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

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43 Holiday homes

Holiday home in St. Michaels

St. Michaels house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

from £1,832 / night

£12,824 / week

1 / 41

St. Michaels holiday home let

St. Michaels house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

from £1,512 / night

£10,992 / week

1 / 38

Cottage letting in St. Michaels

St. Michaels cottage

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

from £305 / night

£2,135 / week

1 / 25

St. Michaels holiday home rental

St. Michaels house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

from £1,832 / night

£12,824 / week

1 / 39

Holiday home in St. Michaels

St. Michaels house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from £282 / night

£1,970 / week

1 / 27

Holiday home rental

St. Michaels house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £573 / night

£2,016 / week

1 / 4

Holiday home in St. Michaels

St. Michaels house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £687 / night

£4,122 / week

1 / 18

Holiday cottage rental

St. Michaels cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from £259 / night

£1,809 / week

1 / 23

St. Michaels holiday cottage rental

St. Michaels cottage

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

from £272 / night

£1,904 / week

1 / 24

Cottage rental in St. Michaels

St. Michaels cottage

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

from £249 / night

£1,742 / week

1 / 24

Holiday home in St. Michaels

St. Michaels house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £220 / night

£1,540 / week

1 / 14

Holiday cottage in St. Michaels

St. Michaels cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from £307 / night

£2,145 / week

1 / 22

Home rental in St. Michaels

St. Michaels house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £258 / night

£1,804 / week

1 / 14

St. Michaels ski cottage to rent.

St. Michaels cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £528 / night

£3,696 / week

1 / 23

Holiday home in St. Michaels

St. Michaels house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £229 / night

£1,602 / week

1 / 11

Holiday home in St. Michaels

St. Michaels house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £397 / night

£2,778 / week

1 / 15

Home rental in St. Michaels

St. Michaels house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

from £1,320 / night

£9,240 / week

1 / 30

Holiday apartment in St. Michaels

St. Michaels apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 3

from £236 / night

£1,652 / week

1 / 30

Ski home to rent in McDaniel

McDaniel house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

from £1,116 / night

£7,812 / week

1 / 30

Ski home to rent in St. Michaels

St. Michaels house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

from £1,040 / night

£7,275 / week

1 / 30

St. Michaels holiday home rental

St. Michaels house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £424 / night

£2,968 / week

1 / 23

St. Michaels holiday home rental

St. Michaels house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £952 / night

£6,664 / week

1 / 30

St. Michaels holiday home accommodation

St. Michaels house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £401 / night

£2,806 / week

1 / 30

Home rental in St. Michaels

St. Michaels house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 9

from £623 / night

£4,357 / week

1 / 30

Home rental in St. Michaels

St. Michaels house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £557 / night

£3,898 / week

1 / 30

St. Michaels holiday apartment rental

St. Michaels apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £200 / night

£1,400 / week

1 / 22

Holiday home in St. Michaels

St. Michaels house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

from £1,139 / night

£7,969 / week

1 / 30

St. Michaels holiday apartment rental

St. Michaels apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £200 / night

£1,400 / week

1 / 11

Holiday studio in St. Michaels

St. Michaels studio

  • Studio
  • 1 bathroom
  • sleeps 2

from £266 / night

£1,860 / week

1 / 22

Home rental in St. Michaels

St. Michaels house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 9

from £496 / night

£3,472 / week

1 / 25

Holiday home in St. Michaels

St. Michaels house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £264 / night

£1,843 / week

1 / 27

Holiday home in St. Michaels

St. Michaels house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

from £1,200 / night

£8,400 / week

1 / 30

Holiday studio in St. Michaels

St. Michaels studio

  • Studio
  • 1 bathroom
  • sleeps 2

from £200 / night

£1,400 / week

1 / 16

Holiday apartment in St. Michaels

St. Michaels apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £200 / night

£1,400 / week

1 / 21

McDaniel holiday home rental

McDaniel house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from £800 / night

£5,600 / week

1 / 30

McDaniel holiday home rental

McDaniel house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £280 / night

£1,960 / week

1 / 30

Holiday home in St. Michaels

St. Michaels house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

from £444 / night

£3,108 / week

1 / 22

Holiday home in St. Michaels

St. Michaels house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from £586 / night

£4,099 / week

1 / 30

Holiday home in St. Michaels

St. Michaels house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

from £1,766 / night

£12,359 / week

1 / 30

Holiday home in St. Michaels

St. Michaels house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Pricing unknown

1 / 13

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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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