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

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Family Vacation Rentals
  3.  USA

  4.  Maryland

  5.  Wittman

Refine your search

Price per night

Amenity Filter

Rating

62 Best Family Vacation Rentals in Wittman (Starting from $238)

Sailor Joes
Sailor Joes
House
Sherwood, MD, USA
2.8k from Wittman center

Security/Safety, Parking, Internet, Child Friendly

1 Bedroom6 Guests
New to Booking
$632
Average price / night
Check Availability
Relaxing Waterfront Cottage Near St Michaels, Maryland
Relaxing Waterfront Cottage Near St Michaels, Maryland
Cottage
Wittman, MD, 21676, United States
1.3k from Wittman center

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

2 Bedrooms4 Guests
9.8

Exceptional

241 reviews

$273
Average price / night
Check Availability
Brand-New Pool! Waterfront Bozman Village Home
Brand-New Pool! Waterfront Bozman Village Home
House
MD, USA
2.9k from Wittman 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
Perfect Waterview Cottage - St. Michaels Getaway
Perfect Waterview Cottage - St. Michaels Getaway
Cottage
Wittman, MD, 21676, United States
1.3k from Wittman center

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

2 Bedrooms4 Guests
9.8

Exceptional

119 reviews

$238
Average price / night
Check Availability
Dragonfly Cove
Dragonfly Cove
House
Mount Pleasant, MD, USA
3.0k from Wittman 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
Waterfront Oyster Farmhouse Built 2018 with Pool/Fence and Dock-23 private acres
Waterfront Oyster Farmhouse Built 2018 with Pool/Fence and Dock-23 private acres
House
Wittman, MD, 21676, United States
2.0k from Wittman center

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

4 Bedrooms8 Guests
10.0

Exceptional

67 reviews

$1091
Average price / night
Check Availability
Baydream Believer
Baydream Believer
House
Saint Michaels, MD, USA
3.1k from Wittman 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
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
2.2k from Wittman 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
The Weekender
The Weekender
House
Mount Pleasant, MD, USA
3.2k from Wittman center

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

1 Bedroom4 Guests
New to Booking
$441
Average price / night
Check Availability
Skipjack House | an ESVR property
Skipjack House | an ESVR property
House
Mcdaniel, MD, 21647, United States
2.9k from Wittman center

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

3 Bedrooms6 Guests
New to Booking
$641
Average price / night
Check Availability
Waterfront St Michaels Vacation Rental with Fire Pit
Waterfront St Michaels Vacation Rental with Fire Pit
House
MD, USA
4.1k from Wittman 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. Michaels | Character Filled
Minutes from Downtown St. Michaels | Character Filled
House
Bozman, MD, 21612, United States
3.2k from Wittman center

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

2 Bedrooms4 Guests
New to Booking
$386
Average price / night
Check Availability
Hawkeye Point
Hawkeye Point
House
Mount Pleasant, MD, USA
4.4k from Wittman center

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

1 Bedroom6 Guests
New to Booking
$1175
Average price / night
Check Availability
Mill Point
Mill Point
House
Neavitt, MD, USA
5.1k from Wittman center

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

1 Bedroom10 Guests
New to Booking
$1199
Average price / night
Check Availability
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
3.6k from Wittman center

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

5 Bedrooms10 Guests
10.0

Exceptional

95 reviews

$598
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
6.0k from Wittman 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
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
3.9k from Wittman center

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

5 Bedrooms10 Guests
10.0

Exceptional

11 reviews

$1263
Average price / night
Check Availability
Neavitt Cottage
Neavitt Cottage
House
Neavitt, MD, USA
6.4k from Wittman center

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

1 Bedroom8 Guests
New to Booking
$765
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
4.4k from Wittman 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
Carpenter Alley Cottage
Carpenter Alley Cottage
House
Saint Michaels, MD, USA
6.7k from Wittman center

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

1 Bedroom6 Guests
New to Booking
$666
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
4.4k from Wittman 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 | 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
4.8k from Wittman center

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

6 Bedrooms12 Guests
New to Booking
$1506
Average price / night
Check Availability
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
5.1k from Wittman center

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

5 Bedrooms10 Guests
9.8

Exceptional

8 reviews

$1138
Average price / night
Check Availability
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 Wittman center

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

5 Bedrooms10 Guests
9.8

Exceptional

40 reviews

$1363
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
5.3k from Wittman center

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

3 Bedrooms6 Guests
10.0

Exceptional

6 reviews

$495
Average price / night
Check Availability
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
5.5k from Wittman center

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

8 Bedrooms12 Guests
10.0

Exceptional

37 reviews

$1991
Average price / night
Check Availability
Grandview- Main House
Grandview- Main House
House
Bozman, MD, 21612, United States
6.2k from Wittman center

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

4 Bedrooms9 Guests
9.8

Exceptional

45 reviews

$885
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 Wittman.

Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods

Stay Near Wittman's Top Attractions

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

Wittman Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 62 verified family-friendly vacation rentals in Wittman. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Wittman vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $238 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Wittman 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 Wittman 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 Wittman 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.