GreatRentals Chesapeake Bay Vacation Rental Lodging

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

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

4 BR/4 BA House (sleeps 24) accept credit card, wheelchair accessible, Beach, Waterfront, Jacuzzi, Balcony, Air Conditioning, Internet, Satellite / Cable

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

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

Oxford Oxford Apartment with B&B amenities including waterfront lawn and private beach.

1 BR/1 BA Lodge (sleeps 2) accept credit card, Beach, River, Rural, Town, Village, Waterfront, Daily Maid Service, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television

Deale The True 'Bay Life'

3 BR/1 BA Cottage (sleeps 6) Lawn / Garden, pets considered, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Parking

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

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

Cambridge Sprawling Multi-Family Home with all the best amenities--pool, hot tub, dock, kayaks and more!

6 BR House (sleeps 23) Town, Waterfront, Air Conditioning

Oxford The Don Wilson Cottage, a Cozy Oxford Town Creek Waterfront Home

2 BR/2 BA House (sleeps 5) accept credit card, Town, Village, Waterfront, pets considered, 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

Cambridge Chesapeake Bay Nature-Oriented Recreation & Repose

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

St. Michaels Large Waterfront Estate Located on Miles River

6 BR/4 BA House (sleeps 12) accept credit card, Waterfront, Satellite / Cable, Television, DVD Player, barbecue

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

Port Republic Gorgeous Waterfront Vacation Home - Only One Hour from D.C.!

3 BR/3 BA House (sleeps 8) Waterfront, terrace, Balcony, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

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

Chestertown Historic House, Steps to Shopping, Dining and Chester River

4 BR/2 BA, 1 half bath House (sleeps 8) Downtown, River, Balcony, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Fireplace

Betterton Beautiful Estate + Organic Farm + Pool on 20 acres

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

Tyaskin Waterfront Chesapeake Bay Retreat.

3 BR/1 BA Cottage (sleeps 6) Beach, Waterfront, Air Conditioning, Satellite / Cable, DVD Player, Fireplace

St. Leonard Chesapeake Bay retreat on Flag Harbor Marina. Fantastic!

4 BR/2 BA House (sleeps 10) accept credit card, Beach, Waterfront, pets considered, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Tilghman Island Charming 2 story dutch colonial on the Chesapeake Bay

3 BR/2 BA House (sleeps 6) Village, Waterfront, pets considered, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Parking

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

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

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

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

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

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

St. Michaels Chesapeak Bay oriented waterfront home with private pool and deep water dock

4 BR/3 BA, 1 half bath House (sleeps 8) accept credit card, Balcony, Internet, Satellite / Cable, Television, DVD Player, barbecue, Fireplace

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

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

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

Tilghman Island Tilghman Island Manor - Tranquility

3 BR/2 BA, 1 half bath House (sleeps 6) accept credit card, Near The Ocean, Town, Communal Pool, Lawn / Garden, pets considered, Air Conditioning, Internet, Satellite / Cable

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

North Beach Breathtaking Waterfront House on Chesapeake Bay in North Beach

2 BR/2 BA, 1 half bath House (sleeps 6) Beach, Waterfront, Jacuzzi, Lawn / Garden, terrace, Air Conditioning, Internet, Satellite / Cable, Television

North Beach Waterfront, Water All Around, Peaceful Family Getaway

3 BR/1 BA House (sleeps 6)
$1,400 - $1,600/wk
per property, Beach, Waterfront, Balcony, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Deal Island Elegant, waterview, brand new villa by the Chesapeake Bay

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

$1,100 - $1,500/wk
per property, accept credit card, Beach, Rural, Lawn / Garden, Balcony, pets considered, Air Conditioning, Internet, Satellite / Cable

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

4 BR/3 BA, 1 half bath House (sleeps 17)
$600/nt

$3,200 - $3,700/wk
per property, River, Waterfront, Private Pool, Lawn / Garden, Air Conditioning, Satellite / Cable, Television, DVD Player, Parking

St. Leonard Harbor Cottage at the Chesapeake Bay Vacation Rental

2 BR/2 BA Cottage (sleeps 6)
$780 - $1,110/wk
per property, accept credit card, Beach, Waterfront, Lawn / Garden, pets considered, Air Conditioning, Internet, Satellite / Cable, Television

Tilghman Island Waterfront on Dogwood Harbor with 270 degrees of water view with dock

3 BR/2 BA, 1 half bath House (sleeps 6) River, Waterfront, pets considered, Air Conditioning, Internet, Television, DVD Player, Parking

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

3 BR/2 BA, 1 half bath House (sleeps 6) accept credit card, Waterfront, Balcony, pets considered, Air Conditioning, Internet, Satellite / Cable, Television

St. Michaels Waterfront Country Cottage Close To St Michaels

3 BR/3 BA Cottage (sleeps 6) Village, Waterfront, terrace, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Parking

Solomons Island Cove Point Beach House at Chesapeake Bay near Solomons Island, MD

3 BR/1 BA, 1 half bath House (sleeps 6) accept credit card, Beach, Near The Ocean, Communal Pool, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Deal Island Water Water Everywhere!

3 BR/2 BA House (sleeps 8) Beach, Downtown, Lake, Near The Ocean, River, Rural, Waterfront, Sauna, Lawn / Garden, Balcony, pets considered, Air Conditioning, Internet, Satellite / Cable

Crisfield Luxury Waterfront Condo With Private Boat Slip In Crisfield Maryland

3 BR/2 BA Condo (sleeps 6) wheelchair accessible, Resort, Waterfront, Jacuzzi, Balcony, Air Conditioning, Satellite / Cable, Television, DVD Player

Chesapeake Bay Vacation Rental Lodging - Page 2 of 3

Chesapeake Bay