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

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74 Holiday homes

(19) Excellent 

25

Cottage rental in Annapolis

Maryland / Annapolis

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly

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from £312 / night

£1,872 / week

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Responds fast!
avg. 2 hours 13 minutes

from £312 / night

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26

Holiday villa in Annapolis

Maryland / Annapolis

5 20 min stay varies

  • 5 bedrooms
  • sleeps 20
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly

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from £620 / night

£2,674 - £6,238 / week

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from £620 / night

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55

Annapolis holiday home rental

Maryland / Annapolis

4 11 5 nights min

  • 4 bedrooms
  • sleeps 11
  • 5 nights min
  • Child friendly
  • Pet friendly

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from £446 / night

£3,119 / week

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from £446 / night

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(2) Excellent 

10

Holiday private room in Annapolis

Maryland / Annapolis

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Child friendly
  • Air conditioning

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from £53 / night

£368 / week

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from £53 / night

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15

Holiday apartment in Annapolis

Maryland / Annapolis

2 5 3 nights min

  • 2 bedrooms
  • sleeps 5
  • 3 nights min
  • Car not necessary
  • Air conditioning
  • Private garden

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from £161 / night

£1,123 / week

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from £161 / night

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21

Holiday home letting

Maryland / Annapolis

5 11 min stay varies

  • 5 bedrooms
  • sleeps 11
  • min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

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from £490 / night

£3,119 - £5,169 / week

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from £490 / night

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(1) Excellent 

17

Annapolis holiday home rental

Maryland / Annapolis

3 7 2 nights min

  • 3 bedrooms
  • sleeps 7
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

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from £267 / night

£2,050 / week

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Responds fast!
avg. 2 hours 21 minutes

from £267 / night

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7

Holiday apartment in Annapolis

Maryland / Annapolis

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Ask about pets

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from £268 / night

£981 / week

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from £268 / night

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(6) Excellent 

19

Holiday home rental

Maryland / Annapolis

6 12 min stay varies

  • 6 bedrooms
  • sleeps 12
  • min stay varies
  • Child friendly
  • Air conditioning

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from £669 / night

£4,456 - £7,129 / week

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Responds fast!
avg. 1 hour 34 minutes

from £669 / night

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(2) Excellent 

52

Annapolis holiday home rental

Maryland / Annapolis

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 6 km
  • Child friendly
  • Car not necessary

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from £223 / night

£891 - £2,005 / week

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Responds fast!
avg. 1 hour 49 minutes

from £223 / night

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24

Holiday home in Annapolis

Maryland / Annapolis

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child friendly
  • Air conditioning

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from £80 / night

£556 / week

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Responds fast!
avg. 14 minutes

from £80 / night

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24

Holiday home in Annapolis

Maryland / Annapolis

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Ask owner if suitable for children
  • Air conditioning

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from £335 / night

£2,341 / week

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from £335 / night

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4

Holiday townhouse in Annapolis

Maryland / Annapolis

4 10 2 nights min

  • 4 bedrooms
  • sleeps 10
  • 2 nights min
  • Child friendly

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from £441 / night

£2,674 / week

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from £441 / night

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23

Holiday home in Annapolis

Maryland / Annapolis

3 8 5 nights min

  • 3 bedrooms
  • sleeps 8
  • 5 nights min
  • Child friendly
  • Air conditioning
  • Private garden

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from £223 / night

£1,337 - £2,585 / week

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from £223 / night

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31

Holiday home in Annapolis

Maryland / Annapolis

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

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from £400 / night

£2,801 / week

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Responds fast!
avg. 10 minutes

from £400 / night

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(3) Very Good 

30

Holiday home rental

Maryland / Annapolis

4 9 min stay varies

  • 4 bedrooms
  • sleeps 9
  • min stay varies
  • Child friendly
  • Air conditioning
  • Ask about pets

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from £379 / night

£2,227 - £5,522 / week

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from £379 / night

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24

Holiday apartment in Annapolis

Maryland / Annapolis

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Air conditioning

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from £174 / night

£1,217 / week

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Responds fast!
avg. 15 minutes

from £174 / night

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43

Holiday home in Annapolis

Maryland / Annapolis

6 14 4 nights min

  • 6 bedrooms
  • sleeps 14
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly

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from £887 / night

£6,207 / week

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Responds fast!
avg. 1 hour 32 minutes

from £887 / night

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24

Holiday home in Annapolis

Maryland / Annapolis

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Child friendly
  • Air conditioning

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from £285 / night

£1,989 / week

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from £285 / night

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(2)  

26

Holiday home in Annapolis

Maryland / Annapolis

3 9 2 nights min

  • 3 bedrooms
  • sleeps 9
  • 2 nights min
  • Child friendly
  • Air conditioning

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from £312 / night

£2,184 / week

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Responds fast!
avg. 14 minutes

from £312 / night

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(1)  

7

Holiday home in Annapolis

Maryland / Annapolis

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • Child friendly
  • Car not necessary
  • Ask about pets

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from £401 / night

£3,476 / week

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from £401 / night

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Great rentals within 20 miles that match your search

Distance approx 15.02 miles from Annapolis

6

Holiday home rental

Maryland / Severn

4 10 2 nights min

  • 4 bedrooms
  • sleeps 10
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Private garden

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from £343 / night

£2,402 / week

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Responds fast!
avg. 21 minutes

from £343 / night

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Distance approx 10.59 miles from Annapolis Show on Map

26

Stevensville holiday home rental

Kent Island / Stevensville

3 10 3 nights min

  • 3 bedrooms
  • sleeps 10
  • 3 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

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from £1,247 / night

£6,235 / week

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from £1,247 / night

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Distance approx 17.28 miles from Annapolis

(1) Excellent 

10

Holiday bungalow in Rock Hall

Maryland / Rock Hall

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

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from £254 / night

£1,777 / week

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from £254 / night

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Distance approx 10.13 miles from Annapolis Show on Map

24

Shady Side holiday home rental

Maryland / Shady Side

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Child friendly
  • Air conditioning

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from £165 / night

£1,154 / week

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Responds fast!
avg. 10 minutes

from £165 / night

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Distance approx 17.42 miles from Annapolis

(3) Excellent 

12

Rock Hall holiday home rental

Maryland / Rock Hall

3 10 2 nights min

  • 3 bedrooms
  • sleeps 10
  • 2 nights min
  • Child friendly
  • Pet friendly

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from £303 / night

£1,908 / week

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Responds fast!
avg. 3 hours 15 minutes

from £303 / night

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Distance approx 18.63 miles from Annapolis

9

Holiday home in North Beach

Calvert County / North Beach

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child friendly

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from £268 / night

£1,336 - £1,648 / week

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from £268 / night

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Distance approx 17.56 miles from Annapolis

11

Holiday home in North Beach

Calvert County / North Beach

3 8 1 night min

  • 3 bedrooms
  • sleeps 8
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly

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from £446 / night

£3,118 / week

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from £446 / night

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Distance approx 10.54 miles from Annapolis Show on Map

(14) Excellent 

19

Holiday home rental

Maryland / Kent Island

3 12 3 nights min

  • 3 bedrooms
  • sleeps 12
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Child friendly

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from £223 / night

£1,248 - £2,228 / week

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from £223 / night

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Distance approx 18.61 miles from Annapolis

33

Holiday home in Bowie

Maryland / Bowie

5 16 3 nights min

  • 5 bedrooms
  • sleeps 16
  • 3 nights min
  • Child friendly
  • Air conditioning

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from £437 / night

£3,059 - £3,683 / week

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from £437 / night

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Distance approx 4.68 miles from Annapolis Show on Map

12

Cape Saint Claire holiday home rental

Maryland / Cape Saint Claire

4 9 1 night min

  • 4 bedrooms
  • sleeps 9
  • 1 night min
  • Child friendly
  • Air conditioning
  • Private garden

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from £312 / night

£2,182 / week

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from £312 / night

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Distance approx 18.43 miles from Annapolis

12

St. Michaels holiday cottage rental

Talbot County / St. Michaels

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning

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from £179 / night

£1,247 / week

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from £179 / night

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Distance approx 5.92 miles from Annapolis Show on Map

29

Riva holiday home rental

Maryland / Riva

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

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from £258 / night

£1,802 / week

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Responds fast!
avg. 10 minutes

from £258 / night

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Distance approx 19.8 miles from Annapolis

(5) Excellent 

22

St. Michaels holiday home rental

Talbot County / St. Michaels

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

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from £334 / night

£4,275 / week

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from £334 / night

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Distance approx 12.44 miles from Annapolis Show on Map

15

Glen Burnie holiday guest house rental

Maryland / Glen Burnie

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Private garden

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from £89 / night

£624 / week

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from £89 / night

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Distance approx 10.8 miles from Annapolis Show on Map

6

Townhouse rental in Gambrills

Maryland / Gambrills

3 3 1 night min

  • 3 bedrooms
  • sleeps 3
  • 1 night min
  • Child friendly

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from £14 / night

£94 / week

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from £14 / night

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Distance approx 3.71 miles from Annapolis Show on Map

(1) Excellent 

18

Holiday yacht in Edgewater

Maryland / Edgewater

4 10 1 night min

  • 4 bedrooms
  • sleeps 10
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly

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from £881 / night

£6,166 / week

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from £881 / night

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Distance approx 10.28 miles from Annapolis Show on Map

12

Holiday home in Chester

Kent Island / Chester

4 12 2 nights min

  • 4 bedrooms
  • sleeps 12
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Private garden

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from £268 / night

£1,873 / week

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from £268 / night

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Distance approx 5.36 miles from Annapolis Show on Map

4

Holiday home rental

Maryland / Edgewater

3 2 7 nights min

  • 3 bedrooms
  • sleeps 2
  • 7 nights min
  • Air conditioning
  • Private garden

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from £90 / night

£624 / week

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from £90 / night

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Distance approx 17.45 miles from Annapolis

88

Holiday home in Rock Hall

Maryland / Rock Hall

4 7 1 night min

  • 4 bedrooms
  • sleeps 7
  • 1 night min
  • Child friendly

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from £90 / night

£576 - £2,087 / week

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Responds fast!
avg. 2 hours 9 minutes

from £90 / night

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