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 Vacation Rental Lodging - Page 2 of 3

Go to page 1 2 3 (51-100 of 108) First Previous Next Last
Sort by: Show rentals per page

St. Michaels Europa on the Beach - Architectural contemporary home on the Chesapeake Bay

  • 3 BR/2 BA House (sleeps 6)
    $643 - $650/nt
    $4,500/wk
    per property, Hot Tub, Waterfront, Private Pool, Lawn / Garden, terrace, Balcony, Air Conditioning, Internet

Elkton Stunning 7-Acre Chesapeake Bay Estate

  • 7 BR/5 BA, 1 half bath House (sleeps 18)
    $745 - $1,095/nt
    $6,585 - $7,665/wk
    $18,750/month
    per property, pets considered, Hot Tub, Private Pool, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television

St. Leonard Harbor Cottage at the Chesapeake Bay Vacation Rental

  • 2 BR/2 BA Cottage (sleeps 6)
    $260/nt
    $1,120/wk
    per property, accept credit card, pets considered, Beach, Waterfront, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television

St. Michaels Sunrises AND Sunsets, Panoramic Views with Pool and Deepwater Dock, Sleeps 10

  • 4 BR/5 BA House (sleeps 10)
    $600 - $850/nt
    $4,200 - $5,700/wk
    per property, accept credit card, pets considered, River, Rural, Village, Waterfront, Private Pool, Lawn / Garden, Balcony, Air Conditioning, Internet

Chestertown Fantastic 360 Farm With Grand 5 Bedroom Manor Home

  • 5 BR/2 BA, 1 half bath House (sleeps 10)
    $929 - $1,000/nt
    $6,500/wk
    $20,000/month
    per property, Rural

St. Michaels Summer 2014 Specials! Vineyard at Thornton - magnificent

  • 5 BR/3 BA, 1 half bath House (sleeps 10)
    $900/nt
    $5,600/wk
    $16,800/month
    per property, pets considered, Rural, Waterfront, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

St. Michaels Incredible Waterfront Home 'Wye Provence' ' With Pool And Dock

  • 5 BR/3 BA, 1 half bath House (sleeps 10)
    $850/nt
    $5,250/wk
    per property, pets considered, River, Rural, Private Pool, Lawn / Garden, Balcony, Air Conditioning, Satellite / Cable, Television

St. Michaels St Michaels Extraordinary Waterfront home on 54 acres with pool, dock, beach...

  • 5 BR/5 BA, 1 half bath House (sleeps 10)
    $1,500/nt
    $8,000/wk
    per property, pets considered, River, Private Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable

Easton Genteel, 30 Acre Waterfront Estate, Private, Close to Easton, Shops, and Dining

  • 6 BR/6 BA Estate (sleeps 12)
    $700 - $900/nt
    $5,000 - $6,000/wk
    per property, Private Pool, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Parking

St. Michaels Brand new waterfront estate....luxury and privacy on ten acres!

  • 4 BR/3 BA, 1 half bath House (sleeps 9)
    $475 - $725/nt
    $2,995 - $4,200/wk
    $5,500/month
    per property, accept credit card, pets considered, Rural, Waterfront, Private Pool, Jacuzzi, Balcony, Air Conditioning, Satellite / Cable

North Beach Reserve Your Long Overdue Vacation On the Chesapeake Today With a Sandy Beach !

  • 2 BR Cottage (sleeps 4)
    $350/nt
    per property, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television, Parking

Tilghman Island Charming 2 story dutch colonial on the Chesapeake Bay

  • 3 BR/2 BA House (sleeps 6)
    $350/nt
    $1,800 - $2,000/wk
    per property, pets considered, Downtown, Village, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Parking

Tilghman Island Charming and elegant with a water view of Knapps Narrows

  • 3 BR/2 BA House (sleeps 6)
    $275 - $300/nt
    $1,932/wk
    per property, Village, Waterfront, Private Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Cambridge Fishing Cove Private Waterfront Retreat with Pool and Pier

  • 8 BR/6 BA House (sleeps 22)
    $430 - $800/nt
    $2,200 - $5,200/wk
    per property, accept credit card, pets considered, wheelchair accessible, Waterfront, Private Pool, Jacuzzi, Balcony, Air Conditioning

North East Unique Lighthouse home & tenant houses with waterfront, dock, ramp, beach

  • 4 BR/4 BA House (sleeps 8)
    $575/nt
    $3,100/wk
    per property, accept credit card, Hot Tub, wheelchair accessible, Beach, Waterfront, Jacuzzi, Balcony, Air Conditioning, Satellite / Cable

North East Waterfront home with dock, ramp, beach overlooking sandy beach

  • 4 BR/3 BA House (sleeps 8)
    $465/nt
    $2,500/wk
    per property, Lawn / Garden, Balcony, Air Conditioning, Satellite / Cable, Television, Parking, Fireplace

North East Affordable, unique, completely remodeled waterfront home. dock, ramp, beach

  • 4 BR/1 BA House (sleeps 8)
    $335/nt
    $1,800/wk
    per property, Air Conditioning, Satellite / Cable, Television, Parking, Fireplace

Port Republic Treasure the Chesapeake Bay w/Beachfront Home

  • 3 BR/2 BA House (sleeps 6)
    $300 - $307/nt
    $1,600 - $2,150/wk
    per property, Beach, Waterfront, Communal Pool, Tennis Court, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

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

  • 4 BR/4 BA Estate (sleeps 8)
    $5,500/wk
    per property, Rural, Private Pool, Jacuzzi, Lawn / Garden, terrace, Balcony, Air Conditioning, Internet

Solomons Island Extended Stay for Solomons Island, Pax River NAS and Calvert Cliffs NPP

  • 2 BR/2 BA Condo (sleeps 4)
    $2,790 - $4,650/month
    per property, wheelchair accessible, Communal Pool, Balcony, Fitness Room / Equipment, Air Conditioning, Internet, Satellite / Cable, Television

St. Michaels Reserve Now for Waterfowl Festival! Luxury Waterfront, 13 Acre Estate

  • 4 BR/3 BA, 1 half bath House (sleeps 8)
    $500 - $900/nt
    $3,000 - $5,000/wk
    per property, pets considered, Private Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Deale The True 'Bay Life'

  • 3 BR/1 BA Cottage (sleeps 5)
    $225/nt
    $1,000/wk
    per property, pets considered, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Parking

St. Leonard Charming home with bay views just short walk to the beach.

  • 3 BR/3 BA, 1 half bath House (sleeps 8)
    $200/nt
    $1,100/wk
    per property, Beach, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

North East Water front home with 200 ft. Dock and boat slip

  • 4 BR/2 BA, 1 half bath House (sleeps 10)
    $350/nt
    River, Air Conditioning, Internet, Satellite / Cable, DVD Player

Church Creek 6.5 Acre Waterfront Retreat!

  • 3 BR/2 BA House (sleeps 9)
    $621 - $650/nt
    $4,350/wk
    per property, pets considered, limited accessibility, Beach, River, Waterfront, Private Pool, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable

Deal Island New renovation of home w/garden, on water w/great Chesapeake Bay views

  • 2 BR/1 BA House (sleeps 5)
    $850/wk
    per property, accept credit card, pets considered, Hot Tub, Beach, Waterfront, Jacuzzi, Lawn / Garden, Air Conditioning, Internet

Cambridge Almost new, private waterfront - dock, beach, private pool & more

  • 6 BR/5 BA House (sleeps 16)
    $449 - $741/nt
    $2,990 - $5,190/wk
    per property, accept credit card, pets considered, Beach, Near The Ocean, River, Town, Waterfront, Private Pool, Jacuzzi, Lawn / Garden, terrace, Balcony

St. Michaels Relaxing Waterfront Estate - 7 Bedrooms/Indoor Pool

  • 7 BR/6 BA House (sleeps 20)
    $700 - $1,000/nt
    $4,900/wk
    per property, Waterfront, Air Conditioning, Internet, Satellite / Cable, Television, barbecue, Fireplace

St. Michaels Large Elegant Ralph Lauren Waterfront Cottage Nr St Michaels with Georgous views

  • 3 BR/2 BA Cottage (sleeps 6) accept credit card, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television, Parking, barbecue

Cambridge Heron's View Vacation Rental in the Heart of Chesapeake Country!

  • 3 BR/2 BA House (sleeps 6) pets considered, Hot Tub, Town, Waterfront, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Cambridge Luxury Waterfront Condo on Chesapeake Hyatt Property

  • 2 BR/2 BA Condo (sleeps 6) accept credit card, wheelchair accessible, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable

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

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

Cambridge Chesapeake Bay Nature-Oriented Recreation & Repose

  • 3 BR/2 BA House (sleeps 6) accept credit card, pets considered, River, Jacuzzi, terrace, Air Conditioning, Satellite / Cable, Television

Tilghman Island Tilghman Island Dreamin. A Beautiful Home Overlooking Dogwood Harbor

  • 4 BR/2 BA, 1 half bath Villa (sleeps 10) pets considered, Waterfront, Jacuzzi, Balcony, Air Conditioning, Satellite / Cable, Television, DVD Player

Crisfield Chesapeake Waterfront with Private Dock in Crisfield, Maryland

  • 2 BR/1 BA House (sleeps 6) accept credit card, Town, Waterfront, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Betterton Charming home in beach community in Upper Eastern Shore on Chesapeake Bay

  • 6 BR/2 BA House (sleeps 8) pets considered, Beach, Town, Television, DVD Player, Parking, Fireplace

Elkton Elk River Vacation Rental (Quiet, Open, Relaxing River Front)

  • 3 BR/1 BA, 1 half bath Cabin (sleeps 8) accept credit card, pets considered, River, Waterfront, Air Conditioning, Satellite / Cable, Television, DVD Player, Parking

Betterton Beautiful Estate + Organic Farm + Pool on 20 acres

  • 4 BR/2 BA, 1 half bath Farmhouse (sleeps 16) pets considered, Rural, Private Pool, Lawn / Garden, Air Conditioning, Internet, Television, DVD Player

Church Creek Warm, Welcoming Waterfront, Relaxing and Close to Everything

  • 5 BR/2 BA, 1 half bath Farmhouse (sleeps 18) pets considered, Rural, Waterfront, Communal Pool, Air Conditioning, Satellite / Cable, Television, Parking, barbecue

St. Leonard Chesapeake Bay Luxury Vacation/Rental Home

  • 6 BR/3 BA House (sleeps 12) Beach, Resort, Communal Pool, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Parking

St. Leonard Chesapeake Bay fossil hunting from your own front yard! 50 min. D.C

  • 3 BR/1 BA Cottage (sleeps 6) Beach, Waterfront, Air Conditioning, Internet, Satellite / Cable, Television, Fireplace

St. Michaels Waterfront vacation on a private, historic estate

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

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. Leonard Chesapeake Bay Cottage

  • 2 BR/1 BA House (sleeps 8)
    $90 - $150/nt
    $540 - $900/wk
    $2,160 - $3,600/month
    per property, Lawn / Garden, Internet, Satellite / Cable, Television, DVD Player, Parking

Deal Island Elegant, waterview, villa by the Chesapeake Bay

  • 4 BR/3 BA House (sleeps 10)
    $214 - $250/nt
    $1,250 - $1,500/wk
    per property, accept credit card, pets considered, Beach, Rural, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable

Betterton Comfortable, very clean and well-equipped home near Chesapeake Bay.

  • 3 BR/2 BA House (sleeps 6)
    $125 - $205/nt
    $615 - $1,230/wk
    per property, pets considered, Beach, Town, Air Conditioning, Television, DVD Player, Parking

Cambridge Serenity Acres - Waterfront, 23 Private Acres, Dock W/Slips & Pool

  • 4 BR/3 BA, 1 half bath House (sleeps 17) River, Waterfront, Private Pool, Lawn / Garden, Air Conditioning, Satellite / Cable, Television, DVD Player, Parking

Tilghman Island 'Knapp Shack'-Waterfront townhome overlooking the Bay

  • 3 BR/2 BA, 1 half bath House (sleeps 6)
    $250 - $300/nt
    $1,505 - $1,855/wk
    per property, accept credit card, pets considered, Waterfront, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Deal Island Water Water Everywhere!

  • 3 BR/2 BA House (sleeps 8)
    $1,400/wk
    $4,500/month
    per property, pets considered, Beach, Downtown, Lake, Near The Ocean, River, Rural, Waterfront, Lawn / Garden, Balcony, Fitness Room / Equipment, Air Conditioning, Internet, Satellite / Cable

St. Michaels Waterfront Country Cottage Close To St Michaels

  • 3 BR/3 BA Cottage (sleeps 6)
    $280 - $495/nt
    $1,908 - $2,520/wk
    per property, Village, Waterfront, terrace, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Parking
Go to page 1 2 3 (51-100 of 108) First Previous Next Last

© 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.