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Holiday Houses in St. Michaels

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60 Holiday homes

Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!

St. Michaels cottage

2 bedrooms / 2 bathrooms / sleeps 5

11

from £198 / night

£1,537 - £1,753 / week

Location Location! St Michaels-- In Town Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

24

from £225 / night

£1,354 - £1,606 / week

Large Historic Thomas Harrison House on Harbor in St. Michaels Town

St. Michaels house

7 bedrooms / 4 bathrooms / sleeps 9

14

from £358 / night

£2,248 - £2,707 / week

Historic Waterfront Property with Wi-Fi and Dock

St. Michaels house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 13 minutes

from £696 / night

£3,246 / week

Premier Cottage in St. Michaels- In Town Location!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

14

from £188 / night

£1,445 - £1,661 / week

Phenomenal Vacation Rental by Water in St Michaels - Walk to Town! 4 ADULTS MAX

St. Michaels house

1 bedroom / 1 bathroom / sleeps 6

2

from £165 / night

£964 / week

Pot Pie House

St. Michaels house

3 bedrooms / 2 bathrooms / sleeps 6

2

from £212 / night

£1,410 / week

Waterview Cottage In St. Michaels!

St. Michaels cottage

2 bedrooms / 3 bathrooms / sleeps 5

5

from £197 / night

£1,530 - £1,745 / week

Sandy Pines: Enjoy Harris Creek w/Pool and Boats

St. Michaels house

4 bedrooms / 3 bathrooms / sleeps 8

5

Responds fast! avg. 32 minutes

from £321 / night

£2,247 / week

St. Michael's Premier in Town Summer Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 4

1

from £354 / night

£2,021 / week

Great rentals within 20 miles that match your search

Panoramic Views of Herrington Harbour on the Bay.

North Beach house

3 bedrooms / 2 bathrooms / sleeps 8

from £470 / night

£3,289 / week

6 Bdrm, 3.5 Bath, Cambridge Md Vacation Home

Cambridge house

6 bedrooms / 4 bathrooms / sleeps 12

from £818 / night

£2,824 / week

Excellent Location in Downtown Annapolis- walk to everything !

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 7

1

Responds fast! avg. 41 minutes

from £269 / night

£2,165 / week

Charming Eastport Home

Annapolis house

3 bedrooms / 4 bathrooms / sleeps 8

from £283 / night

£1,883 / week

Cozy Home in Historic Annapolis with Parking

Annapolis house

2 bedrooms / 2 bathrooms / sleeps 6

from £188 / night

£1,312 / week

Renovated Luxury Waterview House

North Beach house

3 bedrooms / 2 bathrooms / sleeps 6

from £283 / night

£1,412 - £1,742 / week

The Heart of Historic Cool in Annapolis

Annapolis house

5 bedrooms / 3 bathrooms / sleeps 10

from £942 / night

£11,295 / week

Stunning Home in the Heart of Downtown Annapolis

Annapolis house

3 bedrooms / 5 bathrooms / sleeps 11

1

from £655 / night

£5,083 / week

Serene Waterfront Apartment on Kent Island

Stevensville apartment

1 bedroom / 1 bathroom / sleeps 2

from £142 / night

£753 / week

Walk to Shops/Eateries Charming Cottage. Dogs Wel.

Annapolis house

3 bedrooms / 1 bathroom / sleeps 6

2

from £236 / night

£941 - £1,072 / week

Luxury Apartment with Private Entrance

Centreville apartment

1 bedroom / 1 bathroom / sleeps 3

from £111 / night

£771 / week

Modern Luxury Rental in North Beach!

North Beach house

1 bedroom / 1 bathroom / sleeps 4

from £127 / night

£800 / week

St. Michaels Waterfront Retreat with pier, pool, kayaks, gas fire pit and bikes

Royal Oak house

5 bedrooms / 4 bathrooms / sleeps 10

from £470 / night

£5,929 / week

Charming Townhouse - Steps to City Dock and USNA

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 8

1

from £424 / night

£6,118 / week

Lakeside Private Apartment

Wye Mills apartment

1 bedroom / 1 bathroom / sleeps 5

from £131 / night

£916 / week

EASTERN SHORE MARYLAND WELCOMES YOU

Preston house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 54 minutes

from £71 / night

£330 - £396 / week

Charming Artists Home in Eastport/Annapolis

Annapolis house

3 bedrooms / 4 bathrooms / sleeps 6

from £353 / night

£2,471 / week

KENT ISLAND-OCEAN VIEW Home for rent -4 bedrooms EASTERN SHORE sleeps 10-12

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

Maryland’s Eastern Shore Welcomes You

Preston house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 54 minutes

from £82 / night

£236 / week

NEW! Quiet Sailor’s Home with Pier and Bay Vistas!

Tilghman house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 5 minutes

from £221 / night

£1,545 / week

Main House at Grandview at Pleasure Point

Bozman house

5 bedrooms / 3 bathrooms / sleeps 13

13

from £628 / night

£2,839 / week

Cottage 2 at Grandview Pleasure Point

Bozman house

2 bedrooms / 1 bathroom / sleeps 6

1

from £352 / night

£1,420 - £2,216 / week

Cottage 1a at Grandview Pleasure Point

Bozman house

1 bedroom / 1 bathroom / sleeps 4

from £223 / night

£828 / week

Cottage 1b at Grandview Pleasure Point

Bozman cottage

1 bedroom / 1 bathroom / sleeps 2

from £223 / night

£801 / week

Beautiful Murray Hill Home (Annapolis)

Annapolis house

4 bedrooms / 3 bathrooms / sleeps 9

3

from £388 / night

£2,279 - £2,949 / week

Waterfront Annapolis Area 3BR/3BA Retreat with Private Pier

Edgewater house

3 bedrooms / 3 bathrooms / sleeps 10

from £298 / night

£2,084 / week

Stunning, Newer Chesapeake Waterfront Estate, Pool - 6/7 Bedrms 5 Baths

Cambridge house

6 bedrooms / 5 bathrooms / sleeps 20

13

from £547 / night

£5,929 - £6,185 / week

Annapolis Crows Nest Cottage: Chesapeake Bay View

Annapolis villa

5 bedrooms / 3 bathrooms / sleeps 21

from £361 / night

£2,738 - £4,021 / week

Love Point Waterfront

Kent Island house

3 bedrooms / 3 bathrooms / sleeps 12

14

from £231 / night

£1,291 - £3,467 / week

Location,location,location,walk to city dock,free

Annapolis apartment

2 bedrooms / 1 bathroom / sleeps 5

from £232 / night

£1,625 / week

Viewing 40 of 60
rentals in St. Michaels