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Holiday Rentals in St. Michaels

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Bedrooms

Bathrooms

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Distance from

5 km
37 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
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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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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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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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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
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
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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St. Michael's Premier In-Town Rental with heated pool-opens 4/22, holiday rental in St. Michaels
St. Michael's Premier In-Town Rental with heated pool-opens 4/22, holiday rental in St. Michaels
St. Michael's Premier In-Town Rental with heated pool-opens 4/22, holiday rental in St. Michaels

St. Michael's Premier In-Town Rental with heated pool-opens 4/22

Holiday Rental House
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
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
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
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
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
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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2025 Renovation Beautiful Waterfront Home w/ Pool In St. Michaels, holiday rental in St. Michaels
2025 Renovation Beautiful Waterfront Home w/ Pool In St. Michaels, holiday rental in St. Michaels
2025 Renovation Beautiful Waterfront Home w/ Pool In St. Michaels, holiday rental in St. Michaels

2025 Renovation Beautiful Waterfront Home w/ Pool In St. Michaels

Holiday Rental House
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
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 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
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
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
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
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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A Winter Getaway At This Waterfront Retreat, holiday rental in St. Michaels
A Winter Getaway At This Waterfront Retreat, holiday rental in St. Michaels
A Winter Getaway At This Waterfront Retreat, holiday rental in St. Michaels

A Winter Getaway At This Waterfront Retreat

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

LUXURY COASTAL FARMHOUSE WATERFRONT W/ HEATED POOL

Holiday Rental House
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, 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
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, holiday rental in St. Michaels
Minutes from Downtown St. Michaels and Tilghman | Private Dock | Hot Tub, holiday rental in St. Michaels
Minutes from Downtown St. Michaels and Tilghman | Private Dock | Hot Tub, holiday rental in St. Michaels

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

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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ST MICHAELS-Private Waterfront, Huge Deck& 19’Swim spa-pool, Kayaks, 2 MBRooms, holiday rental in St. Michaels
ST MICHAELS-Private Waterfront, Huge Deck& 19’Swim spa-pool, Kayaks, 2 MBRooms, holiday rental in St. Michaels
ST MICHAELS-Private Waterfront, Huge Deck& 19’Swim spa-pool, Kayaks, 2 MBRooms, holiday rental in St. Michaels

ST MICHAELS-Private Waterfront, Huge Deck& 19’Swim spa-pool, Kayaks, 2 MBRooms

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
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
6 bedrooms
3 bathrooms
Sleeps 8
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
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
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
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
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
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
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
More info
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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
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Come and get cozy at this Waterfront Escape, holiday rental in St. Michaels
Come and get cozy at this Waterfront Escape, holiday rental in St. Michaels
Come and get cozy at this Waterfront Escape, holiday rental in St. Michaels

Come and get cozy at this Waterfront Escape

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Warm their hearts with a valentine getaway!, holiday rental in St. Michaels
Warm their hearts with a valentine getaway!, holiday rental in St. Michaels
Warm their hearts with a valentine getaway!, holiday rental in St. Michaels

Warm their hearts with a valentine getaway!

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Warm their heart with a valentine getaway!, holiday rental in St. Michaels
Warm their heart with a valentine getaway!, holiday rental in St. Michaels
Warm their heart with a valentine getaway!, holiday rental in St. Michaels

Warm their heart with a valentine getaway!

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, 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
3 bedrooms
2 bathrooms
Sleeps 6
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
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