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Houses in Annapolis and Apartments – Holiday Lettings - Holiday Rentals Annapolis

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80 Holiday homes

Cottage rental in Annapolis

Annapolis cottage

3 bedrooms / 2 bathrooms / sleeps 6

22

Responds fast! avg. 2 hours 23 minutes

from £302 / night

£1,695 / week

Holiday villa in Annapolis

Annapolis villa

5 bedrooms / 3 bathrooms / sleeps 21

from £372 / night

£2,824 - £5,647 / week

Holiday private room in Annapolis

Annapolis private room

1 bedroom / 1 bathroom / sleeps 2

2

from £56 / night

£389 / week

Holiday apartment in Annapolis

Annapolis apartment

1 bedroom / 1 bathroom / sleeps 2

from £283 / night

£1,036 / week

Holiday home letting

Annapolis house

5 bedrooms / 4 bathrooms / sleeps 11

from £447 / night

£3,294 - £5,459 / week

Holiday apartment in Annapolis

Annapolis apartment

2 bedrooms / 1 bathroom / sleeps 5

from £236 / night

£1,648 / week

Holiday home rental

Annapolis house

6 bedrooms / 5 bathrooms / sleeps 12

6

Responds fast! avg. 16 minutes

from £706 / night

£4,706 - £9,412 / week

Annapolis holiday home rental

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 7

1

Responds fast! avg. 41 minutes

from £269 / night

£2,165 / week

Annapolis holiday home rental

Annapolis house

3 bedrooms / 1 bathroom / sleeps 6

2

from £236 / night

£941 - £1,072 / week

Holiday townhouse in Annapolis

Annapolis townhouse

4 bedrooms / 3 bathrooms / sleeps 10

from £466 / night

£2,824 / week

Holiday home in Annapolis

Annapolis house

3 bedrooms / 4 bathrooms / sleeps 6

from £353 / night

£2,471 / week

Holiday home in Annapolis

Annapolis house

3 bedrooms / 4 bathrooms / sleeps 6

Responds fast! avg. 5 minutes

from £546 / night

£3,822 / week

Holiday home in Annapolis

Annapolis house

3 bedrooms / 4 bathrooms / sleeps 8

from £283 / night

£1,883 / week

Holiday home rental

Annapolis house

4 bedrooms / 3 bathrooms / sleeps 9

3

from £400 / night

£2,349 - £3,040 / week

Holiday home in Annapolis

Annapolis house

5 bedrooms / 3 bathrooms / sleeps 11

Responds fast! avg. 4 minutes

from £634 / night

£4,434 / week

Holiday home in Annapolis

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 16 minutes

from £398 / night

£2,780 / week

Holiday home in Annapolis

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 10

from £470 / night

£2,730 - £3,059 / week

Holiday home in Annapolis

Annapolis house

3 bedrooms / 5 bathrooms / sleeps 11

1

from £655 / night

£5,083 / week

Annapolis holiday townhouse accommodation

Annapolis townhouse

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 26 minutes

from £109 / night

£763 / week

Holiday home in Annapolis

Annapolis house

5 bedrooms / 3 bathrooms / sleeps 10

from £942 / night

£11,295 / week

Holiday home in Annapolis

Annapolis house

2 bedrooms / 2 bathrooms / sleeps 6

from £188 / night

£1,312 / week

Holiday home in Annapolis

Annapolis house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 5 minutes

from £248 / night

£1,737 / week

Holiday home in Annapolis

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 8

1

from £424 / night

£6,118 / week

Condo rental in Annapolis

Annapolis condo

3 bedrooms / 3 bathrooms / sleeps 6

from £248 / night

£1,579 - £13,813 / week

Great rentals within 20 miles that match your search

Holiday boathouse in Edgewater

Edgewater boathouse

1 bedroom / 1 bathroom / sleeps 4

from £113 / night

£786 / week

Stevensville holiday home rental

Stevensville house

3 bedrooms / 4 bathrooms / sleeps 10

from £1,308 / night

£6,540 / week

St. Michaels holiday cottage rental

St. Michaels cottage

2 bedrooms / 2 bathrooms / sleeps 5

11

Responds fast! avg. 3 hours 49 minutes

from £202 / night

£1,570 - £1,790 / week

Holiday home in Chester

Chester house

4 bedrooms / 3 bathrooms / sleeps 12

1

from £328 / night

£2,296 / week

Rock Hall holiday home rental

Rock Hall house

3 bedrooms / 2 bathrooms / sleeps 10

3

from £355 / night

£2,480 / week

Holiday home in North Beach

North Beach house

3 bedrooms / 2 bathrooms / sleeps 8

from £470 / night

£3,289 / week

Holiday home rental

Severn house

4 bedrooms / 4 bathrooms / sleeps 14

Responds fast! avg. 19 minutes

from £452 / night

£3,163 / week

Glen Burnie holiday guest house rental

Glen Burnie guest house

1 bedroom / 1 bathroom / sleeps 2

from £95 / night

£659 / week

Holiday boathouse in Edgewater

Edgewater boathouse

1 bedroom / 1 bathroom / sleeps 4

from £113 / night

£791 / week

Holiday home in North Beach

North Beach house

3 bedrooms / 2 bathrooms / sleeps 6

from £283 / night

£1,412 - £1,742 / week

Glen Burnie holiday guest house rental

Glen Burnie guest house

1 bedroom / 1 bathroom / sleeps 2

from £95 / night

£659 / week

Holiday condo in Largo

Largo condo

2 bedrooms / 3 bathrooms / sleeps 4

from £151 / night

£1,055 / week

Edgemere holiday caravan/mobile home rental

Edgemere caravan/mobile home

1 bedroom / 1 bathroom / sleeps 4

1

from £62 / night

£377 - £509 / week

Holiday home in Bowie

Bowie house

5 bedrooms / 3 bathrooms / sleeps 16

from £462 / night

£3,229 - £3,888 / week

Holiday apartment in Gambrills

Gambrills apartment

1 bedroom / 1 bathroom / sleeps 2

from £57 / night

£356 / week

Holiday home in Largo

Largo house

5 bedrooms / 8 bathrooms / sleeps 10

4

from £1,539 / night

£9,154 / week

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rentals in Annapolis

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Annapolis holidays

Come to Annapolis to experience the best of old world style and Chesapeake Bay charm. This distinguished town, located on the salty bay, has provided visitors with the perfect Maryland holiday getaway for centuries. Visit the museums here and learn more about the early settlers of the area, the natural history and the wildlife that populate fragile Maryland ecosystems, and the important events in American history that took place here. Find a holiday rental, summer home, or bayside cottage overlooking the shoreline. Head downtown to experience Maryland's annual festivals celebrating regional music and the famous Maryland blue crab. Go antique and craft shopping in the heart of the city. Explore Annapolis museums and art galleries and spend some time on the emerald green golf courses around the Chesapeake Bay. At night, head downtown for world-class seafood and a live performance at a local theatre.

Here are a few additional suggestions for your trip:

  • Visit the Maryland State House: Annapolis was America's first peacetime capitol, and the statehouse is the oldest still in legislative use.
  • Visit the US Naval Academy: Take a tour of the Naval Academy, one of the proud institutions of Annapolis.
  • Go on a pirate adventure: Take a real life pirate adventure on a ship in Annapolis Harbor. Pirate Adventures on the Chesapeake offers a full day of true buccaneering on an Annapolis boat, complete with face paint, pirate fashions, and a water cannon battle.
  • Experience Annapolis sailing: Nothing can compare with a real sailing adventure aboard an authentic Chesapeake Skipjack. Help man the sails, try your hand at Annapolis fishing and crabbing, or just relax on the deck and watch the Harbor birds sail overhead.
  • Visit the William Paca Garden: This colonial garden offers peace, serenity, and history lessons along with guided tours.
  • Explore Quiet Waters Park: This 340 acre park just outside the city centre offers more than six miles of trails perfect for strolling, jogging, or biking.

Thousands of visitors come to this area every year to enjoy long weekend getaways, family reunions, and beautiful wedding venues in Annapolis. If you're amongst them, find the perfect rental apartment in the heart of downtown, or a bayside condo near the Harbor. While you're here, consider visiting a few other popular holiday destinations in Maryland like Arnold and Lake Shore.

Also consider