Holiday Houses in Annapolis

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79 Holiday homes

Annapolis Crows Nest Cottage: Chesapeake Bay View

Annapolis villa

5 bedrooms / 3 bathrooms / sleeps 20

from £633 / night

£2,730 - £3,494 / week

Charming Annapolis home with stunning water views

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 11

1

from £452 / night

£3,159 / week

C/ean & Cozy

Annapolis private room

1 bedroom / 1 bathroom / sleeps 2

2

from £54 / night

£376 / week

*BOOK NOW* Beautiful Cottage in historic Annapolis

Annapolis cottage

3 bedrooms / 2 bathrooms / sleeps 6

22

Responds fast! avg. 1 hour 32 minutes

from £289 / night

£1,625 / week

Excellent Location in Downtown Annapolis- walk to everything !

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 7

1

Responds fast! avg. 41 minutes

from £260 / night

£2,093 / week

2. Private 20 acre waterfront estate - studio apt

Annapolis apartment

1 bedroom / 1 bathroom / sleeps 2

from £271 / night

£993 / week

Annapolis Area Waterfront Home

Annapolis house

5 bedrooms / 4 bathrooms / sleeps 11

from £429 / night

£3,159 - £5,235 / week

Charming and Spacious Annapolis Victorian

Annapolis house

6 bedrooms / 5 bathrooms / sleeps 12

6

Responds fast! avg. 59 minutes

from £679 / night

£4,527 - £9,054 / week

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

Annapolis apartment

2 bedrooms / 1 bathroom / sleeps 5

from £226 / night

£1,580 / week

Charming Artists Home in Eastport/Annapolis

Annapolis house

3 bedrooms / 4 bathrooms / sleeps 6

from £339 / night

£2,370 / week

Walk to Shops/Eateries Charming Cottage. Dogs Wel.

Annapolis house

3 bedrooms / 1 bathroom / sleeps 6

2

Responds fast! avg. 27 minutes

from £228 / night

£909 - £1,037 / week

Annapolis Townhome w/Deck by Nature Trails & River

Annapolis house

1 bedroom / 2 bathrooms / sleeps 4

Responds fast! avg. 31 minutes

from £81 / night

£563 / week

Charming Eastport Home

Annapolis house

3 bedrooms / 4 bathrooms / sleeps 8

from £273 / night

£1,820 / week

Perfect Annapolis with Lots of Parking & Hot Tub

Annapolis townhouse

4 bedrooms / 3 bathrooms / sleeps 10

from £451 / night

£2,730 / week

Annapolis House w/ Patio in Bay Ridge Maryland!

Annapolis house

3 bedrooms / 4 bathrooms / sleeps 6

Responds fast! avg. 31 minutes

from £564 / night

£3,949 / week

Beautiful Murray Hill Home (Annapolis)

Annapolis house

4 bedrooms / 3 bathrooms / sleeps 9

3

from £387 / night

£2,275 - £2,944 / week

The Heart of Historic Cool in Annapolis

Annapolis house

5 bedrooms / 3 bathrooms / sleeps 10

from £910 / night

£10,919 / week

Your Eastport Annapolis Haven!

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 9 minutes

from £381 / night

£2,667 / week

NEW! Downtown Annapolis Home, Walk to Navy Stadium

Annapolis townhouse

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 31 minutes

from £109 / night

£759 / week

Annapolis Home w/ Bay Views - Near Naval Academy!

Annapolis house

5 bedrooms / 3 bathrooms / sleeps 11

Responds fast! avg. 42 minutes

from £655 / night

£4,581 / week

670-25Americana

Annapolis apartment

3 bedrooms / 2 bathrooms / sleeps 7

from £99 / night

£689 - £2,351 / week

126-2Dock

Annapolis apartment

3 bedrooms / 1 bathroom / sleeps 4

from £90 / night

£626 - £2,016 / week

Stunning Home in the Heart of Downtown Annapolis

Annapolis house

3 bedrooms / 5 bathrooms / sleeps 11

1

from £628 / night

£4,874 / week

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

Annapolis house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 31 minutes

from £288 / night

£2,016 / week

Charming Townhouse - Steps to City Dock and USNA

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 8

1

from £407 / night

£3,520 / week

Great rentals within 20 miles that match your search

Go Redskins! Home close to FedEx Field, BWI, & DC

Bowie house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 1 hour 49 minutes

from £91 / night

£634 / week

Contemporary Pasadena Apt w/Fireplace -Near River!

Pasadena apartment

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 5 minutes

from £80 / night

£558 / 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. 59 minutes

from £1,177 / night

£5,433 - £5,885 / week

Wellspring Manor & Spa

Largo house

5 bedrooms / 8 bathrooms / sleeps 10

3

from £1,481 / night

£8,805 / week

Renovated Luxury Waterview House

North Beach house

3 bedrooms / 2 bathrooms / sleeps 6

from £272 / night

£1,358 - £1,675 / week

Beautiful Home in Nice Community with up to 7 bedrooms

Severn house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 15 minutes

from £351 / night

£2,452 / week

BEULAH Residence (Bedroom 3)

Glen Burnie guest house

1 bedroom / 1 bathroom / sleeps 2

from £91 / night

£637 / week

Annapolis Area Shagrila Resort

Davidsonville house

3 bedrooms / 3 bathrooms / sleeps 6

from £364 / night

£3,640 / week

Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!

St. Michaels cottage

2 bedrooms / 2 bathrooms / sleeps 5

11

Responds fast! avg. 3 hours 23 minutes

from £196 / night

£1,524 / week

Sailors Crossing

Rock Hall house

3 bedrooms / 2 bathrooms / sleeps 10

3

Responds fast! avg. 1 hour 56 minutes

from £342 / night

£2,389 / week

Brookstone RV

Edgemere caravan/mobile home

1 bedroom / 1 bathroom / sleeps 4

from £60 / night

£364 - £492 / week

BEULAH Residence (Bedroom 4)

Glen Burnie guest house

1 bedroom / 1 bathroom / sleeps 2

from £91 / night

£637 / week

Sandy Pines: Enjoy Harris Creek w/Pool and Boats

St. Michaels house

4 bedrooms / 3 bathrooms / sleeps 10

5

from £455 / night

£3,185 / week

Upscale House/12 MINUTES FROM DC

Bowie house

5 bedrooms / 3 bathrooms / sleeps 16

from £446 / night

£3,121 - £3,758 / week

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

St. Michaels house

7 bedrooms / 4 bathrooms / sleeps 9

13

Responds fast! avg. 3 hours 23 minutes

from £355 / night

£2,230 - £2,684 / week

Viewing 40 of 79
rentals in Annapolis

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