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St. Michaels Vacation Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
43 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
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
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
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 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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 Waterview Cottage In St. Michaels!, vacation rental in St. Michaels
 Waterview Cottage In St. Michaels!, vacation rental in St. Michaels
 Waterview Cottage In St. Michaels!, vacation rental in St. Michaels

Waterview Cottage In St. Michaels!

Rental Home
2 bedrooms
3 bathrooms
Sleeps 5
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
2 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 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Luxurious studio in heart of historic St Michaels!, vacation rental in St. Michaels
Luxurious studio in heart of historic St Michaels!, vacation rental in St. Michaels
Luxurious studio in heart of historic St Michaels!, vacation rental in St. Michaels

Luxurious studio in heart of historic St Michaels!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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St. Michael's Premier In-Town Rental with pool and 2023 Designer updates!, vacation rental in St. Michaels
St. Michael's Premier In-Town Rental with pool and 2023 Designer updates!, vacation rental in St. Michaels
St. Michael's Premier In-Town Rental with pool and 2023 Designer updates!, vacation rental in St. Michaels

St. Michael's Premier In-Town Rental with pool and 2023 Designer updates!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Fabulous in town luxury studio, vacation rental in St. Michaels
Fabulous in town luxury studio, vacation rental in St. Michaels
Fabulous in town luxury studio, vacation rental in St. Michaels

Fabulous in town luxury studio

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Carpenter Alley - Newly Renovated Cottage in Center of Historic St. Michaels, vacation rental in St. Michaels
Carpenter Alley - Newly Renovated Cottage in Center of Historic St. Michaels, vacation rental in St. Michaels
Carpenter Alley - Newly Renovated Cottage in Center of Historic St. Michaels, vacation rental in St. Michaels

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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Book 3 nights in July/August 4 night is free!, vacation rental in St. Michaels
Book 3 nights in July/August 4 night is free!, vacation rental in St. Michaels
Book 3 nights in July/August 4 night is free!, vacation rental in St. Michaels

Book 3 nights in July/August 4 night is free!

Condo/Apartment
1 bedroom
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
2 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
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Beautiful Waterfront Home w/ Pool In St. Michaels, vacation rental in St. Michaels
Beautiful Waterfront Home w/ Pool In St. Michaels, vacation rental in St. Michaels
Beautiful Waterfront Home w/ Pool In St. Michaels, vacation rental in St. Michaels

Beautiful Waterfront Home w/ Pool In St. Michaels

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Riverview Retreat - Charming Waterfront Cottage in St Michaels!, vacation rental in St. Michaels
Riverview Retreat - Charming Waterfront Cottage in St Michaels!, vacation rental in St. Michaels
Riverview Retreat - Charming Waterfront Cottage in St Michaels!, vacation rental in St. Michaels

Riverview Retreat - Charming Waterfront Cottage in St Michaels!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Crabber's Cove - Charming Waterfront Near St. Michaels, Kayaks & Bikes!, vacation rental in St. Michaels
Crabber's Cove - Charming Waterfront Near St. Michaels, Kayaks & Bikes!, vacation rental in St. Michaels
Crabber's Cove - Charming Waterfront Near St. Michaels, Kayaks & Bikes!, vacation rental in St. Michaels

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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Modern Studio in heart of town., vacation rental in St. Michaels
Modern Studio in heart of town., vacation rental in St. Michaels
Modern Studio in heart of town., vacation rental in St. Michaels

Modern Studio in heart of town.

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Modern Studio in heart of town, walk everywhere!, vacation rental in St. Michaels
Modern Studio in heart of town, walk everywhere!, vacation rental in St. Michaels
Modern Studio in heart of town, walk everywhere!, vacation rental in St. Michaels

Modern Studio in heart of town, walk everywhere!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Location Location! St Michaels-- In Town Cottage!, vacation rental in St. Michaels
Location Location! St Michaels-- In Town Cottage!, vacation rental in St. Michaels
Location Location! St Michaels-- In Town Cottage!, vacation rental in St. Michaels

Location Location! St Michaels-- In Town Cottage!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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St. Michael's Premier in Town Summer Cottage now with private pool!, vacation rental in St. Michaels
St. Michael's Premier in Town Summer Cottage now with private pool!, vacation rental in St. Michaels
St. Michael's Premier in Town Summer Cottage now with private pool!, vacation rental in St. Michaels

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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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 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Reserve the Nauti-Hideaway in St Michaels today!, vacation rental in St. Michaels
Reserve the Nauti-Hideaway in St Michaels today!, vacation rental in St. Michaels
Reserve the Nauti-Hideaway in St Michaels today!, vacation rental in St. Michaels

Reserve the Nauti-Hideaway in St Michaels today!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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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
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
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Private+Cozy /3br+3ba /1 mile to Historic Downtown Saint Michaels, vacation rental in St. Michaels
Private+Cozy /3br+3ba /1 mile to Historic Downtown Saint Michaels, vacation rental in St. Michaels
Private+Cozy /3br+3ba /1 mile to Historic Downtown Saint Michaels, vacation rental in St. Michaels

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Waterfront Property, Kayaks, Private Dock, Near Town, vacation rental in St. Michaels
Waterfront Property, Kayaks, Private Dock, Near Town, vacation rental in St. Michaels
Waterfront Property, Kayaks, Private Dock, Near Town, vacation rental in St. Michaels

Waterfront Property, Kayaks, Private Dock, Near Town

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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The Kipsy, A fabulous St Michaels Waterfront, vacation rental in St. Michaels
The Kipsy, A fabulous St Michaels Waterfront, vacation rental in St. Michaels
The Kipsy, A fabulous St Michaels Waterfront, vacation rental in St. Michaels

The Kipsy, A fabulous St Michaels Waterfront

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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NEW LUXURY COASTAL FARMHOUSE WATERFRONT W/ HEATED POOL, vacation rental in St. Michaels
NEW LUXURY COASTAL FARMHOUSE WATERFRONT W/ HEATED POOL, vacation rental in St. Michaels
NEW LUXURY COASTAL FARMHOUSE WATERFRONT W/ HEATED POOL, vacation rental in St. Michaels

NEW LUXURY COASTAL FARMHOUSE WATERFRONT W/ HEATED POOL

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
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Crew's Quarters of St. Michaels, vacation rental in St. Michaels
Crew's Quarters of St. Michaels, vacation rental in St. Michaels
Crew's Quarters of St. Michaels, vacation rental in St. Michaels

Crew's Quarters of St. Michaels

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
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Oyster Cottage | Fishing, Crabbing, and Boating Are All at Your Fingertips!, vacation rental in St. Michaels
Oyster Cottage | Fishing, Crabbing, and Boating Are All at Your Fingertips!, vacation rental in St. Michaels
Oyster Cottage | Fishing, Crabbing, and Boating Are All at Your Fingertips!, vacation rental in St. Michaels

Oyster Cottage | Fishing, Crabbing, and Boating Are All at Your Fingertips!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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ST MICHAELS- Private Waterfront Home, Dock, Huge Deck&Heated 19’Swim Spa, 2 MBR, vacation rental in St. Michaels
ST MICHAELS- Private Waterfront Home, Dock, Huge Deck&Heated 19’Swim Spa, 2 MBR, vacation rental in St. Michaels
ST MICHAELS- Private Waterfront Home, Dock, Huge Deck&Heated 19’Swim Spa, 2 MBR, vacation rental in St. Michaels

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

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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*Heated Pool* TRUE IN-TOWN ST MICHAELS 6 ACRE WATERFRONT, vacation rental in St. Michaels
*Heated Pool* TRUE IN-TOWN ST MICHAELS 6 ACRE WATERFRONT, vacation rental in St. Michaels
*Heated Pool* TRUE IN-TOWN ST MICHAELS 6 ACRE WATERFRONT, vacation rental in St. Michaels

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

Rental Home
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Luxury Waterfront with pool and deep water dock, minutes from St Michaels., vacation rental in St. Michaels
Luxury Waterfront with pool and deep water dock, minutes from St Michaels., vacation rental in St. Michaels
Luxury Waterfront with pool and deep water dock, minutes from St Michaels., vacation rental in St. Michaels

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

Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
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RANCH AT ROYAL OAK- Exclusive waterfront pool pier, vacation rental in St. Michaels
RANCH AT ROYAL OAK- Exclusive waterfront pool pier, vacation rental in St. Michaels
RANCH AT ROYAL OAK- Exclusive waterfront pool pier, vacation rental in St. Michaels

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

Rental Home
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
More info
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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
6 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
More info
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Captain's Cove - Fantastic Family Compound Just 1/2 Mile to Historic District!, vacation rental in St. Michaels
Captain's Cove - Fantastic Family Compound Just 1/2 Mile to Historic District!, vacation rental in St. Michaels
Captain's Cove - Fantastic Family Compound Just 1/2 Mile to Historic District!, vacation rental in St. Michaels

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

Rental Home
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
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The Water House | Over The River And Through The Woods!, vacation rental in St. Michaels
The Water House | Over The River And Through The Woods!, vacation rental in St. Michaels
The Water House | Over The River And Through The Woods!, vacation rental in St. Michaels

The Water House | Over The River And Through The Woods!

Rental Home
5 bedrooms
6 bathrooms
Sleeps 9
Match: Sleeps
More info
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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
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
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Fairview Estate | One Of A Kind!, vacation rental in St. Michaels
Fairview Estate | One Of A Kind!, vacation rental in St. Michaels
Fairview Estate | One Of A Kind!, vacation rental in St. Michaels

Fairview Estate | One Of A Kind!

Rental Home
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
More info
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Red Barn Farm of St. Michaels, vacation rental in St. Michaels
Red Barn Farm of St. Michaels, vacation rental in St. Michaels
Red Barn Farm of St. Michaels, vacation rental in St. Michaels

Red Barn Farm of St. Michaels

Rental Home
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
More info
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Waterfront Estate.  **WALK TO ST. MICHAELS!**, vacation rental in St. Michaels
Waterfront Estate.  **WALK TO ST. MICHAELS!**, vacation rental in St. Michaels
Waterfront Estate.  **WALK TO ST. MICHAELS!**, vacation rental in St. Michaels

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

Rental Home
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
More info
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Ship's Cove Inn and Resort in St. Michaels, MD, vacation rental in St. Michaels
Ship's Cove Inn and Resort in St. Michaels, MD, vacation rental in St. Michaels
Ship's Cove Inn and Resort in St. Michaels, MD, vacation rental in St. Michaels

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

Rental Home
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
More info
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TRUE ST MICHAELS 6 ACRE WATERFRONT, vacation rental in St. Michaels
TRUE ST MICHAELS 6 ACRE WATERFRONT, vacation rental in St. Michaels
TRUE ST MICHAELS 6 ACRE WATERFRONT, vacation rental in St. Michaels

TRUE ST MICHAELS 6 ACRE WATERFRONT

Rental Home
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Showing results 1-43 of 43
Frequently Asked Questions about St. Michaels