, holiday rental in St. Michaels
Downtown St. Michaels | Bikes | Kayaks | Private Pier, holiday rental in St. Michaels
Downtown St. Michaels | Bikes | Kayaks | Private Pier, holiday rental in St. Michaels

Downtown St. Michaels | Bikes | Kayaks | Private Pier

Holiday Rental House
5.8 kilometres from Tilghman Island
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly, holiday rental in St. Michaels
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly, holiday rental in St. Michaels
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly, holiday rental in St. Michaels

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

Holiday Rental House
3.7 kilometres from Tilghman Island
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Seasonal Rental: Artisan designed 3 bedroom home., holiday rental in St. Michaels
Seasonal Rental: Artisan designed 3 bedroom home., holiday rental in St. Michaels
Seasonal Rental: Artisan designed 3 bedroom home., holiday rental in St. Michaels

Seasonal Rental: Artisan designed 3 bedroom home.

Holiday Rental House
5.6 kilometres from Tilghman Island
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Warm Up Here! Your Winter Getaway Awaits, holiday rental in St. Michaels
Warm Up Here! Your Winter Getaway Awaits, holiday rental in St. Michaels
Warm Up Here! Your Winter Getaway Awaits, holiday rental in St. Michaels

Warm Up Here! Your Winter Getaway Awaits

Holiday Rental House
6.1 kilometres from Tilghman Island
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Grace Cottage, Saint Michaels Walk to everything!, holiday rental in St. Michaels
Grace Cottage, Saint Michaels Walk to everything!, holiday rental in St. Michaels
Grace Cottage, Saint Michaels Walk to everything!, holiday rental in St. Michaels

Grace Cottage, Saint Michaels Walk to everything!

Holiday Rental House
5.0 kilometres from Tilghman Island
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
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Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels, holiday rental in St. Michaels
Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels, holiday rental in St. Michaels
Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels, holiday rental in St. Michaels

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

Holiday Rental House
4.2 kilometres from Tilghman Island
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Minutes from Downtown St. Michaels | Pool | Hot Tub | Pickle Ball Court, holiday rental in St. Michaels
Minutes from Downtown St. Michaels | Pool | Hot Tub | Pickle Ball Court, holiday rental in St. Michaels
Minutes from Downtown St. Michaels | Pool | Hot Tub | Pickle Ball Court, holiday rental in St. Michaels

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

Holiday Rental House
4.2 kilometres from Tilghman Island
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
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TRUE IN-TOWN ST MICHAELS 6 ACRE WATERFRONT - Heated Pool, holiday rental in St. Michaels
TRUE IN-TOWN ST MICHAELS 6 ACRE WATERFRONT - Heated Pool, holiday rental in St. Michaels
TRUE IN-TOWN ST MICHAELS 6 ACRE WATERFRONT - Heated Pool, holiday rental in St. Michaels

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

Holiday Rental House
7.4 kilometres 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!, holiday rental in St. Michaels
Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!, holiday rental in St. Michaels
Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!, holiday rental in St. Michaels

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

Holiday Rental House
5.0 kilometres 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, holiday rental in St. Michaels
Minutes from Downtown St. Michael's | Game Room | Pool | Hot Tub | Pickle Ball C, holiday rental in St. Michaels
Minutes from Downtown St. Michael's | Game Room | Pool | Hot Tub | Pickle Ball C, holiday rental in St. Michaels

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

Holiday Rental House
4.0 kilometres 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, holiday rental in St. Michaels
Minutes from Downtown St. Michaels | Private Dock | Kayaks | 1000 Ft of Shorelin, holiday rental in St. Michaels
Minutes from Downtown St. Michaels | Private Dock | Kayaks | 1000 Ft of Shorelin, holiday rental in St. Michaels

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

Holiday Rental House
6.0 kilometres from Tilghman Island
5 bedrooms
6 bathrooms
Sleeps 9
Match: Sleeps
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Classic Eastern Shore Waterfront Manor House - ST-936, holiday rental in St. Michaels
Classic Eastern Shore Waterfront Manor House - ST-936, holiday rental in St. Michaels
Classic Eastern Shore Waterfront Manor House - ST-936, holiday rental in St. Michaels

Classic Eastern Shore Waterfront Manor House - ST-936

Holiday Rental House
2.1 kilometres 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, holiday rental in St. Michaels
Minutes from Downtown Easton and St. Michaels | Pool | Private Dock | Golf Cours, holiday rental in St. Michaels
Minutes from Downtown Easton and St. Michaels | Pool | Private Dock | Golf Cours, holiday rental in St. Michaels

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

Holiday Rental House
5.6 kilometres 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, holiday rental in St. Michaels
Minutes from Downtown St. Michaels | Pool | Kayaks | 350 Ft of Shoreline | Luxur, holiday rental in St. Michaels
Minutes from Downtown St. Michaels | Pool | Kayaks | 350 Ft of Shoreline | Luxur, holiday rental in St. Michaels

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

Holiday Rental House
4.0 kilometres from Tilghman Island
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Lovely Cottage in St.Michael’s.Dock 7‘ Depth,Pet Friendly. A VIP Vacation Rental, holiday rental in St. Michaels
Lovely Cottage in St.Michael’s.Dock 7‘ Depth,Pet Friendly. A VIP Vacation Rental, holiday rental in St. Michaels
Lovely Cottage in St.Michael’s.Dock 7‘ Depth,Pet Friendly. A VIP Vacation Rental, holiday rental in St. Michaels

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

Holiday Rental House
4.0 kilometres from Tilghman Island
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Couples Retreat, 2 King Bedrooms!, holiday rental in St. Michaels
Couples Retreat, 2 King Bedrooms!, holiday rental in St. Michaels
Couples Retreat, 2 King Bedrooms!, holiday rental in St. Michaels

Couples Retreat, 2 King Bedrooms!

Condo/Apartment
4.8 kilometres from Tilghman Island
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Bateau Cabin one of three Cove Cabins in St Michaels, holiday rental in St. Michaels
Bateau Cabin one of three Cove Cabins in St Michaels, holiday rental in St. Michaels
Bateau Cabin one of three Cove Cabins in St Michaels, holiday rental in St. Michaels

Bateau Cabin one of three Cove Cabins in St Michaels

Holiday Rental House
6.0 kilometres from Tilghman Island
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Showing results 1-31 of 31