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128 Houses

Why am I receiving these results?

“Unbelievable value” We were a family group of 3 couples plus an infant traveling to a wedding at the Usna chapel. The home was just wonderful, had a great view, was very clean, and was well equipped for the cooking being planned. Stores, restaurants, and liquor store were close by. Easy on and off the freeway into annapolis. Scott was very personable and worked with us to make our visit just right from the moment we first contacted him about renting.

Price per night from

$453

Price per night from

$458

Waterfront home with private pier is A Shore Thing

Chester house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 9

Price per night from

$429

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

Chester house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$1,947

Great rentals within 20 miles that match your search

The Heart of Historic Cool in Annapolis

Annapolis house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$1,154

Great deal 4 Bedroom House Near the Ferry Park

Rock Hall house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 11

Price per night from

$277

Quiet Home Close to Downtown Annapolis and Parks

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

Price per night from

$403

Gourmet Kitchen, Family and Pet Friendly Residence!

Mayo house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$404

TRUE ST MICHAELS 6 ACRE WATERFRONT

St. Michaels house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 38 minutes

Price per night from

$2,308

Luxury Waterfront - 40 Acre Estate - Swimming, Boating, Activities

Royal Oak manor house

  • 25 bedrooms
  • 25 bathrooms
  • sleeps 50

Price per night from

$7,501

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

St. Michaels house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Responds fast! avg. 38 minutes

Price per night from

$2,308

CHESAPEAKE MANSION - NEW POOL/12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

Sherwood house

  • 8 bedrooms
  • 10 bathrooms
  • sleeps 12

Responds fast! avg. 38 minutes

Price per night from

$2,885

Waterfront Condo Amazing Views with Resort Amenities

Annapolis condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Price per night from

$445

Ferry Bridge House

Easton house

  • 3 bedrooms
  • 5 bathrooms
  • sleeps 6

Price per night from

$802

Belle By the Bay

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$370

Waterfront Getaway - View of bay from your bed

Romancoke studio

  • Studio
  • 1 bathroom
  • sleeps 2

Price per night from

$230

Waterfront Getaway, Dock Your Boat and Play!

Mayo camper van

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Price per night from

$345

London Towne Bungalow w/Loft

Edgewater bungalow

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$300

Captain Quarters - Eastport!

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$576

The Fritz

Edgewater house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$1,558

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Annapolis apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$225

New, Book Me! Riverview Retreat on Warehouse Creek

Edgewater house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$318

South River Hangout

Edgewater tented camp

  • 1 bedroom
  • 1 bathroom
  • sleeps 16

Price per night from

$347

Fisher House - Downtown Annapolis!

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Price per night from

$687

Neptunes by the Water

Cape Saint Claire house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$208

Edgewater/Mayo Getaway!

Edgewater house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$461

Charming Charles Retreat

Annapolis house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

Price per night from

$431

Charming 3 bdrm cottage with lovely front porch

Rock Hall house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 8

Price per night from

$229

Ann House Getaway

Annapolis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$443

Ship's Cove Inn and Resort in St. Michaels, MD

St. Michaels house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Price per night from

$1,897

Abay Palace of Kent Narrows in a King Bed

Grasonville apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

Price per night from

$190

Annapolis Woodland Retreat

Cape Saint Claire house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$345

SeaGlass House by-the-Bay

Annapolis house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$673

The Annapolis General House

Parole house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Price per night from

$690

Cozy Downtown Annapolis Apartment

Annapolis apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$249

Nice ambient 5BDR with fast WiFi near Airport & Casino

Riviera Beach house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

Price per night from

$574

Charming Annapolis Waterview home

Annapolis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$804

Family Sized Contemporary in Spacious Neighborhood

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

Price per night from

$631

Viewing 38 of 128
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