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Holiday Rentals in St. Michaels

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34 rentals in St. Michaels.
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Large Luxury Waterfront Home with pool...... 2 1/2 miles from the center of town, holiday rental in St. Michaels
Large Luxury Waterfront Home with pool...... 2 1/2 miles from the center of town, holiday rental in St. Michaels
Large Luxury Waterfront Home with pool...... 2 1/2 miles from the center of town, holiday rental in St. Michaels

Large Luxury Waterfront Home with pool...... 2 1/2 miles from the center of town

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 8
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
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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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
5 bedrooms
3 bathrooms
Sleeps 8
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
2 bedrooms
2 bathrooms
Sleeps 5
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
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Waterfront Property, kayaks, private dock, near town, holiday rental in St. Michaels
Waterfront Property, kayaks, private dock, near town, holiday rental in St. Michaels
Waterfront Property, kayaks, private dock, near town, holiday rental in St. Michaels

Waterfront Property, kayaks, private dock, near town

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Cottage downtown on a quiet street, holiday rental in St. Michaels
Cottage downtown on a quiet street, holiday rental in St. Michaels
Cottage downtown on a quiet street, holiday rental in St. Michaels

Cottage downtown on a quiet street

Holiday Rental House
1 bedroom
2 bathrooms
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
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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ST MICHAELS- Private Waterfront Home, Dock, Huge Deck&Heated 19’Swim Spa, 2 MBR, holiday rental in St. Michaels
ST MICHAELS- Private Waterfront Home, Dock, Huge Deck&Heated 19’Swim Spa, 2 MBR, holiday rental in St. Michaels
ST MICHAELS- Private Waterfront Home, Dock, Huge Deck&Heated 19’Swim Spa, 2 MBR, holiday rental in St. Michaels

ST MICHAELS- Private Waterfront Home, Dock, Huge Deck&Heated 19’Swim Spa, 2 MBR

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Location Location! St Michaels-- In Town Cottage!, holiday rental in St. Michaels
Location Location! St Michaels-- In Town Cottage!, holiday rental in St. Michaels
Location Location! St Michaels-- In Town Cottage!, holiday rental in St. Michaels

Location Location! St Michaels-- In Town Cottage!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Premier Cottage in St. Michaels- In Town Location!, holiday rental in St. Michaels
Premier Cottage in St. Michaels- In Town Location!, holiday rental in St. Michaels
Premier Cottage in St. Michaels- In Town Location!, holiday rental in St. Michaels

Premier Cottage in St. Michaels- In Town Location!

Holiday Rental House
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!, 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
2 bedrooms
3 bathrooms
Sleeps 5
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
6 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Large Historic Thomas Harrison House on Harbor in St. Michaels Town, holiday rental in St. Michaels
Large Historic Thomas Harrison House on Harbor in St. Michaels Town, holiday rental in St. Michaels
Large Historic Thomas Harrison House on Harbor in St. Michaels Town, holiday rental in St. Michaels

Large Historic Thomas Harrison House on Harbor in St. Michaels Town

Holiday Rental House
7 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Luxury Waterfront with pool and deep water dock, minutes from St Michaels., holiday rental in St. Michaels
Luxury Waterfront with pool and deep water dock, minutes from St Michaels., holiday rental in St. Michaels
Luxury Waterfront with pool and deep water dock, minutes from St Michaels., holiday rental in St. Michaels

Luxury Waterfront with pool and deep water dock, minutes from St Michaels.

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Crabber's Cove - Charming Waterfront Near St. Michaels, Kayaks & Bikes!, holiday rental in St. Michaels
Crabber's Cove - Charming Waterfront Near St. Michaels, Kayaks & Bikes!, holiday rental in St. Michaels
Crabber's Cove - Charming Waterfront Near St. Michaels, Kayaks & Bikes!, holiday rental in St. Michaels

Crabber's Cove - Charming Waterfront Near St. Michaels, Kayaks & Bikes!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Riverview Retreat - Charming Waterfront Cottage in St Michaels!, holiday rental in St. Michaels
Riverview Retreat - Charming Waterfront Cottage in St Michaels!, holiday rental in St. Michaels
Riverview Retreat - Charming Waterfront Cottage in St Michaels!, holiday rental in St. Michaels

Riverview Retreat - Charming Waterfront Cottage in St Michaels!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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 Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!, holiday rental in St. Michaels
 Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!, holiday rental in St. Michaels
 Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!, holiday rental in St. Michaels

Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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 Waterview Cottage In St. Michaels!, holiday rental in St. Michaels
 Waterview Cottage In St. Michaels!, holiday rental in St. Michaels
 Waterview Cottage In St. Michaels!, holiday rental in St. Michaels

Waterview Cottage In St. Michaels!

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
More info
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Mallard Point Cottage - Relaxing Waterfront Home, Kayaks, Bikes, Pet-Friendly!, holiday rental in St. Michaels
Mallard Point Cottage - Relaxing Waterfront Home, Kayaks, Bikes, Pet-Friendly!, holiday rental in St. Michaels
Mallard Point Cottage - Relaxing Waterfront Home, Kayaks, Bikes, Pet-Friendly!, holiday rental in St. Michaels

Mallard Point Cottage - Relaxing Waterfront Home, Kayaks, Bikes, Pet-Friendly!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Charming 1930's Cottage including wide dock with 7 foot depth, holiday rental in St. Michaels
Charming 1930's Cottage including wide dock with 7 foot depth, holiday rental in St. Michaels
Charming 1930's Cottage including wide dock with 7 foot depth, holiday rental in St. Michaels

Charming 1930's Cottage including wide dock with 7 foot depth

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Carpenter Alley - Newly Renovated Cottage in Center of Historic St. Michaels, holiday rental in St. Michaels
Carpenter Alley - Newly Renovated Cottage in Center of Historic St. Michaels, holiday rental in St. Michaels
Carpenter Alley - Newly Renovated Cottage in Center of Historic St. Michaels, holiday rental in St. Michaels

Carpenter Alley - Newly Renovated Cottage in Center of Historic St. Michaels

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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The Water House - Unique 3600-SqFt Home Near St. Michaels!, holiday rental in St. Michaels
The Water House - Unique 3600-SqFt Home Near St. Michaels!, holiday rental in St. Michaels
The Water House - Unique 3600-SqFt Home Near St. Michaels!, holiday rental in St. Michaels

The Water House - Unique 3600-SqFt Home Near St. Michaels!

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
More info
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Captain's Cove - Fantastic Family Compound Just 1/2 Mile to Historic District!, holiday rental in St. Michaels
Captain's Cove - Fantastic Family Compound Just 1/2 Mile to Historic District!, holiday rental in St. Michaels
Captain's Cove - Fantastic Family Compound Just 1/2 Mile to Historic District!, holiday rental in St. Michaels

Captain's Cove - Fantastic Family Compound Just 1/2 Mile to Historic District!

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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St. Michael's Premier in Town Summer Cottage now with private pool!, holiday rental in St. Michaels
St. Michael's Premier in Town Summer Cottage now with private pool!, holiday rental in St. Michaels
St. Michael's Premier in Town Summer Cottage now with private pool!, holiday rental in St. Michaels

St. Michael's Premier in Town Summer Cottage now with private pool!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Private+Cozy /3br+3ba /1 mile to Historic Downtown Saint Michaels, holiday rental in St. Michaels
Private+Cozy /3br+3ba /1 mile to Historic Downtown Saint Michaels, holiday rental in St. Michaels
Private+Cozy /3br+3ba /1 mile to Historic Downtown Saint Michaels, holiday rental in St. Michaels

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront Property, Kayaks, Private Dock, Near Town, holiday rental in St. Michaels
Waterfront Property, Kayaks, Private Dock, Near Town, holiday rental in St. Michaels
Waterfront Property, Kayaks, Private Dock, Near Town, holiday rental in St. Michaels

Waterfront Property, Kayaks, Private Dock, Near Town

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Ship's Cove Inn and Resort in St. Michaels, MD, holiday rental in St. Michaels
Ship's Cove Inn and Resort in St. Michaels, MD, holiday rental in St. Michaels
Ship's Cove Inn and Resort in St. Michaels, MD, holiday rental in St. Michaels

Ship's Cove Inn and Resort in St. Michaels, MD

Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Charming St Michaels Home, holiday rental in St. Michaels
Charming St Michaels Home, holiday rental in St. Michaels
Charming St Michaels Home, holiday rental in St. Michaels

Charming St Michaels Home

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Fabulous rates, Luxury Flat, Heart of St Michaels!, holiday rental in St. Michaels
Fabulous rates, Luxury Flat, Heart of St Michaels!, holiday rental in St. Michaels
Fabulous rates, Luxury Flat, Heart of St Michaels!, holiday rental in St. Michaels

Fabulous rates, Luxury Flat, Heart of St Michaels!

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 3
Match: Sleeps
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Waterfront Estate.  **WALK TO ST. MICHAELS!**, holiday rental in St. Michaels
Waterfront Estate.  **WALK TO ST. MICHAELS!**, holiday rental in St. Michaels
Waterfront Estate.  **WALK TO ST. MICHAELS!**, holiday rental in St. Michaels

Waterfront Estate. **WALK TO ST. MICHAELS!**

Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
More info
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NEW LUXURY COASTAL FARMHOUSE WATERFRONT W/ HEATED POOL, holiday rental in St. Michaels
NEW LUXURY COASTAL FARMHOUSE WATERFRONT W/ HEATED POOL, holiday rental in St. Michaels
NEW LUXURY COASTAL FARMHOUSE WATERFRONT W/ HEATED POOL, holiday rental in St. Michaels

NEW LUXURY COASTAL FARMHOUSE WATERFRONT W/ HEATED POOL

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
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Eastern Shore Vacation Home on the Water!, holiday rental in St. Michaels
Eastern Shore Vacation Home on the Water!, holiday rental in St. Michaels
Eastern Shore Vacation Home on the Water!, holiday rental in St. Michaels

Eastern Shore Vacation Home on the Water!

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
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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
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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