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Holiday Houses in Talbot County

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47 Holiday homes

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

Wittman log cabin

5 bedrooms / 5 bathrooms / sleeps 10

3

from £852 / night

£5,461 / week

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

Royal Oak house

5 bedrooms / 4 bathrooms / sleeps 10

from £718 / night

£5,478 / week

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

St. Michaels cottage

2 bedrooms / 2 bathrooms / sleeps 5

11

Travellers’ Choice award

from £188 / night

£1,464 / week

Location Location! St Michaels-- In Town Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

24

from £214 / night

£1,289 - £1,529 / week

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

St. Michaels house

7 bedrooms / 4 bathrooms / sleeps 9

14

from £341 / night

£2,141 - £2,578 / week

Waterfront Property, Kayaks, Private Dock, Near Town

St. Michaels house

3 bedrooms / 3 bathrooms / sleeps 6

1

Responds fast! avg. 1 hour 55 minutes

from £666 / night

£3,995 / week

Premier Cottage in St. Michaels- In Town Location!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

15

from £180 / night

£1,381 - £1,587 / week

Cottage 1a at Grandview Pleasure Point

Bozman house

1 bedroom / 1 bathroom / sleeps 4

from £213 / night

£792 / 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

Responds fast! avg. 3 hours 53 minutes

from £157 / night

£918 / 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 / 4 bathrooms / sleeps 6

Responds fast! avg. 2 hours 46 minutes

from £5,242 / night

£65,522 / week

St. Michaels Area Cottage - Walk to Water & Marina

Neavitt house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 44 minutes

from £135 / night

£940 / week

Waterview Cottage In St. Michaels!

St. Michaels cottage

2 bedrooms / 3 bathrooms / sleeps 5

5

from £188 / night

£1,464 / week

Cottage 2 at Grandview Pleasure Point

Bozman house

2 bedrooms / 1 bathroom / sleeps 6

1

from £336 / night

£1,357 - £2,117 / week

Cottage 1b at Grandview Pleasure Point

Bozman cottage

1 bedroom / 1 bathroom / sleeps 2

from £213 / night

£765 / 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 £310 / night

£2,164 / week

Main House at Grandview at Pleasure Point

Bozman house

5 bedrooms / 3 bathrooms / sleeps 13

13

from £600 / night

£2,713 / week

St. Michael's Premier in Town Summer Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 4

1

from £342 / night

£1,951 / week

6942 Travelers Rest

Royal Oak house

4 bedrooms / 4 bathrooms / sleeps 10

from £322 / night

£1,995 - £8,428 / week

Bay Cottage Resort

St. Michaels house

6 bedrooms / 5 bathrooms / sleeps 14

from £1,767 / night

£10,599 / week

Great rentals within 20 miles that match your search

Retreat at a quiet, water front cottage

Chestertown house

3 bedrooms / 3 bathrooms / sleeps 8

3

from £278 / night

£1,875 / 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

Serene Waterfront Apartment on Kent Island

Stevensville apartment

1 bedroom / 1 bathroom / sleeps 2

from £142 / night

£753 / week

Charming Townhouse - Steps to City Dock and USNA

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 8

1

from £424 / night

£6,118 / 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

Clean & Spacious

Cape Saint Claire house

4 bedrooms / 5 bathrooms / sleeps 14

from £740 / night

£5,180 / week

Bay Cottage

Rock Hall house

2 bedrooms / 1 bathroom / sleeps 5

from £252 / night

£1,762 / week

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

Annapolis apartment

2 bedrooms / 1 bathroom / sleeps 5

from £227 / night

£1,587 / week

Sailors Crossing

Rock Hall house

3 bedrooms / 2 bathrooms / sleeps 10

3

from £330 / night

£2,305 / week

Maryland’s Eastern Shore Welcomes You

Preston house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 55 minutes

from £61 / night

£175 / week

Bayside Retreat

Rock Hall house

3 bedrooms / 2 bathrooms / sleeps 6

from £255 / night

£1,779 / week

EASTERN SHORE MARYLAND WELCOMES YOU

Preston house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 55 minutes

from £63 / night

£179 - £241 / week

Love Point Waterfront

Kent Island house

3 bedrooms / 3 bathrooms / sleeps 12

14

from £222 / night

£1,240 - £2,975 / week

Huge Stevensville Home w/Pool & Eastern Shore View

Stevensville house

3 bedrooms / 5 bathrooms / sleeps 10

1

Responds fast! avg. 20 minutes

from £364 / night

£2,546 / week

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

Chester house

4 bedrooms / 2 bathrooms / sleeps 8

3

from £252 / night

£1,765 / week

Stunning Home in the Heart of Downtown Annapolis

Annapolis house

3 bedrooms / 5 bathrooms / sleeps 11

1

from £609 / night

£4,731 / week

Walk to Shops/Eateries Charming Cottage. Dogs Wel.

Annapolis house

3 bedrooms / 1 bathroom / sleeps 6

2

from £219 / night

£873 - £1,026 / week

Private setting, enjoy nature, kayaking and total relaxation

Bethlehem house

3 bedrooms / 2 bathrooms / sleeps 8

from £175 / night

£961 - £1,573 / week

Charming Annapolis Waterview home

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 10

from £436 / night

£2,534 - £2,840 / week

Viewing 40 of 47
rentals in Talbot County