Vacation Rentals & Apartments in Annapolis

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137 apartments

2. Private 20 acre waterfront estate - studio apt

Annapolis apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$345

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

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$477

Perfect Annapolis with Lots of Parking & Hot Tub

Annapolis townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$798

Beautiful Murray Hill Home (Annapolis)

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

“Comfortable and secure in a great home - almost as good as at ho” The house is set is a terrific neighborhood of annapolis within easy walking distance to two small parks on the water and to town. We all found the house a delight - the design, decorating, furnishings are tasteful and match the age and the imagery of the house. It is well equipped with comfortable bedrooms, adequate bathrooms and linens, utensils and staple supplies. We certainly will attempt to stay at this house again if we ever return to annapolis.

Price per night from

$488

The Heart of Historic Cool in Annapolis

Annapolis house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$1,148

Charming Annapolis Waterview home

Annapolis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$802

Stay just steps from the Waterfront in the modern Historic Fleet's Inn

Annapolis house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$405

Free parking Historic Union House Downtown with private patio

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$403

The Carrollton Cottage House

Annapolis house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$253

2 parking spots and Walkable to Main Street at Seashell in the City

Annapolis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$465

Take your Leave of Absence around gardens with driveway parking

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Price per night from

$426

King George Downtown Annapolis Getaway

Annapolis apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$431

Duke's Den Downtown home with 2 PARKING spots!

Annapolis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 14

Price per night from

$639

Price per night from

$439

Hanover House across from USNA Gate 3 with private back patio

Annapolis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$465

Price per night from

$500

1 Block to USNA with Chapel Views big back patio and off-site parking!

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$465

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

Annapolis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$500

Modern and cozy Captain’s Crossing Cape house in West Annapolis

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$406

Walk to Main Street from Waterfront Condo with pool and parking

Annapolis condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$395

Captain Quarters - Eastport!

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$573

Family Sized Contemporary in Spacious Neighborhood

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

Price per night from

$630

Comfort & Luxury near downtown, mall, coffee shops and more

Annapolis apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$195

Price per night from

$400

Cottage by the Bay on one level in family-friendly community

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$367

Waterfront Condo Amazing Views with Resort Amenities

Annapolis condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Price per night from

$442

Fisher House - Downtown Annapolis!

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Price per night from

$683

Historic Carriage House in the Heart of Downtown Annapolis

Annapolis house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$343

Free Parking at Randall House in Downtown Annapolis

Annapolis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 11

Price per night from

$729

Stay at Lux Red Door Gem with 3 Parking Spots

Annapolis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$382

Price per night from

$637

Steps to Gate 1 and Free Parking at Naval-Academy Themed Home

Annapolis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 11

Price per night from

$610

History & Charm Near the Annapolis City Dock

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Price per night from

$394

Steps from the water, Easy parking and private backyard patio

Annapolis house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$378

Cozy Downtown Annapolis Apartment

Annapolis apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$248

Steps from USNA Gates 1 & 3 with large private patio

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$408

Price per night from

$338

Price per night from

$370

Viewing 38 of 137
rentals in Annapolis

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About Annapolis

Come to Annapolis to experience the best of old world style and Chesapeake Bay charm. This distinguished town, located on the salty bay, has provided visitors with the perfect Maryland vacation getaway for centuries. Visit the museums here and learn more about the early settlers of the area, the natural history and the wildlife that populate fragile Maryland ecosystems, and the important events in American history that took place here. Find a vacation rental, summer home, or bayside cottage overlooking the shoreline. Head downtown to experience Maryland's annual festivals celebrating regional music and the famous Maryland blue crab. Go antique and craft shopping in the heart of the city. Explore Annapolis museums and art galleries and spend some time on the emerald green golf courses around the Chesapeake Bay. At night, head downtown for world-class seafood and a live performance at a local theater.

Here are a few additional suggestions for your trip:

  • Visit the Maryland State House: Annapolis was America's first peacetime capitol, and the statehouse is the oldest still in legislative use.
  • Visit the US Naval Academy: Take a tour of the Naval Academy, one of the proud institutions of Annapolis.
  • Go on a pirate adventure: Take a real life pirate adventure on a ship in Annapolis Harbor. Pirate Adventures on the Chesapeake offers a full day of true buccaneering on an Annapolis boat, complete with face paint, pirate fashions, and a water cannon battle.
  • Experience Annapolis sailing: Nothing can compare with a real sailing adventure aboard an authentic Chesapeake Skipjack. Help man the sails, try your hand at Annapolis fishing and crabbing, or just relax on the deck and watch the harbor birds sail overhead.
  • Visit the William Paca Garden: This colonial garden offers peace, serenity, and history lessons along with guided tours.
  • Explore Quiet Waters Park: This 340 acre park just outside the city center offers more than six miles of trails perfect for strolling, jogging, or biking.

Thousands of visitors come to this area every year to enjoy long weekend getaways, family reunions, and beautiful wedding venues in Annapolis. If you're among them, find the perfect rental apartment in the heart of downtown, or a bayside condo near the harbor. While you're here, consider visiting a few other popular vacation destinations in Maryland like Arnold and Lake Shore.

Top Destination reviews

Beautiful Murray Hill Home (Annapolis)
wonderful homey feel

The house worked out great for 3 couples and one 3 year old. The 3 year old loved having his own room with a great selection of books and toys. Everyone else enjoed the feel of house. Roomy and a great location. We walked to downtown annapolis twice during our short weekend visit. Completely supplied with an assortment of food and anything you could think of. The homemade muffins and bottle of wine was a treat. I am a very critical person that expects alot.see more

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