Vacation Rentals by Owner

Annapolis Vacation Rentals Show this location only Back to top

•   Spacious Annapolis Waterfront Home with Multiple Decks, Private Pier, and Views! 3BR+/3BA – Sleeps 10 – Annapolis #80753
  20
  $350 - $500 per night 2 night min stay

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•   Annapolis/Boaters/ Waterfront,Pool,Beach,Slip, Wi Fi ,Family/Retreat 5BR+/3BA – Sleeps 13-15 – Annapolis #200683
  32
  $400 - $975 per night 2-3 night min stay

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•   Stunning Downtown Home Steps from the Academy! 3BR+/3.5+BA – Sleeps 9 – Annapolis #146252
  12
  $750 - $875 per night 2 night min stay

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•   Annapolis Condominium in the Heart of Historic Downtown 3BR/2BA – Sleeps 6 – Annapolis #133608
  12
  $250 per night 3 night min stay

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•   Waterfront Cottage - Scenic River Off Chesapeake Bay 2BR/2BA – Sleeps 4-6 – Annapolis #58142
  41
  $1995 per week 7 night min stay

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•   Comfort & Style: Chesapeake Bay Views, Beach, Pier, Spa! 5BR+/3BA – Sleeps 4-20 – Annapolis #390303
  23
  $495 - $695 per night 2-3 night min stay

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•   Amazing Waterfront in Annapolis, Easy Walk to Navy Stadium & Downtown 4BR/4BA – Sleeps 13 – Annapolis #369296
  12
  $500 - $1200 per night 1 night min stay

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•   Beautiful Renovation in Historic District 2BR/2.5BA – Sleeps 6 – Annapolis #203247
  7
  $101 - $425 per night 2-30 night min stay

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•   A Minute's Walk to City Dock! 3BR+/2BA – Sleeps 6-8 – Annapolis #16821
  2
  $350- $450/nt

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•   Renovated Historic Home Located Downtown -Walk Everywhere! 3BR+/2BA – Sleeps 6-8 – Annapolis #361241
  27
  From $250/nt

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•   Historic Stone Riverfront Villa - with Your Own Boat 5BR+/5BA – Sleeps 15 – Annapolis #386641
  7
  $643 per night

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•   Beautiful Annapolis Getaway - Walk Everywhere! 3BR/2BA – Sleeps 7-8 – Annapolis #461541
  3
  $300 - $400 per night 2 night min stay

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•   Luxurious Historic Home in the Heart of Downtown Annapolis! 3BR+/2.75BA – Sleeps 6-9 – Annapolis #131054
  57
  $450/nt - $2900/wk

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•   Walk to Dwtn or Enjoy the Free Ecruiser! Great Location! 4BR+/3.5BA – Sleeps 8-10 – Annapolis #129519
  26
  Starting at $400 per night

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•   Annapolis Area Severn River Waterfront 5BR+/3BA – Sleeps 11 – Annapolis #259512
  10
  $500 per night 4 night min stay

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•   Gorgeous Southern Colonial on the Water in Annapolis- 6BR+/4.5BA – Sleeps 16 – Annapolis #230476
  44
  795. per night.

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•   5BR/3 BA Luxury Waterfront, Featured in 'Waterfront Living' 4BR+/3BA – Sleeps 10-12 – Annapolis #168663
  14
  $340 - $850 per night 2-3 night min stay

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•   Casa Arundel 3BR+/2BA – Sleeps 8-9 – Annapolis #181461
  13
  From $1500- $2000/wk

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•   Charming Vintage Cottage.Walk to Pubs,Shops. Dogs Ok. 2BR+/1BA – Sleeps 4-6 – Annapolis #245985
  38
  $225 per night 2 night min stay

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•   Annapolis, Md Waterfront Rental Home 5BR/3BA – Sleeps 16 – Annapolis #176040
  16
  $6800/wk

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•   Cozy Usna Sailor Cottage-1 Mi City Dock in Eastport $175/nt Slps 8 Avail Cw'14 4BR+/2BA – Sleeps 8-9 – Annapolis #306997
  18
  $150/nt $1200/month great value

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•   Beautiful Upscale Accomodations in Annapolis - Eastport 4BR+/3BA – Sleeps 9-11 – Annapolis #105746
  19
  $175- $475/nt

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•   Perfect Annapolis Family Gathering Place! Steps from the Usna Stadium! 5BR+/4.5BA – Sleeps 11-13 – Annapolis #242904
  11
  $600 - $850 per night 3-7 night min stay

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•   Charming Historic Home Just Steps from Main Street! 3BR/2.5BA – Sleeps 8 – Annapolis #458610
  5
  $450 per night 2 night min stay

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•   Striking Annapolis Home; Walk to Stadium; Ideal Entertaining Venue 4BR+/4.5BA – Sleeps 10-12 – Annapolis #430388
  10
  $500 per night Dollars

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•   Looking for Comm Week 2013? Look No Farther-I Have a Beautiful House! 4BR+/2.5BA – Sleeps 8 – Annapolis #79375
  0
  $500- $800/nt

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•   Romantic Gothic Revival Church in Historic District 2BR+/2.5BA – Sleeps 4-6 – Annapolis #314887
  8
  From $395/nt (3- nt minimum)

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•   Stunning Annapolis Home! 4 Flat Screen Tvs in One Great Room. 4BR+/4.5BA – Sleeps 12 – Annapolis #362729
  9
  $500/night

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•   Largest Fully Refurbished Rental Home in Historic District 7BR/6.5BA – Sleeps 14 – Annapolis #313972
  0
  $1500/nt - $9000/wk

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•   Annapolis Historic District Rowhome- Walk to Everything!! 3BR+/2.5BA – Sleeps 6-8 – Annapolis #346541
  0
  $500 per night 3 night min stay

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•   Charming Cottage Downtown Historic Annapolis 3BR+/2BA – Sleeps 6 – Annapolis #271336
  0
  $1,800 to $4,500/wk

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•   Beautiful 5BR / 3.5BA Annapolis Home - Only 1 Mile from Downtown 5BR+/3.5BA – Sleeps 9-13 – Annapolis #424542
  2
  $500/night

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•   Memories on the Bay 5BR/4.5+BA – Sleeps 10-14 – Annapolis #430086
  0
  $4,000- $8000/week

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•   Awesome Annapolis 4BR House W/ Pool! 1 Mile from Downtown! 4BR+/3.5BA – Sleeps 8-10 – Annapolis #362652
  3
  $500 a nt

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•   Historic Annapolis ! 2BR+/2.75BA – Sleeps 4-6 – Annapolis #356058
  0
  From $250/nt

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•   Beautiful 7800sf Home in Annapolis, 2 Mi to Usna, Sleeps 15 7BR+/4.5BA – Sleeps 15 – Annapolis #374363
  1
  $650- $1000/nt

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•   Walk to Just About Everything! Stay in Eastport! 2BR/1.5BA – Sleeps 4-5 – Annapolis #271903
  10
  $220-$250nt - 1400wk - $2700 mo

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•   Visit Annapolis and Stay in Charming Eastport 4BR+/2.5BA – Sleeps 8-10 – Annapolis #373566
  2
  From $400/nt

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•   Annapolis Vacations, Getaways or Touring Dc 3BR+/3.5BA – Sleeps 6-8 – Annapolis #122383
  10
  $500 per night 3 night min stay

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•   Annapolis Area Waterfront Home on South River and Chesapeake 3BR+/3BA – Sleeps 6 – Annapolis #68630
  15
  $1500- $2000/wk

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•   Beautiful Waterfront Home in Prestigious Lindstead Community. 4BR+/3.5BA – Sleeps 8-10 – Annapolis #336337
  5
  $ 350 - $ 900/nt

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•   Waterfront Relaxing Retreat in Annapolis Area 3BR+/3.5BA – Sleeps 8-10 – Annapolis #432131
  10
  $375 per night 3 night min stay

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•   Waterfront Accommodations - on the Water ! 2BR+/1BA – Sleeps 4 – Annapolis #202132
  5
  From $200/nt

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•   Water Access 7 Bedrooms, Sleeps 8-20, Modern 38' Boat 7BR+/3.5BA – Sleeps 15-20 – Annapolis #334363
  2
  $800 per night 2 night min stay

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•   Spectacular Home - Walk to Downtown Annapolis ! 4BR+/3.5BA – Sleeps 10-13 – Annapolis #253868
  18
  $450-$650/nt-

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•   Beautiful Home in the Heart of Eastport 2BR+/2.5BA – Sleeps 6 – Annapolis #370192
  1
  $425 per night 2 night min stay

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•   Still Available - Commissioning Week 2013! 4BR+/2.5BA – Sleeps 8-10 – Annapolis #197979
  0
  $395/nt

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•   Elegant and Convenient Waterfront Carriage House Apartment 1BR+/1BA – Sleeps 4 – Annapolis #215151
  1
  $150 - $200 per night 3 night min stay

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•   Annapolis Waterfront Home with a Private Pool & Dock 3BR/2BA – Sleeps 6-8 – Annapolis #470943
  0
  $500 per night 3 night min stay

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•   Waterfront Estate with Dock - Annapolis, Md - New Listing for Summer 2013! 5BR/5.5BA – Sleeps 12-16 – Annapolis #471735
  0
  $7210 per week 7 night min stay

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•   Waterman's Cottage in Annapolis 2BR+/1.5BA – Sleeps 4-6 – Annapolis #191110
  0
  $250/nt - $1750/wk

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•   Beautiful Condo-Water View Near City Dock 1BR+/1BA – Sleeps 2-4 – Annapolis #314894
  13
  $150 per night 2 night min stay

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•   Annapolis Luxury, Convenience and Family Friendly! Usna Events & More! 5BR+/2.5+BA – Sleeps 11-13 – Annapolis #430593
  1
  $800 per night 3 night min stay

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•   The Best of Historic Annapolis is Right Outside Your Door! 3BR+/2.5BA – Sleeps 6-8 – Annapolis #140886
  9
  $325- $475/nt

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•   Waterfront 5BR Home - Annapolis/Severna Park 5BR/3.5BA – Sleeps 11-12 – Annapolis #64039
  1
  $2300- $2800/wk

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•   Annapolis Chesapeakebaycharmer Sleeps 14+ on 3 Lvls W 3.5baths 5BR+/3.5BA – Sleeps 12-16 – Annapolis #370852
  2
  $650 per night 2 night min stay

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•   Annapolis Cove 6 Bed 5 Bath - Usna Commissioning 2014 6BR+/5BA – Sleeps 10-14 – Annapolis #247531
  0
  $7490 per week 7 night min stay

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•   Comfortable Timber Frame Deep Waterfront Home in Annapolis 3BR/2BA – Sleeps 2-6 – Annapolis #369980
  15
  $575/weekend and up , date dependant

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•   Historic District - 1 Block to Naval Academy & State House 2BR+/1.5BA – Sleeps 4-6 – Annapolis #209767
  5
  $275/nt

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•   Annapolis - Eastport House, Walk to Everything 3BR+/2.5BA – Sleeps 6-8 – Annapolis #100673
  0
  $450/nt

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•   One Block from the Naval Academy Entrance!! Historical Annapolis!! 3BR/2.5+BA – Sleeps 8 – Annapolis #989211ha
  0
  $450 per night 2 night min stay

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•   Commissioning Week 2014 Available! Family-Friendly. 2BR/1BA – Sleeps 8-10 – Annapolis #465773
  1
  $300 - $325 per night 2 night min stay

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•   Lovely Artists Townhouse Style Apartment Eastport-Annapolis 1BR+/1BA – Sleeps 4 – Annapolis #90263
  0
  From $175-325/nt - 800/wk - $2000/mo

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•   Waterfront Post and Beam New Environmentally Friendly Home 3BR+/3BA – Sleeps 8-10 – Annapolis #339058
  6
  From $150/nt

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•   On the Water in Annapolis - Close to Navel Academy 2BR+/1.75BA – Sleeps 4-6 – Annapolis #243941
  0
  $1250- $2400/wk

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•   Quiet, Relaxing Waterfront Suisse Chalet with Dock for Boats 3BR+/2.5BA – Sleeps 8 – Annapolis #905951ha
  5
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•   Navy Grads 2013 Best Location- Directly Across from Navy Stadium! 3BR+/2BA – Sleeps 8-10 – Annapolis #204368
  0
  $500/nt

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•   Annapolis Waterfront/Beach/Pool (June 2013 Dates Still Available!) 7BR+/7.5BA – Sleeps 12-14 – Annapolis #394973
  2
  $4,550- $6,300/wk

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•   Gorgeous Remodeled Home in Water Access Community with Screened Deck!! 3BR+/3BA – Sleeps 8-12 – Annapolis #379471
  0
  $3,000 - $4,500/wk, $2,000/wknd

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•   Perfect for Family Gatherings in Annapolis, Md! Book Now for Summer! 6BR/4.5+BA – Sleeps 14 – Annapolis #442815
  0
  $950 per night 3 night min stay

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•   Secluded Waterfront Home Minutes from Down Town Annapolis 3BR+/2.5BA – Sleeps 6-12 – Annapolis #378636
  1
  $400/nt

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•   Near Annapolis - Chesapeake Bay/Kent Island Waterfront Cottage 4BR/1.5BA – Sleeps 8-10 – Annapolis #75876
  10
  $1100- $1925/wk

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•   Our Home on the Cove: Waterfront, Peaceful, Wooded, Comfy, Family Friendly 5BR+/2BA – Sleeps 15 – Annapolis #33145
  10
  $350 - $407 per night

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•   Elegant and Luxurious Home Facing the Annapolis Harbor 5BR/4.5BA – Sleeps 10 – Annapolis #55453
  0
  $1043 - $1050 per night

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•   Charming Spacious Eastport Home Easy Walk to Everything 3BR+/3BA – Sleeps 8 – Annapolis #60381
  0
  $385 per night 2 night min stay

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•   Large Contemporary in Wooded Privacy 5BR+/3.5BA – Sleeps 10-12 – Annapolis #82464
  35
  From $450+/nt - $2800/wk

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•   Walk/Boat Show, Downtown, Yacht Clubs, Capital, Naval Academy 2BR/1.5BA – Sleeps 6 – Annapolis #199140
  8
  $325/nt - $2100/wk

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•   Cute Waterfront Cottage with Beach - Winter Rate is Only $750 Per Week 2BR+/2BA – Sleeps 4-7 – Annapolis #86077
  10
  $750- $1,750/wk

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•   Downtown Annapolis... Steps from City Dock!! 4BR+/3BA – Sleeps 8-10 – Annapolis #270585
  3
  $450 - $550 per night 2 night min stay

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•   Charming Cottage Near Navy Marine Corp Stadium in Annapolis 1BR/1BA – Sleeps 2-4 – Annapolis #400862
  9
  $165 per night 1 night min stay

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•   Victorian Home in Heart of Historic Annapolis 5BR/3.5BA – Sleeps 10 – Annapolis #198133
  4
  $1100/nt

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•   Downtown Historic District Apt; Pool / Nicest Street Downtown 1BR+/1BA – Sleeps 2-3 – Annapolis #393178
  10
  $149/nt (3 nt min) $745/wk / $1,975./mo

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•   The Yellow Cottage on Harness Creek 2BR+/1BA – Sleeps 4-6 – Annapolis #300511
  29
  $175- $225/nt

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•   Recently Renovated Annapolis Historic District Apartment 1BR+/1BA – Sleeps 5 – Annapolis #422800
  7
  $175 per night 1 night min stay

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•   Walk to Naval Academy Stadium, Only 1.5 Mile to City Dock 2BR+/2BA – Sleeps 4 – Annapolis #325410
  6
  $350/nt - $950.00 wknd $1750/wk

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•   Recently Renovated Annapolis Historic District Apartment 1BR+/1BA – Sleeps 5 – Annapolis #435647
  6
  $175 per night 1 night min stay

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•   Family-Friendly Beachfront Home on Chesapeake Bay 4BR/2BA – Sleeps 6 – Annapolis #467482
  0
  $325 - $550 per night 3-5 night min stay

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•   2014 Commissioning Week Open! Private Setting on Private Road 3BR+/2BA – Sleeps 8 – Annapolis #137636
  0
  $300- $700/nt

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•   Beautiful Annapolis Home with Water-Access! Minutes to Downtown 4BR/2.5BA – Sleeps 9 – Annapolis #440780
  2
  $500 per night 2 night min stay

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•   Perfect Annapolis Home for Football Games or a Holiday Weekend! 4BR+/2.5BA – Sleeps 7-9 – Annapolis #436066
  0
  $500 per night 1-3 night min stay

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•   Memorial Day Specials Available!!! Peaceful 3BR House on Oyster Creek W/ Amazing Views of the Chesapeake Bay 3BR/3.5BA – Sleeps 9 – Annapolis #3537177ha
  0
  $214 - $1200 per night

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•   Commissioning Week Property Walking Distance to Navy Stadium 3BR/2BA – Sleeps 8 – Annapolis #449253
  0
  $3108 per week 7 night min stay

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•   Beautiful Waterfront Townhome in Historic Annapolis 3BR/3.5BA – Sleeps 8-10 – Annapolis #452191
  0
  $475 per night 2 night min stay

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•   Annapolis/Waterfront 4BR/3.5BA – Sleeps 10-12 – Annapolis #454732
  0
  $675 - $975 per night 5 night min stay

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•   Family Friendly Home in Quiet Community Close to Downtown Annapolis 4BR/3.5BA – Sleeps 7-12 – Annapolis #454353
  0
  $500 per night 2 night min stay

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•   In the Heart of Downtown, One Block to City Dock 1BR+/1BA – Sleeps 5 – Annapolis #3021341ha
  0
  $101 - $250 per night 2-30 night min stay

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•   Fantastic Annapolis Eastport Rental - Available for 2013 Comm'G Week! 3BR+/3.5BA – Sleeps 6-8 – Annapolis #229757
  0
  $6000/wk

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•   Large Annapolis Waterfront Home with View's !! 4BR+/3BA – Sleeps 12-13 – Annapolis #305101
  0
  $450/nt - $3000/wk

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•   Large Annapolis Home Available for Weekly Rentals 3BR+/3BA – Sleeps 12-15 – Annapolis #437875
  0
  $4,000.00/week

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•   Luxury and Convenience - Minutes to Annapolis City Dock 4BR+/3.5BA – Sleeps 8-12 – Annapolis #307410
  4
  $1,000

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