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Annapolis Holiday Rentals

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197 rentals in Annapolis.
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Vintage Bungalow-cozy, walkable, free pkg.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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New! Renovated Pet-friendly Annapolis Townhome

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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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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Beautiful Annapolis Getaway - Walk Everywhere, Parking & Private Backyard!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 7
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Charming historic home just steps from Main Street!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Annapolis waterfront 'tiny house' in garden setting

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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The Yellow Cottage on Harness Creek

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

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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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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Beautiful Waterfront Townhome In Historic Annapolis

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Renovated Historic Home located downtown with parking - Walk everywhere !

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Stunning Waterfront Cottage with Breathtaking Views!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
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Fresh and Sunny and Relaxing ! with assigned parking

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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PERFECT LOCATION in the heart of history

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Historic Home With Great Location!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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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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Historic Downtown Charmer, Water Views and Parking!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
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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 House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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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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Heart of the Historic District!

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
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Two Blocks to Town, Underground Parking Garage

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Come enjoy Historic Annapolis!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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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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Historic Annapolis Home And Garden

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming Annapolis Victorian

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Welcome Aboard the Kathleen Marie!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Charming Historic Annapolis with Impressive Updates Throughout

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Annapolis Condominium in the Heart of Historic Downtown

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Newly renovated Eastport Annapolis house with water views

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Stunning Annapolis Home! Available 2020 USNA Commisioning Week!

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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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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Stunning waterfront house - ideal weekend getaway

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Walk to Naval Academy + City Dock

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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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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Extended Stays Available Please contact for Availability and Pricing.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful Condo - Water View Near City Dock

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Walk everywhere . . .just minutes to historic Annapolis, Updated.

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Charming waterfront home located in Downtown Historic Annapolis

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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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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Eastport Cottage .5 mi from Downtown Annapolis

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Historic District Home with Gorgeous Renovation

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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0146 BLUE ANGELS NEST - Downtown Annapolis. Green Outdoor Space!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Historic District'Crab Cakes and Football'

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Brand new Renovation - Fleet Street Retreat in Historic Downtown Annapolis

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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CIRCA 1885 - DOWNTOWN HISTORIC ANNAPOLIS

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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