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Holiday Lettings
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> Houses and Apartments in Annapolis

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

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  • Apartment (2)
  • Cottage (1)
  • House (24)
  • Townhouse (2)
  • Condo (2)

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77 Holiday homes

Holiday home in Annapolis

Annapolis house

2 bedrooms • 2 bathrooms • sleeps 6

from £138 / night

£964 / week

1 / 10

Annapolis holiday home rental

Annapolis house

4 bedrooms • 4 bathrooms • sleeps 8

from £284 / night

£1,916 - £4,807 / week

1 / 53

Holiday home in Annapolis

Annapolis house

3 bedrooms • 4 bathrooms • sleeps 6

from £482 / night

£3,373 / week

1 / 30

Holiday home in Annapolis

Annapolis house

3 bedrooms • 5 bathrooms • sleeps 11

1 review

from £584 / night

£4,538 / week

1 / 18

Holiday home in Annapolis

Annapolis house

4 bedrooms • 2 bathrooms • sleeps 8

from £141 / night

£912 - £7,344 / week

1 / 39

Holiday condo in Annapolis

Annapolis condo

3 bedrooms • 2 bathrooms • sleeps 6

from £163 / night

£1,138 / week

1 / 33

Holiday home in Annapolis

Annapolis house

4 bedrooms • 4 bathrooms • sleeps 10

from £580 / night

£3,235 - £3,525 / week

1 / 28

Annapolis holiday townhouse accommodation

Annapolis townhouse

3 bedrooms • 2 bathrooms • sleeps 6

from £87 / night

£604 / week

1 / 24

Holiday townhouse in Annapolis

Annapolis townhouse

4 bedrooms • 3 bathrooms • sleeps 10

from £411 / night

£2,489 / week

1 / 4

Holiday home in Annapolis

Annapolis house

4 bedrooms • 2 bathrooms • sleeps 10

from £267 / night

£1,864 - £3,658 / week

1 / 41

Holiday apartment in Annapolis

Annapolis apartment

1 bedroom • 1 bathroom • sleeps 2

from £250 / night

£914 / week

1 / 7

Holiday home in Annapolis

Annapolis house

4 bedrooms • 2 bathrooms • sleeps 11

from £379 / night

£2,067 - £7,048 / week

1 / 37

Holiday home in Annapolis

Annapolis house

4 bedrooms • 2 bathrooms • sleeps 8

from £279 / night

£1,893 - £4,099 / week

1 / 48

Holiday cottage in Annapolis

Annapolis cottage

1 bedroom • 1 bathroom • sleeps 4

from £158 / night

£976 - £1,916 / week

1 / 38

Holiday home in Annapolis

Annapolis house

4 bedrooms • 4 bathrooms • sleeps 12

from £276 / night

£1,916 - £4,024 / week

1 / 42

Holiday home in Annapolis

Annapolis house

3 bedrooms • 2 bathrooms • sleeps 6

from £92 / night

£581 - £4,773 / week

1 / 45

Holiday home rental

Annapolis house

4 bedrooms • 2 bathrooms • sleeps 8

from £276 / night

£1,864 - £8,221 / week

1 / 31

Home rental in Annapolis

Annapolis house

4 bedrooms • 4 bathrooms • sleeps 11

from £297 / night

£2,067 - £7,321 / week

1 / 32

Holiday home letting

Annapolis house

5 bedrooms • 4 bathrooms • sleeps 11

from £479 / night

£3,164 - £4,579 / week

1 / 21

Annapolis holiday home rental

Annapolis house

2 bedrooms • 2 bathrooms • sleeps 7

from £282 / night

£1,754 - £2,886 / week

1 / 29

Holiday home in Annapolis

Annapolis house

3 bedrooms • 2 bathrooms • sleeps 6

from £141 / night

£912 - £4,773 / week

1 / 50

Holiday home in Annapolis

Annapolis house

4 bedrooms • 4 bathrooms • sleeps 10

from £276 / night

£1,864 - £9,980 / week

1 / 50

Holiday home in Annapolis

Annapolis house

3 bedrooms • 3 bathrooms • sleeps 10

from £426 / night

£2,764 - £5,858 / week

1 / 52

Annapolis holiday home rental

Annapolis house

2 bedrooms • 2 bathrooms • sleeps 5

from £141 / night

£912 - £4,703 / week

1 / 41

Home rental in Annapolis

Annapolis house

3 bedrooms • 3 bathrooms • sleeps 8

from £208 / night

£1,452 - £3,919 / week

1 / 30

Holiday home rental

Annapolis house

4 bedrooms • 3 bathrooms • sleeps 9

3 reviews

from £355 / night

£2,086 - £2,699 / week

1 / 30

Condo rental in Annapolis

Annapolis condo

3 bedrooms • 3 bathrooms • sleeps 6

from £219 / night

£1,527 / week

1 / 64

Holiday home in Annapolis

Annapolis house

5 bedrooms • 3 bathrooms • sleeps 10

from £841 / night

£10,091 / week

1 / 12

Holiday home rental

Annapolis house

6 bedrooms • 5 bathrooms • sleeps 12

6 reviews

from £625 / night

£4,164 - £4,372 / week

1 / 19

Annapolis holiday home rental

Annapolis house

3 bedrooms • 1 bathroom • sleeps 6

2 reviews

from £208 / night

£829 - £974 / week

1 / 52

Annapolis holiday apartment rental

Annapolis apartment

2 bedrooms • 1 bathroom • sleeps 5

from £258 / night

£1,603 - £2,148 / week

1 / 20

Great rentals within 20 miles that match your search

Cape Saint Claire holiday home rental

Cape Saint Claire house

4 bedrooms • 5 bathrooms • sleeps 14

from £666 / night

£4,663 / week

1 / 19

Glen Burnie holiday home rental

Glen Burnie house

1 bedroom • 1 bathroom • sleeps 2

from £38 / night

£250 / week

1 / 7

Holiday apartment in Gambrills

Gambrills apartment

1 bedroom • 1 bathroom • sleeps 2

from £50 / night

£315 / week

1 / 6

Guest house rental in Glen Burnie

Glen Burnie guest house

1 bedroom • 1 bathroom • sleeps 2

from £84 / night

£583 / week

1 / 15

Guest house rental in Glen Burnie

Glen Burnie guest house

1 bedroom • 1 bathroom • sleeps 2

from £84 / night

£583 / week

1 / 15

Glen Burnie holiday guest house rental

Glen Burnie guest house

1 bedroom • 1 bathroom • sleeps 2

from £84 / night

£583 / week

1 / 15

Glen Burnie holiday guest house rental

Glen Burnie guest house

1 bedroom • 1 bathroom • sleeps 2

from £84 / night

£583 / week

1 / 15

Holiday home in Largo

Largo house

5 bedrooms • 8 bathrooms • sleeps 10

4 reviews

from £1,362 / night

£8,097 / week

1 / 6

Holiday guest house in Baltimore

Baltimore guest house

2 bedrooms • 1 bathroom • sleeps 4

1 review

from £50 / night

£344 / week

1 / 8

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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