Vacation Rentals by Owner

Eastern Shore Vacation Rentals Show this location only Back to top

•   Our Porch is the Best Seat in Town 8BR/3.5BA – Sleeps 14 – #34166
  0
  $5800- $8300/wk

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•   Beautifully Decorated Th, 3 BR, 2 1/2 Bath, Tennis, Pool, Den 3BR+/2.5BA – Sleeps 6-7 – #163305
  0
  $1,200 - $1,895/wk

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•   Ocean Front 3 Bedroom Condo 3BR+/2BA – Sleeps 8 – #286435
  2
  $150 - $345 per night 2-7 night min stay

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•   Spacious Bay Front Home — Gr8 Views — Ez Walk 2 Pools & Private Beach! 4BR+/4.5BA – Sleeps 10-12 – #346859
  2
  $239-$499/night or $1195-$3795/week

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•   A Million Dollar View, Direct Bayfront, Luxury Home Pool, Hot Tub 4BR/3.5BA – Sleeps 12 – West Ocean City #456235
  0
  $1250 - $4500 per week 7 night min stay

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•   Ocean Block 2000+ Sqft Condo - Wi-Fi, Pool & Views - Ez Walk 2 Beach! 3BR/3.5BA – Sleeps 8 – #346624
  2
  $190-$459/3nt min - $950-$2995/wk

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•   Beautiful 3BR Condo, North Oc, Walk to Beach! Great Rates! 3BR/2BA – Sleeps 8 – #405476
  1
  From $800- $1425

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•   Stay Downtown on Boardwalk — Free Wi-Fi & Pool — Gr8 Bay & Inlet Views 2BR+/2BA – Sleeps 4-6 – #344893
  1
  $259-$530/night or $1295-$2650/week

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•   Gr8 Value Vacation – Ocean Block Condo W/ Pool – Walk 2 Beach! 2BR+/2BA – Sleeps 4-8 – #345523
  1
  $995- $1495/week

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•   Newly Renovated! Bayside 2bd/2BA Condo. Boat Slip Avail. Near Harbor Island. 2BR+/2BA – Sleeps 6 – #421141
  0
  From $130 per night

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•   Ocean Block, Ocean View - Ocean City, Md 2BR+/2BA – Sleeps 6 – #404433
  4
  In season from $1100 - $1400/wk Cash or check

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•   Oceanfront, One Block from North End of Boardwalk 2BR+/2BA – Sleeps 10 – #82593
  6
  $1500- $2000/wk

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•   Oceanfront 2BR Condo Ocean City ~ Sleeps 8 ~ 2nd Fl End Unit 2BR+/2BA – Sleeps 6-8 – #402708
  7
  From $840 - $1,680/wk

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•   Ocean City Getaway Close to Beach, Boardwalk and Bay 2BR+/1BA – Sleeps 7-9 – #38527
  9
  $400- $1300/wk

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•   Bayside Condo with Boat Slip and Close Walk to the Beach 2BR+/2BA – Sleeps 7-8 – #172514
  10
  $499- $1099/wk

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•   Ocean Block-Gorgeous, 2000 Square Foot W/Parking. Sleeps 14! 4BR+/4BA – Sleeps 14 – #51588
  4
  $2700- $4000/wk

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•   Luxury 4 Bedroom Vacation Condo W/ Private Beach 4BR/3.5BA – Sleeps 8 – Chester #417762
  4
  $1700 to $2100/ week

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•   3 BR Condo in Downtown-Few Summer Wks Left-Great Rates!! 3BR+/1BA – Sleeps 7-9 – #316706
  10
  $600 - $1375 wk

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•   Spacious Bay Front Home — Wrap-Around Balconies & Panoramic Bay Views 5BR+/4.5BA – Sleeps 12 – #352529
  0
  $2595- $5200/week

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•   Luxurious Ocean City, Maryland Vacation Home 4BR+/2BA – Sleeps 10 – Ocean Pines #364535
  9
  $1100- $1600 wkly inc cleaning

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•   Historic 1928 Cottage in Old Down Town Ocean City 2BR/1BA – Sleeps 4 – #471198
  2
  $756 - $1085 per week 7 night min stay

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•   Bay Front Home with Pool – Romantic Sunsets @ No Add'l Cost 2BR+/2BA – Sleeps 4-6 – #244592
  0
  $525- $1200/wk

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•   Five Star Direct Ocean Front Condo 2BR/2BA – Sleeps 4-6 – #283853
  13
  $120-$165/nt - $700- $2250/wk

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•   Fabulous Private 29 Acres and 2,000' Shoreline Yet You Can Bike to Village 3BR/2BA – Sleeps 6 – Oxford #449001
  9
  $222 - $423 per night

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•   Beautiful Oceanside Condo with Ocean View 3BR/3BA – Sleeps 10 – #424685
  2
  $300 - $500 per night 2-7 night min stay

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•   Ocean Front Condo - Weekly - Weekend & Mid-Weeks Also Available 3BR+/2BA – Sleeps 6-8 – #352328
  1
  $1,200 - $2,500 Saturday to Saturday

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•   Family Vacation Getaway 4BR+/3.5BA – Sleeps 10 – #294621
  5
  $1500- $2650wk

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•   Belmont Towers Beauty in the Heart of Ocean City 2BR+/2BA – Sleeps 10 – #393106
  13
  From $200/nt

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•   Spectacular - Ocean Front Townhouse - Midtown! 4BR/3.5BA – Sleeps 11 – #170266
  0
  $2500- $4950/wk

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•   Magnificent Waterfront Cottage on 5 Acres with Private Beach and Dock 3BR+/2BA – Sleeps 6 – Stevensville #409507
  8
  $400 nt

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•   Spacious 5 Bedroom Home Pet Friendly Family Vacation Pool Table 5BR/2.5BA – Sleeps 10-16 – Ocean Pines #467296
  0
  $1355 - $1550 per week 7 night min stay

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•   Luxurious Condo - Fitness Rm, Sauna, Outdoor Pool, Great Loc. 2BR+/2BA – Sleeps 6-8 – #80093
  6
  $125/nt - $750- $1600/wk

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•   Ocean Block Th, 3BR 2BA, Pet Friendly 3BR/2BA – Sleeps 8 – #420374
  2
  $104 - $242 per night 3 night min stay

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•   Great Location in Ocean City Maryland 2BR+/2BA – Sleeps 4-6 – #394818
  0
  $1000- $1500 wk

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•   Perfect Blend-Oceanfront/Boardwak/ Location & Exquisite Luxury 3BR/3BA – Sleeps 10 – #194047
  0
  $1900- $4100/wk

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•   Charming, Family-Friendly, Beach-Town Cottage 3BR/2BA – Sleeps 9 – Ocean Pines #472922
  0
  $170 per night 6 night min stay

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•   Ocean City Condominium 2BR+/2BA – Sleeps 8 – #39371
  1
  $900- $1400wk

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•   Stunning 2BR/2BA Condo - Spectacular Views, Remodeled/Everything New 2BR/2BA – Sleeps 6 – North Ocean City #466285
  0
  Rates from $620/wk - $1645/wk

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•   4 Bedroom + Loft Oceanfront Townhouse W/Pool, June 2-8 is Open/Price Just Cut 4BR+/3BA – Sleeps 12 – #398894
  0
  $286 - $686 per night

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•   Tilghman Island Waterfront Home - Views of Historic Skipjacks 4BR+/2.75BA – Sleeps 8-10 – Tilghman Island #43781
  0
  $250nt - $1000- $1500/wk

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•   3 Bedroom Home in Quiet Montego Bay Community of Ocean City 3BR+/2BA – Sleeps 6-8 – #171717
  0
  $160/nt - $1100/wk Seasonal

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•   3 Bedroom Cottage Close to Ocean City, Md 3BR+/1BA – Sleeps 6-8 – Berlin #394272
  0
  $625 - $750

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•   Oceanfront Townhouse, Ocean City Maryland. 3 BR 3BR/3BA – Sleeps 10 – #237249
  2
  $1400- $3200/wk

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•   Beautiful Ocean Condo 3BR+/3BA – Sleeps 10-12 – #319498
  1
  $1500- $2950/wk

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•   Luxury Oceanside Townhouse with Swimming Pool 4BR+/3.5.5BA – Sleeps 14 – North Ocean City #435883
  2
  $1200-$3500/wk - $900-$1500/wkend

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•   Eastern Shore Waterfront Estate, Private Beach, Deep Water 8BR/6.5BA – Sleeps 16-18 – Oxford #196387
  0
  $25/wk; offseason $490-$700/nt Dollars

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•   Vacation Home - Enjoy Peace and Quiet Time.... 4BR/2BA – Sleeps 9 – Ocean Pines #121742
  0
  $550- $1075/wk

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•   1/2 Block to White Sand Beach, 78th Street Ocean Block 2BR+/2BA – Sleeps 6 – #335321
  16
  $95/n - $900 - $1025 per wk

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•   Waterfront Townhouse Views, Views, Views in Prestigious Heron Harbour 3BR+/3.5BA – Sleeps 8 – #445417
  0
  $2555 per week 7 night min stay

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•   Fully Renovated, Bayfront, Sunset, Pool, 1 Blk to Beach, View! 2BR/2BA – Sleeps 6 – #392678
  2
  From $600- $1500/wk

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•   Contemporary Upscale Direct Oceanfront Condominium 2BR+/2BA – Sleeps 7 – #419375
  7
  $2090 - $2530 per week Dollars

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•   Beautiful View of the Ocean and Bay - Steps from the Ocean 2BR+/2BA – Sleeps 4-6 – #131426
  5
  $100-$135/nt - $1600/wk

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•   4 Bedroom 2 1/2 Bath Ocean Front Townhouse with Outdoor Pool 4BR/2.5BA – Sleeps 10-12 – #217020
  0
  $1295- $4200/wk

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•   Ocean Views and Steps to the Beach 2BR+/1BA – Sleeps 4-6 – #165278
  0
  $ 1400/week with taxes included.

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•   Waterfront Luxury Condo 3BR/2BA – Sleeps 6-7 – Crisfield #357989
  1
  $900- $1150

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•   Beautiful Oceanfront Condominium in N. Ocean City, Maryland 1BR+/1.5BA – Sleeps 4 – #125829
  1
  $316- $925/wk

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•   Pretty 2BR, 2BA Condo in Well Appointed Oceanfront Building 2BR/2BA – Sleeps 8 – #420378
  0
  10.5

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•   Newly Renovated Oceanfront Sea Watch Condo 3BR/2BA – Sleeps 7 – #184592
  3
  From $1195 - $2200/wk

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•   5 BR Bayside Townhouse End Unit in Sunset Island - New Rental! 5BR/4BA – Sleeps 8-10 – #450001
  0
  200 - 3550 night - week

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•   Newly Remodled, Great Amenities on Site,1 1/2 Blocks to Beach 2BR+/2BA – Sleeps 4-6 – #396812
  2
  $700.00 - $1450/wk

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•   Penthouse Renovated- 2 Levels - Quay 2504 - Direct Oceanfront Bld 3BR+/2.5BA – Sleeps 12 – #423444
  1
  2100.00 - $3600.00 per week

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•   Dream 3-Level Bayside Townhome- Only a Few Weeks Left!! 4BR+/3.5BA – Sleeps 10-12 – #405184
  1
  $1,600 to 2,300/wk

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•   Waterfront Condo Bayside Overlooking Serene Sanctuary Preserve 3BR/2BA – Sleeps 6 – #338519
  0
  From $1000- $2000/wk

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•   Oceanfront Condo - Book Early to Get the Week You Want! 3BR+/2BA – Sleeps 6-8 – #136058
  5
  $1200- $2425/wk

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•   Beautiful Ocean Block 3 BR W/2 Car Garage Overlooking Pool 3BR+/3.5BA – Sleeps 6-8 – #168337
  1
  $850- $3500/wk

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•   Luxury Bayside Condo with Pool and Spectacular Views 3BR+/2.5BA – Sleeps 6-10 – #401716
  11
  $225 - $370 per night 3-7 night min stay

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•   Ocean Block Condo – Indoor/Outdoor Pools – Easy Walk 2 Beach 2BR+/2BA – Sleeps 7-9 – #389701
  2
  $795 - $1895/Week

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•   Big Beach Block Home – Wi-Fi, Hi-Def Cable & Balcony W/ Ocean Views 5BR/4.5BA – Sleeps 14 – #305858
  3
  $1995- $4995/week

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•   Ocean Front Family-Friendly Condo on the Beach 3BR/2BA – Sleeps 8-9 – #458082
  0
  $2450 per week 7 night min stay

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•   Perfect Oceanfront Family Getaway 2BR/2BA – Sleeps 6 – #395022
  4
  $900- $1,995/wk

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•   Our Place on the Bay - Boating, Fishing, Swimming, Sunsets 2BR+/2BA – Sleeps 6 – #288140
  4
  $750- $1300/wk

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•   3BR/3BA Condo-Indoor Pool - Ocean View - Sleeps 8 - 10. 3BR+/3BA – Sleeps 10 – #114755
  4
  $600- $2400/wk

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•   Gorgeous Direct Bay Front, Close to Beach, New Gourmet Kitchen! 2BR+/2BA – Sleeps 5-7 – #350205
  9
  From $750 to $1400 wk

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•   Guest Favorite- Vacation Home - Minutes from the Beach & Fun 3BR+/2BA – Sleeps 8-10 – Ocean Pines #102554
  4
  $650- $1395/wk

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•   Ocean Front, Spectacular View, up to Date, More 2BR+/2BA – Sleeps 6-10 – #405597
  0
  In season 100- 400/nt, 750-2850/wk

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•   A Perfect Ocean City Bayside Retreat for a Perfect Vacation! 2BR+/2BA – Sleeps 9 – #418511
  1
  Rates vary & range from 850 -1200

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•   Georgeous Oc Townhouse on the Canal in North Ocean City. 3BR+/2.5BA – Sleeps 8 – #404613
  6
  From $135- $185/nt or $850-$1750/wk

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•   Coconut Malorie Resort Ocean City Md 1BR/1BA – Sleeps 4 – #982672ha
  0
  $150 - $200 per night

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•   Water View Condo in the Heart of Rock Hall's Waterfront 2BR/2BA – Sleeps 3-5 – Rock Hall #445394
  0
  $325 per night 2 night min stay

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•   Direct Oceanfront W/Pool - 74th St - Beautiful Views!! 1BR+/1BA – Sleeps 6 – #257112
  12
  From $90/nt.

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•   Direct Oceanfront Penthouse 3BR+/2BA – Sleeps 8 – #394371
  0
  $450 per night 2 night min stay

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•   Oceanfront 3 BR Condo in Carouselhotel-Family Friendly 3BR+/2BA – Sleeps 9-10 – #341192
  5
  $150-$300/nt - $700- $3000/wk

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•   Ocean Front at 127th 2BR+/2BA – Sleeps 7-8 – #101325
  3
  $500- $1600/wk

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•   Eastern Shore Waterfront Estate, Private Beach, Deep Water 8BR/6.5BA – Sleeps 16 – St. Michaels #235779
  0
  $2,500- $6,800/wk

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•   Oceanfront! 2BR/2BA – Sleeps 8 – #395450
  5
  $129 - $329 per night

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•   Dog-Friendly Home – 10 Minutes from O.C.M.D. – Golf, Marina & Pools! 3BR+/2BA – Sleeps 6-8 – Ocean Pines #403225
  2
  $150-$250/night or $700-$1400/week

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•   Eastern Shore Cambridge Secluded Waterfront Home with Pool 4BR/2.5+BA – Sleeps 8 – Cambridge #403317
  1
  $575 per night 4 night min stay

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•   Close to Beaches, Shopping and Casino Wi-Fi and Cable 2BR+/1BA – Sleeps 4-5 – Berlin #394252
  0
  550.00- 600.00/wk

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•   Ocean Front Luxery 2BR/2BA Condo Indoor Pool $1,950 wk 2BR+/2BA – Sleeps 6-8 – #362279
  0
  $1950 per week 7 night min stay

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•   Beautiful Oceanfront Condo in Breakaway East ! 2BR+/2BA – Sleeps 4-6 – #344417
  0
  $1750 per week 7 night min stay

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•   Oceanfront Condo in North Ocean City at 127th Street 2BR+/2BA – Sleeps 4-6 – #308508
  2
  $650- $1500/wk

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•   Ocean City Townhome - 3 Blocks to Beach with Yard and Deck 3BR+/2.5BA – Sleeps 8-10 – #395023
  1
  $150/nt or wekly rate

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•   Assateague Pointe Cottage!!$80-180nt- Beautiful! 2pools/Private Home 2BR+/1BA – Sleeps 8 – #358066
  1
  $ 80- 180.00. nt SPRING -SUMMER !

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•   Newly Renovated, Ocean Front Condo on 7th Floor. Free Wifi. 1BR+/1BA – Sleeps 2-4 – #357302
  0
  From $130 per night US Dollars only

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•   Beautiful Luxury Townhome Walking Distance to Beach and Boardwalk 3BR+/3.5BA – Sleeps 8-10 – #402968
  1
  From $200/nt and $1095/wk

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•   Luxurious, Ocean Blk, Gr8 Price, Gr8 View, 2 Master Bedrooms 3BR+/3BA – Sleeps 10 – #309496
  2
  $700-900/nt - $1600- $4500/wk

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•   Hop, Skip, or Jump to the Beach!! Studio/1BA – Sleeps 2 – #455222
  0
  $125 - $150 per night 2 night min stay

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•   Ocean Front Beautiful 2 BR/2 BA Condo - No Stairs to Climb! 2BR+/2BA – Sleeps 6 – North Ocean City #287770
  5
  $1550- $1755/wk

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•   Ocean View Townhouse 3BR+/2BA – Sleeps 6-8 – #159545
  0
  $1500- $1750/wk

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•   Waterfront Cottage with Pier, Pool and Amazing Sunsets 3BR+/1BA – Sleeps 8 – Rock Hall #440251
  0
  $300 per night 3 night min stay

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