Family-Friendly Vacation Rentals in Tilghman, MD: Compare 10+ Sites & Save

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26 Best Family Vacation Rentals in Tilghman (Starting from $175)

Clearview
Clearview
House
Tilghman Island, MD, USA
2.0k from Tilghman center

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

1 Bedroom6 Guests
New to Booking
$765
Average price / night
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 Artists, writers & creative minds  IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Cottage
Tilghman Island, MD, 21671, United States
0.9k from Tilghman center

AC, Barbecue, Breakfast Available, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

2 Bedrooms4 Guests
10.0

Exceptional

13 reviews

$421
Average price / night
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Crepe Myrtle
Crepe Myrtle
House
Tilghman, MD, USA
2.4k from Tilghman center

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

1 Bedroom6 Guests
New to Booking
$572
Average price / night
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House on the Chesapeake Bay
House on the Chesapeake Bay
House
Tilghman Island, MD, 21671, United States
1.3k from Tilghman center

AC, Barbecue, Crib, Dryer, Extra Bed, Fitness Equipment, Free Parking, Heater, Internet

3 Bedrooms6 Guests
10.0

Exceptional

15 reviews

$511
Average price / night
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Tranquil Waters
Tranquil Waters
House
Tilghman, MD, USA
2.5k from Tilghman center

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

1 Bedroom12 Guests
New to Booking
$1897
Average price / night
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Tilghman | Pool | Private Dock | Pet Friendly
Tilghman | Pool | Private Dock | Pet Friendly
House
Tilghman, MD, 21671, United States
2.0k from Tilghman center

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

3 Bedrooms6 Guests
9.4

Superb

15 reviews

$761
Average price / night
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Tilghman Island Retreat By Knapps Narrows!
Tilghman Island Retreat By Knapps Narrows!
House
MD, USA
2.7k from Tilghman center

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

2 Bedrooms4 Guests
8.0

Good

1 reviews

$274
Average price / night
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Tilghman | Fenced Yard | Pet Friendly | Charming
Tilghman | Fenced Yard | Pet Friendly | Charming
House
Tilghman, MD, 21671, United States
2.4k from Tilghman center

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

3 Bedrooms6 Guests
6.0

Review score

2 reviews

$473
Average price / night
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Waterfront Bliss- Ultimate Tilghman Retreat home
Waterfront Bliss- Ultimate Tilghman Retreat home
House
MD, USA
2.8k from Tilghman center

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

4 Bedrooms8 Guests
9.0

Fabulous

1 reviews

$683
Average price / night
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Tilghman Waterfront | Indoor Pool | Private Dock | Pool House
Tilghman Waterfront | Indoor Pool | Private Dock | Pool House
House
Tilghman, MD, 21671, United States
2.5k from Tilghman center

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

7 Bedrooms12 Guests
9.6

Exceptional

7 reviews

$1657
Average price / night
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St Michaels Area Cottage - Walk to Water and Marina
St Michaels Area Cottage - Walk to Water and Marina
House
Neavitt, MD, USA
5.6k from Tilghman center

Internet, Pet Friendly, Parking, Kitchen, Wheelchair Accessible, Child Friendly

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$175
Average price / night
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ST. MICHAELS ESTATE OFFERS WATERFRONT POOL, PIER, DOCK AND 15 ACS\nPET FRIENDLY
ST. MICHAELS ESTATE OFFERS WATERFRONT POOL, PIER, DOCK AND 15 ACS\nPET FRIENDLY
House
Sherwood, MD, 21665, United States
5.3k from Tilghman center

AC, Arcade, Barbecue, Breakfast Available, Dryer, Fireplace, Free Parking, Heater, Internet

5 Bedrooms10 Guests
9.8

Exceptional

40 reviews

$1363
Average price / night
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Neavitt Cottage
Neavitt Cottage
House
Neavitt, MD, USA
5.7k from Tilghman center

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

1 Bedroom8 Guests
New to Booking
$765
Average price / night
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Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
House
Sherwood, MD, 21665, United States
5.7k from Tilghman center

AC, Arcade, Barbecue, Dryer, Elevator, Fireplace, Fitness Equipment, Free Parking, Heater

8 Bedrooms12 Guests
10.0

Exceptional

37 reviews

$1991
Average price / night
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Mill Point
Mill Point
House
Neavitt, MD, USA
6.1k from Tilghman center

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

1 Bedroom10 Guests
New to Booking
$1199
Average price / night
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Grandview- Main House
Grandview- Main House
House
Bozman, MD, 21612, United States
5.8k from Tilghman center

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

4 Bedrooms9 Guests
9.8

Exceptional

45 reviews

$885
Average price / night
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Sailor Joes
Sailor Joes
House
Sherwood, MD, USA
7.8k from Tilghman center

Security/Safety, Parking, Internet, Child Friendly

1 Bedroom6 Guests
New to Booking
$632
Average price / night
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Eastern Shore Waterside Cottage Near St. Michaels
Eastern Shore Waterside Cottage Near St. Michaels
Cottage
Neavitt, MD, 21652, United States
5.8k from Tilghman center

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

3 Bedrooms6 Guests
10.0

Exceptional

24 reviews

$426
Average price / night
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25 Bedrooms - Retreat Center Waterfront Renovated
25 Bedrooms - Retreat Center Waterfront Renovated
House
MD, USA
9.8k from Tilghman center

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

25 Bedrooms40 Guests
New to Booking
$14533
Average price / night
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Breathtaking Waterfront Estate
Breathtaking Waterfront Estate
Villa
Neavitt, MD, 21652, United States
5.9k from Tilghman center

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

6 Bedrooms12 Guests
10.0

Exceptional

73 reviews

$1941
Average price / night
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Minutes from Downtown St. Michaels | Pool | Kayaks | Private Dock | Newly Renova
Minutes from Downtown St. Michaels | Pool | Kayaks | Private Dock | Newly Renova
House
Bozman, MD, 20815, United States
6.1k from Tilghman center

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

5 Bedrooms10 Guests
9.8

Exceptional

8 reviews

$1138
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
7.1k from Tilghman 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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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
7.6k from Tilghman 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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Minutes from Downtown St. Michaels and Tilghman | Private Dock | Outdoor Dining
Minutes from Downtown St. Michaels and Tilghman | Private Dock | Outdoor Dining
House
Sherwood, MD, 21665, United States
8.4k from Tilghman center

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

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$537
Average price / night
Check Availability
Waterfront Farmhouse Retreat on 18 Acres, Pool
Waterfront Farmhouse Retreat on 18 Acres, Pool
House
Royal Oak, MD, 21662, United States
9.8k from Tilghman center

AC, Balcony, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Internet

8 Bedrooms16 Guests
10.0

Exceptional

1 reviews

$2682
Average price / night
Check Availability
Moofy's Farmhouse: Main Lodge ; Private Waterfront Retreat Center, New Reno on 18 Acres
Moofy's Farmhouse: Main Lodge ; Private Waterfront Retreat Center, New Reno on 18 Acres
House
Royal Oak, MD, 21662, United States
9.8k from Tilghman center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking

1 Bedroom50 Guests
New to Booking
$10158
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 Tilghman.

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Tilghman Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 26 verified family-friendly vacation rentals in Tilghman. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Tilghman vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $175 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Tilghman 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 Tilghman 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 Tilghman 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.