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Apartments in St. Michaels and Villas - Holiday Lettings - Holiday Rentals St. Michaels

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7 Holiday homes

St. Michaels holiday home let

St. Michaels house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

from £1,493 / night

£10,859 / week

1 / 38

Holiday home in St. Michaels

St. Michaels house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

from £1,810 / night

£12,669 / week

1 / 41

St. Michaels holiday home rental

St. Michaels house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

from £1,810 / night

£12,669 / week

1 / 39

Holiday home in St. Michaels

St. Michaels house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from £278 / night

£1,946 / week

1 / 27

Cottage letting in St. Michaels

St. Michaels cottage

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

from £302 / night

£2,109 / week

1 / 25

Holiday home rental

St. Michaels house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £566 / night

£1,991 / week

1 / 4

Holiday home in St. Michaels

St. Michaels house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £679 / night

£4,072 / week

1 / 18

Great rentals within 20 miles that match your search

Holiday home rental

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

from £385 / night

£2,263 - £2,928 / week

1 / 30

Holiday home in Chester

Chester house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from £358 / night

£2,502 / week

1 / 16

Holiday home with shared pool in Bozman

Bozman house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £181 / night

£670 / week

1 / 13

Bozman holiday home rental

Bozman house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £263 / night

£1,026 - £1,817 / week

1 / 17

Holiday cottage with shared pool in Bozman

Bozman cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £181 / night

£670 / week

1 / 17

Holiday home with swimming pool in Bozman

Bozman house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

from £543 / night

£2,444 / week

1 / 22

Annapolis holiday home rental

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £376 / night

£2,629 / week

1 / 30

Holiday cottage in Cambridge

Cambridge cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

from £198 / night

£1,383 / week

1 / 50

Holiday home with golf nearby in Stevensville

Stevensville house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

from £634 / night

£2,896 - £3,937 / week

1 / 66

Holiday home rental

Kent Island house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

from £362 / night

£2,263 - £3,783 / week

1 / 20

Holiday home with swimming pool in Kent Island

Kent Island house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

from £1,539 / night

£7,692 - £9,276 / week

1 / 34

Holiday home in Chester

Chester house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £1,539 / night

£6,787 - £8,371 / week

1 / 50

Holiday home in Annapolis

Annapolis house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

from £905 / night

£10,859 / week

1 / 12

Holiday home in Sherwood

Sherwood house

  • 8 bedrooms
  • 10 bathrooms
  • sleeps 12

from £2,263 / night

£15,836 / week

1 / 25

Holiday home in Annapolis

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

from £316 / night

£2,211 / week

1 / 16

Annapolis holiday home rental

Annapolis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from £349 / night

£2,444 / week

1 / 21

Holiday home in East New Market

East New Market house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

from £996 / night

£6,968 / week

1 / 18

Annapolis holiday condo rental

Annapolis condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from £349 / night

£2,439 / week

1 / 14

Holiday home rental

Easton house

  • 3 bedrooms
  • 5 bathrooms
  • sleeps 6

from £629 / night

£4,403 / week

1 / 21

Holiday studio with swimming pool in Romancoke

Romancoke studio

  • Studio
  • 1 bathroom
  • sleeps 2

from £180 / night

£1,261 / week

1 / 42

Holiday home in Annapolis

Annapolis house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 10

from £530 / night

£2,806 / week

1 / 32

Holiday home rental

Bethlehem house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £272 / night

£1,539 - £2,172 / week

1 / 14

Holiday home in Mayo

Mayo house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £317 / night

£1,884 / week

1 / 19

Annapolis holiday apartment rental

Annapolis apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £196 / night

£1,369 / week

1 / 12

Holiday manor house rental

Royal Oak manor house

  • 25 bedrooms
  • 25 bathrooms
  • sleeps 50

from £5,882 / night

£31,672 / week

1 / 125

Holiday home with shared pool in Royal Oak

Royal Oak house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £720 / night

£5,036 / week

1 / 21

Holiday home in Easton

Easton house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from £5,430 / night

£67,867 / week

1 / 15

Holiday apartment in Grasonville

Grasonville apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

from £150 / night

£889 / week

1 / 9

Holiday home in Edgewater

Edgewater house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 8

from £453 / night

£3,168 / week

1 / 13

Holiday apartment in Annapolis

Annapolis apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £340 / night

£2,138 / week

1 / 11

Holiday home in Chester

Chester house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

from £362 / night

£2,534 / week

1 / 12

Royal Oak holiday home rental

Royal Oak house

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 14

from £1,222 / night

£8,552 / week

1 / 28

Holiday home rental

Royal Oak house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £589 / night

£4,118 / week

1 / 21

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St. Michaels holidays

St. Michaels has been a popular holiday destination for years – find out why by booking your holiday rental with Holiday Lettings, today!

About St. Michaels, Maryland

This small town in Talbot County is famous throughout the east coast for being the perfect getaway spot.

It's slightly unusual, as it wasn't built in a grid form like so many other American towns. Instead, it centres around the town square and progresses outwards in layers.

Way back in the past, it was a tobacco growing and shipbuilding town. A real taste of old-time Americana. But, now its trade focuses on tourism and oysters – the latter are always delicious and well worth trying during your stay.

Plans to improve the town have been underway since the 60s. There's now a museum, waterfront restaurants and tour boats that make it a much more exciting place to stay. Cheque them out for yourself when you come here.

You may recognise this small town as it's starred in a few movies. Clara's Heart (starring Whoopi Goldberg and Neil Patrick Harris), and The Wedding Crashers (with Owen Wilson and Vince Vaughn) were both filmed here – how about that for a bit of Hollywood glitz and glamour?

What to do

FIrst stop, go to the Chesapeake Bay Maritime Museum. It's a really interesting place for sailing enthusiasts and history nuts. The exhibits are mostly historic bay vessels, including the ‘Chesapeake Bay bugeye’ named Edna E. Lockwood – ask the guide about that one!

For a little more history, go to the St. Michael's Mill. It’s a grist mill that dates back to the 19th century, and was a major part of the town life for the locals of yesteryear.

If you want some culture, there are three art galleries to choose from. The Clark Gallery, Hopkins and Gregario – all with something a little different for you to explore.

If you're looking for some fun activities to try during your stay, there are plenty. Take a boat out on the water and explore the area. Or, try stand up paddleboarding – it's hard work but great fun!

There are several running and kayaking trails for you to discover. Or, you could spend a day fishing in the shallow waters.

Top St. Michaels, Maryland travel tips

Most of St. Michaels is dog-friendly, so bring your pooch along on holiday and let them explore someplace new.

You'll have your pick of riverfront restaurants during your stay. Make sure to try the fresh seafood, but remember to tip as gratuity is not included.

For a peaceful trip away by the water, choose St. Michaels as your next holiday destination. Pick your St. Michaels holiday rental on Holiday Lettings and let the adventure begin!

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