St. Michaels with Pools(48)
Historic Waterfront Home in St. Michaels, w/Wi-Fi, Dock & Pet Friendly
- 4 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 8
$650 -
$700
per night
2 - 3 night minimum stay
- 4 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 8
Thistle Dew - Will Do!! Waterfront, Pool, Decor, Location
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 8
$535 -
$752
per night
2 - 7 night minimum stay
- 4 BR,
- 3 BA,
- Sleeps 8
Friends & Family "Crash Pad" - Views, Pool, Kayaks, Bikes, Firepit & More
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 8
$710 -
$869
per night
2 - 7 night minimum stay
- 4 BR,
- 3 BA,
- Sleeps 8
Ultimate family vacation home! Pool, dock, games barn, hot tub and more!
- 5 Bedrooms,
- 4 Bathrooms, Sleeps 10
$1,118 -
$1,185
per night
2 - 7 night minimum stay
- 5 BR,
- 4 BA,
- Sleeps 10
Luxury Waterfront Home....ONE SUMMER WEEK LEFT 6/23-6/30
- 5 Bedrooms,
- 4 Bathrooms, Sleeps 10
$650 -
$800
per night
2 - 7 night minimum stay
- 5 BR,
- 4 BA,
- Sleeps 10
St. Michaels Waterfront 5 Bedroom, Sleeps 10 $2,500/Week
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 10
$800
per night
2 night minimum stay
- 4 BR,
- 3 BA,
- Sleeps 10
Luxury St. Michaels Waterfront 6 Bedrooms/6 Baths $4900/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
Total Privacy and Relaxation! 90 Acre Waterfront Farm with wraparound views
- 4 Bedrooms,
- 2 Bathrooms, Sleeps 8
$475 -
$750
per night
2 - 7 night minimum stay
- 4 BR,
- 2 BA,
- Sleeps 8
Acreage, Amenities and All You Need for Family and Friend Gatherings
- 5 Bedrooms,
- 5 Bathrooms, Sleeps 12
$654 -
$1,150
per night
2 - 7 night minimum stay
- 5 BR,
- 5 BA,
- Sleeps 12
Breezy Point Waterfront Cottage-Pool-Dock-Recreation Pavilion
- 5 Bedrooms,
- 3 Bathrooms, Sleeps 6
$2,380 -
$3,800
per week
7 night minimum stay
- 5 BR,
- 3 BA,
- Sleeps 6
1900 Circa Duel Cottages Decorated to Die For
- 3 Bedrooms,
- 3 Bathrooms, Sleeps 6
$592 -
$768
per night
2 - 7 night minimum stay
- 3 BR,
- 3 BA,
- Sleeps 6
Luxury home with pool and deep water dock.
- 4 Bedrooms,
- 4 Bathrooms, Sleeps 8
- 4 BR,
- 4 BA,
- Sleeps 8
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
Waterfront Home in Historic St. Michaels
- 4 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 8
- 4 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 8
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
New listing with rural country charm, pool, and a deep water dock
- 3 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 10
$350 -
$600
per night
2 - 3 night minimum stay
- 3 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 10
Great amenities---close to town, pool, dock, hot tub!
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 8
$640 -
$790
per night
2 - 7 night minimum stay
- 4 BR,
- 3 BA,
- Sleeps 8
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
Premier Waterfront Vacation Home/St. Michaels (Sept./Oct. Availability)
- 4 Bedrooms,
- 4 Bathrooms, Sleeps 8
$250 -
$350
per night
3 night minimum stay
- 4 BR,
- 4 BA,
- Sleeps 8
Single family vacation cottage with pool, kayaks, play gym and dock
- 3 Bedrooms,
- 1 Bathroom,
- 1 Half Bath, Sleeps 6
$532 -
$678
per night
2 - 7 night minimum stay
- 3 BR,
- 1 BA,
- 1 HF BA,
- Sleeps 6
Ultimate family vacation home! Pool, dock, games barn, hot tub and more!
- 5 Bedrooms,
- 4 Bathrooms, Sleeps 10
$1,147 -
$1,204
per night
2 - 7 night minimum stay
- 5 BR,
- 4 BA,
- Sleeps 10
'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
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 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
'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
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