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Wireless Internet
Air conditioning
Swimming pool
Private pool

Heated pool
Private indoor pool
Balcony or terrace
Washing machine
Garden
Internet access
DVD player
Grill
Fireplace
Cot available
High chair
Sea view
Safe
Dishwasher
Children's pool
Private outdoor pool (unheated)
Private outdoor pool (heated)
Shared indoor pool
Pool or snooker table
Shared outdoor pool (heated)
Clothes dryer
Cribs
Ceiling Fans
Games room
Table tennis
Shared outdoor pool (unheated)
Trampoline
Fax machine
Microwave
Kettle
Toaster
Iron
Hair dryer
Stove
Fridge
Freezer
Linen provided
Video player
Towels provided
Bicycles available
Climbing frame
Swing set or jungle gym
Private fishing lake or river
Staffed property
Boat available
Housekeeping Included

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Pets
Pets allowed
Parking
Car not required

Children under 5
Smoking allowed
Non-Smoking property
Smoking - Ask
Wheelchair adapted
Wheelchair accessible

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Beach or lakeside relaxation
City breaks
Tennis in town
Water sports

Horse riding
Fishing
Golf within 30mins drive
Waterfront

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53 houses

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Annapolis Area Waterfront Home

Annapolis house

5 bedrooms / 4 bathrooms / sleeps 11

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Price per night from

$662

Walk to Shops/Eateries Charming Cottage. Dogs Wel.

Annapolis house

3 bedrooms / 1 bathroom / sleeps 6

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Price per night from

$287

Charming and Spacious Annapolis Victorian

Annapolis house

6 bedrooms / 5 bathrooms / sleeps 12

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Price per night from

$857

Annapolis House w/ Patio in Bay Ridge Maryland!

Annapolis house

3 bedrooms / 4 bathrooms / sleeps 6

Responds fast! avg. 1 hour 48 minutes

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Price per night from

$859

Beautiful Murray Hill Home (Annapolis)

Annapolis house

4 bedrooms / 3 bathrooms / sleeps 9

“Comfortable and secure in a great home - almost as good as at ho” The house is set is a terrific neighborhood of annapolis within easy walking distance to two small parks on the water and to town. We all found the house a delight - the design, decorating, furnishings are tasteful and match the age and the imagery of the house. It is well equipped with comfortable bedrooms, adequate bathrooms and linens, utensils and staple supplies. We certainly will attempt to stay at this house again if we ever return to annapolis.

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Price per night from

$486

The Heart of Historic Cool in Annapolis

Annapolis house

5 bedrooms / 3 bathrooms / sleeps 10

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Price per night from

$1,151

Cozy Home in Historic Annapolis with Parking

Annapolis house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 40 minutes

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Price per night from

$228

Stunning Home in the Heart of Downtown Annapolis

Annapolis house

3 bedrooms / 5 bathrooms / sleeps 11

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Price per night from

$796

Charming Annapolis Waterview home

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 10

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Price per night from

$801

Charming Townhouse - Steps to City Dock and USNA

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 58 minutes

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Price per night from

$520

New - Play at the beach just minutes to downtown Annapolis

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 2 hours 4 minutes

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Price per night from

$381

Newly furnished home, perfect for Naval Academy Football games!

Annapolis house

4 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 2 hours 4 minutes

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Price per night from

$369

New Luxury Home Walkable to Main Street w Parking!

Annapolis house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 4 minutes

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Price per night from

$182

New Lux Downtown Annapolis Home with 3 parking spots!

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 2 hours 4 minutes

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Price per night from

$369

Spend the night in Historic Downtown Annapolis

Annapolis house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 4 minutes

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Price per night from

$369

Naval Academy Themed at the Gates with parking!

Annapolis house

4 bedrooms / 2 bathrooms / sleeps 11

Responds fast! avg. 2 hours 4 minutes

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Price per night from

$524

New! Steps to Main Street with views of the Capital

Annapolis house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 4 minutes

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Price per night from

$289

Annapolis-themed home in Downtown Annapolis with Parking

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 4 minutes

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Price per night from

$182

Renovated Eastport Firehouse in Annapolis

Annapolis house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 4 minutes

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Price per night from

$287

USNA-themed 3 Bedroom home off West Street with parking!

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 4 minutes

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Price per night from

$232

Historic Charm! Walk to Annapolis Waterfront & Academy

Annapolis house

3 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 2 hours 4 minutes

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Price per night from

$575

Walkable to Downtown Annapolis

Annapolis house

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 2 hours 4 minutes

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Price per night from

$182

Great rentals within 20 miles that match your search

Private Room Close To Baltimore and BWI Airport + EXTRAS

Glen Burnie house

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$59

Bay Cottage Resort

St. Michaels house

6 bedrooms / 5 bathrooms / sleeps 12

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Price per night from

$2,404

Clean & Spacious

Cape Saint Claire house

4 bedrooms / 5 bathrooms / sleeps 14

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Price per night from

$917

Wellspring Manor & Spa

Largo house

5 bedrooms / 8 bathrooms / sleeps 10

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Price per night from

$1,839

Bayside Retreat

Rock Hall house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$258

Holistic Getaway

Bowie house

2 bedrooms / 1 bathroom / sleeps 6

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Price per night from

$167

Bay Cottage

Rock Hall house

2 bedrooms / 1 bathroom / sleeps 5

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Price per night from

$312

Sandy Pines: Enjoy Harris Creek w/Pool and Boats

St. Michaels house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 34 minutes

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Price per night from

$782

Peaceful, Waterfront Home on 3 Acres (pier + western view w/gorgeous sunsets)

Chester house

4 bedrooms / 2 bathrooms / sleeps 8

“Unbelievable value” We were a family group of 3 couples plus an infant traveling to a wedding at the Usna chapel. The home was just wonderful, had a great view, was very clean, and was well equipped for the cooking being planned. Stores, restaurants, and liquor store were close by. Easy on and off the freeway into annapolis. Scott was very personable and worked with us to make our visit just right from the moment we first contacted him about renting.

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Price per night from

$337