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Holiday Houses in St. Michaels

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54 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 £239 / night

£1,672 / week

Location Location! St Michaels-- In Town Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

24

from £223 / night

£1,441 / week

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

St. Michaels house

7 bedrooms / 4 bathrooms / sleeps 9

14

from £445 / night

£2,594 / week

Waterfront Property, Kayaks, Private Dock, Near Town

St. Michaels house

3 bedrooms / 3 bathrooms / sleeps 6

1

Responds fast! avg. 2 hours 3 minutes

from £618 / night

£3,705 / week

Premier Cottage in St. Michaels- In Town Location!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

15

from £239 / night

£1,490 / 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 £148 / night

£865 / week

Waterview Cottage In St. Michaels!

St. Michaels cottage

2 bedrooms / 3 bathrooms / sleeps 5

6

from £239 / night

£1,672 / week

Sandy Pines: Enjoy Harris Creek w/Pool and Boats

St. Michaels house

4 bedrooms / 3 bathrooms / sleeps 8

5

Responds fast! avg. 34 minutes

from £564 / night

£3,948 / week

St. Michael's Premier in Town Summer Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 4

1

from £317 / night

£1,808 / week

Bay Cottage Resort

St. Michaels house

6 bedrooms / 5 bathrooms / sleeps 12

from £1,730 / night

£10,376 / week

Great rentals within 20 miles that match your search

The Heart of Historic Cool in Annapolis

Annapolis house

5 bedrooms / 3 bathrooms / sleeps 10

from £828 / night

£9,931 / week

Charming Townhouse - Steps to City Dock and USNA

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 8

1

Responds fast! avg. 58 minutes

from £374 / night

£2,617 / week

Cottage 1a at Grandview Pleasure Point

Bozman house

1 bedroom / 1 bathroom / sleeps 4

from £144 / night

£554 - £780 / week

1

Responds fast! avg. 27 minutes

from £288 / night

£2,014 / week

Beautiful Murray Hill Home (Annapolis)

Annapolis house

4 bedrooms / 3 bathrooms / sleeps 9

3

from £350 / night

£2,055 - £2,659 / week

Walk to Shops/Eateries Charming Cottage. Dogs Wel.

Annapolis house

3 bedrooms / 1 bathroom / sleeps 6

2

from £206 / night

£823 - £967 / week

Stunning Home in the Heart of Downtown Annapolis

Annapolis house

3 bedrooms / 5 bathrooms / sleeps 11

1

from £573 / night

£4,448 / week

Main House at Grandview at Pleasure Point

Bozman house

5 bedrooms / 3 bathrooms / sleeps 13

13

from £468 / night

£1,854 - £2,657 / week

Serene Waterfront Apartment on Kent Island

Stevensville apartment

1 bedroom / 1 bathroom / sleeps 2

from £132 / night

£659 / week

Indoor pool and spa located in beautiful Southern Maryland woodlands

Chesapeake Beach house

3 bedrooms / 3 bathrooms / sleeps 8

from £412 / night

£2,882 / week

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

Cambridge house

6 bedrooms / 5 bathrooms / sleeps 18

16

from £494 / night

£3,452 / week

Annapolis Home w/ Deck & Whitehall Bay Access

Cape Saint Claire house

4 bedrooms / 2 bathrooms / sleeps 8

from £177 / night

£1,239 / week

Waterfront Chesapeake Cottage in Oyster Bay - Dock

Mayo cottage

4 bedrooms / 1 bathroom / sleeps 8

from £369 / night

£2,582 / week

Chesapeake Beach Apt. Walk to Bay, Beach & Marina!

Chesapeake Beach apartment

1 bedroom / 1 bathroom / sleeps 2

from £60 / night

£421 / week

Annapolis House w/ Patio in Bay Ridge Maryland!

Annapolis house

3 bedrooms / 4 bathrooms / sleeps 6

from £622 / night

£4,351 / week

Waterfront Annapolis Home: Fire Pit & Fishing Pier

Cape Saint Claire house

3 bedrooms / 1 bathroom / sleeps 6

from £238 / night

£1,666 / week

NEW! Beautiful Colonial Home on the Choptank River

Cambridge house

4 bedrooms / 2 bathrooms / sleeps 8

from £421 / night

£2,945 / week

NEW! Coastal Pet-Friendly Cottage <½ Mi to Beaches

North Beach cottage

3 bedrooms / 1 bathroom / sleeps 6

from £74 / night

£513 / week

NEW! Waterfront Home w/ Rowboat, Kayaks & Fishing

Chesapeake Beach house

2 bedrooms / 2 bathrooms / sleeps 4

from £234 / night

£1,637 / week

Cambridge Colonial Home, Walk to Town & Waterfront

Cambridge house

3 bedrooms / 3 bathrooms / sleeps 12

from £252 / night

£1,764 / week

Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!

Shady Side house

3 bedrooms / 2 bathrooms / sleeps 6

1

from £343 / night

£2,398 / week

Abay Palace of Kent Narrows in a King Bed

Grasonville apartment

1 bedroom / 1 bathroom / sleeps 5

1

from £136 / night

£809 - £1,024 / week

Charming Annapolis Waterview home

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 10

from £576 / night

£3,211 - £3,499 / week

Cottage 1b at Grandview Pleasure Point

Bozman cottage

1 bedroom / 1 bathroom / sleeps 2

from £144 / night

£556 - £783 / week

Cottage 2 at Grandview Pleasure Point

Bozman house

2 bedrooms / 1 bathroom / sleeps 6

1

from £318 / night

£1,359 - £2,079 / week

St. Michaels Area Cottage - Walk to Water & Marina

Neavitt house

2 bedrooms / 2 bathrooms / sleeps 4

from £219 / night

£1,528 / week

NEW! Chic Condo w/ Balcony 1Mi to Annapolis Harbor

Annapolis condo

3 bedrooms / 2 bathrooms / sleeps 6

from £191 / night

£1,332 / week

Tranquil Easton Waterfront Property

Easton house

3 bedrooms / 4 bathrooms / sleeps 6

Responds fast! avg. 2 hours 31 minutes

from £4,940 / night

£61,746 / week

Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview

Wittman log cabin

5 bedrooms / 5 bathrooms / sleeps 10

3

from £803 / night

£5,146 / week

Cozy Home in Historic Annapolis with Parking

Annapolis house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 28 minutes

from £164 / night

£1,147 / week

Viewing 40 of 54
rentals in St. Michaels