Maryland Vacation Rentals - 868 Properties

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.

Search results

  1. 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...

  2. 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...

  3. 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...

  4. 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...

  5. Sleeps 6, $155 to $410/night

    City : Ocean City
    Bedrooms : 2
    Bathrooms : 2
    Pool

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

  6. 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...

  7. Sleeps 8, ~$200/night

    City : Ocean City
    Bedrooms : 3
    Bathrooms : 2.5

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

  8. Sleeps 6, $285 to $915/night

    City : Ocean City
    Bedrooms : 3
    Bathrooms : 3
    Pool

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

  9. 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...

  10. Sleeps 4, $125 to $240/night

    City : Ocean City
    Bedroom : studio
    Bathroom : 1
    Pool

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

  11. Sleeps 10, $270 to $785/night

    City : Ocean City
    Bedrooms : 3
    Bathrooms : 3
    Pool

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

  12. 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-...

  13. 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...

  14. 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...

  15. Sleeps 6, $235 to $435/night

    City : Ocean City
    Bedrooms : 2
    Bathroom : 1

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

  16. 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....

  17. 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...

  18. 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...

  19. 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...

  20. 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...

  21. 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...

  22. Sleeps 6, $305 to $670/night

    City : Ocean City
    Bedrooms : 3
    Bathrooms : 2
    Pool

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

  23. 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....

  24. 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...

  25. Sleeps 8, $245 to $785/night

    City : Ocean City
    Bedrooms : 3
    Bathrooms : 3
    Pool

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

  26. 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...

  27. Sleeps 4, ~$90/night

    City : Ocean City
    Bedroom : 1
    Bathroom : 1
    Pool

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

  28. Sleeps 7, $190 to $585/night

    City : Ocean City
    Bedrooms : 2
    Bathrooms : 2

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

  29. Sleeps 10, $315 to $795/night

    City : Ocean City
    Bedrooms : 3
    Bathrooms : 3.5
    Pool

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

  30. 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...