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Wittman Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Wittman vacation rentals

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

1. 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 CA $129
CA $416 total
includes taxes & fees
Oct 18 - Oct 19
Charming Coastal/Country Home w/3 Acres & Sauna!
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

2. 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)
"Our host Adam was wonderful and very communicative. We love the house and the location was just great. It was close to everything and had water views. We will certainly come back again."
United States
Rebecca B.
The price is CA $136
CA $426 total
includes taxes & fees
Oct 20 - Oct 21
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A modern kitchen with a central island, stainless steel appliances, and a window with butterfly decals.

3. 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 CA $169
CA $411 total
includes taxes & fees
Oct 17 - Oct 18
The Cozy Crab- Your Charming Haven in Lovely North Beach!
A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

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, (24 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is CA $137
CA $479 total
includes taxes & fees
Oct 20 - Oct 21
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A living room with two grey sofas, a coffee table, and a ceiling fan.

5. Cambridge Apt in Walkable Neighborhood

Cambridge Apt in Walkable Neighborhood
3.0 star property
Cambridge
10.0 out of 10, Exceptional, (1 review)
"This apt was built in the 50’s, or back when fewer outlets were needed, and it has window air conditioners. It was just what we were looking for as we visited the ste for family reunions"
United States
LOIS
The price is CA $135
CA $459 total
includes taxes & fees
Oct 17 - Oct 18
Cambridge Apt in Walkable Neighborhood
A living room with two grey sofas, a coffee table, and a ceiling fan.

6. Cambridge Apt in Walkable Neighborhood

Cambridge Apt in Walkable Neighborhood
Cambridge
8.0 out of 10, Very good, (4 reviews)
"great location."
United States
Anonymous traveller
The price is CA $94
CA $471 total
includes taxes & fees
Oct 17 - Oct 18
Cambridge Apt in Walkable Neighborhood
An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

7. 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)
"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 CA $214
CA $663 total
includes taxes & fees
Nov 9 - Nov 10
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A living room with a sofa, coffee table, fireplace, and artwork on the wall.

8. 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 CA $256
CA $621 total
includes taxes & fees
Oct 18 - Oct 19
3-bedroom house in Deale located on Bay many amenities and great views
A deck with outdoor furniture, a red door, and a house with windows.

9. 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 CA $243
CA $540 total
includes taxes & fees
Oct 21 - Oct 22
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
A modern kitchen with a large window, a dishwasher, and a ceiling fan.

10. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 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 CA $349
CA $719 total
includes taxes & fees
Nov 10 - Nov 11
Sunset Cottage - West River Access and Views!
A beach with chairs and a pier in the background.

11. 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 CA $339
CA $766 total
includes taxes & fees
Oct 19 - Oct 20
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Pool

12. Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views
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 CA $205
CA $652 total
includes taxes & fees
Oct 27 - Oct 28
Family Beach House: Spacious Deck, Grill & Views
A bunk bed with a wooden frame, white bedding, and a blue pillow with a floral design.

13. Rose Haven Coastal Cottage

Rose Haven Coastal Cottage
North Beach
10.0 out of 10, Exceptional, (2 reviews)
"We had a great stay at this home in North Beach, MD! The house was clean, comfortable, and conveniently located near The Inn at Herrington Harbour, making it a great choice for our visit. Everything worked well for our stay, and we appreciated having a nice place to relax. We would happily recommend this property to anyone looking for a comfortable and convenient place to stay in the area!"
United States
Jeremy P.
The price is CA $320
CA $616 total
includes taxes & fees
Oct 18 - Oct 19
Rose Haven Coastal Cottage
A waterfront town with historic buildings, a dock with boats, and a prominent white dome structure in the background.

14. 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 CA $320
CA $788 total
includes taxes & fees
Nov 1 - Nov 2
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
A two-story house with a red roof, a brick chimney, and a small porch.

15. 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 CA $1,024
CA $1,498 total
includes taxes & fees
Oct 18 - Oct 19
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
A modern living room with a sofa, armchair, and coffee table. A kitchen with white cabinets and appliances is visible in the background.

16. 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 CA $376
CA $1,048 total
includes taxes & fees
Oct 21 - Oct 22
Family Home on Mayo Peninsula | Deck | Sleeps 10
A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

17. 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 CA $316
CA $853 total
includes taxes & fees
Nov 3 - Nov 4
Annapolis Retreat - 7 mins from downtown Annapolis!
A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

18. 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, (16 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is CA $391
CA $783 total
includes taxes & fees
Oct 19 - Oct 20
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
A modern kitchen with white cabinets, a stainless steel stove, a microwave, and a sink.

19. Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (40 reviews)
"Wonderful place to stay."
United States
Sharon D.
The price is CA $220
CA $362 total
includes taxes & fees
Oct 18 - Oct 19
Sailwinds Loft at Cambridge Creek
Three birds perched on a wooden structure by the water.

20. 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 CA $1,067
CA $1,880 total
includes taxes & fees
Oct 18 - Oct 19
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
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

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"Perfect place to stay! Classy. Clean comfortable amazing staff"
Nila 2-night trip
Posted 13 hours ago
Annapolis Waterfront Hotel, Autograph Collection

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, cottages, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Wittman vacation rentals we have selected for you start as low as CA $435 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 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.