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 Accommodations Vacation Cottages

Go to page 1 (1-18 of 18)
Sort by: Show rentals per page

Tilghman Island Cozy winter hideaway with wide water views and new kitchen

  • 2 BR/1 BA, 1 half bath Cottage (sleeps 4)
    $425 - $581/nt
    $1,670 - $2,537/wk
    per property, pets considered, Near The Ocean, Waterfront, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Fireplace

St. Michaels Private cottage just one mile to St. Michaels. Great for kayaking and biking!

  • 3 BR/3 BA Cottage (sleeps 6)
    $502 - $721/nt
    $2,104 - $3,219/wk
    per property, pets considered, Waterfront, Communal Pool, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

St. Michaels Sea Glass Cottage on the Bay! Location! Views! MAY bookings 3 + days discount

  • 3 BR/1 BA, 1 half bath Cottage (sleeps 6)
    $275 - $400/nt
    $1,800 - $2,700/wk
    $6,000/month
    per property, Beach, Near The Ocean, Village, Waterfront, Communal Pool, Lawn / Garden, terrace, Air Conditioning, Satellite / Cable, Television, DVD Player

Point Lookout Renovated cottage with Chesapeake Bay sandy beach direct access

  • 1 BR/1 BA Cottage (sleeps 3)
    $132 - $160/nt
    per property, accept credit card, pets considered, Beach, Rural, Air Conditioning, Internet, Satellite / Cable, DVD Player

Tyaskin Waterfront Chesapeake Bay Retreat.

  • 3 BR/1 BA Cottage (sleeps 6)
    $150 - $193/nt
    $950 - $1,350/wk
    $3,000 - $4,800/month
    per property, accept credit card, Beach, Waterfront, Air Conditioning, Satellite / Cable, DVD Player, Fireplace

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

  • 2 BR/1 BA Cottage (sleeps 6)
    $214 - $248/nt
    $1,095 - $1,495/wk
    per property, Beach, Rural, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, barbecue

St. Leonard Summer Availability!! Charming 1BR Bungalow Overlooking Wells Cove

  • 1 BR Cottage (sleeps 2)
    $75 - $90/nt
    $525 - $630/wk
    $2,250 - $2,700/month
    per property, Private Pool, Air Conditioning, Internet, Television

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

  • 3 BR/1 BA Cottage (sleeps 5)
    $190 - $250/nt
    $1,075/wk
    per property, Hot Tub, Rural, Waterfront, Jacuzzi, Lawn / Garden, Air Conditioning, Television, DVD Player, Parking

North East Cozy Cottage with Vaulted Ceiling, minutes from Main St cafes and shops

  • 1 BR/1 BA Cottage (sleeps 4)
    $109 - $129/nt
    $779 - $799/wk
    $2,799 - $2,999/month
    per property, pets considered, Village, Lawn / Garden, Air Conditioning, Satellite / Cable, Television, Parking

Deal Island Relaxing Sunset and Water View Cottage

  • 2 BR/1 BA Cottage (sleeps 5)
    $100 - $150/nt
    $600 - $850/wk
    per property, pets considered, Beach, Waterfront, Air Conditioning, Satellite / Cable, Television, DVD Player, Parking, barbecue

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

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

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. 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

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 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

St. Michaels St. Michael's premier in town summer vacation cottage!

  • 2 BR/2 BA Cottage (sleeps 4)
    $257 - $400/nt
    $1,700 - $1,800/wk
    $7,200/month
    per property, pets considered, Beach, Downtown, Communal Pool, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television

Deal Island Vintage Waterfront Cottage with Fishing Pier on the Chesapeake Bay.

  • 2 BR/1 BA Cottage (sleeps 5)
    $145 - $160/nt
    $3,580/wk
    per property, pets considered, Beach, Rural, Internet, Satellite / Cable, Television, DVD Player
Go to page 1 (1-18 of 18)

© 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.