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Wittman Holiday Rentals

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Wittman holiday rentals

A wooden deck with a table and chairs, surrounded by a wooden railing, overlooking a green landscape.

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, (56 reviews)
"very clean home, quiet neighborhood in a great location."
United States
Anthony P.
The price is HK$1,177
HK$2,845 total
includes taxes & fees
23 Nov - 24 Nov
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A two-story house with a red roof, a brick chimney, and a small porch.

2. 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
8.4 out of 10, Very good, (6 reviews)
"The house was clean. It is clear someone lives there full time and vacated the house for our stay. Their food and clothes remained in the property. It did not bother us, but not something we expected. The AC worked well. The owner communicated there were issues before we arrived that they were working to fix and left the number of the contractor in case we experienced issues. We were there the hottest weekend so far this year and did not have any issues. It does look like they are still...
United States
Michele F.
The price is HK$5,648
HK$8,266 total
includes taxes & fees
1 Nov - 2 Nov
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
A dining area with a wooden table and chairs, a kitchen in the background, and a staircase leading to another level.

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (50 reviews)
"Great stay"
United States
Michael V.
The price is HK$678
HK$2,224 total
includes taxes & fees
2 Nov - 3 Nov
Charming Coastal/Country Home w/3 Acres & Sauna!
Three birds perched on a wooden structure by the water.

4. 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, (75 reviews)
"Just what was needed for our weekend stay."
United States
barbara s.
The price is HK$5,484
HK$9,747 total
includes taxes & fees
1 Dec - 2 Dec
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
A living room with a sofa, coffee table, fireplace, and artwork on the wall.

5. 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
10.0 out of 10, Exceptional, (1 review)
"Everything at this location was as shown on the listing and it was very clean. We were very satisfied with all elements of this stay. We were there for a weekend and did not use the place heavily, but it suited our needs. It's a quiet location. They had all the major points covered. The only negative comment I have is that the water out of the tap was smelly. I suggest bringing a couple of bottles of water and not drinking the water out of the taps. This is obviously a well maintained home...
United States
Amelia
The price is HK$1,412
HK$3,425 total
includes taxes & fees
1 Nov - 2 Nov
3-bedroom house in Deale located on Bay many amenities and great views
Living area

6. 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, (25 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is HK$660
HK$2,379 total
includes taxes & fees
1 Nov - 2 Nov
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A two-story house with a backyard swimming pool, surrounded by trees and a well-maintained lawn.

7. 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (44 reviews)
"Fantastic, property, location and positive interaction with owner."
United States
David R.
The price is HK$5,484
HK$9,747 total
includes taxes & fees
1 Dec - 2 Dec
4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
A modern kitchen with a central island, stainless steel appliances, and a window with butterfly decals.

8. The Cozy Crab- Your Charming Haven in Lovely North Beach!

The Cozy Crab- Your Charming Haven in Lovely North Beach!
North Beach
9.6 out of 10, Exceptional, (30 reviews)
"Wonderful place to visit "
United States
James L.
The price is HK$1,138
HK$2,337 total
includes taxes & fees
1 Nov - 2 Nov
The Cozy Crab- Your Charming Haven in Lovely North Beach!
A hot tub with a white deck and railing, surrounded by trees and a house in the background.

9. 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)
"Super clean, well furnished and in a nice quiet neighborhood close to downtown Annapolis. Great place to stay!"
United States
Ryan C.
The price is HK$1,518
HK$3,582 total
includes taxes & fees
3 Nov - 4 Nov
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A deck with a view of a marina, including boats and docks.

10. Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (54 reviews)
"Love This rental. One of our favorites. Small but everything needed. And the view is absolutely wonderful."
United States
Yamilet
The price is HK$706
HK$2,014 total
includes taxes & fees
12 Nov - 13 Nov
Cass-N-Reel Luxury Houseboat
Living area

11. EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places

EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places
Easton
10.0 out of 10, Exceptional, (1 review)
"Fabulous location in town location! It was much larger than we expected - 2 levels. Nice open layout on the main level with 2 BR/BA and a 3rd BR/BA on 2nd floor. Owners are very responsive before and during the trip. We could not connect to the TV, but owner quickly offered assistance. Bathrooms can use some towel racks and shelves. Beds/pillows were comfy! We were very happy with our stay."
United States
Lynn G.
The price is HK$1,765
HK$3,143 total
includes taxes & fees
9 Nov - 10 Nov
EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places
A modern kitchen with a large window, a dishwasher, and a ceiling fan.

12. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
9.8 out of 10, Exceptional, (6 reviews)
"Our family enjoyed staying at the Sunset Cottage. It was clean, had everything we needed for a great trip and the communion was amazing."
United States
Michelle H.
The price is HK$1,569
HK$3,185 total
includes taxes & fees
4 Nov - 5 Nov
Sunset Cottage - West River Access and Views!
A house with a yellow door and a window with a lamp outside.

13. 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 HK$1,138
HK$2,504 total
includes taxes & fees
15 Nov - 16 Nov
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
A modern living room with a sofa, armchair, and coffee table. A kitchen with white cabinets and appliances is visible in the background.

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

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (6 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is HK$1,899
HK$5,036 total
includes taxes & fees
1 Nov - 2 Nov
Family Home on Mayo Peninsula | Deck | Sleeps 10
A deck with outdoor furniture, a red door, and a house with windows.

15. 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
9.0 out of 10, Wonderful, (2 reviews)
"The location was spectacular, the host was communicative, and we had a great time! A beautiful and clean home with everything needed to make a trip a success. One small issue with some needed essentials meant a quick run to the store (TP!) but otherwise a great location, great stay, and would stay again!"
United States
David S.
The price is HK$1,341
HK$2,978 total
includes taxes & fees
5 Nov - 6 Nov
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

16. WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (17 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is HK$2,050
HK$3,637 total
includes taxes & fees
9 Nov - 10 Nov
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
A cozy outdoor seating area with a fire pit, a wooden table, and chairs.

17. 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, (40 reviews)
"This property and host were excellent. Property was as advertised. Lovely, clean, quiet and comfortable. Owner was super responsive and check in and check out was easy. 100% recommend."
United States
Sarah
The price is HK$1,429
HK$3,748 total
includes taxes & fees
16 Nov - 17 Nov
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A kitchen with wooden cabinets, granite countertops, and a dining table set with blue and white dishes.

18. Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is HK$1,765
HK$4,132 total
includes taxes & fees
10 Nov - 11 Nov
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

19. 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 HK$1,647
HK$4,346 total
includes taxes & fees
10 Nov - 11 Nov
Annapolis Retreat - 7 mins from downtown Annapolis!
A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

20. Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.6 out of 10, Exceptional, (14 reviews)
"This is a cute place. Well stocked nicely renovated kitchen. Having coffee and a bottle of wine was a definite plus. "
United States
Diane D.
The price is HK$1,640
HK$4,150 total
includes taxes & fees
4 Nov - 5 Nov
Renovated Bungalow | Walk to Beach | Dog-Friendly
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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Our stay was as always, exceptional. Spotless room, accommodating and friendly staff, great valet parking, very comfortable room."
Thomas 2-night trip
Posted 5 hours ago
Historic Inns of Annapolis

Find out more about Wittman

Search for holiday rentals in Wittman on Expedia! You can easily find your home rentals, villas, holiday apartments in Wittman using one of the methods below:

  • View our selection of featured holiday rentals in Wittman
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  • Enter your travel dates to view the best deals on holiday rentals in Wittman while they last

Look no further and take a look at our great range of rental properties in Wittman!

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?

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: This holiday home rental outside of Wittman is located near the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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.