Chesapeake Bay Vacation Home Rentals(25)
Historic Waterfront Home in St. Michaels, w/Wi-Fi, Dock & Pet Friendly
- 4 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 8
$400 -
$700
per night
2 - 3 night Minimum Stay
- 4 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 8
Magical Bayfront Home
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 8
$350 -
$425
per night
2 night Minimum Stay
- 3 BR,
- 2 BA,
- Sleeps 8
Chesa. Bay Vacation Rental, quiet, beachy, open, bay view, LAST MIN. SPECIALS!
- 4 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 12
$300 -
$450
per night
2 - 7 night Minimum Stay
- 4 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 12
Chesapeake Bay retreat on Flag Harbor Marina. Fantastic!
- 4 Bedrooms,
- 2 Bathrooms, Sleeps 10
- 4 BR,
- 2 BA,
- Sleeps 10
Premier Waterfront Vacation Home/St. Michaels (August Availability)
- 4 Bedrooms,
- 4 Bathrooms, Sleeps 8
$250 -
$350
per night
3 night Minimum Stay
- 4 BR,
- 4 BA,
- Sleeps 8
Waterfront, Water All Around, Peaceful Family Getaway
- 3 Bedrooms,
- 1 Bathroom, Sleeps 6
$300 -
$325
per night
3 - 7 night Minimum Stay
- 3 BR,
- 1 BA,
- Sleeps 6
Bayberry Cove Private 11 Acre Chesapeake Waterfront 5 Bedroom w/Pool & Hot Tub
- 5 Bedrooms,
- 4 Bathrooms, Sleeps 15
$450 -
$625
per night
2 - 7 night Minimum Stay
- 5 BR,
- 4 BA,
- Sleeps 15
Cove Point Beach House at Chesapeake Bay near Solomons Island, MD
- 3 Bedrooms,
- 1 Bathroom,
- 1 Half Bath, Sleeps 6
$125 -
$220
per night
2 - 5 night Minimum Stay
- 3 BR,
- 1 BA,
- 1 HF BA,
- Sleeps 6
Private Beachfront Home with Beautiful Bay View
- 4 Bedrooms,
- 2 Bathrooms, Sleeps 12
$1,701 -
$2,401
per week
7 night Minimum Stay
- 4 BR,
- 2 BA,
- Sleeps 12
Elegant, waterview, brand new villa by the Chesapeake Bay
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 10
$250
per night
2 - 7 night Minimum Stay
- 4 BR,
- 3 BA,
- Sleeps 10
Osprey's Nest, Spacious, Peaceful, Bay Views, Sunrises, Relaxing
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 10
$300 -
$450
per night
2 - 7 night Minimum Stay
- 4 BR,
- 3 BA,
- Sleeps 10
Waterfront Country Living - Fishing, Crabbing, Boating & Chillin'
- 3 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 9
$200 -
$300
per night
2 night Minimum Stay
- 3 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 9
Cedar Beach Lodge is a Modern Year-Round Retreat on the Chesapeake Bay
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 8
$300 -
$350
per night
2 night Minimum Stay
- 3 BR,
- 2 BA,
- Sleeps 8
Herrington Harbour - Beautiful Single Family Home - Rose Haven
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 7
$217 -
$275
per night
2 night Minimum Stay
- 3 BR,
- 2 BA,
- Sleeps 7
Stone's Throw - Bayfront Log Cabin with 180 degree View in Exclusive Community
- 2 Bedrooms,
- 1 Bathroom, Sleeps 5
$180 -
$300
per night
3 - 6 night Minimum Stay
- 2 BR,
- 1 BA,
- Sleeps 5
Brand new, luxury home with large rooms and lots of windows
- 4 Bedrooms,
- 3 Bathrooms,
- 1 Half Bath, Sleeps 11
$275 -
$450
per night
3 night Minimum Stay
- 4 BR,
- 3 BA,
- 1 HF BA,
- Sleeps 11
Enjoy the Water? Fishing, Crabbing, Boating? Here it is!
- 4 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 9
$2,200
per week
7 night Minimum Stay
- 4 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 9
Treasure the Chesapeake Bay w/Beachfront Home
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 6
$1,950
per week
7 night Minimum Stay
- 3 BR,
- 2 BA,
- Sleeps 6
Luxury Chesapeake Bay Waterfront House - Enjoy Miles of Sandy Beach
- 5 Bedrooms,
- 5 Bathrooms, Sleeps 12
$2,900
per week
2 night Minimum Stay
- 5 BR,
- 5 BA,
- Sleeps 12
The Don Wilson Cottage, a Cozy Oxford Town Creek Waterfront Home
- 2 Bedrooms,
- 2 Bathrooms, Sleeps 5
- 2 BR,
- 2 BA,
- Sleeps 5
Life On The Water
- 3 Bedrooms,
- 3 Bathrooms, Sleeps 8
$375
per night
3 night Minimum Stay
- 3 BR,
- 3 BA,
- Sleeps 8
Spacious beachfront getaway overlooking Chesapeake Bay
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 10
$300
per night
2 night Minimum Stay
- 3 BR,
- 2 BA,
- Sleeps 10
Water Water Everywhere!
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 8
$1,400
per week
7 night Minimum Stay
- 3 BR,
- 2 BA,
- Sleeps 8
Adorable, Fully Remodeled, Heart of Quaint Historic District
- 2 Bedrooms, Sleeps 4
$135 -
$175
per night
2 night Minimum Stay
- 2 BR,
- Sleeps 4
Historic House, Steps to Shopping, Dining and Chester River
- 4 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 8
- 4 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 8