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

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11 Best Oceanfront Rentals in St. Michaels (Starting from $294)

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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St. Michael's Premier In-Town Rental with heated pool. Pool opens 4/3
St. Michael's Premier In-Town Rental with heated pool. Pool opens 4/3
Cottage
St. Michaels, MD, 21663, United States
0.6k from St. Michaels center

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

2 Bedrooms4 Guests
10.0

Exceptional

147 reviews

$824
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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Two Oysters House 2025 Remodel waterfront w/ pool in St. Michaels
Two Oysters House 2025 Remodel waterfront w/ pool in St. Michaels
House
St Michaels, MD, 21663, United States
2.1k from St. Michaels center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

4 Bedrooms8 Guests
9.4

Superb

59 reviews

$1014
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
Check Availability
Cottage #4 Chesapeake Blue  down the drive way.
Cottage #4 Chesapeake Blue down the drive way.
Cottage
Saint Michaels, MD, 21663, United States
4.2k from St. Michaels center

AC, Barbecue, Free Parking, Internet, Kitchen, Microwave, No Smoking, Outdoor Space, TV

1 Bedroom4 Guests
New to Booking
$294
Average price / night
Check Availability
Cottage #5 White Swan At Water with Deck
Cottage #5 White Swan At Water with Deck
Cottage
Saint Michaels, MD, 21663, United States
4.2k from St. Michaels center

AC, Barbecue, Free Parking, Internet, Kitchen, Microwave, No Smoking, Outdoor Space, TV

1 Bedroom4 Guests
New to Booking
$315
Average price / night
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Hurry, reserve your stay for \nSummer & Fall of 2025\nSTR #22-30
Hurry, reserve your stay for \nSummer & Fall of 2025\nSTR #22-30
House
Bozman, MD, 21612, United States
6.9k from St. Michaels center

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

5 Bedrooms10 Guests
10.0

Exceptional

95 reviews

$598
Average price / night
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Amazing Waterfront Views, Private Pool and Dock
Amazing Waterfront Views, Private Pool and Dock
House
Sherwood, MD, 21665, United States
8.6k from St. Michaels center

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

6 Bedrooms12 Guests
New to Booking
$1404
Average price / night
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Heated pool, sandy beach, pier, and playground set punch point apart!
Heated pool, sandy beach, pier, and playground set punch point apart!
House
Sherwood, MD, 21665, United States
9.7k from St. Michaels center

AC, Arcade, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

5 Bedrooms10 Guests
10.0

Exceptional

11 reviews

$1263
Average price / night
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Early Booking Discount! Waterfront, Elevator, Hot Tub, Dock, Gazebo, Beach.
Early Booking Discount! Waterfront, Elevator, Hot Tub, Dock, Gazebo, Beach.
House
Royal Oak, MD, 21662, United States
9.7k from St. Michaels center

AC, Barbecue, Dryer, Elevator, Extra Bed, Fireplace, Free Parking, Heater, Hot Tub

4 Bedrooms8 Guests
9.2

Superb

16 reviews

$563
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 Oceanfront Rentals in St. Michaels.

Stay Near St. Michaels's Top Attractions

VacationByOwnerRentals can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.

St. Michaels Oceanfront Rentals on the Map

Frequently Asked Questions

You can explore 11 verified oceanfront rentals in St. Michaels. These properties are located directly along the shoreline, offering uninterrupted access to the beach and ocean views.

Oceanfront rental prices in St. Michaels vary depending on the property size, exact beachfront location, and season. Rates typically start from around $294 per night, with higher prices for larger homes or peak travel periods. Properties located directly on popular stretches of coastline tend to command premium rates.

Many oceanfront rentals in St. Michaels offer direct access to the beach, often through private walkways or dedicated entry paths. Some properties may share access points, so it’s helpful to review the listing details to understand the type of beach access provided.

Yes, some oceanfront rentals in St. Michaels welcome pets. Currently, 5 listings allow pets, although policies can vary by property. It’s recommended to check specific house rules for details such as size limits or additional fees.

Oceanfront properties are often in high demand, especially during peak travel seasons, so booking 90 to 120 days in advance is recommended for the best selection. During quieter periods, you may still find availability closer to your travel dates.

Oceanfront rentals in St. Michaels often include features designed for a comfortable coastal stay, such as View, Ocean View, and Oceanfront. These amenities help guests make the most of their time by the water.

Yes, there is a clear difference. "Oceanfront" means the property is located directly on the beach with no obstructions between the home and the water. "Ocean View" typically means the ocean is visible from certain angles or rooms, but the property may not be right on the shoreline.