Wittman Holiday Rentals

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Our top choices for Wittman holiday rentals

Condo in Historic District

Upscale Condo in Annapolis
10.0 out of 10, Exceptional, (2)
"Great condo! Very clean and convenient to everything in Annapolis. We will definitely be back."
United States
Scott P.
The price is NZ$851
includes taxes & fees
20 Jan - 21 Jan
Upscale Condo in Annapolis
10.0 out of 10, Exceptional, (7)
The price is NZ$603
includes taxes & fees
10 Jan - 11 Jan
Station House East: Upscale Loft in the Historic District Cambridge, MD
10.0 out of 10, Exceptional, (17)
"We loved our stay! The property was just as advertised and had everything we needed. Quiet area and felt very safe. The owners provided excellent communication as well!"
United States
Jennifer B.
The price is NZ$556
includes taxes & fees
25 Jan - 26 Jan
Walk to Beach! King Bed & Free Beach Passes
9.8 out of 10, Exceptional, (11)
"This was such a cozy, comfortable space for a girls weekend away. We loved the charm of the old building paired with thoughtful amenities. "
United States
Lauren V.
The price is NZ$576
includes taxes & fees
2 Feb - 3 Feb
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
9.6 out of 10, Exceptional, (4)
"Great place in a wonderful area! So cozy & well situated! A perfect weekend getaway!"
United States
Jana S.
The price is NZ$505
includes taxes & fees
10 Jan - 11 Jan
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
10.0 out of 10, Exceptional, (6)
"Beautiful home. Very nice and quiet neighborhood on the water. "
United States
shannan t.
The price is NZ$1,487
includes taxes & fees
11 Jan - 12 Jan
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
10.0 out of 10, Exceptional, (7)
"Very clean and very convenient location for our trip. "
United States
Greg S.
The price is NZ$961
includes taxes & fees
11 Jan - 12 Jan
Charming Pet-Friendly Stay - Near Bay & Beaches.
10.0 out of 10, Exceptional, (31)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is NZ$702
includes taxes & fees
21 Jan - 22 Jan
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
9.6 out of 10, Exceptional, (20)
"The place was wonderful beautiful views of harbor, extremely clean and well appointed. Great restaurants we ate at RAR, great beer and food. Christopher’ Corner great dinner food fabulous and cocktails, highly recommend. Blackwater Cafe wonderful breakfast. "
United States
deb j.
The price is NZ$587
includes taxes & fees
12 Jan - 13 Jan
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
8.4 out of 10, Very good, (6)
"Perfectly located in town and well appointed, comfortable quarters. We would stay again."
United States
Richard D.
The price is NZ$466
includes taxes & fees
12 Jan - 13 Jan
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
9.6 out of 10, Exceptional, (12)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
The price is NZ$718
includes taxes & fees
12 Jan - 13 Jan
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
9.6 out of 10, Exceptional, (32)
"Very nice house! We had 3 people in our party and didn't want to rent 2 hotel rooms, this is a great way to save money and enjoy time together. "
United States
Pamela
The price is NZ$432
includes taxes & fees
11 Jan - 12 Jan
Charming Coastal/Country Home w/3 Acres & Sauna!
10.0 out of 10, Exceptional, (81)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is NZ$707
includes taxes & fees
10 Jan - 11 Jan
Waterfront Oasis of Annapolis Star
10.0 out of 10, Exceptional, (50)
"Beautiful place! Loved all the activities, will return in the future! Our family and friends had a blast! Thank you so much!!"
United States
Karen L.
The price is NZ$543
includes taxes & fees
12 Jan - 13 Jan
Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, (10)
"Just a beautiful place. I would stay here again. Everything was walking distance. "
United States
Sylvie G.
The price is NZ$597
includes taxes & fees
12 Jan - 13 Jan
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
10.0 out of 10, Exceptional, (1)
"Great stay, host was super amazing and we had the best time!!"
United States
Kirstyn I.
Annapolis Boat Life - Overnight Stays

Apartment in Cambridge

Sailwinds Loft at Cambridge Creek
10.0 out of 10, Exceptional, (24)
"What a great place to relax after exploring and enjoying the area. Definitely will visit again "
United States
Chris S.
The price is NZ$433
includes taxes & fees
10 Jan - 11 Jan
Sailwinds Loft at Cambridge Creek
9.8 out of 10, Exceptional, (43)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
The price is NZ$432
includes taxes & fees
11 Jan - 12 Jan
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Holiday Home in Annapolis

Mins to DTA - King Beds - Parking
2.0 star property
10.0 out of 10, Exceptional, (4)
"Great house & great location! We will definitely be returning! Thank you Jessica!"
United States
Holly W.
Mins to DTA - King Beds - Parking
10.0 out of 10, Exceptional, (14)
"Amazing news out of the back.Great for kayaking.We brought our own kayaksAnd also use yoursThere were four of usWe also took a nice trip over to Saint Michael’s"
United States
Sandy S.
The price is NZ$898
includes taxes & fees
10 Jan - 11 Jan
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Wittman Hotel Reviews

Find out more about Wittman

Everything you need to know about Wittman holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Wittman holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Wittman holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Wittman holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Wittman. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Wittman holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Wittman holiday rentals we have selected for you start as low as NZ$543 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Wittman rentals

At Expedia, we put the best Wittman holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Wittman rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Wittman holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Wittman. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Wittman?

Yes, there are holiday rentals close to the most popular sights in Wittman, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Wittman has to offer?

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA: This holiday home rental outside of Wittman is located in the city centre, and offers a selection of games, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals will I find in Wittman?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Wittman stay.

What’s there to see and do in Wittman?

While exploring the area, visit family-friendly sights like Chesapeake Bay Maritime Museum, or get outside and enjoy nature at Chesapeake Bay Environmental Center. In the wider area, you’ll find St. Michaels Winery and St. Michaels Marina.

What’s a holiday rental in Wittman like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Wittman. Holiday rentals feature extras like WiFi and washers and dryers so you'll feel right at home. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from public hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great option for family trips or small group gatherings.