Vacation Rentals & Apartments in Annapolis

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39 apartments

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Vintage Bungalow-cozy, walk to shops, water, free pkg.

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Balcony or terrace

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Price per night from

$474

Perfect Annapolis with Lots of Parking & Hot Tub

Annapolis townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Balcony or terrace

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Price per night from

$793

The Heart of Historic Cool in Annapolis

Annapolis house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Balcony or terrace

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Price per night from

$1,141

Charming Annapolis Waterview home

Annapolis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Balcony or terrace

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Price per night from

$798

Match: Balcony or terrace

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Price per night from

$407

Match: Balcony or terrace

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Price per night from

$785

Free Parking at Randall House in Downtown Annapolis

Annapolis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 11

Match: Balcony or terrace

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Price per night from

$729

Eastport Gem - Popular house walk to Downtown & USNA

Annapolis house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Balcony or terrace

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Price per night from

$400

Take your Leave of Absence around gardens with driveway parking

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Match: Balcony or terrace

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Price per night from

$426

Hanover House across from USNA Gate 3 with private back patio

Annapolis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Balcony or terrace

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Price per night from

$465

History & Charm Near the Annapolis City Dock

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Match: Balcony or terrace

All filters match

Price per night from

$394

Luxury Waterfront home with private pier and guest house

Annapolis house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Balcony or terrace

All filters match

Price per night from

$907

Match: Balcony or terrace

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Price per night from

$500

Popular Historic Firehouse fully renovated with Parking and Pet Friendly

Annapolis house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Balcony or terrace

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Price per night from

$465

Parking at Stunning On Cloud 9 with private patio pet-friendly

Annapolis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Balcony or terrace

All filters match

Price per night from

$500

Walk to Main Street from Waterfront Condo with pool and parking

Annapolis condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Match: Balcony or terrace

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Price per night from

$407

Captain Quarters - Eastport!

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Balcony or terrace

All filters match

Price per night from

$570

Still Available for 2024 Commissioning Week! Historic gem steps to USNA

Annapolis house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Balcony or terrace

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Price per night from

$465

Match: Balcony or terrace

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Price per night from

$359

Great rentals within 20 miles that match your search

KENT ISLAND-OCEAN VIEW Home for rent-4 bedrooms EASTERN SHORE sleeps 10-12

Kent Island house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

Match: Balcony or terrace

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Price per night from

$1,940

DOLCE VIDA AT Kent Island- 4 bedrooms House for rent-SLEEPS 10-12

Chester house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Balcony or terrace

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Price per night from

$1,940

Eat..Sleep..Fish..Repeat! Who needs a desk (there is one upstairs) when you can

Stevensville house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

Match: Balcony or terrace

All filters match

Price per night from

$799

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

St. Michaels house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Responds fast! avg. 38 minutes

Match: Balcony or terrace

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Price per night from

$2,282

Edgewater/Mayo Getaway!

Edgewater house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Balcony or terrace

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Price per night from

$456

The Fritz

Edgewater house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Balcony or terrace

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Price per night from

$1,540

Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview

Wittman log cabin

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Balcony or terrace

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Price per night from

$1,113

Waterfront pier, putting green just minutes from downtown Annapolis

Riva house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Balcony or terrace

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Price per night from

$725

Waterfront home with private pier is A Shore Thing

Chester house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 9

Match: Balcony or terrace

All filters match

Price per night from

$429

Private pier by Kurtz Beach pet-friendly Dock of the Bay

Riviera Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Match: Balcony or terrace

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Price per night from

$424

Private Waterfront Retreat with Pool, Hot Tub and Game Room

Tracys Landing house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 14

Match: Balcony or terrace

All filters match

Price per night from

$727

Waterfront Jolly Roger with Private Pier mins to Annapolis

Crownsville house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

Match: Balcony or terrace

All filters match

Price per night from

$454

180-degree water views at unique round house

Shady Side house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Balcony or terrace

All filters match

Price per night from

$367

Stunning Waterfront Home in Round Bay

Severna Park house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Balcony or terrace

All filters match

Price per night from

$1,451

Available for 2024 Commissioning Week Waterfront home mins to USNA

Crownsville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Balcony or terrace

All filters match

Price per night from

$361

Match: Balcony or terrace

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Price per night from

$355

Private Waterview Estate with 4 bedroom Suites & Hot Tub

Shady Side house

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 14

Match: Balcony or terrace

All filters match

Price per night from

$429

Pool and Bay Views on wrap around deck in Kent Island

Stevensville house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

Match: Balcony or terrace

All filters match

Price per night from

$321

Sprawling Family home on a Cul De Sac sleeps 10-14!

Severna Park house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Match: Balcony or terrace

All filters match

Price per night from

$382

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