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Annapolis Vacation Rentals

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111 rentals in Annapolis.
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Ultra Contemporary waterfront home very close to downtown Annapolis with stunnin, vacation rental in Annapolis

Ultra Contemporary waterfront home very close to downtown Annapolis with stunnin

4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Annapolis Getaway - Walk Everywhere, Parking & Private Backyard!, vacation rental in Annapolis

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

4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Annapolis waterfront 'tiny house' in garden setting, vacation rental in Annapolis

Annapolis waterfront 'tiny house' in garden setting

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Charming historic home  just steps from Main Street!, vacation rental in Annapolis

Charming historic home just steps from Main Street!

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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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

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Charming Historic Annapolis Home With Two Off-street Parking Places!, vacation rental in Annapolis

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

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The Yellow Cottage on Harness Creek, vacation rental in Annapolis

The Yellow Cottage on Harness Creek

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Two Blocks to Town, Underground Parking Garage, vacation rental in Annapolis

Two Blocks to Town, Underground Parking Garage

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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PERFECT LOCATION in the heart of history, vacation rental in Annapolis

PERFECT LOCATION in the heart of history

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Waterfront Townhome In Historic Annapolis, vacation rental in Annapolis

Beautiful Waterfront Townhome In Historic Annapolis

3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Renovated Historic Home located downtown with parking - Walk everywhere !, vacation rental in Annapolis

Renovated Historic Home located downtown with parking - Walk everywhere !

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown, vacation rental in Annapolis

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

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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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

4 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
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Historic Downtown Charmer, Water Views and Parking!, vacation rental in Annapolis

Historic Downtown Charmer, Water Views and Parking!

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Waterfront Oasis in Eastport - Walk to Downtown and USNA, vacation rental in Annapolis

Waterfront Oasis in Eastport - Walk to Downtown and USNA

5 bedrooms
4 bathrooms
Sleeps 13
Match: Sleeps
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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

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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The Cottage on Spa Creek, vacation rental in Annapolis

The Cottage on Spa Creek

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Magical Memories - Annapolis Chesapeake Bay Waterfront Home w/Pool., vacation rental in Annapolis

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

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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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 !

4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Beautiful Historic Home With Great Location!, vacation rental in Annapolis

Beautiful Historic Home With Great Location!

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Walk Everywhere with Off-Street Parking !!!, vacation rental in Annapolis

Walk Everywhere with Off-Street Parking !!!

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Impeccable, near Navy Stadium, vacation rental in Annapolis

Impeccable, near Navy Stadium

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Cozy Cottage by the Beach, vacation rental in Annapolis

Cozy Cottage by the Beach

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Come enjoy Historic Annapolis!, vacation rental in Annapolis

Come enjoy Historic Annapolis!

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Historic Annapolis Home And Garden, vacation rental in Annapolis

Historic Annapolis Home And Garden

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Heart of the Historic District!, vacation rental in Annapolis

Heart of the Historic District!

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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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.

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Pristine Renovation: Perfect Downtown  Location walk to the Academy or Stadium!, vacation rental in Annapolis

Pristine Renovation: Perfect Downtown Location walk to the Academy or Stadium!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District, vacation rental in Annapolis

Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Annapolis Condominium in the Heart of Historic Downtown, vacation rental in Annapolis

Annapolis Condominium in the Heart of Historic Downtown

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Location Location Location!!!50 Steps from Main Street and all of the action, vacation rental in Annapolis

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

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Welcome Aboard the Kathleen Marie!, vacation rental in Annapolis

Welcome Aboard the Kathleen Marie!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Eastport Cottage with Waterview  - Minutes from Downtown Annapolis and USNA, vacation rental in Annapolis

Eastport Cottage with Waterview - Minutes from Downtown Annapolis and USNA

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Charming waterfront home located in Downtown Historic Annapolis, vacation rental in Annapolis

Charming waterfront home located in Downtown Historic Annapolis

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Adorable cottage! Walking distance to USNA & downtown! (VRBO only), vacation rental in Annapolis

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

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Extended Stays Available Please contact for Availability and Pricing., vacation rental in Annapolis

Extended Stays Available Please contact for Availability and Pricing.

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Walk to Naval Academy + City Dock, vacation rental in Annapolis

Walk to Naval Academy + City Dock

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Brand new Renovation - Fleet Street Retreat in Historic Downtown Annapolis, vacation rental in Annapolis

Brand new Renovation - Fleet Street Retreat in Historic Downtown Annapolis

2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Walk everywhere . . .just minutes to historic Annapolis,  Updated., vacation rental in Annapolis

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

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Sleeps 10! Great Reviews., vacation rental in Annapolis

Sleeps 10! Great Reviews.

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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0210 Submariners Gate. Downtown with PARKING! Rich in Naval History!, vacation rental in Annapolis

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

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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CIRCA 1885 - DOWNTOWN HISTORIC ANNAPOLIS, vacation rental in Annapolis

CIRCA 1885 - DOWNTOWN HISTORIC ANNAPOLIS

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Charming Historic Annapolis with Impressive Updates Throughout, vacation rental in Annapolis

Charming Historic Annapolis with Impressive Updates Throughout

5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Views! Charming Renovated Beachfront House in Bay Ridge Annapolis. 10 min dwntwn, vacation rental in Annapolis

Views! Charming Renovated Beachfront House in Bay Ridge Annapolis. 10 min dwntwn

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Heart of Downtown, superior location!, vacation rental in Annapolis

Heart of Downtown, superior location!

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Historic beach Cottage, vacation rental in Annapolis

Historic beach Cottage

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Eastport Cottage .5 mi from Downtown Annapolis, vacation rental in Annapolis

Eastport Cottage .5 mi from Downtown Annapolis

2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Large Luxury Apartment In Downtown Annapolis, vacation rental in Annapolis

Large Luxury Apartment In Downtown Annapolis

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Waterside with it All! Private Pier, Hot Tub and Pool., vacation rental in Annapolis

Waterside with it All! Private Pier, Hot Tub and Pool.

6 bedrooms
6 bathrooms
Sleeps 18
Match: Sleeps
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0198 Days Landing. Your Chesapeake Family Getaway! Lake, Pool, Hot Tub, Dock., vacation rental in Annapolis

0198 Days Landing. Your Chesapeake Family Getaway! Lake, Pool, Hot Tub, Dock.

6 bedrooms
7 bathrooms
Sleeps 14
Match: Sleeps
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