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

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54 Holiday homes

Cottage letting in St. Michaels

St. Michaels cottage

2 bedrooms • 3 bathrooms • sleeps 5

from £281 / night

£1,966 / week

1 / 25

St. Michaels holiday home rental

St. Michaels house

1 bedroom • 1 bathroom • sleeps 6

from £151 / night

£886 / week

1 / 18

St. Michaels holiday home let

St. Michaels house

6 bedrooms • 6 bathrooms • sleeps 12

from £1,681 / night

£10,087 / week

1 / 6

Holiday home in St. Michaels

St. Michaels house

2 bedrooms • 2 bathrooms • sleeps 5

from £219 / night

£1,528 / week

1 / 24

St. Michaels holiday cottage rental

St. Michaels cottage

2 bedrooms • 2 bathrooms • sleeps 5

from £317 / night

£2,219 / week

1 / 23

Holiday home in St. Michaels

St. Michaels house

2 bedrooms • 2 bathrooms • sleeps 5

from £260 / night

£1,814 / week

1 / 27

Holiday home in St. Michaels

St. Michaels house

7 bedrooms • 4 bathrooms • sleeps 9

“Perfect in every way!” I stayed at the Thomas Harrison house a few weeks ago and all I can say is..."if you are planning on coming to St. Michael's you need to stay at this house." This house is perfect in every way. It has all the accommodations that you could ever need and is very unique and quaint. The location is more than perfect (we literally were in walking distance of everything, shops, restaurants, etc.) and did not even have to get into the car to drive anywhere the entire time. The backyard has a wonderful porch where you can sit outside and converse with friends or even sip your coffee in the morning. The view is phenomenal! You have a wonderful panoramic view of the water from your bedroom window and the beds are very comfortable (which is a must for me). If you are planning on a trip to experience St. Michael's whether it is a romantic weekend getaway or a family (group) outing I would hands down recommend this house.

from £380 / night

£2,658 / week

1 / 30

St. Michaels holiday home rental

St. Michaels house

4 bedrooms • 3 bathrooms • sleeps 8

from £578 / night

£4,046 / week

1 / 22

Holiday home in St. Michaels

St. Michaels house

3 bedrooms • 3 bathrooms • sleeps 6

from £631 / night

£3,783 / week

1 / 18

Great rentals within 20 miles that match your search

Holiday cottage with shared pool in Bozman

Bozman cottage

1 bedroom • 1 bathroom • sleeps 2

from £160 / night

£580 - £925 / week

1 / 17

Holiday home with shared pool in Bozman

Bozman house

1 bedroom • 1 bathroom • sleeps 4

from £160 / night

£580 - £925 / week

1 / 13

Bozman holiday home rental

Bozman house

2 bedrooms • 1 bathroom • sleeps 6

from £236 / night

£820 - £1,555 / week

1 / 17

Holiday home with swimming pool in Bozman

Bozman house

5 bedrooms • 3 bathrooms • sleeps 9

from £488 / night

£1,976 - £2,816 / week

1 / 22

Annapolis holiday home rental

Annapolis house

3 bedrooms • 2 bathrooms • sleeps 6

from £358 / night

£2,501 / week

1 / 61

Holiday home rental

Kent Island house

3 bedrooms • 3 bathrooms • sleeps 12

from £295 / night

£2,102 - £3,514 / week

1 / 21

Holiday home in Annapolis

Annapolis house

5 bedrooms • 3 bathrooms • sleeps 10

from £841 / night

£10,087 / week

1 / 12

Holiday tented camp in Grasonville

Grasonville tented camp

1 bedroom • 1 bathroom • sleeps 6

from £169 / night

£1,330 - £1,530 / week

1 / 15

Holiday home in Chester

Chester house

4 bedrooms • 2 bathrooms • sleeps 8

from £334 / night

£2,333 / week

1 / 16

Holiday home in Chester

Chester house

4 bedrooms • 3 bathrooms • sleeps 12

from £338 / night

£2,363 / week

1 / 12

Holiday home in Annapolis

Annapolis house

3 bedrooms • 5 bathrooms • sleeps 11

from £587 / night

£4,556 / week

1 / 18

Holiday home rental

Annapolis house

4 bedrooms • 3 bathrooms • sleeps 9

from £359 / night

£2,110 - £2,730 / week

1 / 30

Holiday home in Easton

Easton house

3 bedrooms • 4 bathrooms • sleeps 6

from £5,063 / night

£63,279 / week

1 / 15

Holiday log cabin with swimming pool in Wittman

Wittman log cabin

5 bedrooms • 5 bathrooms • sleeps 10

from £823 / night

£5,274 / week

1 / 36

Holiday apartment in Grasonville

Grasonville apartment

1 bedroom • 1 bathroom • sleeps 5

from £140 / night

£829 / week

1 / 9

Condo rental in Annapolis

Annapolis condo

2 bedrooms • 2 bathrooms • sleeps 4

from £160 / night

£1,117 - £1,412 / week

1 / 40

Holiday home rental

Bethlehem house

3 bedrooms • 2 bathrooms • sleeps 8

from £169 / night

£928 - £1,519 / week

1 / 14

Holiday home in Annapolis

Annapolis house

2 bedrooms • 2 bathrooms • sleeps 6

from £66 / night

£461 / week

1 / 10

Holiday home with shared pool in Chesapeake Beach

Chesapeake Beach house

3 bedrooms • 3 bathrooms • sleeps 8

from £815 / night

£5,700 / week

1 / 11

Holiday home in Annapolis

Annapolis house

4 bedrooms • 4 bathrooms • sleeps 10

from £590 / night

£3,291 - £3,586 / week

1 / 28

Holiday home in Edgewater

Edgewater house

2 bedrooms • 1 bathroom • sleeps 8

from £422 / night

£2,953 / week

1 / 13

Condo rental in Annapolis

Annapolis condo

3 bedrooms • 3 bathrooms • sleeps 6

from £223 / night

£1,556 / week

1 / 64

Stevensville holiday apartment rental

Stevensville apartment

1 bedroom • 1 bathroom • sleeps 2

from £136 / night

£676 / week

1 / 17

Annapolis holiday home rental

Annapolis house

4 bedrooms • 4 bathrooms • sleeps 11

from £281 / night

£1,952 - £4,051 / week

1 / 47

Annapolis holiday home rental

Annapolis house

2 bedrooms • 2 bathrooms • sleeps 7

from £287 / night

£1,786 - £2,939 / week

1 / 29

Annapolis holiday home rental

Annapolis house

2 bedrooms • 2 bathrooms • sleeps 5

from £143 / night

£929 - £2,720 / week

1 / 41

Holiday home with swimming pool in Stevensville

Stevensville house

3 bedrooms • 3 bathrooms • sleeps 13

from £272 / night

£1,899 - £4,536 / week

1 / 36

Holiday home in Annapolis

Annapolis house

4 bedrooms • 2 bathrooms • sleeps 8

from £143 / night

£929 - £7,481 / week

1 / 39

Annapolis holiday home rental

Annapolis house

4 bedrooms • 4 bathrooms • sleeps 14

from £307 / night

£2,135 - £7,711 / week

1 / 49

Holiday home in Annapolis

Annapolis house

4 bedrooms • 2 bathrooms • sleeps 8

from £284 / night

£1,928 - £4,015 / week

1 / 48

Holiday home in Annapolis

Annapolis house

3 bedrooms • 3 bathrooms • sleeps 10

from £310 / night

£2,052 - £5,967 / week

1 / 52

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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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