Chesapeake Bay Home Rentals by Owner

Port Republic Spacious beachfront getaway overlooking Chesapeake Bay

3 BR/2 BA House (sleeps 10) Beach, Waterfront, pets considered, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Parking

Port Republic Charming 1BR Bungalow Overlooking Wells Cove

1 BR House (sleeps 2)
$75 - $85/nt

$500/wk
per property, Beach, Waterfront, Lawn / Garden, Balcony, Air Conditioning, Internet, Television

St. Leonard Hidden Cove Apartment resting on the Shores of Wells Cove

1 BR/1 BA House (sleeps 2)
$90 - $125/nt
per property, Beach, Waterfront, pets considered, Air Conditioning, Internet, Television, Parking

Tyaskin Nanticoke Farmhouse - Luxury and Charm at the Chesapeake Bay

3 BR/2 BA, 1 half bath House (sleeps 6) Beach, River, Lawn / Garden, pets considered, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

St. Michaels Endless Waterfront Sunsets on Eastern Bay!!

3 BR/3 BA, 1 half bath House (sleeps 8)
$300 - $550/nt

$1,900 - $3,000/wk
per property, accept credit card, River, Rural, Village, Waterfront, Communal Pool, Jacuzzi, Lawn / Garden, Balcony, Air Conditioning, Internet

North East Unique Waterfront Home with Breathtaking Views

6 BR/3 BA, 1 half bath House (sleeps 11)
$440/nt

$2,950/wk
per property, Beach, River, Rural, Waterfront, Lawn / Garden, pets considered, DVD Player

St. Michaels Luxury Waterfront Home, Sunsets, Pool, 2 miles from Town Center!

5 BR/4 BA House (sleeps 10)
$650 - $800/nt

$3,500 - $6,500/wk
per property, Town, Waterfront, Private Pool, Lawn / Garden, terrace, Air Conditioning, Internet, Satellite / Cable, Television

Deale Million Dollar View on the Chesapeake Bay

4 BR/3 BA House (sleeps 10)
$250 - $300/nt

$1,500 - $1,900/wk
per property, Waterfront, Jacuzzi, Balcony, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Deal Island Chesapeake Bay-Deal Island Vacation Bay views- fishing-crabbing -boating

3 BR/2 BA House (sleeps 8)
$110 - $150/nt

$750 - $895/wk

$2,800 - $3,500/month
per property, Village, Waterfront, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

St. Michaels St Michaels Premier Waterfront home with pool and dock

5 BR/4 BA House (sleeps 10) River, Private Pool, Lawn / Garden, pets considered, 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) River, Rural, Private Pool, Lawn / Garden, Balcony, pets considered, Air Conditioning, Satellite / Cable, Television

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

3 BR/2 BA House (sleeps 6) Waterfront, Private Pool, Lawn / Garden, terrace, Balcony, Air Conditioning, Internet, Satellite / Cable

St. Michaels 'Chez Bonheur' magnificent 5 bedroom home on 1000 acre estate with pool and dock

6 BR/2 BA, 2 half baths House (sleeps 6)
$7,000/wk
per property, River, Rural, Waterfront, Private Pool, terrace, pets considered, Air Conditioning, Internet, Satellite / Cable, Television

St. Michaels Exquisite 360 acre farm with 5 bedroom Manor, pool and vineyard

5 BR/3 BA, 1 half bath House (sleeps 10) Rural, Waterfront, Lawn / Garden, Balcony, pets considered, Air Conditioning, Internet, Satellite / Cable, Television

Oxford Updated Historic Sprawling Waterfront Estate minutes to Oxford

5 BR/3 BA House (sleeps 10)
$595 - $942/nt

$3,035 - $5,960/wk
per property, Near The Ocean, Rural, Village, Private Pool, pets considered, Air Conditioning, Internet, Fireplace

St. Michaels Ultimate family vacation home! Pool, dock, games barn, hot tub and more!

5 BR/4 BA House (sleeps 10)
$1,020 - $1,185/nt

$4,985 - $7,240/wk
per property, Beach, Village, Private Pool, Air Conditioning, Internet, Fireplace

Cobb Island Potomac River Waterfront - Private Beach & Dock- Fish, Swim, Crab

4 BR/2 BA House (sleeps 9)
$1,950 - $2,450/wk
per property, accept credit card, River, Waterfront, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Parking

Port Republic Stone's Throw - Bayfront Log Cabin with 180 degree View in Exclusive Community

2 BR/1 BA House (sleeps 5)
$180 - $300/nt

$1,100 - $1,500/wk
per property, accept credit card, Beach, Resort, Rural, Waterfront, Communal Pool, Tennis Court, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable

St. Leonard Chesa. Bay Vacation Rental, quiet, beachy, open, bay view, LAST MIN. SPECIALS!

4 BR/2 BA, 1 half bath House (sleeps 12)
$300 - $450/nt

$1,700 - $2,000/wk
per property, accept credit card, Beach, Near The Ocean, Balcony, pets considered, Air Conditioning, Internet, Satellite / Cable, Television

St. Leonard Osprey's Nest, Spacious, Peaceful, Bay Views, Sunrises, Relaxing

4 BR/3 BA House (sleeps 10)
$300 - $450/nt

$2,000 - $2,500/wk
per property, accept credit card, wheelchair accessible, Beach, Rural, Balcony, pets considered, Air Conditioning, Internet, Satellite / Cable

Cambridge Welcome Home to Sunset Bay

5 BR/3 BA, 1 half bath House (sleeps 13) Waterfront, Private Pool, Jacuzzi, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

St. Michaels Historic Waterfront Home in St. Michaels, w/Wi-Fi, Dock & Pet Friendly

4 BR/2 BA, 1 half bath House (sleeps 8)
$400 - $700/nt

$1,950 - $3,150/wk
per property, accept credit card, wheelchair accessible, River, Waterfront, Communal Pool, Lawn / Garden, Balcony, pets considered, Air Conditioning

Port Republic Treasure the Chesapeake Bay w/Beachfront Home

3 BR/2 BA House (sleeps 6)
$1,950/wk
per property, Beach, Waterfront, Communal Pool, Tennis Court, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

St. Michaels 2 Weeks Still Open in June - $2000 Off $6300/Week!

6 BR/6 BA, 2 half baths House (sleeps 12)
$4,900/wk
per property, accept credit card, Beach, Downtown, Resort, River, Rural, Town, Village, Waterfront, Private Pool, Jacuzzi, Lawn / Garden, terrace, Balcony, Air Conditioning

Solomons Island Cedar Beach Lodge is a Modern Year-Round Retreat on the Chesapeake Bay

3 BR/2 BA House (sleeps 8)
$350/nt

$1,850/wk
per property, accept credit card, Beach, Rural, Waterfront, Lawn / Garden, pets considered, Air Conditioning, Internet, Satellite / Cable, Television

St. Michaels 'Sandy Pines' 4 BR Home on Harris Creek w/Pool, Dock, Kayaks, Sunfish

4 BR/3 BA House (sleeps 10)
$2,600 - $4,600/wk
per property, River, Waterfront, Private Pool, Lawn / Garden, terrace, Air Conditioning, Internet, Satellite / Cable, Television

North East Lovely waterfront home with pier. Wonderful quiet getaway!

2 BR/2 BA House (sleeps 6)
$150/nt

$1,000/wk
per property, River, Waterfront, pets considered, Air Conditioning, Satellite / Cable, Television, DVD Player

Port Republic Private Beachfront Home with Beautiful Bay View

4 BR/2 BA House (sleeps 12)
$1,600 - $2,300/wk
per property, accept credit card, Beach, Waterfront, Communal Pool, Tennis Court, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable

North Beach Relaxing House on Chesapeake Bay

3 BR/2 BA, 1 half bath House (sleeps 8) Waterfront, Balcony, Air Conditioning, Satellite / Cable, Television, DVD Player, barbecue, Fireplace

North East Top of the Chesapeake - Minutes from Historic Charlestown

5 BR/2 BA House (sleeps 11)
$359 - $429/nt

$2,499 - $2,699/wk
per property, accept credit card, River, Waterfront, Balcony, pets considered, Air Conditioning, Internet, Satellite / Cable, Television

St. Michaels Premier Waterfront Vacation Home/St. Michaels (August Availability)

4 BR/4 BA House (sleeps 8)
$2,200/wk
per property, accept credit card, limited accessibility, Rural, Waterfront, Communal Pool, Jacuzzi, Sauna, Lawn / Garden, Air Conditioning

Point Lookout Luxury Chesapeake Bay Waterfront House - Enjoy Miles of Sandy Beach

5 BR/5 BA House (sleeps 12)
$2,900/wk
per property, accept credit card, Beach, Balcony, 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)
$200/nt

$1,200/wk
per property, Beach, Town, pets considered, Television, DVD Player, Parking, Fireplace

North East Life On The Water

3 BR/3 BA House (sleeps 8) limited accessibility, River, Waterfront, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Cobb Island Enjoy the Water? Fishing, Crabbing, Boating? Here it is!

4 BR/2 BA, 1 half bath House (sleeps 9)
$2,200/wk
per property, accept credit card, River, Rural, Waterfront, Lawn / Garden, Balcony, pets considered, Air Conditioning, Internet, Satellite / Cable

Point Lookout Waterfront Country Living - Fishing, Crabbing, Boating & Chillin'

3 BR/2 BA, 1 half bath House (sleeps 9) Rural, Lawn / Garden, Air Conditioning, Satellite / Cable, Television, Parking, Fireplace

Kent Island Peaceful, Waterfront Cottage w/Pier (close to St. Michaels & Annapolis)

4 BR/2 BA House (sleeps 8)
$180 - $375/nt

$1,260 - $1,960/wk
per property, limited accessibility, Rural, Waterfront, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Port Republic Magical Bayfront Home

3 BR/2 BA House (sleeps 8) accept credit card, limited accessibility, wheelchair accessible, Beach, Waterfront, pets considered, Air Conditioning, Internet, Satellite / Cable

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

3 BR/3 BA, 1 half bath House (sleeps 8)
$250/nt

$1,450/wk
per property, Beach, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

North Beach Herrington Harbour - Beautiful Single Family Home - Rose Haven

3 BR/2 BA House (sleeps 7)
$275/nt

$1,300/wk
per property, accept credit card, Resort, Waterfront, Private Pool, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

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

4 BR/5 BA House (sleeps 10)
$4,500 - $6,500/wk
per property, accept credit card, River, Rural, Village, Waterfront, Private Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable

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

3 BR/2 BA House (sleeps 6)
$300/nt

$1,800/wk
per property, Village, Waterfront, Private Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Cambridge Renovated Historic Waterfront Home with Pool, Dock, 200 acres

7 BR/3 BA, 1 half bath House (sleeps 18) wheelchair accessible, River, Rural, Waterfront, Lawn / Garden, pets considered, Air Conditioning, Internet, Satellite / Cable, Television

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

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

Tilghman Island In the Heart of Chesapeake Bay on Maryland’s Scenic Eastern Shore

7 BR/7 BA, 1 half bath House (sleeps 14)
$2,000 - $2,500/wk
per property, Beach, Downtown, Near The Ocean, Resort, Town, Village, Waterfront, Lawn / Garden, pets considered, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Church Creek 6.5 Acre Waterfront Retreat!

3 BR/2 BA House (sleeps 9) limited accessibility, Beach, River, Waterfront, Private Pool, Lawn / Garden, pets considered, 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, Beach, Waterfront, Jacuzzi, Lawn / Garden, pets considered, Air Conditioning, Internet, Satellite / Cable

Chesapeake Beach Chesapeake Beach House -- 30 Miles from DC or Annapolis Md

6 BR/5 BA, 1 half bath House (sleeps 13)
$850 - $875/nt

$5,000 - $5,500/wk
per property, accept credit card, Beach, Town, Waterfront, Jacuzzi, terrace, Balcony, pets considered, Air Conditioning, Internet

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

6 BR/5 BA House (sleeps 16) accept credit card, Beach, Near The Ocean, River, Town, Waterfront, Private Pool, Jacuzzi, Lawn / Garden, terrace, Balcony, pets considered

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

7 BR/6 BA House (sleeps 20) Waterfront, Air Conditioning, Internet, Satellite / Cable, Television, barbecue, Fireplace