We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Annapolis Vacation Rentals

List your property
Owner log in
Where to?
Check in
— / — / —
Check out
— / — / —
Guests
0 rooms, 2+ guests

Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

1 mi
378 rentals in Annapolis.
Sort by:
Tripadvisor Sort
Revenue impacts this sort order. Learn more.
Charming historic home  just steps from Main Street!, vacation rental in Annapolis
Charming historic home  just steps from Main Street!, vacation rental in Annapolis
Charming historic home  just steps from Main Street!, vacation rental in Annapolis

Charming historic home just steps from Main Street!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Gorgeous Annapolis Getaway - Walk Everywhere, Parking & Private Backyard!, vacation rental in Annapolis
Gorgeous Annapolis Getaway - Walk Everywhere, Parking & Private Backyard!, vacation rental in Annapolis
Gorgeous Annapolis Getaway - Walk Everywhere, Parking & Private Backyard!, vacation rental in Annapolis

Gorgeous Annapolis Getaway - Walk Everywhere, Parking & Private Backyard!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Charming Historic Annapolis Home With Two Off-street Parking Places!, vacation rental in Annapolis
Charming Historic Annapolis Home With Two Off-street Parking Places!, vacation rental in Annapolis
Charming Historic Annapolis Home With Two Off-street Parking Places!, vacation rental in Annapolis

Charming Historic Annapolis Home With Two Off-street Parking Places!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Annapolis waterfront "tiny house" in garden setting, vacation rental in Annapolis
Annapolis waterfront "tiny house" in garden setting, vacation rental in Annapolis
Annapolis waterfront "tiny house" in garden setting, vacation rental in Annapolis

Annapolis waterfront "tiny house" in garden setting

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Stunning Waterfront Cottage with Breathtaking Views!, vacation rental in Annapolis
Stunning Waterfront Cottage with Breathtaking Views!, vacation rental in Annapolis
Stunning Waterfront Cottage with Breathtaking Views!, vacation rental in Annapolis

Stunning Waterfront Cottage with Breathtaking Views!

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

The Yellow Cottage on Harness Creek, vacation rental in Annapolis
The Yellow Cottage on Harness Creek, vacation rental in Annapolis
The Yellow Cottage on Harness Creek, vacation rental in Annapolis

The Yellow Cottage on Harness Creek

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

One of a kind renovation in the center of it all - THE BEST LOCATION DOWNTOWN !, vacation rental in Annapolis
One of a kind renovation in the center of it all - THE BEST LOCATION DOWNTOWN !, vacation rental in Annapolis
One of a kind renovation in the center of it all - THE BEST LOCATION DOWNTOWN !, vacation rental in Annapolis

One of a kind renovation in the center of it all - THE BEST LOCATION DOWNTOWN !

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Brand new Renovation in Historic District with 2 parking spots -walk everywhere, vacation rental in Annapolis
Brand new Renovation in Historic District with 2 parking spots -walk everywhere, vacation rental in Annapolis
Brand new Renovation in Historic District with 2 parking spots -walk everywhere, vacation rental in Annapolis

Brand new Renovation in Historic District with 2 parking spots -walk everywhere

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Two Blocks to Town, Underground Parking Garage, vacation rental in Annapolis
Two Blocks to Town, Underground Parking Garage, vacation rental in Annapolis
Two Blocks to Town, Underground Parking Garage, vacation rental in Annapolis

Two Blocks to Town, Underground Parking Garage

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

PERFECT LOCATION in the heart of history, vacation rental in Annapolis
PERFECT LOCATION in the heart of history, vacation rental in Annapolis
PERFECT LOCATION in the heart of history, vacation rental in Annapolis

PERFECT LOCATION in the heart of history

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Save time - get the best Annapolis rentals sent straight to your email!
Waterfront Oasis in Eastport - Walk to Downtown and USNA, vacation rental in Annapolis
Waterfront Oasis in Eastport - Walk to Downtown and USNA, vacation rental in Annapolis
Waterfront Oasis in Eastport - Walk to Downtown and USNA, vacation rental in Annapolis

Waterfront Oasis in Eastport - Walk to Downtown and USNA

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Beautiful Historic Home With Great Location!, vacation rental in Annapolis
Beautiful Historic Home With Great Location!, vacation rental in Annapolis
Beautiful Historic Home With Great Location!, vacation rental in Annapolis

Beautiful Historic Home With Great Location!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Renovated Historic Home located downtown with parking - Walk everywhere !, vacation rental in Annapolis
Renovated Historic Home located downtown with parking - Walk everywhere !, vacation rental in Annapolis
Renovated Historic Home located downtown with parking - Walk everywhere !, vacation rental in Annapolis

Renovated Historic Home located downtown with parking - Walk everywhere !

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Space & Relaxation you Crave ! With plenty of Parking!, vacation rental in Annapolis
Space & Relaxation you Crave ! With plenty of Parking!, vacation rental in Annapolis
Space & Relaxation you Crave ! With plenty of Parking!, vacation rental in Annapolis

Space & Relaxation you Crave ! With plenty of Parking!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Beautiful Waterfront Townhome In Historic Annapolis, vacation rental in Annapolis
Beautiful Waterfront Townhome In Historic Annapolis, vacation rental in Annapolis
Beautiful Waterfront Townhome In Historic Annapolis, vacation rental in Annapolis

Beautiful Waterfront Townhome In Historic Annapolis

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Stunning Home in Historic District, Steps to USNA & Downtown, vacation rental in Annapolis
Stunning Home in Historic District, Steps to USNA & Downtown, vacation rental in Annapolis
Stunning Home in Historic District, Steps to USNA & Downtown, vacation rental in Annapolis

Stunning Home in Historic District, Steps to USNA & Downtown

Rental Home
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Stunning waterfront house - ideal weekend getaway, vacation rental in Annapolis
Stunning waterfront house - ideal weekend getaway, vacation rental in Annapolis
Stunning waterfront house - ideal weekend getaway, vacation rental in Annapolis

Stunning waterfront house - ideal weekend getaway

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Tastefully decorated Eastport Annapolis house with water views, vacation rental in Annapolis
Tastefully decorated Eastport Annapolis house with water views, vacation rental in Annapolis
Tastefully decorated Eastport Annapolis house with water views, vacation rental in Annapolis

Tastefully decorated Eastport Annapolis house with water views

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Historic Downtown Charmer, Water Views and Parking!, vacation rental in Annapolis
Historic Downtown Charmer, Water Views and Parking!, vacation rental in Annapolis
Historic Downtown Charmer, Water Views and Parking!, vacation rental in Annapolis

Historic Downtown Charmer, Water Views and Parking!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

The Cottage on Spa Creek, vacation rental in Annapolis
The Cottage on Spa Creek, vacation rental in Annapolis
The Cottage on Spa Creek, vacation rental in Annapolis

The Cottage on Spa Creek

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Charming garden row home, easy 4 block walk to the heart of Annapolis., vacation rental in Annapolis
Charming garden row home, easy 4 block walk to the heart of Annapolis., vacation rental in Annapolis
Charming garden row home, easy 4 block walk to the heart of Annapolis., vacation rental in Annapolis

Charming garden row home, easy 4 block walk to the heart of Annapolis.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport, vacation rental in Annapolis
Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport, vacation rental in Annapolis
Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport, vacation rental in Annapolis

Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport

Rental Home
4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Historic Annapolis Home And Garden, vacation rental in Annapolis
Historic Annapolis Home And Garden, vacation rental in Annapolis
Historic Annapolis Home And Garden, vacation rental in Annapolis

Historic Annapolis Home And Garden

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Heart of Historic District!, vacation rental in Annapolis
Heart of Historic District!, vacation rental in Annapolis
Heart of Historic District!, vacation rental in Annapolis

Heart of Historic District!

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown, vacation rental in Annapolis
Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown, vacation rental in Annapolis
Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown, vacation rental in Annapolis

Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Charming Annapolis Victorian, vacation rental in Annapolis
Charming Annapolis Victorian, vacation rental in Annapolis
Charming Annapolis Victorian, vacation rental in Annapolis

Charming Annapolis Victorian

Rental Home
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Annapolis Condominium in the heart of the historic center, vacation rental in Annapolis
Annapolis Condominium in the heart of the historic center, vacation rental in Annapolis
Annapolis Condominium in the heart of the historic center, vacation rental in Annapolis

Annapolis Condominium in the heart of the historic center

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

THE SHIPS BRIDGE featuring the most sought after Chesapeake Bay Views! 4 BR Wate, vacation rental in Annapolis
THE SHIPS BRIDGE featuring the most sought after Chesapeake Bay Views! 4 BR Wate, vacation rental in Annapolis
THE SHIPS BRIDGE featuring the most sought after Chesapeake Bay Views! 4 BR Wate, vacation rental in Annapolis

THE SHIPS BRIDGE featuring the most sought after Chesapeake Bay Views! 4 BR Wate

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District, vacation rental in Annapolis
Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District, vacation rental in Annapolis
Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District, vacation rental in Annapolis

Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown, vacation rental in Annapolis
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown, vacation rental in Annapolis
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown, vacation rental in Annapolis

Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Welcome Aboard the Kathleen Marie!, vacation rental in Annapolis
Welcome Aboard the Kathleen Marie!, vacation rental in Annapolis
Welcome Aboard the Kathleen Marie!, vacation rental in Annapolis

Welcome Aboard the Kathleen Marie!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Historic District Home with Gorgeous Renovation, vacation rental in Annapolis
Historic District Home with Gorgeous Renovation, vacation rental in Annapolis
Historic District Home with Gorgeous Renovation, vacation rental in Annapolis

Historic District Home with Gorgeous Renovation

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Charming Historic Annapolis with Impressive Updates Throughout, vacation rental in Annapolis
Charming Historic Annapolis with Impressive Updates Throughout, vacation rental in Annapolis
Charming Historic Annapolis with Impressive Updates Throughout, vacation rental in Annapolis

Charming Historic Annapolis with Impressive Updates Throughout

Rental Home
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Walk to Naval Academy + City Dock, vacation rental in Annapolis
Walk to Naval Academy + City Dock, vacation rental in Annapolis
Walk to Naval Academy + City Dock, vacation rental in Annapolis

Walk to Naval Academy + City Dock

Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Eastport Cottage .5 mi from Downtown Annapolis, vacation rental in Annapolis
Eastport Cottage .5 mi from Downtown Annapolis, vacation rental in Annapolis
Eastport Cottage .5 mi from Downtown Annapolis, vacation rental in Annapolis

Eastport Cottage .5 mi from Downtown Annapolis

Rental Home
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

CIRCA 1885 - DOWNTOWN HISTORIC ANNAPOLIS, vacation rental in Annapolis
CIRCA 1885 - DOWNTOWN HISTORIC ANNAPOLIS, vacation rental in Annapolis
CIRCA 1885 - DOWNTOWN HISTORIC ANNAPOLIS, vacation rental in Annapolis

CIRCA 1885 - DOWNTOWN HISTORIC ANNAPOLIS

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Charming cottage - easy walk to downtown with parking, vacation rental in Annapolis
Charming cottage - easy walk to downtown with parking, vacation rental in Annapolis
Charming cottage - easy walk to downtown with parking, vacation rental in Annapolis

Charming cottage - easy walk to downtown with parking

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Walk everywhere . . .just minutes to historic Annapolis,  Updated., vacation rental in Annapolis
Walk everywhere . . .just minutes to historic Annapolis,  Updated., vacation rental in Annapolis
Walk everywhere . . .just minutes to historic Annapolis,  Updated., vacation rental in Annapolis

Walk everywhere . . .just minutes to historic Annapolis, Updated.

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Beautiful Condo - Water View Near City Dock, vacation rental in Annapolis
Beautiful Condo - Water View Near City Dock, vacation rental in Annapolis
Beautiful Condo - Water View Near City Dock, vacation rental in Annapolis

Beautiful Condo - Water View Near City Dock

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Brand new Renovation - Fleet Street Retreat in Historic Downtown Annapolis, vacation rental in Annapolis
Brand new Renovation - Fleet Street Retreat in Historic Downtown Annapolis, vacation rental in Annapolis
Brand new Renovation - Fleet Street Retreat in Historic Downtown Annapolis, vacation rental in Annapolis

Brand new Renovation - Fleet Street Retreat in Historic Downtown Annapolis

Rental Home
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Cozy Cottage by the Beach - Waterview
Minutes from Downtown Annapolis, vacation rental in Annapolis
Cozy Cottage by the Beach - Waterview
Minutes from Downtown Annapolis, vacation rental in Annapolis
Cozy Cottage by the Beach - Waterview
Minutes from Downtown Annapolis, vacation rental in Annapolis

Cozy Cottage by the Beach - Waterview Minutes from Downtown Annapolis

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!, vacation rental in Annapolis
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!, vacation rental in Annapolis
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!, vacation rental in Annapolis

421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Historic Downtown Annapolis Waterfront, 1936, with a deep water dock, and kayaks, vacation rental in Annapolis
Historic Downtown Annapolis Waterfront, 1936, with a deep water dock, and kayaks, vacation rental in Annapolis
Historic Downtown Annapolis Waterfront, 1936, with a deep water dock, and kayaks, vacation rental in Annapolis

Historic Downtown Annapolis Waterfront, 1936, with a deep water dock, and kayaks

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Adorable cottage! Walking distance to USNA & downtown! (VRBO only), vacation rental in Annapolis
Adorable cottage! Walking distance to USNA & downtown! (VRBO only), vacation rental in Annapolis
Adorable cottage! Walking distance to USNA & downtown! (VRBO only), vacation rental in Annapolis

Adorable cottage! Walking distance to USNA & downtown! (VRBO only)

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Stunning Annapolis Home! Across from the library, walk to Naval Graduation, vacation rental in Annapolis
Stunning Annapolis Home! Across from the library, walk to Naval Graduation, vacation rental in Annapolis
Stunning Annapolis Home! Across from the library, walk to Naval Graduation, vacation rental in Annapolis

Stunning Annapolis Home! Across from the library, walk to Naval Graduation

Rental Home
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Eastport Cottage with Waterview  - Minutes from Downtown Annapolis and USNA, vacation rental in Annapolis
Eastport Cottage with Waterview  - Minutes from Downtown Annapolis and USNA, vacation rental in Annapolis
Eastport Cottage with Waterview  - Minutes from Downtown Annapolis and USNA, vacation rental in Annapolis

Eastport Cottage with Waterview - Minutes from Downtown Annapolis and USNA

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Historic Charm! Walk to Annapolis Waterfront & Academy with Parking, vacation rental in Annapolis
Historic Charm! Walk to Annapolis Waterfront & Academy with Parking, vacation rental in Annapolis
Historic Charm! Walk to Annapolis Waterfront & Academy with Parking, vacation rental in Annapolis

Historic Charm! Walk to Annapolis Waterfront & Academy with Parking

Rental Home
5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Come enjoy Historic Annapolis!, vacation rental in Annapolis
Come enjoy Historic Annapolis!, vacation rental in Annapolis
Come enjoy Historic Annapolis!, vacation rental in Annapolis

Come enjoy Historic Annapolis!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

0210 Submariners Gate. Downtown with PARKING! Rich in Naval History!, vacation rental in Annapolis
0210 Submariners Gate. Downtown with PARKING! Rich in Naval History!, vacation rental in Annapolis
0210 Submariners Gate. Downtown with PARKING! Rich in Naval History!, vacation rental in Annapolis

0210 Submariners Gate. Downtown with PARKING! Rich in Naval History!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

0180 Anchors Aweigh - Your Downtown Annapolis Home Aweigh from Home!, vacation rental in Annapolis
0180 Anchors Aweigh - Your Downtown Annapolis Home Aweigh from Home!, vacation rental in Annapolis
0180 Anchors Aweigh - Your Downtown Annapolis Home Aweigh from Home!, vacation rental in Annapolis

0180 Anchors Aweigh - Your Downtown Annapolis Home Aweigh from Home!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

PreviousNext
123456