Search Holiday Rentals in Wittman

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May 4 - May 5
Tomorrow
May 5 - May 6
Next weekend
May 10 - May 12

Top Holiday Rentals in Wittman

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Fridge, microwave, oven, stovetop
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (2)
"My rugby team traveled down for a competition. Erin met us there walked us around the property and gave us great recommendations for food in the area. She was an amazing manager, always answering questions and getting us anything we needed. The property was beautiful and fit our entire team comfortably. The large slace and outdoor activity allowed for a lot of team building and we had a blast llaying pickle ball and basketball with each other. We wish we coukd have spent more time there."
The price is £1,138
includes taxes & fees
6 May - 7 May
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
The Blue Crab Beach House - Free beach passes
Beach nearby, sun-loungers, beach umbrellas, beach towels
The Blue Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, (37)
"This property is in a great location! The house is adorable and the owner was very responsive and accommodating when I needed to add an extra day. I would definitely recommend!"
The Blue Crab Beach House - Free beach passes
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Exterior
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, (186)
"The cottage is fully stocked, clean, and cozy. We thoroughly enjoyed sitting on the deck and watching all the wildlife."
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
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Directly Across from Gate One & Steps from the Waterfront
Fridge, microwave, oven, stovetop
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, (178)
"Great location! The owner was very easy to communicate with and very accommodating. We had a great time exploring Annapolis."
Directly Across from Gate One & Steps from the Waterfront
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Property grounds
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
10.0 out of 10, Exceptional, (22)
"My family and I had an amazing stay!! Jacob’s correspondence was timely and very friendly from beginning to end. We had some problems with cleanliness (sheets not being washed, cobwebs, dead beetles in windowsills), and Jacob refunded our cleaning fee. Despite that, the house was beautiful and had plenty of space for our big family to move around. Be warned that there are A LOT of stairs! But nothing my older parents couldn’t handle. The views are absolutely breathtaking and every single room...
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Amazing views, short walks to great dining!
Smart TV, Netflix, DVD player, streaming services
Amazing views, short walks to great dining!
10.0 out of 10, Exceptional, (63)
"My husband and I stayed at the Weems creek cottage for a childless getaway weekend. Everything was excellent, from communication with Jim, to the gorgeous property and the time we had in the city of Annapolis. Not to mention the weather was nice! We spent Friday and most of Saturday in the city of Annapolis. On Saturday evening we just enjoyed our stay at the cottage, we had two fires, relaxing in the Adirondack chairs overlooking the water. THIS was exactly what we needed and what we enjoy...
Amazing views, short walks to great dining!
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
10.0 out of 10, Exceptional, (72)
"The house has a beautiful view of the water. Being so close to the Happy Harbor restaurant, we could order carryout & listen to the bands from the screened-in porch. It was a perfect getaway for someone who had relaxation on the mind. Thanks for sharing your lovely home."
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Recently Renovated Annapolis Home - Conveniently Located
Fridge, microwave, oven, stovetop
Recently Renovated Annapolis Home - Conveniently Located
10.0 out of 10, Exceptional, (43)
"Great location - walkable to Downtown Annapolis and the stadium. House was very clean and has all the features and amenities you need for a comfortable stay!"
Recently Renovated Annapolis Home - Conveniently Located
Firefly Cottage at the Cape, HOT TUB, E.V. community beach, Commissioning Week
Exterior
Firefly Cottage at the Cape, HOT TUB, E.V. community beach, Commissioning Week
10.0 out of 10, Exceptional, (57)
"My wife and I stayed here for a weekend and everthing was perfect. The house looks professionally decorated and sits in a very quiet and safe neighbohhod that was fun to walk for miles. As night falls, the enchanting lights in the backyard transform the space into a serene oasis, inviting you to unwind under the stars. The addition of a hot tub and corn hole adds a playful touch, perfect for relaxation and entertainment. Our stay was nothing short of perfection. Pat and Ken were great host and...
Firefly Cottage at the Cape, HOT TUB, E.V. community beach, Commissioning Week
Charming Cottage with Hot Tub 1 Block from the Bay
Property grounds
Charming Cottage with Hot Tub 1 Block from the Bay
10.0 out of 10, Exceptional, (6)
"Was a super comfortable spot my 5 friends and I. Super comfy couches and beds, nice TV, well appointed kitchen. Took a nice walk down to the water in the am. Would stay again!"
The price is £460
includes taxes & fees
5 May - 6 May
Charming Cottage with Hot Tub 1 Block from the Bay
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Fridge, microwave, oven, stovetop
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
10.0 out of 10, Exceptional, (78)
"A wonderfully located cottage, walking distance to quant breakfast eaterys and upscale restaurants. The sunroom was wonderful. Even tho it was still chilly outside, we did enjoy the upstairs deck and even had some wine poolside. Def recommend The Chart House Prime, just a quick walk to a restaurant with a superb wine selection and 5 Star food. Host was quick to respond to questions and very amenable to any issue we may have had. We absolutely will stay here again!"
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Cozy place close to the city dock
Beach
Cozy place close to the city dock
10.0 out of 10, Exceptional, (52)
"We were in town for a family wedding, and we also able to enjoy the atmosphere of downtown Annapolis."
Cozy place close to the city dock
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
Fridge, microwave, oven, stovetop
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
10.0 out of 10, Exceptional, (30)
"Great place to recharge for a few days as a family! Beautiful and peaceful in the fall — though my kids are ready to come back and use the pool in warmer weather!!!"
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
3 Story Stunner in Murray Hill <1 mile from USNA!
Terrace/patio
3 Story Stunner in Murray Hill <1 mile from USNA!
10.0 out of 10, Exceptional, (13)
"The location and the house were perfect. Spacious and beautiful!"
The price is £687
includes taxes & fees
6 May - 7 May
3 Story Stunner in Murray Hill <1 mile from USNA!
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Sun-loungers, beach towels
Secluded Waterfront Cottage on 200 acre farm near Queenstown
10.0 out of 10, Exceptional, (89)
"Lovely visit. I have a 1 and 3 year old. They loved the water and meeting the llama. The room set up is confusing in the listing. Its 3 bedrooms with 2person beds and a forth bedroom w a 1person bed."
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Great location, free parking
Fridge, microwave, oven, stovetop
Great location, free parking
10.0 out of 10, Exceptional, (24)
"The house is in a great location near the water and close to downtown Annapolis. The house itself was perfect for our group and had everything we needed. The owner, Gibson, was very helpful and communicative and if this house was ever available again would definitely stay there."
Great location, free parking
7 mins away from Downtown Annapolis
Property grounds
7 mins away from Downtown Annapolis
10.0 out of 10, Exceptional, (5)
"The home was very clean and beautifully set up. The property managers were very helpful and communicative. they even had complimentary snack, beverages, and even a hand written note with a wine bottle. Bathrooms were clean and stocked with everything incase you forgot something at home. Everyone enjoyed the home, we were planning our next visit before we even left!"
7 mins away from Downtown Annapolis
Relaxing Waterfront Cottage Near St Michaels, Maryland
Exterior
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, (194)
"Lovely setting, comfy home. Planning on staying there again."
Relaxing Waterfront Cottage Near St Michaels, Maryland
Charming Annapolis WaterVIEW Home
Property grounds
Charming Annapolis WaterVIEW Home
9.8 out of 10, Exceptional, (41)
"We were friends gathering for a visit to relax and catch up and the house was perfect for that! It was very comfortable, in a quiet neighborhood, but close to enjoy going to local restaurants and shopping. We loved the large windows that looked out over the Bay! The decor was unique interesting touches."
The price is £551
includes taxes & fees
8 May - 9 May
Charming Annapolis WaterVIEW Home
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Fridge, microwave, oven, stovetop
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, (25)
"My family and I enjoyed our stay at the Carpenter Alley Cottage in Saint Michaels! The location was perfect -- walking distance from everything! Appreciated that there was a ground floor bedroom for my parents so they didn't have to climb the stairs and my daughter loved having her own bunk bed room! I did have a few questions about the cottage and the check-in process and my inquiries were all met with a prompt response. Would love to stay here again! (One note though is that it is a smaller,...
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
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See all available properties in Wittman
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.

Wittman Holiday Rental Travel Info

Number of holiday rentals
21
Popular accommodation
Wittman private holiday homes
Known landmarks
St. Michaels Winery, Tilghman Watermen’s Museum and St. Michaels Museum
International airport
Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)

Other types of properties in Wittman you may be interested in

Relaxing Waterfront Cottage Near St Michaels, Maryland
Exterior
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, (194)
"Lovely setting, comfy home. Planning on staying there again."
Relaxing Waterfront Cottage Near St Michaels, Maryland
Graduate Annapolis
View from property
Graduate Annapolis
4.0 star property
9.4 out of 10, Exceptional, (1070)
"Lovely hotel - everything was perfect except the coffee situation. Rubbish provision in room and then had to pay in the lobby."
The price is £170
includes taxes & fees
2 Jun - 3 Jun
Graduate Annapolis
Historic Inns of Annapolis
Exterior
Historic Inns of Annapolis
3.5 star property
9.0 out of 10, Wonderful, (1607)
"This hotel was a marvelous surprise! It could not be in a better location. Just loved it! I want to stay in all 3 buildings now. "
The price is £165
includes taxes & fees
16 May - 17 May
Historic Inns of Annapolis
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.

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, apart-hotels, 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 £183 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.

How many holiday rentals will I find in Wittman?

With 4 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 Avalon Theatre.

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.

Recent reviews of Wittman properties
Expedia verified reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

5/5 Excellent
Best location ever!
"This hotel was a marvelous surprise! It could not be in a better location. Just loved it! I want to stay in all 3 buildings now. "
A verified traveller stayed at Historic Inns of Annapolis
Posted 2 days ago
Historic Inns of Annapolis