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St. Michaels Vacation Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
37 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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Delightful Close to town, vacation rental in St. Michaels
Delightful Close to town, vacation rental in St. Michaels
Delightful Close to town, vacation rental in St. Michaels

Delightful Close to town

Rental Home
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!, 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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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 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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St. Michael's Premier In-Town Rental with heated pool - Pool is open!, vacation rental in St. Michaels
St. Michael's Premier In-Town Rental with heated pool - Pool is open!, vacation rental in St. Michaels
St. Michael's Premier In-Town Rental with heated pool - Pool is open!, vacation rental in St. Michaels

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

Rental Home
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
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 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
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 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
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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 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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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
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 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
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
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
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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
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Unwind at this Waterfront Retreat, vacation rental in St. Michaels
Unwind at this Waterfront Retreat, vacation rental in St. Michaels
Unwind at this Waterfront Retreat, vacation rental in St. Michaels

Unwind at this Waterfront Retreat

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

LUXURY COASTAL FARMHOUSE WATERFRONT W/ HEATED POOL

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
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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
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
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Minutes from Downtown St. Michaels and Tilghman | Private Dock | Hot Tub, vacation rental in St. Michaels
Minutes from Downtown St. Michaels and Tilghman | Private Dock | Hot Tub, vacation rental in St. Michaels
Minutes from Downtown St. Michaels and Tilghman | Private Dock | Hot Tub, vacation rental in St. Michaels

Minutes from Downtown St. Michaels and Tilghman | Private Dock | Hot Tub

Rental Home
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
6 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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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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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
7 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
More info
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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
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
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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
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
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
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
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
More info
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Celebrate the Season! Cozy Waterfront Escape, vacation rental in St. Michaels
Celebrate the Season! Cozy Waterfront Escape, vacation rental in St. Michaels
Celebrate the Season! Cozy Waterfront Escape, vacation rental in St. Michaels

Celebrate the Season! Cozy Waterfront Escape

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
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2BR Waterfront Family Escape, vacation rental in St. Michaels
2BR Waterfront Family Escape, vacation rental in St. Michaels
2BR Waterfront Family Escape, vacation rental in St. Michaels

2BR Waterfront Family Escape

Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Couples Retreat, 2 King Bedrooms!, vacation rental in St. Michaels
Couples Retreat, 2 King Bedrooms!, vacation rental in St. Michaels
Couples Retreat, 2 King Bedrooms!, vacation rental in St. Michaels

Couples Retreat, 2 King Bedrooms!

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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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
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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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
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Showing results 1-37 of 37
Frequently Asked Questions about St. Michaels