St. Michaels with Parking Included(41)
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
Luxury Waterfront Home, Sunsets, Pool, 2 miles from Town Center!
- 5 Bedrooms,
- 4 Bathrooms, Sleeps 10
$650 -
$800
per night
2 - 7 night Minimum Stay
- 5 BR,
- 4 BA,
- Sleeps 10
Special $1,000 Off May and June Weeks
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 10
$800
per night
2 night Minimum Stay
- 4 BR,
- 3 BA,
- Sleeps 10
2 Weeks Still Open in June - $2000 Off $6300/Week!
- 6 Bedrooms,
- 6 Bathrooms,
- 2 Half Baths, Sleeps 12
$4,900
per week
2 night Minimum Stay
- 6 BR,
- 6 BA,
- 2 HF BA,
- Sleeps 12
Breezy Point Waterfront Cottage-Pool-Dock-Recreation Pavilion
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 6
$340 -
$600
per night
2 night Minimum Stay
- 4 BR,
- 3 BA,
- Sleeps 6
Endless Waterfront Sunsets on Eastern Bay!!
- 3 Bedrooms,
- 3 Bathrooms,
- 1 Half Bath, Sleeps 8
$300 -
$550
per night
2 - 3 night Minimum Stay
- 3 BR,
- 3 BA,
- 1 HF BA,
- Sleeps 8
Premium Waterfront Estate Property - $7,500/Week -
- 5 Bedrooms,
- 7 Bathrooms, Sleeps 10
- 5 BR,
- 7 BA,
- Sleeps 10
Luxury home with pool and deep water dock.
- 4 Bedrooms,
- 4 Bathrooms, Sleeps 8
- 4 BR,
- 4 BA,
- Sleeps 8
Waterfront Home in Historic St. Michaels
- 4 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 8
- 4 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 8
New listing with rural country charm, pool, and a deep water dock
- 3 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 10
$350 -
$550
per night
2 night Minimum Stay
- 3 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 10
Luxurious and Extremely Private Waterfront Estate
- 9 Bedrooms,
- 7 Bathrooms,
- 2 Half Baths, Sleeps 20
$11,500
per week
2 night Minimum Stay
- 9 BR,
- 7 BA,
- 2 HF BA,
- Sleeps 20
Sea Glass Cottage on the Bay - St Michaels MD Area
- 3 Bedrooms,
- 1 Bathroom,
- 1 Half Bath, Sleeps 6
$300 -
$400
per night
2 night Minimum Stay
- 3 BR,
- 1 BA,
- 1 HF BA,
- Sleeps 6
Waterfront Country Cottage Close To St Michaels
- 3 Bedrooms,
- 3 Bathrooms, Sleeps 6
$280 -
$495
per night
2 night Minimum Stay
- 3 BR,
- 3 BA,
- Sleeps 6
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
'Sandy Pines' 4 BR Home on Harris Creek w/Pool, Dock, Kayaks, Sunfish
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 10
$2,600 -
$4,600
per week
2 - 7 night Minimum Stay
- 4 BR,
- 3 BA,
- Sleeps 10
Europa on the Beach - Architectural contemporary home on the Chesapeake Bay
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 6
$500 -
$650
per night
3 night Minimum Stay
- 3 BR,
- 2 BA,
- Sleeps 6
Incredible Waterfront Home 'Wye Provence' ' With Pool And Dock
- 5 Bedrooms,
- 3 Bathrooms,
- 1 Half Bath, Sleeps 10
$850
per night
3 night Minimum Stay
- 5 BR,
- 3 BA,
- 1 HF BA,
- Sleeps 10
St. Michael's premier in town summer vacation cottage!
- 2 Bedrooms,
- 2 Bathrooms, Sleeps 4
- 2 BR,
- 2 BA,
- Sleeps 4
St Michaels Premier Waterfront home with pool and dock
- 5 Bedrooms,
- 4 Bathrooms, Sleeps 10
$1,000
per night
3 night Minimum Stay
- 5 BR,
- 4 BA,
- Sleeps 10
Exquisite 360 acre farm with 5 bedroom Manor, pool and vineyard
- 5 Bedrooms,
- 3 Bathrooms,
- 1 Half Bath, Sleeps 10
$1,000
per night
3 night Minimum Stay
- 5 BR,
- 3 BA,
- 1 HF BA,
- Sleeps 10
'Chez Bonheur' magnificent 5 bedroom home on 1000 acre estate with pool and dock
- 6 Bedrooms,
- 2 Bathrooms,
- 2 Half Baths, Sleeps 6
$1,200
per night
3 night Minimum Stay
- 6 BR,
- 2 BA,
- 2 HF BA,
- Sleeps 6
Sunrises AND Sunsets, Panoramic Views with Pool and Deepwater Dock, Sleeps 10
- 4 Bedrooms,
- 5 Bathrooms, Sleeps 10
$4,500 -
$6,500
per week
7 night Minimum Stay
- 4 BR,
- 5 BA,
- Sleeps 10
Magnificent Vacation Rental home - 'Compass Rose' with pool and dock
- 5 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 8
$5,502
per week
7 night Minimum Stay
- 5 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 8
St. Michaels Premier Waterfront estate close to town, golfcourse, Harbor,Museum
- 6 Bedrooms,
- 5 Bathrooms,
- 1 Half Bath, Sleeps 12
- 6 BR,
- 5 BA,
- 1 HF BA,
- Sleeps 12
Charming historic farmhouse just minutes from all St. Michaels has to offer
- 2 Bedrooms,
- 1 Bathroom, Sleeps 4
- 2 BR,
- 1 BA,
- Sleeps 4
Longview -- Waterfront Estate w/ Pool & 3+ Acres
- 5 Bedrooms,
- 3 Bathrooms, Sleeps 10
- 5 BR,
- 3 BA,
- Sleeps 10
15 More choices from HomeAway International Websites
BOAT HOUSE: New Luxury pool on the water in St. Michaels -
- 4 Bedrooms,
- 2 Bathrooms, Sleeps 9
$380 -
$900
per night
2 - 3 night Minimum Stay
- 4 BR,
- 2 BA,
- Sleeps 9
Relaxing New Waterfront Retreat W/ Private Pier, Pool & Kayaks
- 4 Bedrooms,
- 3 Bathrooms,
- 1 Half Bath, Sleeps 11
$500 -
$700
per night
2 - 7 night Minimum Stay
- 4 BR,
- 3 BA,
- 1 HF BA,
- Sleeps 11
Perfect for Families! Waterfront, 1 mile from downtown St. M's. Mostly 1 level.
- 5 Bedrooms,
- 3 Bathrooms, Sleeps 10
$300 -
$510
per night
2 night Minimum Stay
- 5 BR,
- 3 BA,
- Sleeps 10
On Harbor and on Park! - Only Large Vacation House in Town
- 6 Bedrooms, Sleeps 11
- 6 BR,
- Sleeps 11
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