Wittman holiday rentals

We found 209 holiday rentals — enter your dates for availability

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July 2025

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Discover a selection of holiday rentals in Wittman that are perfect for your trip. Whether you're staying in a holiday rental with family or friends, you'll find the amenities that you need and want, which might include Wi-Fi and a washer and dryer. You're sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Wittman

Showing deals for:10 Oct - 17 Oct

Exceptional

(9 reviews)

Grace Cottage, Saint Michaels Walk to everything!

St. Michaels, MD

8% off

AU$937 per night

includes taxes & fees

Waterfront 5+ bedroom home on the Miles River!

Exceptional

(88 reviews)

Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

Easton, MD

8% off

AU$1,371 per night

includes taxes & fees

Baja Deck with umbrella- sit in pool on plastic adirondack chairs and read!

Exceptional

(133 reviews)

Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

Easton, MD

8% off

AU$1,714 per night

includes taxes & fees

Kent Island Beach House:Winter, Spring, Summer & Fall there is something for All

Exceptional

(75 reviews)

Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.

Stevensville, MD

8% off

AU$1,428 per night

includes taxes & fees

Exceptional

(38 reviews)

Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.

Stevensville, MD

8% off

AU$1,428 per night

includes taxes & fees

Exceptional

(51 reviews)

Easter Weekend open WATERFRONT St Michaels area historic home, dog friendly

Neavitt, MD

8% off

AU$644 per night

includes taxes & fees

Front and side view of Blades House from Locust St.

Exceptional

(140 reviews)

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

St. Michaels, MD

8% off

AU$577 per night

includes taxes & fees

Exceptional

(119 reviews)

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

St. Michaels, MD

8% off

AU$531 per night

includes taxes & fees

"Overlook on Dun's Cove" -- luxury, year-round waterfront vacation rental

Exceptional

(140 reviews)

Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels

Sherwood, MD

10% off

AU$526 per night

includes taxes & fees

House and Garage as seen from above (pool on left)

Exceptional

(87 reviews)

Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)

Royal Oak, MD

8% off

AU$3,756 per night

includes taxes & fees

Exceptional

(23 reviews)

Jellyfish Cottage - Waterfront. Spectacular Sunsets over Chesapeake Bay

Tilghman, MD

12% off

AU$705 per night

includes taxes & fees

Exceptional

(134 reviews)

Charming cottage along water with private pier, near St. Michaels Winery

Bozman, MD

12% off

AU$450 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Wittman

Enjoy views of the Chesapeake Bay, pool and garden through a wall of glass!

Comfortable Spacious Fun! 6+Acres Pool+Bay Waterfront St Michaels-Yes Weddings!

Sleeps 16 · 5 bedrooms · 5 bathrooms

Waterfront Oyster Farmhouse Built 2018 with Pool/Fence and Dock-23 private acres

Sleeps 8 · 4 bedrooms · 4+ bathrooms

Cozy getaway! Centrally located between St. Michaels and Tilghman Island

Sleeps 6 · 3 bedrooms · 1 bathroom

Minutes from Downtown St. Michaels and Tilghman | Private Dock | Pool | 8.6 Acre

Sleeps 8 · 4 bedrooms · 3+ bathrooms

Peace of mind
Our Book with Confidence Guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Relaxing Wittman will entice you

Learn about the unique charm of Wittman with a stay in a holiday home rental. Travellers appreciate the cycling in this relaxing city. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in and around Wittman

Do you want to find attractions to see in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Wittman a fun place to get away to. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

St. Michaels Winery (4 mi / 6.4 km)
Chesapeake Beach Water Park (14.8 mi / 23.8 km)
Queenstown Harbor Golf Links (15.1 mi / 24.3 km)
Queenstown Harbor Golf Club (15.1 mi / 24.3 km)
Hog Neck Golf Course (12.9 mi / 20.8 km)
Paul Reed Smith Guitars (13.5 mi / 21.7 km)

Exploring the natural features in Wittman

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Wittman is a great spot to appreciate mother nature. These are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

Chesapeake Bay Environmental Center (11.2 mi / 18.1 km)
Shadyside Park (12.5 mi / 20.1 km)
Bay Ridge Beach (13.8 mi / 22.1 km)
Carrs Beach (14.6 mi / 23.5 km)
Maryland Quiet Waters Park (15.1 mi / 24.3 km)
Sandy Point Beach (16 mi / 25.8 km)

How to get to and around Wittman

Fly into Easton, MD (ESN-Easton - Newnam), the closest airport, located 12.4 mi (20 km) from the city centre.

Frequently asked questions

What is the most popular type of holiday home accommodation in Wittman?

Based on our research, houses are the most desirable property type in Wittman. But that goes without saying, everyone's idea of the perfect trip will differ. Stayz has holiday homes with every size, shape and budget in mind, so you're sure to find the perfect match.

How much does it cost to rent a holiday home in Wittman?

The average price for a holiday home in Wittman can vary based on factors like season, property type and length of stay. Whether you're looking for a sprawling house with room for friends and family or a quaint cottage just for the two of you, just add your travel dates to find stays that offer great value.

How much does it cost to rent a beach house in Wittman?

The average price for a holiday home by the beach in Wittman depends on when you'll be there and the size and style of property you're looking for. You can easily and quickly find prices on Stayz by entering your travel dates and destination. Then use the handy filter tool to select the number of bedrooms and amenities that you need, like WiFi, a pool and air conditioning.

Are there pet-friendly holiday homes in Wittman?

With eight holiday homes that welcome four-legged guests, your furry buddy can join you on your Wittman holiday. Use our filter tool to search our pet-friendly holiday homes and find a holiday home that'll set tails wagging on Stayz.

Can I rent a house with a pool in Wittman?

Add a new level of fun to your holiday by booking your family into one of the seven houses with a private pool in Wittman. Use our handy search filter to find the kind of property you want on Stayz, and then spend your days splashing and playing in a swimming pool that's all your own.

What are popular home amenities in Wittman?

The most popular home amenities people search for in Wittman include nearby museums, tennis and a barbecue grill. Whether you're hitting the road with buddies, family or even pets, Stayz holiday properties feature the best amenities for ultimate relaxation with your loved ones.

Are there large group holiday homes in Wittman?

You can pick from two holiday properties in Wittman that can sleep 10 or more people. Whether you're organising a family holiday or a celebration like an anniversary, there's ample space to get your loved ones together under one roof.

Are there holiday homes in Wittman that welcome kids?

With eight family-friendly holiday homes to pick from in Wittman, now is a great time to introduce the kiddos to the pleasures of travel. Just click on our "Properties good for families" filter to find stays packed with amenities perfect for holidaying families, like dining rooms, private pools, entertainment areas and bunk beds.

What are the top attractions for families in Wittman?

Keep the kids occupied at these awesome family-friendly attractions in Wittman:

Chesapeake Bay Maritime Museum
St. Michaels Museum
Tilghman Watermen's Museum

Can I find two-bedroom holiday homes in Wittman?

Gather your family and experience complete comfort and privacy in one of the two two-bedroom holiday homes Wittman has to offer.

Are there holiday homes with WiFi in Wittman?

Choose from three holiday homes with WiFi in Wittman. If you want to disconnect from the world on your trip, but still need to be connected to the internet, these properties have just what you need. Narrow your search by applying the WiFi filter on Stayz.

How can I find holiday homes with air conditioning in Wittman?

You'll find eight Stayz holiday homes with air conditioning in Wittman giving you that cool, cool breeze and extra touch of comfort. Enter your desired travel dates and then make use of our filters to locate stays with air conditioning.

How old do you have to be to rent a holiday home in Wittman?

The minimum age requirements can vary across properties on Stayz, so be sure to look at the rules of the holiday home in Wittman you want. But normally, it's 16, 18 or 21.

How long can I rent a holiday home in Wittman for?

How long you can rent a holiday home in Wittman is down to the property. Just enter your selected dates to look at a list of options offering extended stays. With plenty of features such as air conditioning and full kitchens, as well as some offering weekly or monthly discounted prices, you're sure to find somewhere just right to call your home away from home in Wittman.