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St. Michaels
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556,649
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556,358
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531,450
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516,647
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411,329
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374,305
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240,486
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218,143
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130,768
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117,846
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71,433
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65,203
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39,602
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23,070
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90,255
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165,531
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146,096
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79,052
)
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33,998
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28,953
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Vacation Rentals
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World
>
USA
>
Maryland
>
Chesapeake Bay
>
St. Michaels
3
BR /
2
BA /
Sleeps
6
From $425/nt
Featured
4
BR /
3
BA /
Sleeps
8
From $535/nt
Featured
4
BR /
4
BA /
Sleeps
8
Featured
5
BR /
3
BA /
Sleeps
6
From $2,250/wk
Featured
5
BR /
4
BA /
Sleeps
10
From $1,118/nt
Featured
St. Michaels Vacation Rental Estates
(11)
sort by
HomeAway Sort
HomeAway Sort
Average Rating
Availability Last Updated
Accepts Online Payments
Bedrooms: Least to Most
Bedrooms: Most to Least
Price: High to Low
Price: Low to High
Number of Reviews
Special Offers First
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
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
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
$290 - $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
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 estate close to town, golfcourse, Harbor,Museum
6 Bedrooms,
5
Bathrooms
,
1
Half Bath
, Sleeps 12
St. Michaels Premier Waterfront estate close to town, golfcourse, Harbor,Museum
6
BR,
5
BA,
1
HF BA,
Sleeps
12
Chesapeake Bay
>
St. Michaels Estate
#113980
Compare
Waterfront vacation on a private, historic estate
5 Bedrooms,
3
Bathrooms
,
1
Half Bath
, Sleeps 12
Waterfront vacation on a private, historic estate
5
BR,
3
BA,
1
HF BA,
Sleeps
12
Chesapeake Bay
>
St. Michaels Estate
#297871
Compare
Longview -- Waterfront Estate w/ Pool & 3+ Acres
5 Bedrooms,
3
Bathrooms
, Sleeps 10
Longview -- Waterfront Estate w/ Pool & 3+ Acres
5
BR,
3
BA,
Sleeps
10
Chesapeake Bay
>
St. Michaels Estate
#109333
(3)
Compare
Willows on the Miles - Private, waterfront farmhouse estate- Miles River
5 Bedrooms,
3
Bathrooms
, Sleeps 12
Willows on the Miles - Private, waterfront farmhouse estate- Miles River
5
BR,
3
BA,
Sleeps
12
Chesapeake Bay
>
St. Michaels Estate
#966959
2 Reviews
Compare
Relaxing New Waterfront Retreat W/ Private Pier, Pool & Kayaks
4 Bedrooms,
3
Bathrooms
,
1
Half Bath
, Sleeps 11
$425 - $700
per night
Relaxing New Waterfront Retreat W/ Private Pier, Pool & Kayaks
Book it Now!
2 - 7 night minimum stay
4
BR,
3
BA,
1
HF BA,
Sleeps
11
Chesapeake Bay
>
St. Michaels Estate
#347588vb
(25)
Compare
Beautiful, Quiet, Waterfront Home Close to St. Michaels/Easton
5 Bedrooms, Sleeps 13
Beautiful, Quiet, Waterfront Home Close to St. Michaels/Easton
5
BR,
Sleeps
13
Chesapeake Bay
>
St. Michaels Estate
#304091vb
2 Reviews
Compare
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