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Vacation Rentals
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World
>
USA
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Maryland
>
Chesapeake Bay
>
St. Michaels
3
BR /
3
BA /
1
HF BA /
Sleeps
8
From $300/nt
Featured
3
BR /
2
BA /
Sleeps
8
From $675/nt
Featured
3
BR /
3
BA /
Sleeps
6
From $592/nt
Featured
4
BR /
3
BA /
Sleeps
8
From $710/nt
Featured
3
BR /
3
BA /
Sleeps
6
From $473/nt
Featured
St. Michaels with Internet Access
(48)
sort by
HomeAway Sort
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Availability Last Updated
Accepts Online Payments
Bedrooms: Least to Most
Bedrooms: Most to Least
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Price: Low to High
Number of Reviews
Special Offers First
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
Historic Waterfront Home in St. Michaels, w/Wi-Fi, Dock & Pet Friendly
2 - 3 night minimum stay
4
BR,
2
BA,
1
HF BA,
Sleeps
8
Chesapeake Bay
>
St. Michaels House
#123352
(18)
Compare
Thistle Dew - Will Do!! Waterfront, Pool, Decor, Location
4 Bedrooms,
3
Bathrooms
, Sleeps 8
$535 - $752
per night
Thistle Dew - Will Do!! Waterfront, Pool, Decor, Location
2 - 7 night minimum stay
4
BR,
3
BA,
Sleeps
8
Chesapeake Bay
>
St. Michaels Cottage
#449007vb
(10)
Compare
Private Cottage just outside St. Michaels with kayak and bikes included!
3 Bedrooms,
3
Bathrooms
, Sleeps 6
$473 - $610
per night
Private Cottage just outside St. Michaels with kayak and bikes included!
2 - 3 night minimum stay
3
BR,
3
BA,
Sleeps
6
Chesapeake Bay
>
St. Michaels Cottage
#389515vb
(11)
Compare
Ultimate family vacation home! Pool, dock, games barn, hot tub and more!
5 Bedrooms,
4
Bathrooms
, Sleeps 10
$1,118 - $1,185
per night
Ultimate family vacation home! Pool, dock, games barn, hot tub and more!
2 - 7 night minimum stay
5
BR,
4
BA,
Sleeps
10
Chesapeake Bay
>
St. Michaels House
#922712
(15)
Compare
Luxury Waterfront Home....ONE SUMMER WEEK LEFT 6/23-6/30
5 Bedrooms,
4
Bathrooms
, Sleeps 10
$650 - $800
per night
Luxury Waterfront Home....ONE SUMMER WEEK LEFT 6/23-6/30
2 - 7 night minimum stay
5
BR,
4
BA,
Sleeps
10
Chesapeake Bay
>
St. Michaels House
#233398
(13)
Compare
Luxury St. Michaels Waterfront 6 Bedrooms/6 Baths $4900/Week
6 Bedrooms,
6
Bathrooms
,
2
Half Baths
, Sleeps 12
$4,900
per week
Luxury St. Michaels Waterfront 6 Bedrooms/6 Baths $4900/Week
2 night minimum stay
6
BR,
6
BA,
2
HF BA,
Sleeps
12
Chesapeake Bay
>
St. Michaels House
#272472
Compare
Total Privacy and Relaxation! 90 Acre Waterfront Farm with wraparound views
4 Bedrooms,
2
Bathrooms
, Sleeps 8
$475 - $750
per night
Total Privacy and Relaxation! 90 Acre Waterfront Farm with wraparound views
2 - 7 night minimum stay
4
BR,
2
BA,
Sleeps
8
Chesapeake Bay
>
St. Michaels House
#146900vb
(27)
Compare
Private Cottage just outside St. Michaels with kayak and bikes included!
3 Bedrooms,
3
Bathrooms
, Sleeps 6
$473 - $610
per night
Private Cottage just outside St. Michaels with kayak and bikes included!
2 - 3 night minimum stay
3
BR,
3
BA,
Sleeps
6
Chesapeake Bay
>
St. Michaels Cottage
#960147
(11)
Compare
Acreage, Amenities and All You Need for Family and Friend Gatherings
5 Bedrooms,
5
Bathrooms
, Sleeps 12
$654 - $1,150
per night
Acreage, Amenities and All You Need for Family and Friend Gatherings
2 - 7 night minimum stay
5
BR,
5
BA,
Sleeps
12
Chesapeake Bay
>
St. Michaels House
#449016vb
(3)
Compare
Breezy Point Waterfront Cottage-Pool-Dock-Recreation Pavilion
5 Bedrooms,
3
Bathrooms
, Sleeps 6
$2,380 - $3,800
per week
Breezy Point Waterfront Cottage-Pool-Dock-Recreation Pavilion
7 night minimum stay
5
BR,
3
BA,
Sleeps
6
Chesapeake Bay
>
St. Michaels Cottage
#254824
Compare
1900 Circa Duel Cottages Decorated to Die For
3 Bedrooms,
3
Bathrooms
, Sleeps 6
$592 - $768
per night
1900 Circa Duel Cottages Decorated to Die For
2 - 7 night minimum stay
3
BR,
3
BA,
Sleeps
6
Chesapeake Bay
>
St. Michaels Cottage
#449015vb
(3)
Compare
Luxury home with pool and deep water dock.
4 Bedrooms,
4
Bathrooms
, Sleeps 8
Luxury home with pool and deep water dock.
4
BR,
4
BA,
Sleeps
8
Chesapeake Bay
>
St. Michaels Estate
#336403
(4)
Compare
Endless Waterfront Sunsets on Eastern Bay!!
3 Bedrooms,
3
Bathrooms
,
1
Half Bath
, Sleeps 8
$300 - $550
per night
Endless Waterfront Sunsets on Eastern Bay!!
2 - 3 night minimum stay
3
BR,
3
BA,
1
HF BA,
Sleeps
8
Chesapeake Bay
>
St. Michaels House
#246578
(6)
Compare
Premium Waterfront Estate Property - $7,500/Week -
5 Bedrooms,
7
Bathrooms
, Sleeps 10
Premium Waterfront Estate Property - $7,500/Week -
5
BR,
7
BA,
Sleeps
10
Chesapeake Bay
>
St. Michaels Estate
#388823
(8)
Compare
Waterfront Home in Historic St. Michaels
4 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 8
Waterfront Home in Historic St. Michaels
4
BR,
2
BA,
1
HF BA,
Sleeps
8
Chesapeake Bay
>
St. Michaels Farmhouse
#410694vb
(5)
Compare
Luxurious and Extremely Private Waterfront Estate
9 Bedrooms,
7
Bathrooms
,
2
Half Baths
, Sleeps 20
$11,500
per week
Luxurious and Extremely Private Waterfront Estate
2 night minimum stay
9
BR,
7
BA,
2
HF BA,
Sleeps
20
Chesapeake Bay
>
St. Michaels Estate
#942769
(5)
Compare
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
New listing with rural country charm, pool, and a deep water dock
2 - 3 night minimum stay
3
BR,
2
BA,
1
HF BA,
Sleeps
10
Chesapeake Bay
>
St. Michaels Estate
#3021814
(6)
Compare
Waterfront Country Cottage Close To St Michaels
3 Bedrooms,
3
Bathrooms
, Sleeps 6
$280 - $495
per night
Waterfront Country Cottage Close To St Michaels
2 night minimum stay
3
BR,
3
BA,
Sleeps
6
Chesapeake Bay
>
St. Michaels Cottage
#185818
(10)
Compare
Premier Waterfront Vacation Home/St. Michaels (Sept./Oct. Availability)
4 Bedrooms,
4
Bathrooms
, Sleeps 8
$250 - $350
per night
Premier Waterfront Vacation Home/St. Michaels (Sept./Oct. Availability)
3 night minimum stay
4
BR,
4
BA,
Sleeps
8
Chesapeake Bay
>
St. Michaels House
#3177402
(8)
Compare
Ultimate family vacation home! Pool, dock, games barn, hot tub and more!
5 Bedrooms,
4
Bathrooms
, Sleeps 10
$1,147 - $1,204
per night
Ultimate family vacation home! Pool, dock, games barn, hot tub and more!
2 - 7 night minimum stay
5
BR,
4
BA,
Sleeps
10
Chesapeake Bay
>
St. Michaels House
#3471873
(15)
Compare
'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
'Sandy Pines' 4 BR Home on Harris Creek w/Pool, Dock, Kayaks, Sunfish
2 - 7 night minimum stay
4
BR,
3
BA,
Sleeps
10
Chesapeake Bay
>
St. Michaels House
#314049
(7)
Compare
Europa on the Beach - Architectural contemporary home on the Chesapeake Bay
3 Bedrooms,
2
Bathrooms
, Sleeps 6
$500 - $650
per night
Europa on the Beach - Architectural contemporary home on the Chesapeake Bay
3 night minimum stay
3
BR,
2
BA,
Sleeps
6
Chesapeake Bay
>
St. Michaels House
#234151
(3)
Compare
Incredible Waterfront Home 'Wye Provence' ' With Pool And Dock
5 Bedrooms,
3
Bathrooms
,
1
Half Bath
, Sleeps 10
$850
per night
Incredible Waterfront Home 'Wye Provence' ' With Pool And Dock
3 night minimum stay
5
BR,
3
BA,
1
HF BA,
Sleeps
10
Chesapeake Bay
>
St. Michaels House
#909433
Compare
St. Michael's premier in town summer vacation cottage!
2 Bedrooms,
2
Bathrooms
, Sleeps 4
St. Michael's premier in town summer vacation cottage!
2
BR,
2
BA,
Sleeps
4
Chesapeake Bay
>
St. Michaels Cottage
#287681
(27)
Compare
Sunrises AND Sunsets, Panoramic Views with Pool and Deepwater Dock, Sleeps 10
4 Bedrooms,
5
Bathrooms
, Sleeps 10
$4,500 - $6,500
per week
Sunrises AND Sunsets, Panoramic Views with Pool and Deepwater Dock, Sleeps 10
7 night minimum stay
4
BR,
5
BA,
Sleeps
10
Chesapeake Bay
>
St. Michaels House
#254760
Compare
Magnificent Vacation Rental home - 'Compass Rose' with pool and dock
5 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 8
$5,502
per week
Magnificent Vacation Rental home - 'Compass Rose' with pool and dock
7 night minimum stay
5
BR,
2
BA,
1
HF BA,
Sleeps
8
Chesapeake Bay
>
St. Michaels Estate
#234152
Compare
St Michaels Premier Waterfront home with pool and dock
5 Bedrooms,
4
Bathrooms
, Sleeps 10
$1,000
per night
St Michaels Premier Waterfront home with pool and dock
3 night minimum stay
5
BR,
4
BA,
Sleeps
10
Chesapeake Bay
>
St. Michaels House
#138986
1 Review
Compare
'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
'Chez Bonheur' magnificent 5 bedroom home on 1000 acre estate with pool and dock
3 night minimum stay
6
BR,
2
BA,
2
HF BA,
Sleeps
6
Chesapeake Bay
>
St. Michaels House
#909425
Compare
Exquisite 360 acre farm with 5 bedroom Manor, pool and vineyard
5 Bedrooms,
3
Bathrooms
,
1
Half Bath
, Sleeps 10
$1,000
per night
Exquisite 360 acre farm with 5 bedroom Manor, pool and vineyard
3 night minimum stay
5
BR,
3
BA,
1
HF BA,
Sleeps
10
Chesapeake Bay
>
St. Michaels House
#120889
1 Review
Compare
Chesapeak Bay oriented waterfront home with private pool and deep water dock
4 Bedrooms,
3
Bathrooms
,
1
Half Bath
, Sleeps 8
Chesapeak Bay oriented waterfront home with private pool and deep water dock
4
BR,
3
BA,
1
HF BA,
Sleeps
8
Chesapeake Bay
>
St. Michaels House
#376538
Compare
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