Vacation Rentals with Private Pool in Wittman, MD: Compare 10+ Sites & Save

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36 Best Vacation Rentals with Private Pool in Wittman (Starting from $273)

Tranquil Waters
Tranquil Waters
House
Tilghman, MD, USA
8.1k from Wittman 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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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
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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
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Brand-New Pool! Waterfront Bozman Village Home
Brand-New Pool! Waterfront Bozman Village Home
House
Bozman, MD, 21612, United States
2.9k from Wittman center

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

4 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$549
Average price / night
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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
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Minutes from Downtown St. Michaels | Pool | Hot Tub
Minutes from Downtown St. Michaels | Pool | Hot Tub
House
Bozman, MD, 21612, United States
3.0k from Wittman center

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

2 Bedrooms4 Guests
9.8

Exceptional

10 reviews

$680
Average price / night
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Minutes from Downtown St. Michaels | Pool | Cabana | Kayaks | Private Dock
Minutes from Downtown St. Michaels | Pool | Cabana | Kayaks | Private Dock
House
St. Michaels, MD, 21663, United States
3.5k from Wittman center

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

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$1085
Average price / night
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Baydream Believer
Baydream Believer
House
Talbot County, MD, 21663, United States
3.5k from Wittman center

AC, Arcade, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub

5 Bedrooms8 Guests
10.0

Exceptional

87 reviews

$1392
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
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
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GRATITUDE FARM - A Tranquil Waterfront Renovated Farmhouse - Bozman, MD
GRATITUDE FARM - A Tranquil Waterfront Renovated Farmhouse - Bozman, MD
House
Bozman, MD, 21612, United States
4.1k from Wittman center

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

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$682
Average price / night
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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
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Waterfront | Pet Friendly & Close to St. Michaels
Waterfront | Pet Friendly & Close to St. Michaels
House
Bozman, MD, 21612, United States
4.6k from Wittman center

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

4 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$797
Average price / night
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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
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St. Michaels Waterfront | Pool and Sunset Views
St. Michaels Waterfront | Pool and Sunset Views
House
Saint Michaels, MD, 21663, United States
4.9k from Wittman center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Microwave

5 Bedrooms10 Guests
New to Booking
$1891
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
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Saint Michaels Summer Retreat with Pool & Hot Tub
Saint Michaels Summer Retreat with Pool & Hot Tub
House
Saint Michaels, MD, 21663-2402, United States
5.2k from Wittman center

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

3 Bedrooms6 Guests
9.8

Exceptional

9 reviews

$788
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 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
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Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock
Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock
House
St. Michaels, MD, 21663, United States
5.3k from Wittman center

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

4 Bedrooms8 Guests
8.0

Good

2 reviews

$913
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
5.5k 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
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6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
House
Sherwood, MD, 21665, United States
5.8k from Wittman center

AC, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub

6 Bedrooms12 Guests
10.0

Exceptional

22 reviews

$1239
Average price / night
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ENDLESS SUNSETS ON THE EASTERN BAY
ENDLESS SUNSETS ON THE EASTERN BAY
House
Claiborne, MD, 21624, United States
6.2k from Wittman center

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

2 Bedrooms4 Guests
9.8

Exceptional

79 reviews

$667
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
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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
6.2k from Wittman 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
St. Michaels Escape | Pool, Hot Tub & Fire Pit
St. Michaels Escape | Pool, Hot Tub & Fire Pit
House
Saint Michaels, MD, 21663, United States
6.2k from Wittman center

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

3 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$709
Average price / night
Check Availability
Eastern Shore Waterside Cottage Near St. Michaels
Eastern Shore Waterside Cottage Near St. Michaels
Cottage
Neavitt, MD, 21652, United States
6.7k from Wittman center

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

3 Bedrooms6 Guests
10.0

Exceptional

24 reviews

$426
Average price / night
Check Availability
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
7.1k from Wittman 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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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
7.1k from Wittman 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
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 with Private Pool in Wittman.

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Wittman Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 36 verified vacation rentals with a private pool in Wittman. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Wittman vary depending on the property size, location, and travel season. Rates typically start from around $273 per night, with higher prices for larger homes, prime locations, or peak travel periods.

Yes, properties listed with private pools are intended for the exclusive use of guests staying at that home. You can review listing photos and descriptions to better understand the layout and level of privacy offered.

Yes, some vacation rentals with private pools in Wittman also welcome pets. Currently, 16 listings allow pets, although policies may vary. It’s a good idea to review any rules related to pets and outdoor areas before booking.

Private pool properties are often in high demand, especially during holidays and warmer months, so booking 90 to 120 days in advance is recommended. During quieter periods, you may still find availability closer to your travel dates.

Vacation rentals with private pools in Wittman often include additional features such as Pool, Private Pool, and Bedding/Linens. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Wittman include safety features such as pool fences, covers, or screened enclosures. It’s recommended to check the property details to confirm whether a specific rental meets your safety preferences.