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Holiday Houses in Talbot County

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61 Holiday homes

Waterfront Room Rentals 1 with Private Beach

Trappe private room

1 bedroom / 1 bathroom / sleeps 2

1

Responds fast! avg. 1 hour 54 minutes

from £123 / night

£735 / week

Waterfront Room Rentals 2 with Private Beach

Trappe private room

1 bedroom / 1 bathroom / sleeps 2

1

Responds fast! avg. 1 hour 54 minutes

from £95 / night

£565 / week

Waterfront Vacation Home with Private Beach

Trappe house

3 bedrooms / 3 bathrooms / sleeps 6

5

Responds fast! avg. 1 hour 54 minutes

from £310 / night

£1,861 / week

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

Wittman log cabin

5 bedrooms / 5 bathrooms / sleeps 10

3

from £906 / night

£5,803 - £6,778 / week

Waterfront Room Rentals 3 with Private Beach

Trappe private room

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 54 minutes

from £95 / night

£565 / 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

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

St. Michaels cottage

2 bedrooms / 2 bathrooms / sleeps 5

11

Responds fast! avg. 3 hours 49 minutes

from £200 / night

£1,553 - £1,771 / week

Location Location! St Michaels-- In Town Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

24

Responds fast! avg. 3 hours 49 minutes

from £228 / night

£1,368 - £1,623 / week

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

St. Michaels house

7 bedrooms / 4 bathrooms / sleeps 9

14

Responds fast! avg. 3 hours 49 minutes

from £362 / night

£2,272 - £2,735 / week

Historic Waterfront Property with Wi-Fi and Dock

St. Michaels house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 14 minutes

from £706 / night

£3,294 / week

Premier Cottage in St. Michaels- In Town Location!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

14

Responds fast! avg. 3 hours 49 minutes

from £190 / night

£1,461 - £1,678 / week

Cottage 1a at Grandview Pleasure Point

Bozman house

1 bedroom / 1 bathroom / sleeps 4

from £177 / night

£605 - £857 / 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 £166 / night

£974 / week

Pot Pie House

St. Michaels house

3 bedrooms / 2 bathrooms / sleeps 6

2

from £212 / night

£1,410 / week

Tranquil Easton Waterfront Property

Easton house

3 bedrooms / 3 bathrooms / sleeps 12

from £706 / night

£6,589 / week

St. Michaels Area Cottage - Walk to Water & Marina

Neavitt house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 5 minutes

from £142 / night

£993 / week

Waterview Cottage In St. Michaels!

St. Michaels cottage

2 bedrooms / 3 bathrooms / sleeps 5

5

Responds fast! avg. 3 hours 49 minutes

from £203 / night

£1,577 - £1,798 / week

Cottage 2 at Grandview Pleasure Point

Bozman house

2 bedrooms / 1 bathroom / sleeps 6

1

from £278 / night

£932 - £2,288 / week

Cottage 1b at Grandview Pleasure Point

Bozman cottage

1 bedroom / 1 bathroom / sleeps 2

from £177 / night

£605 - £829 / week

Lakeside Private Apartment

Wye Mills apartment

1 bedroom / 1 bathroom / sleeps 5

from £131 / night

£916 / week

Sandy Pines: Enjoy Harris Creek w/Pool and Boats

St. Michaels house

4 bedrooms / 3 bathrooms / sleeps 8

5

from £325 / night

£2,275 / week

Main House at Grandview at Pleasure Point

Bozman house

5 bedrooms / 3 bathrooms / sleeps 13

13

from £528 / night

£2,048 - £2,897 / week

St. Michael's Premier in Town Summer Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 4

1

from £363 / night

£2,071 / week

St. Michaels award-winning waterfront BayCottage, pool, docks, sundeck, grounds

St. Michaels villa

6 bedrooms / 6 bathrooms / sleeps 12

1

Responds fast! avg. 3 hours 21 minutes

from £940 / night

£5,826 / week

6942 Travelers Rest

Royal Oak house

4 bedrooms / 4 bathrooms / sleeps 10

from £300 / night

£1,824 - £6,075 / 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

Great rentals within 20 miles that match your search

Love Point Luxury Waterfront in Stevensville

Stevensville house

3 bedrooms / 4 bathrooms / sleeps 10

from £1,308 / night

£6,540 / week

Retreat at a quiet, water front cottage

Chestertown house

3 bedrooms / 3 bathrooms / sleeps 8

3

from £278 / night

£1,875 / week

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

Annapolis apartment

2 bedrooms / 1 bathroom / sleeps 5

from £236 / night

£1,648 / week

Charming Eastport Home

Annapolis house

3 bedrooms / 4 bathrooms / sleeps 8

from £283 / night

£1,883 / 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

C/ean & Cozy

Annapolis private room

1 bedroom / 1 bathroom / sleeps 2

2

from £56 / night

£389 / 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

Peaceful, Waterfront Home on 3 Acres (pier + western view w/gorgeous sunsets)

Chester house

4 bedrooms / 2 bathrooms / sleeps 8

3

from £269 / night

£1,878 / week

Annapolis Crows Nest Cottage: Chesapeake Bay View

Annapolis villa

5 bedrooms / 3 bathrooms / sleeps 21

from £372 / night

£2,824 - £5,647 / week

Charming Townhouse - Steps to City Dock and USNA

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 8

1

from £424 / night

£6,118 / 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

Viewing 40 of 61
rentals in Talbot County