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Holiday Apartments in St. Michaels

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 km
43 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
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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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
More info
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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
More info
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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
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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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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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
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
More info
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Luxurious studio in heart of historic St Michaels!, holiday rental in St. Michaels
Luxurious studio in heart of historic St Michaels!, holiday rental in St. Michaels
Luxurious studio in heart of historic St Michaels!, holiday rental in St. Michaels

Luxurious studio in heart of historic St Michaels!

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

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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Fabulous in town luxury studio, holiday rental in St. Michaels
Fabulous in town luxury studio, holiday rental in St. Michaels
Fabulous in town luxury studio, holiday rental in St. Michaels

Fabulous in town luxury studio

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
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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Book 3 nights in July/August 4 night is free!, holiday rental in St. Michaels
Book 3 nights in July/August 4 night is free!, holiday rental in St. Michaels
Book 3 nights in July/August 4 night is free!, holiday rental in St. Michaels

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

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 3
Match: Sleeps
More info
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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
More info
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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
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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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
More info
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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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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
More info
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Modern Studio in heart of town., holiday rental in St. Michaels
Modern Studio in heart of town., holiday rental in St. Michaels
Modern Studio in heart of town., holiday 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!, holiday rental in St. Michaels
Modern Studio in heart of town, walk everywhere!, holiday rental in St. Michaels
Modern Studio in heart of town, walk everywhere!, holiday 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!, 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
More info
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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
More info
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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
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Reserve the Nauti-Hideaway in St Michaels today!, holiday rental in St. Michaels
Reserve the Nauti-Hideaway in St Michaels today!, holiday rental in St. Michaels
Reserve the Nauti-Hideaway in St Michaels today!, holiday rental in St. Michaels

Reserve the Nauti-Hideaway in St Michaels today!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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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
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, 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
More info
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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
More info
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The Kipsy, A fabulous St Michaels Waterfront, holiday rental in St. Michaels
The Kipsy, A fabulous St Michaels Waterfront, holiday rental in St. Michaels
The Kipsy, A fabulous St Michaels Waterfront, holiday rental in St. Michaels

The Kipsy, A fabulous St Michaels Waterfront

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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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Crew's Quarters of St. Michaels, holiday rental in St. Michaels
Crew's Quarters of St. Michaels, holiday rental in St. Michaels
Crew's Quarters of St. Michaels, holiday rental in St. Michaels

Crew's Quarters of St. Michaels

Holiday Rental House
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!, holiday rental in St. Michaels
Oyster Cottage | Fishing, Crabbing, and Boating Are All at Your Fingertips!, holiday rental in St. Michaels
Oyster Cottage | Fishing, Crabbing, and Boating Are All at Your Fingertips!, holiday rental in St. Michaels

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

Holiday Rental House
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, 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
More info
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*Heated Pool* TRUE IN-TOWN ST MICHAELS 6 ACRE WATERFRONT, holiday rental in St. Michaels
*Heated Pool* TRUE IN-TOWN ST MICHAELS 6 ACRE WATERFRONT, holiday rental in St. Michaels
*Heated Pool* TRUE IN-TOWN ST MICHAELS 6 ACRE WATERFRONT, holiday rental in St. Michaels

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

Holiday Rental House
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., 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
More info
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RANCH AT ROYAL OAK- Exclusive waterfront pool pier, holiday rental in St. Michaels
RANCH AT ROYAL OAK- Exclusive waterfront pool pier, holiday rental in St. Michaels
RANCH AT ROYAL OAK- Exclusive waterfront pool pier, holiday rental in St. Michaels

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

Holiday Rental House
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!, 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
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
More info
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The Water House | Over The River And Through The Woods!, holiday rental in St. Michaels
The Water House | Over The River And Through The Woods!, holiday rental in St. Michaels
The Water House | Over The River And Through The Woods!, holiday rental in St. Michaels

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

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

Fairview Estate | One Of A Kind!

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

Red Barn Farm of St. Michaels

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

TRUE ST MICHAELS 6 ACRE WATERFRONT

Holiday Rental House
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