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

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58 Holiday homes

St. Michaels holiday home rental

St. Michaels house

1 bedroom / 1 bathroom / sleeps 6

2

from £167 / night

£976 / week

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.

14

from £360 / night

£2,258 - £2,719 / week

Holiday home in St. Michaels

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

24

from £228 / night

£1,370 - £1,626 / week

Holiday home in St. Michaels

St. Michaels house

3 bedrooms / 2 bathrooms / sleeps 6

2

from £212 / night

£1,410 / week

Holiday home in St. Michaels

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

14

from £189 / night

£1,452 - £1,669 / week

Holiday home in St. Michaels

St. Michaels house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 13 minutes

from £696 / night

£3,246 / week

Cottage letting in St. Michaels

St. Michaels cottage

2 bedrooms / 3 bathrooms / sleeps 5

5

from £197 / night

£1,530 - £1,745 / week

St. Michaels holiday cottage rental

St. Michaels cottage

2 bedrooms / 2 bathrooms / sleeps 5

11

from £200 / night

£1,556 - £1,774 / week

St. Michaels holiday home rental

St. Michaels house

4 bedrooms / 3 bathrooms / sleeps 8

5

Responds fast! avg. 3 hours 42 minutes

from £323 / night

£2,259 / week

Great rentals within 20 miles that match your search

Holiday home in North Beach

North Beach house

3 bedrooms / 2 bathrooms / sleeps 8

from £470 / night

£3,289 / week

Holiday home in Cambridge

Cambridge house

6 bedrooms / 4 bathrooms / sleeps 12

from £818 / night

£2,824 / week

Annapolis holiday home rental

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 7

1

Responds fast! avg. 41 minutes

from £269 / night

£2,165 / week

Holiday home in Annapolis

Annapolis house

3 bedrooms / 4 bathrooms / sleeps 8

from £283 / night

£1,883 / week

Holiday home in Annapolis

Annapolis house

2 bedrooms / 2 bathrooms / sleeps 6

from £188 / night

£1,312 / week

Holiday home in North Beach

North Beach house

3 bedrooms / 2 bathrooms / sleeps 6

from £283 / night

£1,412 - £1,742 / week

Holiday home in Annapolis

Annapolis house

5 bedrooms / 3 bathrooms / sleeps 10

from £942 / night

£11,295 / week

Holiday home in Annapolis

Annapolis house

3 bedrooms / 5 bathrooms / sleeps 11

1

from £655 / night

£5,083 / week

Stevensville holiday apartment rental

Stevensville apartment

1 bedroom / 1 bathroom / sleeps 2

from £142 / night

£753 / week

Annapolis holiday home rental

Annapolis house

3 bedrooms / 1 bathroom / sleeps 6

2

from £236 / night

£941 - £1,072 / week

Holiday apartment in Centreville

Centreville apartment

1 bedroom / 1 bathroom / sleeps 3

from £111 / night

£771 / week

Holiday home in North Beach

North Beach house

1 bedroom / 1 bathroom / sleeps 4

from £127 / night

£800 / week

Home rental in Royal Oak with swimming pool

Royal Oak house

5 bedrooms / 4 bathrooms / sleeps 10

from £470 / night

£5,929 / week

Holiday home in Annapolis

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 8

1

from £424 / night

£6,118 / week

Wye Mills holiday apartment rental

Wye Mills apartment

1 bedroom / 1 bathroom / sleeps 5

from £131 / night

£916 / week

Holiday home with shared pool in Preston

Preston house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 54 minutes

from £71 / night

£330 - £396 / week

Holiday home in Annapolis

Annapolis house

3 bedrooms / 4 bathrooms / sleeps 6

from £353 / night

£2,471 / week

Holiday home with swimming pool in Kent Island

Kent Island house

4 bedrooms / 3 bathrooms / sleeps 10

1

Responds fast! avg. 1 hour 17 minutes

from £1,224 / night

£5,647 - £6,118 / week

Preston holiday home rental

Preston house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 54 minutes

from £82 / night

£236 / week

Home accommodation in Tilghman

Tilghman house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 5 minutes

from £221 / night

£1,545 / week

Holiday home with swimming pool in Bozman

Bozman house

5 bedrooms / 3 bathrooms / sleeps 13

13

from £628 / night

£2,839 / week

Bozman holiday home rental

Bozman house

2 bedrooms / 1 bathroom / sleeps 6

1

from £352 / night

£1,420 - £2,216 / week

Holiday home with shared pool in Bozman

Bozman house

1 bedroom / 1 bathroom / sleeps 4

from £223 / night

£828 / week

Holiday cottage with shared pool in Bozman

Bozman cottage

1 bedroom / 1 bathroom / sleeps 2

from £223 / night

£801 / week

Holiday home rental

Annapolis house

4 bedrooms / 3 bathrooms / sleeps 9

3

from £388 / night

£2,279 - £2,949 / week

Holiday home in Edgewater

Edgewater house

3 bedrooms / 3 bathrooms / sleeps 10

from £298 / night

£2,084 / week

Holiday villa in Annapolis

Annapolis villa

5 bedrooms / 3 bathrooms / sleeps 21

from £361 / night

£2,738 - £4,021 / week

Holiday home rental

Kent Island house

3 bedrooms / 3 bathrooms / sleeps 12

14

from £231 / night

£1,291 - £3,467 / week

Holiday apartment in Annapolis

Annapolis apartment

2 bedrooms / 1 bathroom / sleeps 5

from £232 / night

£1,625 / week

Holiday home in Chester

Chester house

4 bedrooms / 3 bathrooms / sleeps 12

1

from £325 / night

£2,276 / week

Holiday home in Chester

Chester house

4 bedrooms / 2 bathrooms / sleeps 8

3

from £265 / night

£1,853 / week

Viewing 40 of 58
rentals in St. Michaels

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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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