Destination: Search
Great Rentals is part of HomeAway.com, the world's leading vacation rentals marketplace. Search over 170,000 vacation rentals properties now! Click here to see more Chesapeake Bay Vacation Rentals

Chesapeake Bay Estate Homes for Rent

Go to page 1 (1-9 of 9)
Sort by: Show rentals per page

View all 112 Chesapeake Bay Vacation Rentals or all 762 Maryland Vacation Rentals

Advertise your rental in Chesapeake Bay, Maryland

St. Michaels Magnificent Vacation Rental home - 'Compass Rose' with pool and dock

  • 5 BR/2 BA, 1 half bath Estate (sleeps 8) wheelchair accessible, Downtown, River, Town, Waterfront, Private Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable

St. Michaels New listing with rural country charm, pool, and a deep water dock

  • 3 BR/2 BA, 1 half bath Estate (sleeps 10) limited accessibility, Rural, Waterfront, Private Pool, Lawn / Garden, pets considered, Fitness Room / Equipment, Air Conditioning, Internet

St. Michaels Luxurious and Extremely Private Waterfront Estate

  • 9 BR/7 BA, 2 half baths Estate (sleeps 20)
    $11,500/wk
    $39,500/month
    per property, Rural, Waterfront, Private Pool, Daily Maid Service, Tennis Court, Lawn / Garden, terrace, Balcony, pets considered

St. Michaels Willows on the Miles - Private, waterfront farmhouse estate- Miles River

  • 5 BR/3 BA Estate (sleeps 12) Waterfront, Private Pool, pets considered, Satellite / Cable, Television, DVD Player, Fireplace

St. Michaels Luxury home with pool and deep water dock.

  • 4 BR/4 BA Estate (sleeps 8) Rural, Waterfront, Private Pool, Jacuzzi, Lawn / Garden, terrace, Balcony, Air Conditioning, Internet

St. Michaels Longview -- Waterfront Estate w/ Pool & 3+ Acres

  • 5 BR/3 BA Estate (sleeps 10) Waterfront, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Parking, Fireplace

St. Michaels Waterfront vacation on a private, historic estate

  • 5 BR/3 BA, 1 half bath Estate (sleeps 12) accept credit card, Waterfront, Private Pool, pets considered, Air Conditioning, Internet, Satellite / Cable, Television

St. Michaels St. Michaels Premier Waterfront estate close to town, golfcourse, Harbor,Museum

  • 6 BR/5 BA, 1 half bath Estate (sleeps 12) accept credit card, Resort, Waterfront, Private Pool, Jacuzzi, Lawn / Garden, Balcony, Air Conditioning, Internet

Oxford Eastern Shore Waterfront Estate, Private Beach, Deep Water

  • 8 BR/6 BA, 1 half bath Estate (sleeps 15) wheelchair accessible, Rural, Waterfront, Private Pool, Air Conditioning, Television, DVD Player, Parking, barbecue
Go to page 1 (1-9 of 9)

© 1996-Present HomeAway.com, Inc. All rights reserved.

Use of this Web site constitutes acceptance of the GreatRentals.com Terms and Conditions and Privacy Policy.