Vacation Rentals in St. Michaels, MD: Compare 10+ Sites & Save

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145 Best Vacation Rentals in St. Michaels (Starting from $277)

Carpenter Alley Cottage
Carpenter Alley Cottage
House
Saint Michaels, MD, USA
0.1k from St. Michaels center

Security/Safety, Parking, Pet Friendly, Internet, Child Friendly

1 Bedroom6 Guests
New to Booking
$666
Average price / night
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Elegant 2-Bedroom Retreat in Historic Saint Michaels – Walk to Dining & Shops
Elegant 2-Bedroom Retreat in Historic Saint Michaels – Walk to Dining & Shops
Apartment
Saint Michaels, MD, 21663, United States
0.0k from St. Michaels center

AC, Free Parking, Heater, Internet, Microwave, No Smoking, TV

2 Bedrooms4 Guests
9.8

Exceptional

7 reviews

$519
Average price / night
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Riverview Retreat
Riverview Retreat
House
Saint Michaels, MD, USA
1.1k from St. Michaels center

Security/Safety, Parking, Internet, Child Friendly

1 Bedroom6 Guests
New to Booking
$879
Average price / night
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Downtown St. Michaels | Porch + Pet-Friendly
Downtown St. Michaels | Porch + Pet-Friendly
Apartment
Saint Michaels, MD, 21663, United States
0.1k from St. Michaels center

AC, Balcony, Dryer, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$790
Average price / night
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Crews Quarters
Crews Quarters
House
Saint Michaels, MD, USA
1.2k from St. Michaels center

Parking, Pool, Security/Safety, Hot Tub, Internet, Wellness Facilities, Child Friendly

1 Bedroom6 Guests
New to Booking
$800
Average price / night
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Captains Cove
Captains Cove
House
Saint Michaels, MD, USA
1.3k from St. Michaels center

Parking, Pool, Sports/Activities, Security/Safety, Hot Tub, Internet, Wellness Facilities

1 Bedroom10 Guests
New to Booking
$1180
Average price / night
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Downtown Flat • Walk to Dining & Shops • Sleeps 4
Downtown Flat • Walk to Dining & Shops • Sleeps 4
House
Saint Michaels, MD, 21663, United States
0.1k from St. Michaels center

AC, Balcony, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Living Area

1 Bedroom4 Guests
New to Booking
$427
Average price / night
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Waterfront Retreat on Chesapeake Bay in St Michaels
Waterfront Retreat on Chesapeake Bay in St Michaels
House
Saint Michaels, MD, USA
2.0k from St. Michaels center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

2 Bedrooms4 Guests
New to Booking
$459
Average price / night
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Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Cottage
Saint Michaels, MD, 21663, United States
0.1k from St. Michaels center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms5 Guests
9.8

Exceptional

200 reviews

$480
Average price / night
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Waterfront St Michaels Vacation Rental with Fire Pit
Waterfront St Michaels Vacation Rental with Fire Pit
House
MD, USA
2.6k from St. Michaels center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings

3 Bedrooms6 Guests
8.0

Good

1 reviews

$1551
Average price / night
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Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
House
St. Michaels, MD, 21663, United States
0.1k from St. Michaels center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
9.8

Exceptional

49 reviews

$750
Average price / night
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Hawkeye Point
Hawkeye Point
House
Mount Pleasant, MD, USA
2.7k from St. Michaels center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom6 Guests
New to Booking
$1175
Average price / night
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Charming Intown Cottage – The Ultimate Walkable Getaway steps from Downtown!
Charming Intown Cottage – The Ultimate Walkable Getaway steps from Downtown!
Cottage
St. Michaels, MD, 21663, United States
0.2k from St. Michaels center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

1 Bedroom2 Guests
9.8

Exceptional

59 reviews

$277
Average price / night
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Baydream Believer
Baydream Believer
House
Saint Michaels, MD, USA
3.7k from St. Michaels center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Hot tubs, Places to stay

5 Bedrooms8 Guests
New to Booking
$1015
Average price / night
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John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Cottage
Saint Michaels, MD, 21663, United States
0.2k from St. Michaels center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Kitchen, Laundry, Living Area

2 Bedrooms5 Guests
9.6

Exceptional

126 reviews

$366
Average price / night
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Brand-New Pool! Waterfront Bozman Village Home
Brand-New Pool! Waterfront Bozman Village Home
House
MD, USA
4.1k from St. Michaels center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Hot tubs

4 Bedrooms8 Guests
New to Booking
$494
Average price / night
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Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Cottage
St Michaels, MD, 21663, United States
0.2k from St. Michaels center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms5 Guests
9.4

Superb

130 reviews

$335
Average price / night
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Dragonfly Cove
Dragonfly Cove
House
Mount Pleasant, MD, USA
4.1k from St. Michaels center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Hot tubs, Places to stay

1 Bedroom4 Guests
New to Booking
$590
Average price / night
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Premier St. Michaels Cottage - T. Blades House -  Walk to Everything in Town
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Cottage
St Michaels, MD, 21663, United States
0.2k from St. Michaels center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms5 Guests
9.6

Exceptional

147 reviews

$374
Average price / night
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Fairview Estate
Fairview Estate
House
Saint Michaels, MD, USA
4.1k from St. Michaels center

Parking, Pool, Security/Safety, Internet, Pet Friendly, Child Friendly

1 Bedroom12 Guests
New to Booking
$1880
Average price / night
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Stay in the HEART of Saint Michaels!
Stay in the HEART of Saint Michaels!
House
St Michaels, MD, 21663, United States
0.2k from St. Michaels center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
10.0

Exceptional

385 reviews

$333
Average price / night
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The Weekender
The Weekender
House
Mount Pleasant, MD, USA
4.5k from St. Michaels center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$441
Average price / night
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Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!
Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!
House
St. Michaels, MD, 21663, United States
0.2k from St. Michaels center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

6 Bedrooms9 Guests
9.4

Superb

136 reviews

$774
Average price / night
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Walk to Everything House
Walk to Everything House
House
Saint Michaels, MD, 21663, United States
0.2k from St. Michaels center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms6 Guests
10.0

Exceptional

87 reviews

$358
Average price / night
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Dollhouse in Central Historic St Michaels
Dollhouse in Central Historic St Michaels
House
St Michaels, MD, 21663, United States
0.2k from St. Michaels center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
9.8

Exceptional

59 reviews

$297
Average price / night
Check Availability
Grace Cottage, St Michaels Walk to everything!
Grace Cottage, St Michaels Walk to everything!
House
Saint Michaels, MD, 21663, United States
0.4k from St. Michaels center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Laundry, Microwave, No Smoking

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$664
Average price / night
Check Availability
Grace Cottage, Saint Michaels Walk to everything!
Grace Cottage, Saint Michaels Walk to everything!
House
Saint Michaels, MD, 21663, United States
0.4k from St. Michaels center

Internet, No Smoking

2 Bedrooms4 Guests
10.0

Exceptional

14 reviews

$694
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in St. Michaels.

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Frequently Asked Questions

You can explore 145 verified vacation rentals in St. Michaels. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in St. Michaels vary depending on the season, property size, and location. Rates typically start from around $277 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in St. Michaels include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in St. Michaels welcome pets. Currently, 42 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in St. Michaels often include amenities such as Internet, Fireplace/Heating, and Pet Friendly. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.