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

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129 Best Vacation Rentals in Wittman (Starting from $230)

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
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Lovely 2-bedroom waterfront cottage in charming Wittman
Lovely 2-bedroom waterfront cottage in charming Wittman
Cottage
Wittman, MD, 21676, United States
1.3k from Wittman center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, No Smoking, Outdoor Space

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$313
Average price / night
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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
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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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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
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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
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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
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Charming 3 Bedroom Cottage – 6 Miles to St. Michaels
Charming 3 Bedroom Cottage – 6 Miles to St. Michaels
House
Wittman, MD, 21676, United States
1.5k from Wittman center

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

3 Bedrooms6 Guests
8.0

Good

1 reviews

$255
Average price / night
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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
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Cozy getaway! Centrally located between St. Michaels and Tilghman Island\n\n
Cozy getaway! Centrally located between St. Michaels and Tilghman Island\n\n
House
Wittman, MD, 21676, United States
1.6k from Wittman center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

3 Bedrooms6 Guests
10.0

Exceptional

7 reviews

$230
Average price / night
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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
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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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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
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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
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
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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
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Amazing Waterfront Views, Private Pool and Dock
Amazing Waterfront Views, Private Pool and Dock
House
Sherwood, MD, 21665, United States
2.5k from Wittman 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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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
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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
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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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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
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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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Waterfront  - pier & acreage to run & play.   Pet friendly Oct/Nov dates open!
Waterfront - pier & acreage to run & play. Pet friendly Oct/Nov dates open!
House
Saint Michaels, MD, 21663, United States
3.0k from Wittman center

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

4 Bedrooms8 Guests
9.8

Exceptional

22 reviews

$917
Average price / night
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Cottage #4 Chesapeake Blue  down the drive way.
Cottage #4 Chesapeake Blue down the drive way.
Cottage
Saint Michaels, MD, 21663, United States
3.1k from Wittman center

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

1 Bedroom4 Guests
New to Booking
$294
Average price / night
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#3 Mallard Cottage  (located 3rd down drive)
#3 Mallard Cottage (located 3rd down drive)
Cottage
Saint Michaels, MD, 21663, United States
3.1k from Wittman center

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

1 Bedroom4 Guests
10.0

Exceptional

1 reviews

$294
Average price / night
Check Availability
#2 Egret Cottage Harris Cove
#2 Egret Cottage Harris Cove
Cottage
Saint Michaels, MD, 21663, United States
3.1k from Wittman center

AC, Barbecue, Free Parking, Internet, Kitchen, No Smoking, TV

10.0

Exceptional

1 reviews

$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
3.1k from Wittman center

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

1 Bedroom4 Guests
New to Booking
$315
Average price / night
Check Availability
Cottage #8 Herons Nest Lg 2 rooms Under Main House
Cottage #8 Herons Nest Lg 2 rooms Under Main House
Cottage
Saint Michaels, MD, 21663, United States
3.1k from Wittman center

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

1 Bedroom6 Guests
10.0

Exceptional

1 reviews

$371
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 in Wittman.

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Frequently Asked Questions

You can explore 129 verified vacation rentals in Wittman. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Wittman vary depending on the season, property size, and location. Rates typically start from around $230 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Wittman include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Wittman welcome pets. Currently, 29 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Wittman often include amenities such as Internet, Fireplace/Heating, and Child Friendly. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.