COVID-19 Update

The impact of COVID-19 on travel is unprecedented. Like you, we’re monitoring the situation. Rest assured, we’re here to help with questions about your plans. Learn more here: About the coronavirus outbreak (COVID-19)

Holiday Houses in Talbot County

Updating

age 0-16
45 Results

Relevance

Price low to high

Price high to low

Reviews

45 Holiday homes

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

Wittman log cabin

5 bedrooms / 5 bathrooms / sleeps 10

3

from £841 / night

£5,387 / week

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

Royal Oak house

5 bedrooms / 4 bathrooms / sleeps 10

from £725 / night

£5,070 / 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 £186 / night

£1,444 / week

Location Location! St Michaels-- In Town Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

24

from £212 / night

£1,272 - £1,509 / week

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

St. Michaels house

7 bedrooms / 4 bathrooms / sleeps 9

14

from £337 / night

£2,112 - £2,543 / 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 £177 / night

£1,358 - £1,560 / 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 £155 / night

£905 / 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 £5,171 / night

£64,635 / week

St. Michaels Area Cottage - Walk to Water & Marina

Neavitt house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 18 minutes

from £132 / night

£923 / week

Waterview Cottage In St. Michaels!

St. Michaels cottage

2 bedrooms / 3 bathrooms / sleeps 5

5

from £186 / night

£1,444 / 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

from £304 / night

£2,126 / 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 £335 / night

£1,915 / week

6942 Travelers Rest

Royal Oak house

4 bedrooms / 4 bathrooms / sleeps 10

from £340 / night

£2,070 - £8,283 / 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

Retreat at a quiet, water front cottage

Chestertown house

3 bedrooms / 3 bathrooms / sleeps 8

3

from £278 / night

£1,875 / week

The Heart of Historic Cool in Annapolis

Annapolis house

5 bedrooms / 3 bathrooms / sleeps 10

from £942 / night

£11,295 / 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

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

from £62 / night

£176 / week

EASTERN SHORE MARYLAND WELCOMES YOU

Preston house

1 bedroom / 1 bathroom / sleeps 2

from £62 / night

£176 - £237 / week

Bayside Retreat

Rock Hall house

3 bedrooms / 2 bathrooms / sleeps 6

from £256 / night

£1,788 / week

Bay Cottage

Rock Hall house

2 bedrooms / 1 bathroom / sleeps 5

from £241 / night

£1,684 / week

Serene Waterfront Apartment on Kent Island

Stevensville apartment

1 bedroom / 1 bathroom / sleeps 2

from £131 / night

£697 / week

1

Responds fast! avg. 27 minutes

from £305 / night

£2,131 / week

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

Chester house

4 bedrooms / 2 bathrooms / sleeps 8

3

from £248 / night

£1,731 / week

Stunning Home in the Heart of Downtown Annapolis

Annapolis house

3 bedrooms / 5 bathrooms / sleeps 11

1

from £599 / night

£4,654 / week

Walk to Shops/Eateries Charming Cottage. Dogs Wel.

Annapolis house

3 bedrooms / 1 bathroom / sleeps 6

2

from £216 / night

£861 - £1,012 / week

Newly-Listed Naval Academy Themed Home at the Gates!

Annapolis house

4 bedrooms / 2 bathrooms / sleeps 11

from £473 / night

£3,288 - £4,965 / week

Private setting, enjoy nature, kayaking and total relaxation

Bethlehem house

3 bedrooms / 2 bathrooms / sleeps 8

from £173 / night

£948 - £1,552 / week

Waterfront Chesapeake Cottage in Oyster Bay - Dock

Mayo cottage

4 bedrooms / 1 bathroom / sleeps 8

Responds fast! avg. 1 hour 18 minutes

from £195 / night

£1,364 / week

Waterfront Annapolis Home: Fire Pit & Fishing Pier

Cape Saint Claire house

3 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 1 hour 18 minutes

from £128 / night

£893 / week

Viewing 40 of 45
rentals in Talbot County