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Holiday Houses in Annapolis

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70 Holiday homes

*BOOK NOW* Beautiful Cottage in historic Annapolis

Annapolis cottage

3 bedrooms / 2 bathrooms / sleeps 6

22

from £288 / night

£1,619 / week

2. Private 20 acre waterfront estate - studio apt

Annapolis apartment

1 bedroom / 1 bathroom / sleeps 2

from £283 / night

£1,036 / week

Annapolis Area Waterfront Home

Annapolis house

5 bedrooms / 4 bathrooms / sleeps 11

from £427 / night

£3,146 - £5,033 / week

Excellent Location in Downtown Annapolis- walk to everything !

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 7

1

Responds fast! avg. 8 minutes

from £257 / night

£2,068 / week

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

Annapolis apartment

2 bedrooms / 1 bathroom / sleeps 5

from £227 / night

£1,587 / week

Charming and Spacious Annapolis Victorian

Annapolis house

6 bedrooms / 5 bathrooms / sleeps 12

6

Responds fast! avg. 22 minutes

from £656 / night

£4,369 - £4,587 / 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

Perfect Annapolis with Lots of Parking & Hot Tub

Annapolis townhouse

4 bedrooms / 3 bathrooms / sleeps 10

from £466 / night

£2,824 / week

Annapolis House w/ Patio in Bay Ridge Maryland!

Annapolis house

3 bedrooms / 4 bathrooms / sleeps 6

Responds fast! avg. 44 minutes

from £508 / night

£3,553 / week

Charming Eastport Home

Annapolis house

3 bedrooms / 4 bathrooms / sleeps 8

from £283 / night

£1,883 / week

Beautiful Murray Hill Home (Annapolis)

Annapolis house

4 bedrooms / 3 bathrooms / sleeps 9

3

from £373 / night

£2,195 - £2,840 / week

Charming Annapolis Waterview home

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 10

from £436 / night

£2,534 - £2,840 / week

The Heart of Historic Cool in Annapolis

Annapolis house

5 bedrooms / 3 bathrooms / sleeps 10

from £942 / night

£11,295 / week

Stunning Home in the Heart of Downtown Annapolis

Annapolis house

3 bedrooms / 5 bathrooms / sleeps 11

1

from £609 / night

£4,731 / week

Downtown Annapolis Home, Walk to Navy Stadium

Annapolis townhouse

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 44 minutes

from £82 / night

£569 / week

Cozy Home in Historic Annapolis with Parking

Annapolis house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 14 minutes

from £174 / night

£1,217 / week

Charming Annapolis Home w/ Yard - 5 Mins to Dwtn!

Annapolis house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 44 minutes

from £231 / night

£1,615 / week

Charming Townhouse - Steps to City Dock and USNA

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 8

1

from £424 / night

£6,118 / week

22 Fleet St. - Best Spot for Commissioning Week, Newly-Renovated & Historic!

Annapolis condo

3 bedrooms / 3 bathrooms / sleeps 6

from £369 / night

£2,026 - £6,906 / week

NEW! Chic Condo w/ Balcony 1Mi to Annapolis Harbor

Annapolis condo

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 44 minutes

from £100 / night

£698 / week

Great rentals within 20 miles that match your search

Little Boat in Annapolis!

Edgewater boathouse

1 bedroom / 1 bathroom / sleeps 4

from £113 / night

£786 / week

Panoramic Views of Herrington Harbour on the Bay.

North Beach house

3 bedrooms / 2 bathrooms / sleeps 8

from £470 / night

£3,289 / week

BEULAH Residence (Bedroom 4)

Glen Burnie guest house

1 bedroom / 1 bathroom / sleeps 2

from £95 / night

£659 / week

Edgewater boathouse

1 bedroom / 1 bathroom / sleeps 4

from £113 / night

£791 / week

BEULAH Residence (Bedroom 3)

Glen Burnie guest house

1 bedroom / 1 bathroom / sleeps 2

from £95 / night

£659 / week

2 Bedroom Condo minutes away from DC & VA

Largo condo

2 bedrooms / 3 bathrooms / sleeps 4

from £151 / night

£1,055 / week

Metromax Lovely Private Studio!

Gambrills apartment

1 bedroom / 1 bathroom / sleeps 2

from £57 / night

£356 / week

Wellspring Manor & Spa

Largo house

5 bedrooms / 8 bathrooms / sleeps 10

4

from £1,539 / night

£9,154 / week

Private Room - Creek Side

Glen Burnie townhouse

1 bedroom / 1 bathroom / sleeps 1

from £47 / night

£330 / week

Serene Waterfront Apartment on Kent Island

Stevensville apartment

1 bedroom / 1 bathroom / sleeps 2

from £142 / night

£753 / week

Lochhaven house for rent

Edgewater house

3 bedrooms / 1 bathroom / sleeps 2

from £95 / night

£659 / week

BEULAH Residence (Bedroom 2)

Glen Burnie guest house

1 bedroom / 1 bathroom / sleeps 2

from £95 / night

£659 / week

Private Room Close To Baltimore and BWI Airport + EXTRAS

Glen Burnie house

1 bedroom / 1 bathroom / sleeps 2

from £43 / night

£283 / week

Simply Severn - Comfortable and Close to Everything in the DC Area.

Severn house

3 bedrooms / 3 bathrooms / sleeps 8

from £165 / night

£1,106 - £1,370 / week

BEULAH Residence (Bedroom 1)

Glen Burnie guest house

1 bedroom / 1 bathroom / sleeps 2

from £95 / night

£659 / week

Holistic Getaway

Bowie house

2 bedrooms / 1 bathroom / sleeps 6

from £137 / night

£956 / 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

2 Bedroom Guest House Near Downtown & BWI + Full Office & Kitchenette.

Baltimore guest house

2 bedrooms / 1 bathroom / sleeps 4

1

from £56 / night

£389 / 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

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rentals in Annapolis