Search Vacation Homes in Wittman

Start date: Check-in selected.
To Date
End date: Check-out

  • 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

Next weekend
Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28
In one month
Jan 9 - Jan 11
In two months
Feb 6 - Feb 8

Our top choices for Wittman vacation homes

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

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

Stevensville
9.6 out of 10, Exceptional, (32)
"Very nice house! We had 3 people in our party and didn't want to rent 2 hotel rooms, this is a great way to save money and enjoy time together. "
United States
Pamela
$234 nightly
The price is $248
Dec 11 - Dec 12
Total with taxes and fees
Charming Coastal/Country Home w/3 Acres & Sauna!
Beach nearby
Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes

North Beach
10.0 out of 10, Exceptional, (16)
"We loved our stay! The property was just as advertised and had everything we needed. Quiet area and felt very safe. The owners provided excellent communication as well!"
United States
Jennifer B.
$286 nightly
The price is $315
Dec 10 - Dec 11
Total with taxes and fees
Walk to Beach! King Bed & Free Beach Passes
Marina
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cambridge
9.6 out of 10, Exceptional, (20)
"In town for a family wedding. This worked out perfectly. Would stay there again "
United States
Barbara V.
$339 nightly
The price is $359
Dec 13 - Dec 14
Total with taxes and fees
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Marina
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, (42)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
$227 nightly
The price is $241
Dec 11 - Dec 12
Total with taxes and fees
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Beach nearby, sun loungers, beach towels
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, (31)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
$368 nightly
The price is $407
Dec 10 - Dec 11
Total with taxes and fees
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Interior
Beautiful Waterfront Retreat in Cambridge!

Beautiful Waterfront Retreat in Cambridge!

Cambridge
10.0 out of 10, Exceptional, (49)
"Beautiful place! Loved all the activities, will return in the future! Our family and friends had a blast! Thank you so much!!"
United States
Karen L.
$357 nightly
The price is $378
Dec 14 - Dec 15
Total with taxes and fees
Beautiful Waterfront Retreat in Cambridge!
Exterior
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Shady Side
10.0 out of 10, Exceptional, (4)
"Would stay here again "
United States
Thomas D.
$374 nightly
The price is $426
Dec 10 - Dec 11
Total with taxes and fees
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Marina
Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis

Historic District
10.0 out of 10, Exceptional, (72)
"Great little house easy to walk to West St, Main St & the Yard (USNA). Has parking included which is nice. Great communication we owner. Will stay again. "
United States
Sheldon E.
$288 nightly
The price is $328
Dec 10 - Dec 11
Total with taxes and fees
Cozy 2br home w/ parking in downtown Annapolis
4 bedrooms, desk, iron/ironing board, travel crib
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Homewood
9.8 out of 10, Exceptional, (8)
"This house was perfect for us! We love the ease of getting into town without having to drive and park in a parking garage. I would 10/10 recommend this house!"
United States
Elaina H.
$409 nightly
The price is $466
Dec 10 - Dec 11
Total with taxes and fees
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Pool
Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views

Chesapeake Beach
9.0 out of 10, Wonderful, (6)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
$438 nightly
The price is $462
Jan 8 - Jan 9, 2026
Total with taxes and fees
Family Beach House: Spacious Deck, Grill & Views
Fridge, microwave, oven, stovetop
Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium

Admiral Heights
9.8 out of 10, Exceptional, (7)
"We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!"
United States
Tammy L.
$460 nightly
The price is $520
Dec 15 - Dec 16
Total with taxes and fees
Cute bungalow blocks to Stadium
Smart TV
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, (14)
"Second time staying at this lovely, serene home/property. It’s the perfect getaway if you’re looking to escape into some peace! Highly recommend "
United States
Jill C.
$498 nightly
The price is $528
Dec 11 - Dec 12
Total with taxes and fees
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Property grounds
New! Stylish downtown home w/awesome outdoor area!

New! Stylish downtown home w/awesome outdoor area!

Stevensville
9.8 out of 10, Exceptional, (26)
"The house was spacious, clean, and in a great location. The owners were available, and easy to communicate with."
United States
Marjorie N.
$502 nightly
The price is $532
Dec 25 - Dec 26
Total with taxes and fees
New! Stylish downtown home w/awesome outdoor area!
Fridge, microwave, oven, stovetop
Fisher House: Steps From USNA + Covered Parking!

Fisher House: Steps From USNA + Covered Parking!

Historic District
10.0 out of 10, Exceptional, (13)
"Great house and location. Great communication. We had a great time there!"
United States
Barbara S.
$561 nightly
The price is $602
Dec 10 - Dec 11
Total with taxes and fees
Fisher House: Steps From USNA + Covered Parking!
Exterior
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, (12)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
$395 nightly
The price is $419
Dec 10 - Dec 11
Total with taxes and fees
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
3 bedrooms, iron/ironing board, travel crib, free WiFi
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Prince Frederick
9.6 out of 10, Exceptional, (5)
"We had a short stay after a sporting event in DC, it was a little less than an hour away. Convenient location and a very clean house. Kitchen was well stocked. There was little communication with the owner, which was nice vs a long list of rules, but we would have liked to know any of their local specific favorite spots or more detailed check in/check out. Worked out nicely for our family. "
United States
Carrie K.
$344 nightly
The price is $365
Dec 17 - Dec 18
Total with taxes and fees
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Interior
Historic Row Home with Hot Tub- 1 Block from Gate 1 at USNA!

Historic Row Home with Hot Tub- 1 Block from Gate 1 at USNA!

Historic District
10.0 out of 10, Exceptional, (5)
"Wonderful location. Easy walking to downtown restaurants, shops, city docks and USNA. Enjoyed spending time on front porch and swing.Comfortable beds and home like atmosphere.No need for a vehicle, but if you have one, parking garage is just a few blocks away. "
United States
Katie S.
$617 nightly
The price is $703
Dec 15 - Dec 16
Total with taxes and fees
Historic Row Home with Hot Tub- 1 Block from Gate 1 at USNA!
Interior
Charming Pet-Friendly Stay - Near Bay & Beaches.

Charming Pet-Friendly Stay - Near Bay & Beaches.

Annapolis
10.0 out of 10, Exceptional, (6)
"The property provided the space I needed for my family. It is located in a cute neighborhood. The property was clean and the owner was very responsive to any questions that I had. I really enjoyed staying here."
United States
Kristina
$494 nightly
The price is $563
Dec 15 - Dec 16
Total with taxes and fees
Charming Pet-Friendly Stay - Near Bay & Beaches.
TV, books, offices
Holly Hill Haven - Sleeps 10

Holly Hill Haven - Sleeps 10

Edgewater
10.0 out of 10, Exceptional, (3)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
$494 nightly
The price is $527
Jan 5 - Jan 6, 2026
Total with taxes and fees
Holly Hill Haven - Sleeps 10
Terrace/patio
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
9.8 out of 10, Exceptional, (11)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
$480 nightly
The price is $547
Dec 19 - Dec 20
Total with taxes and fees
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
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

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Great"
stephen 3-night trip
Posted 16 hours ago
DoubleTree by Hilton Hotel Annapolis

Find out more about Wittman

Wittman Vacation Homes information

Number of reviews
363
Accommodation
608 Vacation Homes
Lowest Price
$241
Highest Price
$703

Explore a world of travel with Expedia