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Our top choices for Wittman vacation homes

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
The price is AED 251
AED 912 total
includes taxes & fees
10 Dec - 11 Dec
Charming Coastal/Country Home w/3 Acres & Sauna!

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.
The price is AED 313
AED 1,206 total
includes taxes & fees
10 Dec - 11 Dec
Walk to Beach! King Bed & Free Beach Passes

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.
The price is AED 551
AED 1,320 total
includes taxes & fees
13 Dec - 14 Dec
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

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.
The price is AED 251
AED 912 total
includes taxes & fees
11 Dec - 12 Dec
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

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.
The price is AED 361
AED 1,494 total
includes taxes & fees
10 Dec - 11 Dec
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

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.
The price is AED 595
AED 1,390 total
includes taxes & fees
14 Dec - 15 Dec
Beautiful Waterfront Retreat in Cambridge!

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.
The price is AED 529
AED 1,566 total
includes taxes & fees
10 Dec - 11 Dec
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

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.
The price is AED 488
AED 1,206 total
includes taxes & fees
10 Dec - 11 Dec
Cozy 2br home w/ parking in downtown Annapolis

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.
The price is AED 678
AED 1,710 total
includes taxes & fees
10 Dec - 11 Dec
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

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.
The price is AED 690
AED 1,684 total
includes taxes & fees
8 Jan - 9 January 2026
Family Beach House: Spacious Deck, Grill & Views

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.
The price is AED 536
AED 1,910 total
includes taxes & fees
15 Dec - 16 Dec
Cute bungalow blocks to Stadium

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.
The price is AED 964
AED 1,940 total
includes taxes & fees
11 Dec - 12 Dec
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

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.
The price is AED 900
AED 1,954 total
includes taxes & fees
25 Dec - 26 Dec
New! Stylish downtown home w/awesome outdoor area!

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.
The price is AED 830
AED 2,218 total
includes taxes & fees
10 Dec - 11 Dec
Fisher House: Steps From USNA + Covered Parking!

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.
The price is AED 918
AED 1,538 total
includes taxes & fees
10 Dec - 11 Dec
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

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.
The price is AED 661
AED 1,339 total
includes taxes & fees
17 Dec - 18 Dec
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

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.
The price is AED 496
AED 2,583 total
includes taxes & fees
15 Dec - 16 Dec
Historic Row Home with Hot Tub- 1 Block from Gate 1 at USNA!

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
The price is AED 862
AED 2,067 total
includes taxes & fees
15 Dec - 16 Dec
Charming Pet-Friendly Stay - Near Bay & Beaches.

Holly Hill Haven - Sleeps 10

Edgewater
10.0 out of 10, Exceptional, (3)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is AED 639
AED 1,936 total
includes taxes & fees
5 Jan - 6 January 2026
Holly Hill Haven - Sleeps 10

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.
The price is AED 942
AED 2,050 total
includes taxes & fees
19 Dec - 20 Dec
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.
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Top Wittman Hotel Reviews