A1Vacations is part of HomeAway.com, the world’s leading vacation rentals marketplace.
Search over 150,000 vacation rentals properties now!   Click here to see more Vacation Homes

Search for vacation rental homes in Chesapeake Bay

  • Previous Page
  • Next Page
Go to page
  1. 1
  2. 2
  3. 3
  4. 4
  5. 5
  6. 6
  7. 7
  8. 8
  9. 9
  10. 10
(71 - 80 of 99)

  1. Eventide Cottage
    View Chesapeake Bay Fall Colors- Waterfront home with new reduced Fall Rates — Property 152481

    Vacation Cottage rental in Chesapeake Bay area
    • Cottage
    • 3 bedrooms , sleeps 8
    • 2 bathrooms
    • 1 half bathroom
    • village, waterfront
    • garden
    Rates (shown in USD)
    $995 - $1395 per property per week

  2. Comfortable, well-equipped home in quiet seaside town. Easy drive to Chestertown — Property 186924

    Vacation House rental in Betterton area
    • House
    • 3 bedrooms , sleeps 6
    • 1 bathroom
    • 1 half bathroom
    • beach, river
    • pets considered
    Rates (shown in USD)
    $700 - $1050 per property per week

  3. Charming home in beach community of Upper Eastern Shore on Chesapeake Bay — Property 235930

    Vacation House rental in Betterton area
    • House
    • 6 bedrooms , sleeps 11
    • 2 bathrooms
    • beach, town
    • pets considered
    Rates (shown in USD)
    $850 per property per week

  4. Charming 2 story dutch colonial on the Chesapeake Bay — Property 138016

    Vacation House rental in Tilghman Island area
    • House
    • 3 bedrooms , sleeps 6
    • 2 bathrooms
    • waterfront
    • pets considered
    Rates (shown in USD)
    $1000 - $1500 per property per week

  5. New upside down home overlooking Dogwood Harbor on Tilghman Island — Property 146170

    Vacation House rental in Tilghman Island area
    • House
    • 3 bedrooms , sleeps 6
    • 2 bathrooms
    • 1 half bathroom
    • river, waterfront
    • pets considered
    Rates (shown in USD)
    $1100 per property per week

  6. Chesapeake Waterfront with Dock in Crisfield, Maryland — Property 183195

    Vacation House rental in Crisfield area
    • House
    • 2 bedrooms , sleeps 6
    • 1 bathroom
    • town, waterfront
    • air-conditioning
    Rates (shown in USD)

  7. Historic Waterfront Property in the Town of Saint Michaels — Property 254518

    Vacation House rental in St. Michaels area
    • House
    • 6 bedrooms , sleeps 12
    • 3 bathrooms
    • 1 half bathroom
    • waterfront
    • pool
    Rates (shown in USD)

  8. Sunset Hill — Property 247921

    Vacation House rental in Bozman area
    • House
    • 5 bedrooms , sleeps 10
    • 5 bathrooms
    • village, waterfront
    • air-conditioning
    Rates (shown in USD)
    $2500 per property per week

  9. Luxury Waterfront Condo With Private Boat Slip In Crisfield Maryland — Property 236795

    Vacation Condo rental in Crisfield area
    • Condo
    • 3 bedrooms , sleeps 6
    • 2 bathrooms
    • resort, waterfront
    • jacuzzi
    Rates (shown in USD)
    $700 per property per week

  10. Charming, private waterfront home, close to St. Michaels, Oxford, and Easton. — Property 165697

    Vacation House rental in St. Michaels area
    • House
    • 3 bedrooms , sleeps 6
    • 2 bathrooms
    • 1 half bathroom
    • river, rural
    • jacuzzi
    Rates (shown in USD)

Refine Your Search

You refined by:
Chesapeake Bay remove
(remove all)
Find by availability dates:

Regions

Bedrooms

Sleeps

Baths

Lodging Type

Amenities

Leisure Activities

Suitability

Other

  • Previous Page
  • Next Page
Go to page
  1. 1
  2. 2
  3. 3
  4. 4
  5. 5
  6. 6
  7. 7
  8. 8
  9. 9
  10. 10
(71 - 80 of 99)