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Wittman Holiday Rentals

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Our top choices for Wittman holiday rentals

1. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (55 reviews)
"We had a wonderful stay. The house was perfect and Adam stayed in contact constantly in case we needed anything. But our stay went smoothly and we had everything we needed."
United States
Dawn G.
The price is NZ$539
includes taxes & fees
16 Sept - 17 Sept
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

2. Cass-Away Luxury Houseboat

Cass-Away Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (107 reviews)
"Wonderful stay. House boat was amazing and hosts helpful and responsive! "
United States
Jamie L.
The price is NZ$526
includes taxes & fees
25 Sept - 26 Sept
Cass-Away Luxury Houseboat

3. Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (47 reviews)
"Great location, house was very clean, ample space and Adam was super communicative. Will definitely stay again!"
United States
Michelle P.
The price is NZ$551
includes taxes & fees
17 Sept - 18 Sept
Charming Coastal/Country Home w/3 Acres & Sauna!

4. Beachside Oasis with Beach Passes & King Suite by A Haven Away

Beachside Oasis with Beach Passes & King Suite by A Haven Away
North Beach
10.0 out of 10, Exceptional, (22 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is NZ$509
includes taxes & fees
8 Sept - 9 Sept
Beachside Oasis with Beach Passes & King Suite by A Haven Away

5. Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Deale
8.0 out of 10, Very good, (13 reviews)
"The rental was near our relatives in a quiet community. Neighbors were friendly. The size was perfect for me and my brother while we were in for a funeral (Arlington National). All the comforts of home! I'll definitely look to stay here again."
United States
Maude H.
The price is NZ$549
includes taxes & fees
10 Sept - 11 Sept
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

6. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Shady Side
10.0 out of 10, Exceptional, (1 review)
"Jut as described. Easy in easy out. Great for a few days with the family."
United States
Joshua T.
The price is NZ$663
includes taxes & fees
6 Oct - 7 Oct
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

7. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.6 out of 10, Exceptional, (19 reviews)
"The perfect off-season get-away! "
United States
Pamela B.
The price is NZ$774
includes taxes & fees
9 Sept - 10 Sept
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

8. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (37 reviews)
"We enjoyed our stay in North Beach at this lovely residence. It was spacious, clean, nicely furnished and only a few minutes walk to the bay. The beds were so comfortable too!!"
United States
Penny N.
The price is NZ$768
includes taxes & fees
15 Sept - 16 Sept
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

9. Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (16 reviews)
"This was a lovely find and had more amenities than the pictures provided with seating for 8, an air fryer, and a Keurig. There was a full kitchen, so cooking was easy. The king bed was very comfortable. It is near the outlet malls and is in a great location. The owner is very nice and accommodating. "
United States
Robin
The price is NZ$714
includes taxes & fees
8 Sept - 9 Sept
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

10. Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Chesapeak beach
9.2 out of 10, Wonderful, (7 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is NZ$775
includes taxes & fees
8 Sept - 9 Sept
Beach Front, Bay View, Fishing, chesapeake,Family Getaway

11. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 reviews)
"Lovely place and neighborhood! "
United States
Marci M.
The price is NZ$969
includes taxes & fees
9 Sept - 10 Sept
Sunset Cottage - West River Access and Views!

12. Family Home on Mayo Peninsula | Deck | Sleeps 10

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (5 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is NZ$1,188
includes taxes & fees
8 Sept - 9 Sept
Family Home on Mayo Peninsula | Deck | Sleeps 10

13. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
Stevensville
6.8 out of 10, (3 reviews)
"The place was very clean and Host was ok the shopping was six miles away, not in walking distance, we had no pets on this trip."
United States
Anonymous traveller
The price is NZ$1,743
includes taxes & fees
9 Sept - 10 Sept
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

14. 3-bedroom house in Deale located on Bay many amenities and great views

3-bedroom house in Deale located on Bay many amenities and great views
Deale
The price is NZ$869
includes taxes & fees
6 Oct - 7 Oct
3-bedroom house in Deale located on Bay many amenities and great views

15. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (74 reviews)
"Just what was needed for our weekend stay."
United States
barbara s.
The price is NZ$2,173
includes taxes & fees
8 Sept - 9 Sept
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

16. Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (77 reviews)
"Our family had a wonderful stay at your beautiful home! The views are to die for! House was very clean with all equipment and kitchen appliances all available! Very happy with our stay! "
United States
Whitney M.
The price is NZ$1,299
includes taxes & fees
16 Sept - 17 Sept
Charming Annapolis WaterVIEW Home

17. Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (39 reviews)
"Wonderful place to stay."
United States
Sharon D.
The price is NZ$433
includes taxes & fees
8 Sept - 9 Sept
Sailwinds Loft at Cambridge Creek

18. Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is NZ$996
includes taxes & fees
15 Sept - 16 Sept
Annapolis Retreat - 7 mins from downtown Annapolis!

19. Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (43 reviews)
"Fantastic, property, location and positive interaction with owner."
United States
David R.
The price is NZ$2,278
includes taxes & fees
8 Sept - 9 Sept
Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

20. The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Downtown Cambridge
9.8 out of 10, Exceptional, (13 reviews)
"Great stay! Gorgeous apartment!"
United States
Kristen S.
The price is NZ$627
includes taxes & fees
8 Sept - 9 Sept
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Wittman holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Wittman. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Wittman. Seeing all the best attractions is bound to make you fall in love with Wittman. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Wittman short-term rentals, that won’t be hard to do.

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?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: This holiday home rental outside of Wittman offers a balcony, a garden and a BBQ 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 Northern Chesapeake Bay. 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.