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

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73 Best Family Vacation Rentals in St. Michaels (Starting from $374)

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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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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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
Check Availability
Downtown St. Michaels | Bikes | Kayaks | Private Pier
Downtown St. Michaels | Bikes | Kayaks | Private Pier
House
Saint Michaels, MD, 21663, United States
1.1k from St. Michaels center

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

3 Bedrooms6 Guests
10.0

Exceptional

35 reviews

$792
Average price / night
Check Availability
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
Check Availability
Minutes from Downtown St. Michaels | Pool | Hot Tub | Pickle Ball Court
Minutes from Downtown St. Michaels | Pool | Hot Tub | Pickle Ball Court
House
Saint Michaels, MD, 21663, United States
1.2k from St. Michaels center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms6 Guests
9.6

Exceptional

4 reviews

$677
Average price / night
Check Availability
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
Check Availability
Minutes from Downtown St. Michael's | Game Room | Pool | Hot Tub | Pickle Ball C
Minutes from Downtown St. Michael's | Game Room | Pool | Hot Tub | Pickle Ball C
House
Saint Michaels, MD, 21663, United States
1.3k from St. Michaels center

AC, Arcade, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub

5 Bedrooms10 Guests
10.0

Exceptional

8 reviews

$1402
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
Check Availability
Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels
Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels
House
Saint Michaels, MD, 21663, United States
1.4k from St. Michaels center

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

3 Bedrooms6 Guests
10.0

Exceptional

6 reviews

$495
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
Check Availability
St. Michaels Waterfront w/ Dock, 1 mile from Town
St. Michaels Waterfront w/ Dock, 1 mile from Town
Cottage
St. Michaels, MD, 21663, United States
1.5k from St. Michaels center

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

3 Bedrooms6 Guests
10.0

Exceptional

16 reviews

$736
Average price / night
Check Availability
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
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly
House
St. Michaels, MD, 21663, United States
1.6k from St. Michaels center

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

3 Bedrooms6 Guests
9.6

Exceptional

31 reviews

$742
Average price / night
Check Availability
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
Check Availability
Minutes from Downtown St. Michaels | Pool | Kayaks | 350 Ft of Shoreline | Luxur
Minutes from Downtown St. Michaels | Pool | Kayaks | 350 Ft of Shoreline | Luxur
House
Saint Michaels, MD, 21663, United States
1.9k from St. Michaels center

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

6 Bedrooms12 Guests
New to Booking
$1506
Average price / night
Check Availability
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
Check Availability
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
Check Availability
Minutes from Downtown St. Michaels | Private Dock | Kayaks
Minutes from Downtown St. Michaels | Private Dock | Kayaks
House
Saint Michaels, MD, 21663, United States
2.3k from St. Michaels center

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

4 Bedrooms8 Guests
9.8

Exceptional

11 reviews

$750
Average price / night
Check Availability
Minutes from Downtown St. Michaels | Pool | Dock
Minutes from Downtown St. Michaels | Pool | Dock
House
St Michaels, MD, 21663, United States
2.7k from St. Michaels center

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

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$1004
Average price / night
Check Availability
TRUE IN-TOWN ST MICHAELS 6 ACRE WATERFRONT - Heated Pool
TRUE IN-TOWN ST MICHAELS 6 ACRE WATERFRONT - Heated Pool
House
St Michaels, MD, 21663, United States
2.7k from St. Michaels center

AC, Arcade, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet

5 Bedrooms8 Guests
10.0

Exceptional

68 reviews

$1593
Average price / night
Check Availability
Cozy, Family Friendly, Log Cabin-St. Michaels, MD
Cozy, Family Friendly, Log Cabin-St. Michaels, MD
House
Saint Michaels, MD, 21663, United States
3.6k from St. Michaels center

AC, Arcade, Balcony, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
9.8

Exceptional

7 reviews

$603
Average price / night
Check Availability
Minutes from Downtown Easton and St. Michaels | Pool | Private Dock | Golf Cours
Minutes from Downtown Easton and St. Michaels | Pool | Private Dock | Golf Cours
House
Easton, MD, 21601, United States
4.1k from St. Michaels center

AC, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

6 Bedrooms12 Guests
10.0

Exceptional

2 reviews

$2110
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 Family Vacation Rentals in St. Michaels.

Stay Near St. Michaels's Top Attractions

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St. Michaels Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 73 verified family-friendly vacation rentals in St. Michaels. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in St. Michaels vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $374 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in St. Michaels offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in St. Michaels are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in St. Michaels often include amenities such as Child Friendly, Internet, and Fireplace/Heating. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.