Skip to Main Content.
Download the app button
Download the app button with download icon
Get the app
United States
Trip Boards
List your property
Help
My trips
Sign in
Vrbo just got better
Earn rewards across our family of brands with One Key™
Sign in
Sign in as an owner
Learn about One Key
Feedback
Going to
Going to
Dates
Dates
Travelers
Adults
Adults
Decrease the number of adults
Increase the number of adults
Children
Ages 0 to 17
Decrease the number of children
Increase the number of children
I am traveling with pets
If checked, only properties that allow pets will be shown
Done
Search
Filters
Popular
Price
Rooms & spaces
Sort by recommended
300+ properties
How our sort order works
Opens in a new window
Search results showing properties in US-50, Annapolis, MD, USA
Google map showing 500 properties
Photo gallery for Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Image of Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Show previous image for Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Show next image for Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Premier Host
Cottage · 6.66 mi from address
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Sleeps 11 · 3 bedrooms · 2 bathrooms
10/10
Exceptional
(186 reviews)
10 out of 10 Exceptional (186 reviews)
The price is $309
$309
avg per night
avg per night
More information about Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA, opens in a new tab
Photo gallery for Fox Hollow House- The perfect Annapolis Getaway
Living area
Show previous image for Fox Hollow House- The perfect Annapolis Getaway
Show next image for Fox Hollow House- The perfect Annapolis Getaway
Premier Host
House · 1.78 mi from address
Fox Hollow House- The perfect Annapolis Getaway
Sleeps 8 · 4 bedrooms · 3 bathrooms
The price is $441
$441
avg per night
avg per night
More information about Fox Hollow House- The perfect Annapolis Getaway, opens in a new tab
Photo gallery for Serene Waterfront Apartment on Kent Island
Property grounds
Show previous image for Serene Waterfront Apartment on Kent Island
Show next image for Serene Waterfront Apartment on Kent Island
Apartment · 9.39 mi from address
Serene Waterfront Apartment on Kent Island
Sleeps 2 · 1 bedroom · 1 bathroom
10/10
Exceptional
(71 reviews)
10 out of 10 Exceptional (71 reviews)
The price is $200
$200
avg per night
avg per night
More information about Serene Waterfront Apartment on Kent Island, opens in a new tab
House · 4.62 mi from address
Brand New Luxury Waterfront Home
Sleeps 10 · 6 bedrooms · 6 bathrooms
10/10
Exceptional
(11 reviews)
10 out of 10 Exceptional (11 reviews)
The price is $1,100
$1,100
avg per night
avg per night
More information about Brand New Luxury Waterfront Home, opens in a new tab
House · 7.07 mi from address
Serene, riverfront home with deck, balcony, kitchen & fireplace - dog-friendly
Sleeps 6 · 3 bedrooms · 2+ bathrooms
10/10
Exceptional
(2 reviews)
10 out of 10 Exceptional (2 reviews)
The price is $401
$401
avg per night
avg per night
More information about Serene, riverfront home with deck, balcony, kitchen & fireplace - dog-friendly, opens in a new tab
House · 0.39 mi from address
Charming 4BR 2BA w/ outdoor patio & fire pit! 5 min walk to Navy Stadium and DT
Sleeps 9 · 4 bedrooms · 2 bathrooms
10/10
Exceptional
(14 reviews)
10 out of 10 Exceptional (14 reviews)
The price is $420
$420
avg per night
avg per night
More information about Charming 4BR 2BA w/ outdoor patio & fire pit! 5 min walk to Navy Stadium and DT, opens in a new tab
House · 7.28 mi from address
Searenity Stays, a Cozy Home
Sleeps 6 · 3 bedrooms · 2 bathrooms
10/10
Exceptional
(16 reviews)
10 out of 10 Exceptional (16 reviews)
The price is $249
$249
avg per night
avg per night
More information about Searenity Stays, a Cozy Home, opens in a new tab
House · 2.56 mi from address
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Sleeps 5 · 2 bedrooms · 2 bathrooms
10/10
Exceptional
(78 reviews)
10 out of 10 Exceptional (78 reviews)
The price is $558
$558
avg per night
avg per night
More information about 421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!, opens in a new tab
Apartment · 2.5 mi from address
Well-appointed 1 bedroom, 1 bath in Annapolis / Eastport
Sleeps 4 · 1 bedroom · 1 bathroom
10/10
Exceptional
(38 reviews)
10 out of 10 Exceptional (38 reviews)
The price is $225
$225
avg per night
avg per night
More information about Well-appointed 1 bedroom, 1 bath in Annapolis / Eastport, opens in a new tab
House · 2.3 mi from address
“Athens of America,” Annapolis Apartment One B
Sleeps 4 · 1 bedroom · 1 bathroom
9.4/10
Exceptional
(11 reviews)
9.4 out of 10 Exceptional (11 reviews)
The price is $182
$182
avg per night
avg per night
More information about “Athens of America,” Annapolis Apartment One B, opens in a new tab
House · 1.92 mi from address
Walk to waterfront & USNA with Parking at Historic Wisteria
Sleeps 8 · 4 bedrooms · 4 bathrooms
9.8/10
Exceptional
(46 reviews)
9.8 out of 10 Exceptional (46 reviews)
The price is $424
$424
avg per night
avg per night
More information about Walk to waterfront & USNA with Parking at Historic Wisteria, opens in a new tab
House · 2.8 mi from address
Steps from the water, Easy parking and private backyard patio
Sleeps 7 · 2 bedrooms · 1+ bathroom
10/10
Exceptional
(27 reviews)
10 out of 10 Exceptional (27 reviews)
The price is $353
$353
avg per night
avg per night
More information about Steps from the water, Easy parking and private backyard patio, opens in a new tab
House · 5.92 mi from address
Little Magothy Riverfront Home With Pool
Sleeps 8 · 3 bedrooms · 2 bathrooms
10/10
Exceptional
(42 reviews)
10 out of 10 Exceptional (42 reviews)
The price is $433
$433
avg per night
avg per night
More information about Little Magothy Riverfront Home With Pool, opens in a new tab
House · 6.28 mi from address
Coastal Edgewater Home w/ Private Hot Tub!
Sleeps 9 · 5 bedrooms · 2 bathrooms
8.8/10
Excellent
(8 reviews)
8.8 out of 10 Excellent (8 reviews)
The price is $347
$347
avg per night
avg per night
More information about Coastal Edgewater Home w/ Private Hot Tub!, opens in a new tab
House · 2.03 mi from address
PERFECT LOCATION in the heart of history
Sleeps 8 · 3 bedrooms · 2+ bathrooms
10/10
Exceptional
(177 reviews)
10 out of 10 Exceptional (177 reviews)
The price is $374
$374
avg per night
avg per night
More information about PERFECT LOCATION in the heart of history, opens in a new tab
House · 2.36 mi from address
Upscale home with parking for 4 cars in driveway. Walk to downtown.
Sleeps 10 · 4 bedrooms · 3+ bathrooms
10/10
Exceptional
(139 reviews)
10 out of 10 Exceptional (139 reviews)
The price is $435
$435
avg per night
avg per night
More information about Upscale home with parking for 4 cars in driveway. Walk to downtown., opens in a new tab
House · 1.95 mi from address
Renovated Historic Home located downtown with parking - Walk everywhere !
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.8/10
Exceptional
(232 reviews)
9.8 out of 10 Exceptional (232 reviews)
The price is $295
$295
avg per night
avg per night
More information about Renovated Historic Home located downtown with parking - Walk everywhere !, opens in a new tab
Apartment · 7.68 mi from address
National Historic home w/ Serene & Quiet Setting
Sleeps 4 · 2 bedrooms · 1 bathroom
9.8/10
Exceptional
(36 reviews)
9.8 out of 10 Exceptional (36 reviews)
The price is $184
$184
avg per night
avg per night
More information about National Historic home w/ Serene & Quiet Setting, opens in a new tab
Tell us how we can improve our site
Share feedback