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5 Best St. Michaels Vacation rentals on Holiday Lettings - Apartments

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51 Vacation rentals

St. Michaels Vacation home rental

St. Michaels house

1 bedroom • 1 bathroom • sleeps 6

2 reviews

from $205 / night

$1,203 / week

1 / 18

Vacation home in St. Michaels

St. Michaels house

7 bedrooms • 4 bathrooms • sleeps 9

14 reviews

from $619 / night

$3,607 / week

1 / 30

Vacation home in St. Michaels

St. Michaels house

2 bedrooms • 2 bathrooms • sleeps 5

24 reviews

from $310 / night

$2,004 / week

1 / 27

Vacation home in St. Michaels

St. Michaels house

2 bedrooms • 2 bathrooms • sleeps 5

15 reviews

from $332 / night

$2,073 / week

1 / 24

Vacation home in St. Michaels

St. Michaels house

3 bedrooms • 3 bathrooms • sleeps 6

1 review

from $859 / night

$5,153 / week

1 / 18

Cottage rental in St. Michaels

St. Michaels cottage

2 bedrooms • 3 bathrooms • sleeps 5

5 reviews

from $332 / night

$2,325 / week

1 / 25

St. Michaels Vacation cottage rental

St. Michaels cottage

2 bedrooms • 2 bathrooms • sleeps 5

11 reviews

from $332 / night

$2,325 / week

1 / 23

St. Michaels Vacation home rental

St. Michaels house

4 bedrooms • 3 bathrooms • sleeps 8

5 reviews

from $785 / night

$5,491 / week

1 / 22

St. Michaels Vacation home rental

St. Michaels house

6 bedrooms • 5 bathrooms • sleeps 12

from $2,290 / night

$13,740 / week

1 / 6

Great rentals within 20 miles that match your search

Vacation home in North Beach

North Beach house

3 bedrooms • 2 bathrooms • sleeps 8

from $573 / night

$4,008 / week

1 / 11

Vacation home in Annapolis

Annapolis house

5 bedrooms • 3 bathrooms • sleeps 10

from $1,145 / night

$13,740 / week

1 / 12

Vacation home in Annapolis

Annapolis house

3 bedrooms • 2 bathrooms • sleeps 8

1 review

from $516 / night

$7,443 / week

1 / 7

Bozman Vacation home rental

Bozman house

2 bedrooms • 1 bathroom • sleeps 6

1 review

from $442 / night

$1,890 - $2,892 / week

1 / 20

Vacation cottage with shared pool in Bozman

Bozman cottage

1 bedroom • 1 bathroom • sleeps 2

from $201 / night

$773 - $1,088 / week

1 / 12

Vacation home with shared pool in Bozman

Bozman house

1 bedroom • 1 bathroom • sleeps 4

from $201 / night

$773 - $1,088 / week

1 / 12

Vacation apartment in Annapolis

Annapolis apartment

2 bedrooms • 1 bathroom • sleeps 5

from $287 / night

$2,004 / week

1 / 15

Annapolis Vacation home rental

Annapolis house

3 bedrooms • 1 bathroom • sleeps 6

2 reviews

from $287 / night

$1,144 - $1,345 / week

1 / 52

Vacation home in Chester

Chester house

4 bedrooms • 2 bathrooms • sleeps 8

3 reviews

from $338 / night

$2,365 / week

1 / 21

Vacation home with swimming pool in Bozman

Bozman house

5 bedrooms • 3 bathrooms • sleeps 13

13 reviews

from $651 / night

$2,577 - $3,693 / week

1 / 27

Cape Saint Claire Vacation home rental

Cape Saint Claire house

4 bedrooms • 2 bathrooms • sleeps 8

from $236 / night

$1,651 / week

1 / 24

Vacation apartment rental

Chesapeake Beach apartment

1 bedroom • 1 bathroom • sleeps 2

from $84 / night

$585 / week

1 / 26

Vacation home in Annapolis

Annapolis house

3 bedrooms • 5 bathrooms • sleeps 11

1 review

from $796 / night

$6,183 / week

1 / 18

Home rental in Cambridge

Cambridge house

3 bedrooms • 3 bathrooms • sleeps 12

from $350 / night

$2,445 / week

1 / 41

Vacation home in Shady Side

Shady Side house

3 bedrooms • 2 bathrooms • sleeps 6

1 review

from $447 / night

$3,126 / week

1 / 31

Vacation cottage in Mayo

Mayo cottage

4 bedrooms • 1 bathroom • sleeps 8

from $513 / night

$3,591 / week

1 / 29

Vacation cottage in North Beach

North Beach cottage

3 bedrooms • 1 bathroom • sleeps 6

from $105 / night

$730 / week

1 / 25

Vacation home in Neavitt

Neavitt house

2 bedrooms • 2 bathrooms • sleeps 4

from $385 / night

$2,693 / week

1 / 28

Vacation home in Cambridge

Cambridge house

4 bedrooms • 2 bathrooms • sleeps 8

from $588 / night

$4,112 / week

1 / 34

Vacation home in Annapolis

Annapolis house

3 bedrooms • 4 bathrooms • sleeps 6

from $865 / night

$6,052 / week

1 / 30

Vacation home in Chester

Chester house

4 bedrooms • 3 bathrooms • sleeps 12

1 review

from $401 / night

$2,806 / week

1 / 12

Home rental in Cape Saint Claire

Cape Saint Claire house

3 bedrooms • 1 bathroom • sleeps 6

from $334 / night

$2,333 / week

1 / 30

Vacation home rental

Annapolis house

4 bedrooms • 3 bathrooms • sleeps 9

3 reviews

from $487 / night

$2,863 - $3,704 / week

1 / 30

Vacation condo in Annapolis

Annapolis condo

3 bedrooms • 2 bathrooms • sleeps 6

from $273 / night

$1,908 / week

1 / 33

Annapolis Vacation home rental

Annapolis house

3 bedrooms • 2 bathrooms • sleeps 7

1 review

from $327 / night

$2,634 / week

1 / 17

Vacation home in Easton

Easton house

3 bedrooms • 4 bathrooms • sleeps 6

from $6,870 / night

$85,875 / week

1 / 15

Vacation log cabin with swimming pool in Wittman

Wittman log cabin

5 bedrooms • 5 bathrooms • sleeps 10

3 reviews

from $1,117 / night

$7,157 / week

1 / 36

Stevensville Vacation apartment rental

Stevensville apartment

1 bedroom • 1 bathroom • sleeps 2

from $184 / night

$916 / week

1 / 17

Vacation home with shared pool in Chesapeake Beach

Chesapeake Beach house

3 bedrooms • 3 bathrooms • sleeps 8

from $573 / night

$4,008 / week

1 / 11

Vacation home in Annapolis

Annapolis house

4 bedrooms • 4 bathrooms • sleeps 10

from $801 / night

$4,466 - $4,867 / week

1 / 28

Vacation home rental

Bethlehem house

3 bedrooms • 2 bathrooms • sleeps 8

from $229 / night

$1,260 - $2,061 / week

1 / 14