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Wittman Vacation Rentals

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Dates

November 2026

December 2026

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Our top choices for Wittman vacation rentals

A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

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

Stevensville

Anthony P.

AED 1,340 total

includes taxes & fees

23 Nov - 24 Nov

A lighthouse with a white exterior, a balcony, and a metal roof.

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

Stevensville

Michael V.

AED 1,124 total

includes taxes & fees

10 Nov - 11 Nov

A deck with a view of a marina, including boats and docks.

3. Cass-N-Reel Luxury Houseboat

Grasonville

Yamilet

AED 947 total

includes taxes & fees

12 Nov - 13 Nov

A house with a yellow door and a window with a lamp outside.

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

Deale

Maude H.

AED 1,188 total

includes taxes & fees

15 Nov - 16 Nov

A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

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

North Beach

Johanna S.

AED 1,155 total

includes taxes & fees

1 Dec - 2 Dec

A modern kitchen with a central island, stainless steel appliances, and a window with butterfly decals.

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

North Beach

James L.

AED 1,145 total

includes taxes & fees

9 Nov - 10 Nov

A living room with a sofa, coffee table, fireplace, and artwork on the wall.

7. 3-bedroom house in Deale located on Bay many amenities and great views

Deale

"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...

Amelia

AED 1,604 total

includes taxes & fees

13 Nov - 14 Nov

A deck with outdoor furniture, a red door, and a house with windows.

8. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

Shady Side

David S.

AED 1,319 total

includes taxes & fees

9 Nov - 10 Nov

A modern kitchen with a large window, a dishwasher, and a ceiling fan.

9. Sunset Cottage - West River Access and Views!

Shady Side

Michelle H.

AED 1,608 total

includes taxes & fees

1 Dec - 2 Dec

A beach with chairs and a pier in the background.

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

Arundel on the Bay

Ryan C.

AED 1,692 total

includes taxes & fees

9 Nov - 10 Nov

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

Easton

Lynn G.

AED 1,476 total

includes taxes & fees

10 Nov - 11 Nov

A living room with two grey sofas, a coffee table, and a ceiling fan.

12. Cambridge Apt in Walkable Neighborhood

Cambridge

LOIS

AED 1,185 total

includes taxes & fees

6 Nov - 7 Nov

An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

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

North Beach

Sarah

AED 1,678 total

includes taxes & fees

16 Nov - 17 Nov

A kitchen with wooden cabinets, a stove, and a dining table with chairs.

14. Family Friendly Cozy 3 Bedroom Duplex

Grasonville

AED 1,141 total

includes taxes & fees

6 Nov - 7 Nov

A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

15. Annapolis Retreat - 7 mins from downtown Annapolis!

Hillsmere

Paul C.

AED 2,048 total

includes taxes & fees

30 Nov - 1 Dec

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

Cambridge

Jill C.

AED 1,740 total

includes taxes & fees

11 Nov - 12 Nov

17. Cambridge Apt in Walkable Neighborhood

Cambridge

Anonymous traveler

AED 1,146 total

includes taxes & fees

6 Nov - 7 Nov

A modern living room with a sofa, armchair, and coffee table. A kitchen with white cabinets and appliances is visible in the background.

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

Edgewater

Kristin G.

AED 2,571 total

includes taxes & fees

11 Nov - 12 Nov

A two-story house with a red roof, a brick chimney, and a small porch.

19. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

Stevensville

Anonymous traveler

AED 3,679 total

includes taxes & fees

8 Nov - 9 Nov

A waterfront town with historic buildings, a dock with boats, and a prominent white dome structure in the background.

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

Annapolis

"A nice, clean, roomy place at a good price--gotta love that. The walk-out basement apartment was located in a compound of units on a quiet dead-end street. This unit is actually toward the back and I spent a little time searching for it. Once there, access to the key and apartment was no problem.The home was well-stocked with kitchen and bathroom supplies, and bedding. Would definitely stay there again."

Rob L.

AED 1,842 total

includes taxes & fees

8 Nov - 9 Nov

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Find vacation rentals that suit your style

Top Wittman Hotel Reviews

A marina with several boats docked, a building with multiple levels, and a calm water surface reflecting the structures.

Knapps Narrows Marina & Inn

Sherwood

10/10 Excellent

Stan and Joan

Two Adirondack chairs facing a calm body of water with a clear sky above.

Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

10/10 Excellent

The staff is friendly and helpful. The pool is refreshing, and I love the benches overlooking the waters and jetty from which you can view a lot of nature. There is always complimentary coffee and tea and apples available as well as filtered water. The best for me is that the property is on the Cross Island Trail so I can enjoy a walk/run or bike ride (you can rent bikes) to Terrapin Nature Park on the other side of Kent Island. It's also a short walk to a handful of great restaurants. We look...

Christina

A modern lobby with a stone fireplace, a blue patterned rug, a blue sofa with colorful cushions, a brown leather chair, and a round coffee table.

Fairfield Inn & Suites by Marriott Easton

Easton

10/10 Excellent

The Fairfield Inn on US50 has become our go-to mid-range hotel in Easton. We have stayed here several times in recent years, and once again had a great experience during this Christmas stay. The facilities are clean and in good condition. The staff is friendly, welcoming, and accommodating. When I booked our stay this time through a third-party, I got a little confused about room options, and took the only king-bed room that I saw. The manager didnt know I had any concerns, and when the staff...

Richard

A room with a fireplace, a dining area with chairs, a large window with a view of the outside, and a cabinet with bottles.

Inn at Perry Cabin

Downtown St. Michaels

10/10 Excellent

Norm

St Michaels Inn

St. Michaels

10/10 Excellent

Lori

A spacious living room with a fireplace, a sofa, a coffee table, and a staircase leading to another level.

Best Western Plus Easton Inn & Suites

Easton

10/10 Excellent

Everything was good with checkin ,check out, and the room. The only complaint I can voice is with the breakfast service attendant. She was not very warm or inviting, did not speak to guest. She did have everything out and the area clean, but at the end of breakfast time, she removed all plates and bowls first so no one could get anything else to eat. We were late eating on our 3rd morning, but were in time to get our food before she started putting away. But then put chairs on the tables so...

Nancy

A waterfront property with a covered patio, a dock, and a boat.

Wylder Tilghman Island

Tilghman

10/10 Excellent

We had a great time at the Wylder Inn on Tilghman Island (20-21 May). This is a great spot for a quick getaway, and there are many things to do on site and in the area if you want to stay longer. The staff was welcoming and responsive from our arrival to departure when our key was collected from our car so we didn't have to get out in the rain. The Continental Breakfast had a variety of items to start the day right and the fire pits provided a relaxing venue at the end of the day. We look...

Alan

A modern hotel dining area with a long table, four chairs, and three pendant lights.

Hampton Inn Easton

Easton

10/10 Excellent

Anonymous traveler

An indoor swimming pool with lounge chairs and a no diving sign.

Holiday Inn Express Easton by IHG

Easton

10/10 Excellent

Belinda

A patio with outdoor seating, overlooking a marina with boats.

Hilton Garden Inn Kent Island Marina

Grasonville

10/10 Excellent

Kathie

A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.

The Inn at Chesapeake Bay Beach Club

Stevensville

10/10 Excellent

Chuck

A large, two-story barn-style building with a covered front porch and a garage.

Kent Island Resort

Stevensville

10/10 Excellent

I stayed here for a quick overnight and did not utilize many of the amenities however, the staff was incredibly kind overall and with tips on dinner. This place is historic, which is a nice way of saying old but classic. Don’t expect a huge room, the photos portray the room accurately. Some things were a little rickety, but everything was clean. Overall I recommend this if you’re solo or a couple looking for a place as you enjoy the bay.

John

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with stools.

The Oaks Waterfront

Easton

10/10 Excellent

William

A modern kitchen with a large island, bar stools, and a wine rack.

Anchored Inn at Hidden Harbour Marina

Deale

10/10 Excellent

We needed overnight accommodations before heading out for a day of sailing on the bay and Hidden Harbour popped up as the closest venue geographically and we're glad it did. The accommodations are new, with quality and fixtures and bathrooms that you wouldn't mind taking home with you. The price seemed fair and as we watched the full moon rising from our deck we wished that we were spending a week.

Rico

A hotel room with a bed, a desk, a chair, a large window with curtains, a wall-mounted painting, and a bathtub.

Best Western Kent Narrows Inn

Grasonville

10/10 Excellent

Valerie

A Victorian-style building with a prominent tower, a porch with outdoor seating, and a sign indicating it is a bed and breakfast.

Parsonage Inn

Downtown St. Michaels

10/10 Excellent

A large, stately house with a grand entrance, multiple windows, and a symmetrical facade.

The Tidewater Inn

Easton

10/10 Excellent

Maria

A spacious lobby with a staircase, a reception desk, and a dining area.

Quality Inn Grasonville near Kent Island

Grasonville

10/10 Excellent

My wife and have been staying here off and on for a few years now. We have always found it to a lovely place stay . The staff there is especially courteous and helpful whenever a special need arises ! We give special notice of thanks to general manager Amy Patel for her attention to service and her pleasant attitude at all times ! Her caring manner and attention to detail are par excellence ! The cleanliness , breakfast included , location and the inground pool make this a sure bet for any...

Chuck

Frequently Asked Questions

Can I find a vacation rental in Wittman?

Yes, there are vacation rentals near well known sights in Wittman, or you can select a more remote option if you'd like a relaxing place to stay.

What's the top vacation rental in Wittman?

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: Visitors like this Wittman vacation home rental. It is located near the beach and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals will I find in Wittman?

With 3 Expedia vacation rentals, you're sure 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 larger area, you’ll find St. Michaels Winery and St. Michaels Marina.

What’s a vacation rental in Wittman like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Wittman. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can provide a sense of security away from public hotel elevators and busy concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for small groups.

Wittman Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Wittman vacation rentals

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

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

3. Cass-N-Reel Luxury Houseboat

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

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

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

7. 3-bedroom house in Deale located on Bay many amenities and great views

8. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

9. Sunset Cottage - West River Access and Views!

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

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

12. Cambridge Apt in Walkable Neighborhood

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

14. Family Friendly Cozy 3 Bedroom Duplex

15. Annapolis Retreat - 7 mins from downtown Annapolis!

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

17. Cambridge Apt in Walkable Neighborhood

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

19. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

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

Find vacation rentals that suit your style

Top Wittman Hotel Reviews

Knapps Narrows Marina & Inn

10/10 Excellent

Frequently Asked Questions

Can I find a vacation rental in Wittman?

What's the top vacation rental in Wittman?

How many vacation rentals will I find in Wittman?

What’s there to see and do in Wittman?

What’s a vacation rental in Wittman like?

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