Vacation Rentals By Awesome.

Maryland Vacation Rentals - 868 Properties

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Good morning Baltimore! Home of the Baltimore Ravens and the Chesapeake Bay, Maryland is an absolutely gorgeous place to vacation no matter what time of year. Visit some of the most beautiful beaches and breathtaking mountains in the country, or enjoy some live theatre and some o' Maryland's famous blue crabs. Whatever tickles your fancy, RedAwning has the vacation rental for you. Browse your favorite Baltimore region using the blue location links below, or filter your preferences using the panel on the side. With our simplified booking process you'll have the most important part of your trip buttoned in no time.

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  1. Hidden Harbour 179U
    Hidden Harbour 179U

    Sleeps 8, $145 to $305/night

    City : Ocean City
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Retreat in this 2BR, 2BA condo overlooking the canal in the Hidden...

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  2. OF Villas on Boardwalk 105
    OF Villas on Boardwalk 105

    Sleeps 11, $495 to $930/night

    City : Ocean City
    Bedrooms : 3
    Bathrooms : 2

    As you drive over the Route 50 bridge and see the gateway to Ocean...

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  3. OF Villas on Boardwalk 109
    OF Villas on Boardwalk 109

    Sleeps 11, $435 to $755/night

    City : Ocean City
    Bedrooms : 3
    Bathrooms : 2

    As you drive over the Route 50 bridge and see the gateway to Ocean...

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  4. Sun Spray 602A
    Sun Spray 602A

    Sleeps 8, $145 to $275/night

    City : Ocean City
    Bedrooms : 2
    Bathrooms : 2.5

    Two level townhouse on the canal witha boat dock. Lower level has a...

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  5. White Marlin 108B
    White Marlin 108B

    Sleeps 6, $155 to $410/night

    City : Ocean City
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Fantastic downtown OC location! Walk to the boardwalk and beach....

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  6. Seaway 5
    Seaway 5

    Sleeps 6, $140 to $240/night

    City : Ocean city
    Bedrooms : 2
    Bathrooms : 2

    Seaway 5 is a charming 2 bedroom, 2 bath ocean block condo that...

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  7. Outrigger I D
    Outrigger I D

    Sleeps 8, ~$200/night

    City : Ocean City
    Bedrooms : 3
    Bathrooms : 2.5

    Please note: Linens are not included with this property. Linens are...

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  8. Gateway Grand 909
    Gateway Grand 909

    Sleeps 6, $285 to $915/night

    City : Ocean City
    Bedrooms : 3
    Bathrooms : 3
    Pool

    Experience Ocean city the Grand way. Stunning oceanfront unit, with...

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  9. Gullway Villa 103
    Gullway Villa 103

    Sleeps 6, $130 to $215/night

    City : Ocean City
    Bedrooms : 2
    Bathroom : 1
    Pool

    Gullway Villa 103 is one of Ocean City's finest vacation rentals and...

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  10. Golden Sands 1505
    Golden Sands 1505

    Sleeps 4, $125 to $240/night

    City : Ocean City
    Bedroom : studio
    Bathroom : 1
    Pool

    Golden Sands 1505 is an airy, homey beachfront condominium. This...

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  11. Gateway Grand 314 (Side)
    Gateway Grand 314 (Side)

    Sleeps 10, $270 to $785/night

    City : Ocean City
    Bedrooms : 3
    Bathrooms : 3
    Pool

    Non-Smoking building, except for designated areas. Non-refundable...

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  12. Purnell House 104 (Side)
    Purnell House 104 (Side)

    Sleeps 10, $165 to $350/night

    City : Ocean City
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Enjoy this side unit in an ocean front building. Great location-...

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  13. Windjammer 205
    Windjammer 205

    Sleeps 2, $150 to $275/night

    City : Ocean City
    Bedroom : studio
    Bathroom : 1
    Pets OK

    The Windjammer offers that wonderful retro Ocean City feel. This...

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  14. Windjammer 204
    Windjammer 204

    Sleeps 5, $170 to $355/night

    City : Ocean City
    Bedroom : 1
    Bathroom : 1
    Pets OK

    The Windjammer offers that wonderful retro Ocean City feel. This 1...

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  15. Windjammer 303
    Windjammer 303

    Sleeps 6, $235 to $435/night

    City : Ocean City
    Bedrooms : 2
    Bathroom : 1

    The Windjammer offers that wonderful retro Ocean City feel. This 2...

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  16. Top Royal 404-S
    Top Royal 404-S

    Sleeps 6, $130 to $220/night

    City : Ocean City
    Bedroom : 1
    Bathroom : 1.5
    Pool

    Top Royal 404-S is a homey condominium located on the ocean block....

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  17. Irene 1607- Ocean City Condo
    Irene 1607- Ocean City Condo

    Sleeps 8, $165 to $670/night

    City : Ocean City
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Just Listed! You will be impressed as soon as you open the door to...

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  18. Windjammer 306
    Windjammer 306

    Sleeps 4, $170 to $355/night

    City : Ocean City
    Bedroom : 1
    Bathroom : 1
    Pets OK

    The Windjammer offers that wonderful retro Ocean City feel. This 1...

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  19. Calypso 603
    Calypso 603

    Sleeps 8, $155 to $505/night

    City : Ocean City
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Calypso 603 is one of Ocean City's finest vacation rentals and is...

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  20. Our Place at Beach 203I
    Our Place at Beach 203I

    Sleeps 6, $140 to $330/night

    City : Ocean City
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Truly a sweet summer spot to relax and take in all that Ocean City...

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  21. Windjammer 305
    Windjammer 305

    Sleeps 2, $150 to $275/night

    City : Ocean City
    Bedroom : studio
    Bathroom : 1
    Pets OK

    The Windjammer offers that wonderful retro Ocean City feel. This...

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  22. Captiva Bay 105
    Captiva Bay 105

    Sleeps 6, $305 to $670/night

    City : Ocean City
    Bedrooms : 3
    Bathrooms : 2
    Pool

    We rent to families, married couples, and responsible adults over...

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  23. Bay Princess 406
    Bay Princess 406

    Sleeps 6, $135 to $365/night

    City : Ocean City
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Bay Princess 406 is one of Ocean City's finest vacation rentals....

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  24. Windjammer 300 (Deluxe)
    Windjammer 300 (Deluxe)

    Sleeps 6, $275 to $475/night

    City : Ocean City
    Bedrooms : 2
    Bathroom : 1
    Pets OK

    The Windjammer offers that wonderful retro Ocean City feel. This 2...

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  25. Gateway Grand 303 (Side)
    Gateway Grand 303 (Side)

    Sleeps 8, $245 to $785/night

    City : Ocean City
    Bedrooms : 3
    Bathrooms : 3
    Pool

    Side unit in oceanfront building on 48th street. Deluxe oceanfront...

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  26. Makai 402 (Bay View)
    Makai 402 (Bay View)

    Sleeps 6, $155 to $325/night

    City : Ocean City
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Makai is conveniently located on 42nd Street and the bayfront. Walk...

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  27. Fountainhead 209
    Fountainhead 209

    Sleeps 4, ~$90/night

    City : Ocean City
    Bedroom : 1
    Bathroom : 1
    Pool

    Please Note:  Linens are not included with this property. Linens...

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  28. Misty Sea 102
    Misty Sea 102

    Sleeps 7, $190 to $585/night

    City : Ocean City
    Bedrooms : 2
    Bathrooms : 2

    Misty Sea 102 is a luxury beachfront condominium with newly...

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  29. Belmont Towers TH 7 (Side)
    Belmont Towers TH 7 (Side)

    Sleeps 10, $315 to $795/night

    City : Ocean City
    Bedrooms : 3
    Bathrooms : 3.5
    Pool

    Enjoy the newest luxury condominium building on the Boardwalk....

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  30. Sea Watch 1303
    Sea Watch 1303

    Sleeps 8, $155 to $340/night

    City : Ocean City
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Please note: Linens are not included with this property. Linens are...

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