Vacation Rentals by Owner

Eastern Shore Vacation Rentals Show this location only Back to top

•   Historic Waterfront Home in St. Michaels, W/Wi-Fi, Dock & Pet Friendly 4BR+/2.5BA – Sleeps 8 – St. Michaels #87481
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•   Premier One Level Waterfront Home with Pool, Dock, Every Amenity! 4BR/3BA – Sleeps 8 – St. Michaels #27321
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•   Bayberrycove-Private 11 Acre Waterfront, Pool, Dock, Hot-Tub, Beach 5BR+/4BA – Sleeps 12-15 – Cambridge #56245
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  $525 per night 2 night min stay

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•   1920's Restored Waterman's Cottage with Fantastic Views! 2BR/1.5BA – Sleeps 4 – Tilghman Island #57687
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•   Oceanblk 3story Townhome 56st: 7/6, 8/17 & 8/31 Weeks Remain 4BR/3.5BA – Sleeps 9-10 – #74428
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  $1000- $3600/wk

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•   A Cold Drink, a Waterfront Sunset in Hot Tub Deck 3BR/2.5BA – Sleeps 6 – Tilghman Island #78928
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•   Spectacular Corner Unit - Direct Waterfront Condo in Crisfield, Md 3BR/2BA – Sleeps 6 – Crisfield #187381
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•   Pool, Hot Tub, Big Water Views--What More Could You Ask for in a Cottage 3BR/3BA – Sleeps 7 – Tilghman Island #204687
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•   Ultimate Ocean City Condo-Ocean Front Boardwalk, Pool and More 3BR/3BA – Sleeps 10 – #182142
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  $1,650- $4,450/wk

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•   Luxury Waterfront Home, Sunsets, Pool, 2 Miles from Town Center! 5BR/4BA – Sleeps 10 – St. Michaels #231553
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•   Direct Oceanfront Condo - the Plaza - the Jewel of the Beach 2BR+/2BA – Sleeps 5-8 – #26409
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  $825- $2750/wk

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•   Water View Grande - Beautiful Spacious Condo on the Water 3BR+/2BA – Sleeps 8 – #48595
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  From $550/wk

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•   Water's Edge - Waterfront Living at its Best 5BR+/4.5BA – Sleeps 12 – #120730
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  $1785 - $3175 per week 2 night min stay

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•   You Can't Get Any Closer to the Shoreline Than This Townhome 4BR+/4BA – Sleeps 9-15 – #220552
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  From $ 249/nt - $995/wk- $1995/mo

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•   Stunning Beachside Condo 37th St. **Booking Fall Now** 2BR+/2BA – Sleeps 6 – #429895
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  $695 per week 3 night min stay

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•   Book 2013 Luxury Condo Affordable Rates Top Floor Sleeps 6 2BR+/2BA – Sleeps 6-8 – #395259
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  $249 per night 2 night min stay

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•   Recently Renovated Multi-Family Compound Outside Cambridge 7BR/5.5BA – Sleeps 22 – Cambridge #327216
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•   Luxury Ocean Facing 2 BR Condo,Slps 8,Indoor Pool,Walk 2 Beach 2BR+/2BA – Sleeps 6-8 – #413468
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  $113 per night 3 night min stay

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•   Ultimate Family Vacation Home! Pool, Dock, Games Barn, Hot Tub and More! 5BR/4BA – Sleeps 10 – St. Michaels #922712ha
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•   Luxurious 'Cottage by the Sea' Oceanfront Condo Spring Rate Sale! 3BR+/3BA – Sleeps 10 – #266539
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•   Renovated Waterfront Farm House on 25 Acres with Pool 4BR/3.5BA – Sleeps 10 – Cambridge #367564
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•   All Generations Hanging by Pool and Dock and Happy 7BR/7.5BA – Sleeps 22 – Cambridge #390476
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•   Beautiful 2 BR/2 BA on the Boardwalk in Ocean City, Maryland 2BR/2BA – Sleeps 6 – Ocean City #228008
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  $2996 per week 7 night min stay

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•   Updated Historic Sprawling Waterfront Estate Minutes to Oxford 5BR/3BA – Sleeps 10 – Oxford #327422
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•   Contemporary Cottage on Quiet Creek, Waterside Pool, Tranquil Views 3BR/2BA – Sleeps 8 – St. Michaels #391798
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•   2 Weeks Still Open in June - $2000 Off $6300/Week! 6BR/6.5+BA – Sleeps 12 – St. Michaels #284839
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•   Three Level Family Home Restored 1920s Colonial on 25 Acres, Dock, Pool 5BR/4.5BA – Sleeps 10-13 – Cambridge #390372
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•   Private Cottage Just Outside St. Michaels with Kayak and Bikes Included! 3BR/3BA – Sleeps 6 – St. Michaels #389515
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•   Bay View Condo, New Furnishings, Pool, Gym & Short Walk to the Beach 2BR+/2BA – Sleeps 7 – #401125
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•   Awesome Bayviews! Direct Bayfront Topfloor Condo Sleep6 2BR+/2BA – Sleeps 6-8 – #323184
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  From $159/nt - $1895/wk - $2000/mo

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•   Waterfront Retreat with Pool Located on Taylors Island 5BR+/2BA – Sleeps 12-14 – Cambridge #120352
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  $2200- $3600/wk

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•   Artist Beach Home, Gorgeous 4 BR+ with Dock Bay Front 4BR+/3BA – Sleeps 8-12 – #322773
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  $1290- $3290/wk

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•   Waterfront Getaway Cottage Near St. Michaels, Hot Tub, Kayaks 3BR/2BA – Sleeps 6 – St. Michaels #448997
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•   3 Free Kayaks to Explore the Bay Included 4BR/3BA – Sleeps 4-8 – Cambridge #421120
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•   Luxury Furnished Ocean View Condo for Your Next Vacation 3BR+/2.5BA – Sleeps 8-10 – #347546
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  From $1600 to $4390 a wk

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•   Elegant Ralph Lauren Waterfront Cottage Nr St Michaels 3BR/2BA – Sleeps 6 – St. Michaels #410268
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  2000. wk. Call re: last minute wk ends

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•   Huge Ocean Block Condo – Wi-Fi, 2 Master Brs, Pool & Gr8 Views! 3BR+/3BA – Sleeps 10-12 – #391476ha
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•   Thistle Dew - Will Do!! Waterfront, Pool, Decor, Location 4BR/3BA – Sleeps 8 – St. Michaels #449007
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•   Friends & Family "Crash Pad" - Views, Pool, Kayaks, Bikes, Firepit & More 4BR/3BA – Sleeps 8 – St. Michaels #449003
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•   Ocean City Rental Ocean View Across from Seacrets , 5BR/3BA – Sleeps 12-14 – #399328
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  FROM 2200 A WEEK

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•   1 Block to Boardwalk, Beach, Down Town, Spacious 3 BR / 2 BA 3BR/2BA – Sleeps 4-8 – #397746
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  $2995 Per wk

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•   1,000 Off Full Week $3,900 Rental in May and June! 6BR/5.5BA – Sleeps 14 – St. Michaels #452636
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  $3906 per week 2 night min stay

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•   Wow! Secluded Waterfront Home on Maryland's Charming Eastern Shore 4BR/3.5BA – Sleeps 8 – Centreville #458295
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  $3500 per week 3 night min stay

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•   Special $1,000 Off May and June Weeks 4BR/3BA – Sleeps 8-10 – St. Michaels #454608
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  $3899 per week 2 night min stay

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•   Oceanfront - Boardwalk - 25th Street - on the Quiet North End 2BR+/2BA – Sleeps 8 – #224048
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  $500/3nts - $1050- $1975/wk

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•   Townhouse on the Water Bring Your Boat or Jetski All Ameniti 1BR+/1.5BA – Sleeps 6 – #397928
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  From $95/nt. or $595/wk. to $995/wk.

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•   Beach & Boaters Paradise 4BR/3BA – Sleeps 9-12 – Ocean Pines #448166
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  $225 per night 7 night min stay

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•   Charming Island Home on Chesapeake Bay with Great Water Views 3BR/2BA – Sleeps 6 – Tilghman Island #364943
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  $1225 per week 3 night min stay

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•   The Point of it All-Near Annapolis, Washington D.C., Baltimore 6BR/6BA – Sleeps 14 – Stevensville #447255
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  $6475 per week 7 night min stay

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•   Elegant 3,000-Sqft Oceanfront W/ Jacuzzi — Featured in Coastal Style 3BR+/3.5BA – Sleeps 8 – #3509574ha
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•   Oceanfront Perfection! Huge Luxury Condo W/ Wi-Fi & Pool (60th St) 4BR+/3.5BA – Sleeps 10-12 – #3530540ha
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•   Bradley on the Bay - Bay View Condo - Ocean City, 37th Street 2BR+/2BA – Sleeps 6-8 – #102156
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  $1120 per week 7 night min stay

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•   Waterfront 3 Bedroom Home, Short Walk to Beach, Boat Dock! 3BR+/2BA – Sleeps 8-12 – #219559
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  $2205 per week 7 night min stay

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•   3/2 Hse-3 Blks to Bch*Reserve Your Private Beach House Today! 3BR/2BA – Sleeps 6 – #43272
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  $650- $1000/*3 NIGHT MIN*

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•   Waterfront-Walk to Beach-2BR/2BA - Boat Slip - Newly Listed!!! 2BR/2BA – Sleeps 6 – #351968
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  $850 per week 2 night min stay

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•   Oceanblock 3-Story Townhome with 2-Car Garage at 56th Street 3BR+/3.5BA – Sleeps 6-10 – #130524
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  $200 - $400 per night 2 night min stay

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•   Total Privacy and Relaxation! 90 Acre Waterfront Farm with Wraparound Views 4BR/2BA – Sleeps 6-8 – St. Michaels #146900
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•   Beautiful Single Family Home-Walk to Beach!! 3BR+/3BA – Sleeps 10-12 – #235475
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  $150 per night 3 night min stay

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•   Beautiful Oceanfront Condo - 137th St 2BR/2BA – Sleeps 6 – #82387
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  $1795- $1995/wk Summer

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•   Memorial Day Wknd $1500 * 6/1 Thru 6/8 Open * 8/24 Thru 8/31 Open * Bike wk Open 3BR+/2BA – Sleeps 6-8 – #357255
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  $300 - $400 per night 7 night min stay

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•   St. Michaels Waterfront-7BR-Indoor Pool-Dock 7BR+/5BA – Sleeps 2-14 – St. Michaels #25129
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  $5500 per week 2 night min stay

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•   Sunset Island at 67th Street Townhome for Rent 5BR+/3.5BA – Sleeps 12 – #130267
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  $399-$799/wknd - $1399-$3299/wk

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•   5 BR Bay Front Townhouse in Sunset Island- June Special-20%0ff-Only 2 Weeks Left 5BR+/3.5+BA – Sleeps 9-12 – #58473
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  $175 a night- $495 a night

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•   Townhouse in the Heart of Ocean City, Md. Located on 69th St. 3BR/2.5BA – Sleeps 6 – #181864
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  $1715 per week 3 night min stay

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•   100%Oceanfront, Jacuzzi Over Ocean, Fireplace, 2 Heated Pools, 3BR/2BA – Sleeps 13 – #83999
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•   1940's Sears Cottage in Village 2BR/1BA – Sleeps 4 – Oxford #215987
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•   Beautiful Beachfront Penthouse with Pool - Perfect Location! 2BR+/2.5BA – Sleeps 8 – #61373
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  $1195 - $2295/wk

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•   Beautiful Refinished Ocean Front Condo Beautiful Sunrises 3BR/2BA – Sleeps 10-12 – #270461
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  $165nt- $3090/Wk

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•   Your Vacation Paradise!!Pets Welcome!! Off Season Weekends 2BR+/2BA – Sleeps 6-8 – #56554
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  $395/wknds - $1150- $2100wk

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•   Totally Refinished Direct Ocean Front Condo with Ocean View 3BR+/2BA – Sleeps 10-12 – #341958
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  From$175/nt to $3190 wk

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•   Waterfront, Stylish, Historic Retreat 2BR/2BA – Sleeps 3-4 – Chestertown #328116
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  $1099 per week 2 night min stay

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•   Premier Waterfront Vacation Home/St. Michaels (August Availability) 4BR/4BA – Sleeps 8 – St. Michaels #432739
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  $2200 per week 3 night min stay

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•   Beautiful Four Bedroom Home on Quiet Cul De Sac 4BR+/2BA – Sleeps 8-10 – Ocean Pines #356697
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  $200 - $350 per night 2 night min stay

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•   Luxury Bayfront 2 BR Condo,Sleeps 8,Indoor Pool,Walk to Beach 2BR+/2BA – Sleeps 6-8 – #401145
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  $113 per night 3 night min stay

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•   Serenity Acres - Waterfront, 23 Private Acres, Dock & Pool 4BR+/3.5BA – Sleeps 13-17 – Cambridge #81628
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  $3700/wk

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•   Oceanfront 'Terrific' - Available: 5/31-6/7-Be Our Guest ! 2BR/1BA – Sleeps 6 – #327730
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•   3BR/3.5b 1 Block T-T Beach in & Outdr Pools & W/Wi-Fi 3BR/3.5BA – Sleeps 4-7 – #64477
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  $1300- $2,500/wk

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•   Bayside Resort - Beaches, Golf, Tennis & More! 5BR/4.5BA – Sleeps 12 – #79960
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•   Beautiful 3BR/3 Full BA Builders Model Condo Near Beach 3BR+/3BA – Sleeps 8-10 – #315402
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  $2900 per week 2 night min stay

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•   Awesome Waterfront Beachouse W/Pool&Dock Summer up to 50% Off! 3BR+/3BA – Sleeps 6-12 – #226097
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  $400 per night 2 night min stay

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•   Exquisite Water-Front Chesapeake Bay Home Near Chesapeake City 3BR+/3.5BA – Sleeps 8-10 – Chesapeake City #319105
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  From $595/nt

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•   The Quay 3BR/2BA Direct Ocean Front – Stunning View of Ocean 3BR+/2BA – Sleeps 6-8 – #299134
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  $175/nt - $895- $2850/wk

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•   Oceanfront Paradise Getaway 2BR+/2BA – Sleeps 6-8 – #54340
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  From $425/wknd - $1200-$1800/wk

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•   Lovely Spacious 3 BR Condo - 88th St - 100 Feet to the Beach 3BR/1.5BA – Sleeps 8 – #413073
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  $1785 per week 7 night min stay

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•   Isabella- a Beautiful Townhouse on 1st St., Near B.W. & Ocean 3BR+/3.5BA – Sleeps 6-10 – #158951
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  From $200/nt - $1095/wk

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•   18th Street- Great Location 300 Ft to the Beach and Boardwalk 3BR+/2BA – Sleeps 7-10 – #270928
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  $900- $2000/wk

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•   Crab & Fish on Your Dock in the Seafood Capital of the World. 3BR/3BA – Sleeps 6-8 – Crisfield #64731
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  $250/nt- $1400/wk

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•   Exclusive Chesapeake Bay 250-Acre Estate - Beach,Pool,Dock 11BR+/7.5BA – Sleeps 34 – Cambridge #15537
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  $3500- $7350/wk

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•   Adorable Cottage in Heart of Oxford, Walk to Park, Great Family Spot 3BR/2BA – Sleeps 6 – Oxford #327397
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•   Spectacular Ocean Front!! 2013 Weekly or Mini Weeks Available 2BR+/2BA – Sleeps 4-8 – #158087
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  $700- $1950/wk

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•   Luxury Townhouse Downtown Ocean City! (2nd Street) 3BR+/3.5BA – Sleeps 9 – #182374
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  $100-$350/nt - $700- $2500/wk

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•   Spectacular Waterfront Family Vacation Home -- Views! 6 BR, 5.5b 6BR/5.5BA – Sleeps 14 – #223085
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  $3400- $5400/wk

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•   Chesapeake Bay Nature-Oriented Recreation & Repose 3BR+/2BA – Sleeps 5-6 – Cambridge #224776
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  $200/nt - $550/wknd - $1200/wk

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•   Waterfront Farm with Pool, Private Dock and Kayaks 4BR/4BA – Sleeps 8 – Chestertown #410328
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  $3500 per week 2 night min stay

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•   St. Michael's Premier in-Town Summer Vacation Cottage! 2BR+/2BA – Sleeps 4 – St. Michaels #296266
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  $235-$260/nt and $1400-1600 wkly

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•   Oceanblock 4 BR Townhome /Pool/Ocean View! Off Season Weekends 4BR/3.5BA – Sleeps 10 – #283290
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  $1850- $3850/wk

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•   Fantastic Location & Views, Beach Steps Away, 1 BR/1.5 BA 1BR+/1.5BA – Sleeps 4-6 – #304847
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  $450- $1100/wk

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•   Direct Oceanfront on the Boardwalk! Great Family Vacation Home! 3BR+/2BA – Sleeps 6-8 – #229013
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  $875- $2325/wk

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•   30th St Great Location 150 Yards to the Beach 3BR+/2BA – Sleeps 8-10 – #354056
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  900- 1900wk

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•   Heron Cove *Private Family Retreat* Summer $4000/wk 7BR+/5BA – Sleeps 14-20 – St. Michaels #89088
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  $4000/wk

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