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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 spacious living room with a ceiling fan, a staircase, and a view of the outdoors.

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

Stevensville

Anthony P.

$324 nightly

Nov 23 - Nov 24

Total with taxes and fees

A dining area with a wooden table and chairs, a kitchen in the background, and a staircase leading to another level.

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

Stevensville

Michael V.

$284 nightly

Nov 9 - Nov 10

Total with taxes and fees

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

3. Cass-N-Reel Luxury Houseboat

Grasonville

Yamilet

$233 nightly

Nov 12 - Nov 13

Total with taxes and fees

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.

$284 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

North Beach

Johanna S.

$292 nightly

Dec 1 - Dec 2

Total with taxes and fees

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.

$294 nightly

Nov 9 - Nov 10

Total with taxes and fees

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

$383 nightly

Nov 13 - Nov 14

Total with taxes and fees

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.

$315 nightly

Nov 9 - Nov 10

Total with taxes and fees

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.

$433 nightly

Dec 1 - Dec 2

Total with taxes and fees

A hot tub with a white deck and railing, surrounded by trees and a house in the background.

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

Arundel on the Bay

Ryan C.

$404 nightly

Nov 9 - Nov 10

Total with taxes and fees

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

Easton

Lynn G.

$379 nightly

Nov 10 - Nov 11

Total with taxes and fees

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

12. Cambridge Apt in Walkable Neighborhood

Cambridge

LOIS

$291 nightly

Nov 6 - Nov 7

Total with taxes and fees

A cozy outdoor seating area with a fire pit, a wooden table, and chairs.

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

North Beach

Sarah

$423 nightly

Nov 16 - Nov 17

Total with taxes and fees

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

14. Family Friendly Cozy 3 Bedroom Duplex

Grasonville

$293 nightly

Nov 6 - Nov 7

Total with taxes and fees

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.

$489 nightly

Nov 30 - Dec 1

Total with taxes and fees

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.

$447 nightly

Nov 11 - Nov 12

Total with taxes and fees

17. Cambridge Apt in Walkable Neighborhood

Cambridge

Anonymous traveler

$282 nightly

Nov 6 - Nov 7

Total with taxes and fees

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.

$614 nightly

Nov 11 - Nov 12

Total with taxes and fees

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

$945 nightly

Nov 8 - Nov 9

Total with taxes and fees

A kitchen with wooden cabinets, granite countertops, and a dining table set with blue and white dishes.

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.

$440 nightly

Nov 8 - Nov 9

Total with taxes and fees

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Find vacation rentals that suit your style

Top Wittman Hotel Reviews

A marina with boats docked at wooden piers, surrounded by greenery.

Knapps Narrows Marina & Inn

Sherwood

10/10 Excellent

Stan and Joan

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

A two-story building with a covered entrance and an American flag.

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 wooden sauna with a door, a wooden bench, and a bottle of water on the bench.

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 balcony with a view of a body of water, a row of buildings, and a chair.

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 multi-story hotel with a central entrance, a landscaped garden with flowers, and a metal sculpture.

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 hotel room with a sofa, armchairs, a TV, a bed, and a large window.

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

Find out more about Wittman

Everything you need to know about Wittman vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Wittman vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Wittman vacation 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 low season months. For more hustle and bustle, you may prefer to visit Wittman in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $257 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Wittman rentals

At Expedia, we put the best Wittman vacation 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 vacation.

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 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

Bundle & Save

OneKeyCash

Upfront pricing

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

Find out more about Wittman

Everything you need to know about Wittman vacation rentals

Wittman vacation rentals: An excellent choice for every season

How to find incredible deals on Wittman rentals

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