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Annapolis Holiday Apartments

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225 rentals in Annapolis.
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Charming historic home  just steps from Main Street!, holiday rental in Annapolis
Charming historic home  just steps from Main Street!, holiday rental in Annapolis
Charming historic home  just steps from Main Street!, holiday rental in Annapolis

Charming historic home just steps from Main Street!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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Beautiful Annapolis Getaway - Walk Everywhere, Parking & Private Backyard!, holiday rental in Annapolis
Beautiful Annapolis Getaway - Walk Everywhere, Parking & Private Backyard!, holiday rental in Annapolis
Beautiful Annapolis Getaway - Walk Everywhere, Parking & Private Backyard!, holiday rental in Annapolis

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

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 7
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Annapolis waterfront 'tiny house' in garden setting, holiday rental in Annapolis
Annapolis waterfront 'tiny house' in garden setting, holiday rental in Annapolis
Annapolis waterfront 'tiny house' in garden setting, holiday rental in Annapolis

Annapolis waterfront 'tiny house' in garden setting

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Charming Historic Annapolis Home With Two Off-street Parking Places!, holiday rental in Annapolis
Charming Historic Annapolis Home With Two Off-street Parking Places!, holiday rental in Annapolis
Charming Historic Annapolis Home With Two Off-street Parking Places!, holiday rental in Annapolis

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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The Yellow Cottage on Harness Creek, holiday rental in Annapolis
The Yellow Cottage on Harness Creek, holiday rental in Annapolis
The Yellow Cottage on Harness Creek, holiday rental in Annapolis

The Yellow Cottage on Harness Creek

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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One of a kind renovation in the center of it all - THE BEST LOCATION DOWNTOWN !, holiday rental in Annapolis
One of a kind renovation in the center of it all - THE BEST LOCATION DOWNTOWN !, holiday rental in Annapolis
One of a kind renovation in the center of it all - THE BEST LOCATION DOWNTOWN !, holiday rental in Annapolis

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

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Stunning Waterfront Cottage with Breathtaking Views!, holiday rental in Annapolis
Stunning Waterfront Cottage with Breathtaking Views!, holiday rental in Annapolis
Stunning Waterfront Cottage with Breathtaking Views!, holiday rental in Annapolis

Stunning Waterfront Cottage with Breathtaking Views!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Waterfront Oasis in Eastport - Walk to Downtown and USNA, holiday rental in Annapolis
Waterfront Oasis in Eastport - Walk to Downtown and USNA, holiday rental in Annapolis
Waterfront Oasis in Eastport - Walk to Downtown and USNA, holiday rental in Annapolis

Waterfront Oasis in Eastport - Walk to Downtown and USNA

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful Historic Home With Great Location!, holiday rental in Annapolis
Beautiful Historic Home With Great Location!, holiday rental in Annapolis
Beautiful Historic Home With Great Location!, holiday rental in Annapolis

Beautiful Historic Home With Great Location!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Renovated Historic Home located downtown with parking - Walk everywhere !, holiday rental in Annapolis
Renovated Historic Home located downtown with parking - Walk everywhere !, holiday rental in Annapolis
Renovated Historic Home located downtown with parking - Walk everywhere !, holiday rental in Annapolis

Renovated Historic Home located downtown with parking - Walk everywhere !

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Fresh and Sunny and Relaxing ! with assigned parking, holiday rental in Annapolis
Fresh and Sunny and Relaxing ! with assigned parking, holiday rental in Annapolis
Fresh and Sunny and Relaxing ! with assigned parking, holiday rental in Annapolis

Fresh and Sunny and Relaxing ! with assigned parking

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Waterfront Townhome In Historic Annapolis, holiday rental in Annapolis
Beautiful Waterfront Townhome In Historic Annapolis, holiday rental in Annapolis
Beautiful Waterfront Townhome In Historic Annapolis, holiday rental in Annapolis

Beautiful Waterfront Townhome In Historic Annapolis

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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PERFECT LOCATION in the heart of history, holiday rental in Annapolis
PERFECT LOCATION in the heart of history, holiday rental in Annapolis
PERFECT LOCATION in the heart of history, holiday rental in Annapolis

PERFECT LOCATION in the heart of history

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport, holiday rental in Annapolis
Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport, holiday rental in Annapolis
Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport, holiday rental in Annapolis

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

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Stunning Home in the Historic District, Steps to the Academy, holiday rental in Annapolis
Stunning Home in the Historic District, Steps to the Academy, holiday rental in Annapolis
Stunning Home in the Historic District, Steps to the Academy, holiday rental in Annapolis

Stunning Home in the Historic District, Steps to the Academy

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Brand new Renovation in Historic District with 2 parking spots -walk everywhere, holiday rental in Annapolis
Brand new Renovation in Historic District with 2 parking spots -walk everywhere, holiday rental in Annapolis
Brand new Renovation in Historic District with 2 parking spots -walk everywhere, holiday 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
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Two Blocks to Town, Underground Parking Garage, holiday rental in Annapolis
Two Blocks to Town, Underground Parking Garage, holiday rental in Annapolis
Two Blocks to Town, Underground Parking Garage, holiday rental in Annapolis

Two Blocks to Town, Underground Parking Garage

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Magical Memories - Annapolis Chesapeake Bay Waterfront Home w/Pool., holiday rental in Annapolis
Magical Memories - Annapolis Chesapeake Bay Waterfront Home w/Pool., holiday rental in Annapolis
Magical Memories - Annapolis Chesapeake Bay Waterfront Home w/Pool., holiday rental in Annapolis

Magical Memories - Annapolis Chesapeake Bay Waterfront Home w/Pool.

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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The Cottage on Spa Creek, holiday rental in Annapolis
The Cottage on Spa Creek, holiday rental in Annapolis
The Cottage on Spa Creek, holiday rental in Annapolis

The Cottage on Spa Creek

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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THE SHIPS BRIDGE featuring the most sought after Chesapeake Bay Views! 4 BR Wate, holiday rental in Annapolis
THE SHIPS BRIDGE featuring the most sought after Chesapeake Bay Views! 4 BR Wate, holiday rental in Annapolis
THE SHIPS BRIDGE featuring the most sought after Chesapeake Bay Views! 4 BR Wate, holiday rental in Annapolis

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

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District, holiday rental in Annapolis
Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District, holiday rental in Annapolis
Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District, holiday rental in Annapolis

Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Historic Downtown Charmer, Water Views and Parking!, holiday rental in Annapolis
Historic Downtown Charmer, Water Views and Parking!, holiday rental in Annapolis
Historic Downtown Charmer, Water Views and Parking!, holiday rental in Annapolis

Historic Downtown Charmer, Water Views and Parking!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Heart of the Historic District!, holiday rental in Annapolis
Heart of the Historic District!, holiday rental in Annapolis
Heart of the Historic District!, holiday rental in Annapolis

Heart of the Historic District!

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Historic Annapolis Home And Garden, holiday rental in Annapolis
Historic Annapolis Home And Garden, holiday rental in Annapolis
Historic Annapolis Home And Garden, holiday rental in Annapolis

Historic Annapolis Home And Garden

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming garden row home, easy 4 block walk to the heart of Annapolis., holiday rental in Annapolis
Charming garden row home, easy 4 block walk to the heart of Annapolis., holiday rental in Annapolis
Charming garden row home, easy 4 block walk to the heart of Annapolis., holiday rental in Annapolis

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stunning waterfront house - ideal weekend getaway, holiday rental in Annapolis
Stunning waterfront house - ideal weekend getaway, holiday rental in Annapolis
Stunning waterfront house - ideal weekend getaway, holiday rental in Annapolis

Stunning waterfront house - ideal weekend getaway

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Charming Annapolis Victorian, holiday rental in Annapolis
Charming Annapolis Victorian, holiday rental in Annapolis
Charming Annapolis Victorian, holiday rental in Annapolis

Charming Annapolis Victorian

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Newly renovated Eastport Annapolis house with water views, holiday rental in Annapolis
Newly renovated Eastport Annapolis house with water views, holiday rental in Annapolis
Newly renovated Eastport Annapolis house with water views, holiday rental in Annapolis

Newly renovated Eastport Annapolis house with water views

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown, holiday rental in Annapolis
Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown, holiday rental in Annapolis
Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown, holiday rental in Annapolis

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

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Welcome Aboard the Kathleen Marie!, holiday rental in Annapolis
Welcome Aboard the Kathleen Marie!, holiday rental in Annapolis
Welcome Aboard the Kathleen Marie!, holiday rental in Annapolis

Welcome Aboard the Kathleen Marie!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Come enjoy Historic Annapolis!, holiday rental in Annapolis
Come enjoy Historic Annapolis!, holiday rental in Annapolis
Come enjoy Historic Annapolis!, holiday rental in Annapolis

Come enjoy Historic Annapolis!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Location Location Location!!!50 Steps from Main Street and all of the action, holiday rental in Annapolis
Location Location Location!!!50 Steps from Main Street and all of the action, holiday rental in Annapolis
Location Location Location!!!50 Steps from Main Street and all of the action, holiday rental in Annapolis

Location Location Location!!!50 Steps from Main Street and all of the action

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stunning Annapolis Home! Available 2020 USNA Commisioning Week!, holiday rental in Annapolis
Stunning Annapolis Home! Available 2020 USNA Commisioning Week!, holiday rental in Annapolis
Stunning Annapolis Home! Available 2020 USNA Commisioning Week!, holiday rental in Annapolis

Stunning Annapolis Home! Available 2020 USNA Commisioning Week!

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Annapolis Condominium in the Heart of Historic Downtown, holiday rental in Annapolis
Annapolis Condominium in the Heart of Historic Downtown, holiday rental in Annapolis
Annapolis Condominium in the Heart of Historic Downtown, holiday rental in Annapolis

Annapolis Condominium in the Heart of Historic Downtown

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown, holiday rental in Annapolis
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown, holiday rental in Annapolis
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown, holiday rental in Annapolis

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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Charming Historic Annapolis with Impressive Updates Throughout, holiday rental in Annapolis
Charming Historic Annapolis with Impressive Updates Throughout, holiday rental in Annapolis
Charming Historic Annapolis with Impressive Updates Throughout, holiday rental in Annapolis

Charming Historic Annapolis with Impressive Updates Throughout

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Historic District Home with Gorgeous Renovation, holiday rental in Annapolis
Historic District Home with Gorgeous Renovation, holiday rental in Annapolis
Historic District Home with Gorgeous Renovation, holiday rental in Annapolis

Historic District Home with Gorgeous Renovation

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Walk to Naval Academy + City Dock, holiday rental in Annapolis
Walk to Naval Academy + City Dock, holiday rental in Annapolis
Walk to Naval Academy + City Dock, holiday rental in Annapolis

Walk to Naval Academy + City Dock

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Charming waterfront home located in Downtown Historic Annapolis, holiday rental in Annapolis
Charming waterfront home located in Downtown Historic Annapolis, holiday rental in Annapolis
Charming waterfront home located in Downtown Historic Annapolis, holiday rental in Annapolis

Charming waterfront home located in Downtown Historic Annapolis

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Eastport Cottage with Waterview  - Minutes from Downtown Annapolis and USNA, holiday rental in Annapolis
Eastport Cottage with Waterview  - Minutes from Downtown Annapolis and USNA, holiday rental in Annapolis
Eastport Cottage with Waterview  - Minutes from Downtown Annapolis and USNA, holiday rental in Annapolis

Eastport Cottage with Waterview - Minutes from Downtown Annapolis and USNA

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Beautiful Condo - Water View Near City Dock, holiday rental in Annapolis
Beautiful Condo - Water View Near City Dock, holiday rental in Annapolis
Beautiful Condo - Water View Near City Dock, holiday rental in Annapolis

Beautiful Condo - Water View Near City Dock

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Historic home steps to the State House CW available, holiday rental in Annapolis
Historic home steps to the State House CW available, holiday rental in Annapolis
Historic home steps to the State House CW available, holiday rental in Annapolis

Historic home steps to the State House CW available

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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CIRCA 1885 - DOWNTOWN HISTORIC ANNAPOLIS, holiday rental in Annapolis
CIRCA 1885 - DOWNTOWN HISTORIC ANNAPOLIS, holiday rental in Annapolis
CIRCA 1885 - DOWNTOWN HISTORIC ANNAPOLIS, holiday rental in Annapolis

CIRCA 1885 - DOWNTOWN HISTORIC ANNAPOLIS

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Historic District'Crab Cakes and Football', holiday rental in Annapolis
Historic District'Crab Cakes and Football', holiday rental in Annapolis
Historic District'Crab Cakes and Football', holiday rental in Annapolis

Historic District'Crab Cakes and Football'

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Eastport Cottage .5 mi from Downtown Annapolis, holiday rental in Annapolis
Eastport Cottage .5 mi from Downtown Annapolis, holiday rental in Annapolis
Eastport Cottage .5 mi from Downtown Annapolis, holiday rental in Annapolis

Eastport Cottage .5 mi from Downtown Annapolis

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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0210 Submariners Gate. Downtown with PARKING! Rich in Naval History!, holiday rental in Annapolis
0210 Submariners Gate. Downtown with PARKING! Rich in Naval History!, holiday rental in Annapolis
0210 Submariners Gate. Downtown with PARKING! Rich in Naval History!, holiday rental in Annapolis

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

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Walk everywhere . . .just minutes to historic Annapolis,  Updated., holiday rental in Annapolis
Walk everywhere . . .just minutes to historic Annapolis,  Updated., holiday rental in Annapolis
Walk everywhere . . .just minutes to historic Annapolis,  Updated., holiday rental in Annapolis

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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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0146 BLUE ANGELS NEST - Downtown Annapolis. Green Outdoor Space!, holiday rental in Annapolis
0146 BLUE ANGELS NEST - Downtown Annapolis. Green Outdoor Space!, holiday rental in Annapolis
0146 BLUE ANGELS NEST - Downtown Annapolis. Green Outdoor Space!, holiday rental in Annapolis

0146 BLUE ANGELS NEST - Downtown Annapolis. Green Outdoor Space!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Charming Home In Presidents Hill Area near to the Historic District, holiday rental in Annapolis
Charming Home In Presidents Hill Area near to the Historic District, holiday rental in Annapolis
Charming Home In Presidents Hill Area near to the Historic District, holiday rental in Annapolis

Charming Home In Presidents Hill Area near to the Historic District

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Restored Historic 5 Bedroom/5 Bath Former BnB in Downtown Annapolis, holiday rental in Annapolis
Restored Historic 5 Bedroom/5 Bath Former BnB in Downtown Annapolis, holiday rental in Annapolis
Restored Historic 5 Bedroom/5 Bath Former BnB in Downtown Annapolis, holiday rental in Annapolis

Restored Historic 5 Bedroom/5 Bath Former BnB in Downtown Annapolis

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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