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Cottages, Villas, Apartments in Annapolis
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197 rentals
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Vintage Bungalow-cozy, walkable, free pkg.
2 reviews
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3 bedrooms
2 bathrooms
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New! Renovated Pet-friendly Annapolis Townhome
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3 bedrooms
2 bathrooms
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One of a kind renovation in the center of it all - THE BEST LOCATION DOWNTOWN !
73 reviews
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4 bedrooms
2 bathrooms
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Beautiful Annapolis Getaway - Walk Everywhere, Parking & Private Backyard!
133 reviews
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4 bedrooms
3 bathrooms
Sleeps 7
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Charming historic home just steps from Main Street!
152 reviews
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3 bedrooms
3 bathrooms
Sleeps 8
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Annapolis waterfront 'tiny house' in garden setting
142 reviews
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1 bedroom
1 bathroom
Sleeps 4
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The Yellow Cottage on Harness Creek
85 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
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Charming Historic Annapolis Home With Two Off-street Parking Places!
113 reviews
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3 bedrooms
3 bathrooms
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Waterfront Oasis in Eastport - Walk to Downtown and USNA
51 reviews
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5 bedrooms
4 bathrooms
Sleeps 10
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Brand new Renovation in Historic District with 2 parking spots -walk everywhere
98 reviews
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2 bedrooms
1 bathroom
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Beautiful Waterfront Townhome In Historic Annapolis
89 reviews
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3 bedrooms
4 bathrooms
Sleeps 8
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Renovated Historic Home located downtown with parking - Walk everywhere !
202 reviews
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3 bedrooms
2 bathrooms
Sleeps 7
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Stunning Waterfront Cottage with Breathtaking Views!
131 reviews
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2 bedrooms
1 bathroom
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Fresh and Sunny and Relaxing ! with assigned parking
58 reviews
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3 bedrooms
3 bathrooms
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PERFECT LOCATION in the heart of history
118 reviews
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3 bedrooms
3 bathrooms
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Beautiful Historic Home With Great Location!
53 reviews
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4 bedrooms
3 bathrooms
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Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District
39 reviews
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1 bedroom
1 bathroom
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Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown
79 reviews
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1 bedroom
1 bathroom
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THE SHIPS BRIDGE featuring the most sought after Chesapeake Bay Views! 4 BR Wate
34 reviews
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4 bedrooms
4 bathrooms
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Historic Downtown Charmer, Water Views and Parking!
72 reviews
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2 bedrooms
2 bathrooms
Sleeps 5
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Magical Memories - Annapolis Chesapeake Bay Waterfront Home w/Pool.
30 reviews
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5 bedrooms
3 bathrooms
Sleeps 12
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The Cottage on Spa Creek
44 reviews
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2 bedrooms
2 bathrooms
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Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport
63 reviews
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4 bedrooms
4 bathrooms
Sleeps 10
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Stunning Home in the Historic District, Steps to the Academy
77 reviews
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4 bedrooms
5 bathrooms
Sleeps 12
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Heart of the Historic District!
92 reviews
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5 bedrooms
3 bathrooms
Sleeps 10
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Two Blocks to Town, Underground Parking Garage
94 reviews
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3 bedrooms
4 bathrooms
Sleeps 6
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Come enjoy Historic Annapolis!
84 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
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Charming garden row home, easy 4 block walk to the heart of Annapolis.
62 reviews
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3 bedrooms
2 bathrooms
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Historic Annapolis Home And Garden
53 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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Charming Annapolis Victorian
38 reviews
Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 12
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Welcome Aboard the Kathleen Marie!
38 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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Charming Historic Annapolis with Impressive Updates Throughout
21 reviews
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5 bedrooms
4 bathrooms
Sleeps 14
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Annapolis Condominium in the Heart of Historic Downtown
186 reviews
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3 bedrooms
2 bathrooms
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Newly renovated Eastport Annapolis house with water views
64 reviews
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3 bedrooms
3 bathrooms
Sleeps 6
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Stunning Annapolis Home! Available 2020 USNA Commisioning Week!
40 reviews
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 12
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Eastport Cottage with Waterview - Minutes from Downtown Annapolis and USNA
25 reviews
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1 bedroom
1 bathroom
Sleeps 2
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Stunning waterfront house - ideal weekend getaway
30 reviews
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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Walk to Naval Academy + City Dock
45 reviews
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3 bedrooms
3 bathrooms
Sleeps 7
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Location Location Location!!!50 Steps from Main Street and all of the action
65 reviews
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3 bedrooms
2 bathrooms
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Extended Stays Available Please contact for Availability and Pricing.
60 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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Beautiful Condo - Water View Near City Dock
102 reviews
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1 bedroom
1 bathroom
Sleeps 4
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Walk everywhere . . .just minutes to historic Annapolis, Updated.
30 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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Charming waterfront home located in Downtown Historic Annapolis
29 reviews
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3 bedrooms
3 bathrooms
Sleeps 10
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0210 Submariners Gate. Downtown with PARKING! Rich in Naval History!
24 reviews
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4 bedrooms
3 bathrooms
Sleeps 8
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Eastport Cottage .5 mi from Downtown Annapolis
26 reviews
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2 bedrooms
1 bathroom
Sleeps 3
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Historic District Home with Gorgeous Renovation
51 reviews
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3 bedrooms
3 bathrooms
Sleeps 6
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0146 BLUE ANGELS NEST - Downtown Annapolis. Green Outdoor Space!
17 reviews
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
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Historic District'Crab Cakes and Football'
31 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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Brand new Renovation - Fleet Street Retreat in Historic Downtown Annapolis
23 reviews
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 5
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CIRCA 1885 - DOWNTOWN HISTORIC ANNAPOLIS
28 reviews
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2 bedrooms
1 bathroom
Sleeps 5
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Frequently Asked Questions about Annapolis
Do any holiday rentals in Annapolis have a pool?
Yes, here are some popular holiday rentals in Annapolis that have a pool:\n
\n
Stunning Waterfront Cottage with Breathtaking Views!
\n
Beautiful Waterfront Townhome In Historic Annapolis
\n
DISCOUNTED FOR USNA COMMISSIONING WEEK 2020 ! Check rates through inquiry.
\n
\n
See all holiday rentals with a pool in Annapolis on Tripadvisor
Do any holiday rentals in Annapolis have internet access?
Yes, here are some popular holiday rentals in Annapolis that have internet access:\n
\n
Stunning Home in the Heart of Downtown Annapolis
\n
Beautiful Murray Hill Home (Annapolis)
\n
Charming and Spacious Annapolis Victorian
\n
\n
See all holiday rentals in Annapolis on Tripadvisor
What are the best pet friendly rentals in Annapolis?
The best pet friendly rentals in Annapolis are:\n
\n
Vintage Bungalow-cozy, walkable, free pkg.
\n
The Heart of Historic Cool in Annapolis
\n
Across from Gate 1 - Family's Tribute to Heroic Marine
\n
\n
See all pet friendly holiday rentals in Annapolis on Tripadvisor
What are some great rentals in Annapolis that are kid friendly?
Some of the most popular kid friendly rentals in Annapolis are:\n
\n
Beautiful Murray Hill Home (Annapolis)
\n
Charming and Spacious Annapolis Victorian
\n
Vintage Bungalow-cozy, walkable, free pkg.
\n
\n
See all kid friendly holiday rentals in Annapolis on Tripadvisor