Chesapeake Bay Rentals, Sleeps 5-8

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

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 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 '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

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

Crisfield Waterfront luxury, natural beauty, peace and tranquility

3 BR/2 BA Condo (sleeps 6)
$1,300/wk
per property, wheelchair accessible, Downtown, Waterfront, Private Pool, terrace, Balcony, Air Conditioning, Satellite / Cable, Television

Port Republic Chesapeake Bayfront Cottage - Port Republic, Calvert County, MD

2 BR/1 BA Cottage (sleeps 6) Beach, Rural, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, barbecue

St. Michaels Sea Glass Cottage on the Bay - St Michaels MD Area

3 BR/1 BA, 1 half bath Cottage (sleeps 6)
$300 - $400/nt

$2,000 - $2,700/wk
per property, Beach, Near The Ocean, Village, Waterfront, Communal Pool, Lawn / Garden, terrace, Air Conditioning, 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

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

4 BR/2 BA, 1 half bath House (sleeps 8)
$650 - $700/nt

$2,950 - $3,150/wk
per property, accept credit card, wheelchair accessible, River, Waterfront, Communal Pool, Lawn / Garden, Balcony, pets considered, Air Conditioning

Cambridge Cozy waterfront cottage with hot tub, large screened porch and scenic views

3 BR/1 BA Cottage (sleeps 5) Rural, Waterfront, Jacuzzi, Lawn / Garden, Air Conditioning, Television, DVD Player, Parking

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. Leonard New,Quiet, Fun, Beachy, Colorful,Comfortable, Views,Economical,accessible apt

2 BR/1 BA Apartment (sleeps 6)
$700 - $800/wk
per property, accept credit card, wheelchair accessible, Beach, Rural, Lawn / Garden, pets considered, Air Conditioning, Internet, Satellite / Cable

St. Michaels Private Cottage just outside St. Michaels with kayak and bikes included!

3 BR/3 BA Cottage (sleeps 6)
$473 - $610/nt

$2,002 - $2,783/wk

$7,545/month
per property, Waterfront, pets considered, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

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

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

St. Michaels Premier Waterfront Vacation Home/St. Michaels (Sept./Oct. 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

Chestertown Chester River Water Front Retreat - Sunrise and Sunset Views

3 BR Cottage (sleeps 8)
$350 - $400/nt

$2,100/wk

$8,000/month
per property, River, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Parking

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

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

2 BR/1 BA House (sleeps 5)
$150 - $300/nt

$1,200 - $1,500/wk
per property, accept credit card, Beach, Resort, Rural, Waterfront, Communal Pool, Tennis Court, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable

Tyaskin Waterfront Chesapeake Bay Retreat.

3 BR/1 BA Cottage (sleeps 6)
$950 - $1,350/wk

$4,400/month
per property, accept credit card, Beach, Waterfront, Air Conditioning, Satellite / Cable, DVD Player, Fireplace

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

Crisfield Spectacular Corner Unit - Direct Waterfront Condo in Crisfield, Md

3 BR/2 BA Condo (sleeps 6)
$100 - $200/nt

$600 - $1,200/wk
per property, accept credit card, Village, Waterfront, Communal Pool, Balcony, 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

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

Port Republic Treasure the Chesapeake Bay w/Beachfront Home

3 BR/2 BA House (sleeps 6)
$1,650 - $1,950/wk
per property, Beach, Waterfront, Communal Pool, Tennis Court, 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

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

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

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

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

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) accept credit card, Beach, Waterfront, Jacuzzi, Lawn / Garden, pets considered, Air Conditioning, Internet, Satellite / Cable

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

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

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

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 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

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

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 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

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

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 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

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

4 BR/4 BA House (sleeps 8) accept credit card, wheelchair accessible, Beach, Waterfront, Jacuzzi, Balcony, Air Conditioning, Satellite / Cable, Television

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

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. 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

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