Default HTG hotel image

Wittman Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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!

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.
$240 nightly
The price is $258
Sep 29 - Sep 30
Total with taxes and fees
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A lighthouse with a white exterior, a balcony, and a metal roof.

2. 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.
$240 nightly
The price is $258
Sep 29 - Sep 30
Total with taxes and fees
Charming Coastal/Country Home w/3 Acres & Sauna!
A modern exterior with a black door, a metal staircase, and a lantern.

3. 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.
Cass-Away Luxury Houseboat
A modern kitchen with dark cabinets, a white countertop, and a large window.

4. Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (51 reviews)
"Had a great time, great property and great location."
United States
Danny B.
$235 nightly
The price is $260
Oct 8 - Oct 9
Total with taxes and fees
Cass-N-Reel Luxury Houseboat
An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

5. 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.
$337 nightly
The price is $372
Sep 29 - Sep 30
Total with taxes and fees
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

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, (24 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
$294 nightly
The price is $326
Oct 4 - Oct 5
Total with taxes and fees
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A house with a yellow door and a window with a lamp outside.

7. 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.
$276 nightly
The price is $314
Oct 8 - Oct 9
Total with taxes and fees
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
A beach with chairs and a pier in the background.

8. 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)
$384 nightly
The price is $437
Sep 29 - Sep 30
Total with taxes and fees
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A living room with a sofa, coffee table, fireplace, and artwork on the wall.

9. 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
$413 nightly
The price is $471
Oct 27 - Oct 28
Total with taxes and fees
3-bedroom house in Deale located on Bay many amenities and great views
A bedroom with a bed, a chair, a bedside table with a lamp, a picture on the wall, and a window with curtains.

10. Your Annapolis Waterfront retreat for a weekend or any-day getaway!

Your Annapolis Waterfront retreat for a weekend or any-day getaway!
West Annapolis
10.0 out of 10, Exceptional, (94 reviews)
"Lovely location and Jim was very helpful all the way around!"
United States
Jill R.
$266 nightly
The price is $296
Oct 5 - Oct 6
Total with taxes and fees
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
A dining area with a wooden table and chairs, beige curtains, and a ceiling light fixture.

11. 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
$452 nightly
The price is $479
Sep 29 - Sep 30
Total with taxes and fees
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
A deck with outdoor furniture, a red door, and a house with windows.

12. 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.
$314 nightly
The price is $358
Oct 26 - Oct 27
Total with taxes and fees
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
A modern kitchen with white cabinets, a stainless steel stove, a microwave, and a sink.

13. 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.
$230 nightly
The price is $244
Sep 29 - Sep 30
Total with taxes and fees
Sailwinds Loft at Cambridge Creek
A market with a covered seating area and a sign indicating parking for curbside pickup.

14. Rose Haven Coastal Cottage

Rose Haven Coastal Cottage
North Beach
"Great place to stay! Location was nice and close to water views. House was charming and CLEAN. Owners went above and beyond to make the stay welcoming and convenient. Price was reasonable until additional Vrbo fees were added."
United States
Sharon t.
$370 nightly
The price is $422
Sep 29 - Sep 30
Total with taxes and fees
Rose Haven Coastal Cottage
A covered outdoor area with a view of the water, a wicker chair, a table with a plant, and a sofa with pillows.

15. Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (78 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.
$570 nightly
The price is $650
Sep 29 - Sep 30
Total with taxes and fees
Charming Annapolis WaterVIEW Home
A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

16. 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, (14 reviews)
"Great stay! Gorgeous apartment!"
United States
Kristen S.
$310 nightly
The price is $329
Sep 29 - Sep 30
Total with taxes and fees
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
A two-story house with a red roof, a brick chimney, and a small porch.

17. 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
8.0 out of 10, Very good, (5 reviews)
"We arrived and the air conditioning was broken.The owner did not inform us but installed portable AC’s running vents out of doors that would not close or lock. The old AC unit was installed incorrectly &BR below flooded by 12 am. contacted owner and then was told not to run AC & we would be refunded. Covered mattresses that were being soaked, cleaned up flood, washed all bedding. Owner said trying to find us another rental but there were none & I had service dog. If we moved we would miss...
United States
Suzanne R.
$935 nightly
The price is $991
Sep 29 - Sep 30
Total with taxes and fees
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

18. 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.
$409 nightly
The price is $426
Oct 27 - Oct 28
Total with taxes and fees
Family Beach House: Spacious Deck, Grill & Views
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)
$478 nightly
The price is $545
Oct 20 - Oct 21
Total with taxes and fees
Annapolis Retreat - 7 mins from downtown Annapolis!
A modern kitchen with a large window, a dishwasher, and a ceiling fan.

20. 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.
$531 nightly
The price is $535
Oct 6 - Oct 7
Total with taxes and fees
Sunset Cottage - West River Access and Views!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Wittman Hotel Reviews

Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG

8/10 Good
"The property was very clean and staff was friendly."
Darren 1-night trip
Posted 8 hours ago
Candlewood Suites Annapolis by IHG

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 $258 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.