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Annapolis Apartments & Vacation Rentals - 23 Rentals Available

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4 Vacation rentals

(2)

1 / 20

Annapolis House

  • 2
  • 6
  • Min stay varies
  • Ask about children
  • Air conditioning

$200

Excellent (2 reviews)

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from $200 / night

1 / 24

Annapolis House

  • 4
  • 14
  • 2 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

from $851 / night

1 / 66

Annapolis House

  • 6
  • 15
  • 4 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

from $995 / night

1 / 19

Annapolis Cottage

  • 3
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

from $251 / night

Your search has been expanded 49.9 miles to include more rentals

(2)

1 / 17

Severna Park House - 11 miles away

  • 5
  • 10
  • 3 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

$601

Very Good (2 reviews)

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from $601 / night

(3)

1 / 17

Kent Island House - 13.9 miles away

  • 4
  • 10
  • 2 nights min
  • Ask about children
  • Air conditioning

$501

Excellent (3 reviews)

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from $501 / night

(12)

1 / 35

Chester House - 20.4 miles away

  • 4
  • 10
  • 2 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

$375

Excellent (12 reviews)

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from $375 / night

(1)

1 / 24

Churchton House - 21.4 miles away

  • 3
  • 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$169

Excellent (1 reviews)

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from $169 / night

(3)

1 / 12

Grasonville House - 22.3 miles away

  • 4
  • 12
  • 2 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

$450

Excellent (3 reviews)

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from $450 / night

(3)

1 / 11

Claiborne House - 24.4 miles away

  • 3
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$275

Excellent (3 reviews)

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from $275 / night

(21)

1 / 34

Centreville House - 30.6 miles away

  • 4
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$330

Excellent (21 reviews)

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from $330 / night

1 / 7

Baltimore Townhouse - 34.2 miles away

  • 3
  • 8
  • 2 nights min
  • Ask about children

from $249 / night

1 / 10

Baltimore House - 34.7 miles away

  • 3
  • 10
  • 2 nights min
  • Ask about children
  • Air conditioning

from $249 / night

1 / 9

Baltimore House - 34.7 miles away

  • 2
  • 4
  • 2 nights min
  • Ask about children
  • Air conditioning

from $209 / night

1 / 24

Baltimore House - 34.7 miles away

  • 3
  • 10
  • 2 nights min
  • Ask about children
  • Air conditioning

from $249 / night

(4)

1 / 5

Baltimore Townhouse - 35.1 miles away

  • 3
  • 8
  • 1 night min
  • Ask about children
  • Pet friendly

$326

Very Good (4 reviews)

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from $326 / night

(10)

1 / 9

Royal Oak Cottage - 40.1 miles away

  • 3
  • 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

$280

Excellent (10 reviews)

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from $280 / night

1 / 24

Washington DC House - 45.5 miles away

  • 2
  • 4
  • Min stay varies
  • Ask about children
  • Air conditioning

from $251 / night

(5)

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Washington DC Townhouse - 46.6 miles away

  • 3
  • 10
  • 2 nights min
  • Ask about children
  • Air conditioning

$251

Very Good (5 reviews)

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from $251 / night

(1)

1 / 24

Washington DC Apartment - 46.7 miles away

  • 2
  • 5
  • 1 night min
  • Ask about children
  • Air conditioning

$337

Excellent (1 reviews)

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from $337 / night

(2)

1 / 24

Washington DC Apartment - 46.8 miles away

  • 2
  • 6
  • Min stay varies
  • Ask about children
  • Air conditioning

$200

Very Good (2 reviews)

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from $200 / night

1 / 13

Washington DC Townhouse - 46.9 miles away

  • 3
  • 8
  • 2 nights min
  • Ask about children
  • Air conditioning

from $426 / night

1 / 28

Virginia House - 49.9 miles away

  • 3
  • 7
  • 3 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly

from $326 / night

About Annapolis

With easy access to Baltimore and Washington, D.C., Annapolis, Maryland, is the perfect getaway for a weekend or longer. Its quaint cobblestone streets and harbor filled with sailboats produce some unforgettable vacation pictures and memories. An Annapolis vacation rental is the best way to enjoy this charming town and the Chesapeake Bay.

Things to Do

The water is a major draw with sailing and boat tours. It's also fun to try your hand at crabbing for blue crabs. Quiet Waters Park has trails for biking and/or hiking, playgrounds for children, and even a skating rink Sandy Point Park is a year-round park that is near Chesapeake Bay. Many visit this area for its amazing beaches and water views.

While in town check out the Naval Academy and the USNA Museum. Don't miss the school's breathtaking chapel, and take a guided tour of this active training facility. History buffs enjoy the free Bannecker-Douglass Museum, which displays Maryland’s African-American history, or just walking around the historic downtown. Located at the harbor where slave ships once arrived carrying their human cargo is The Kunta Kinte-Alex Haley Memorial. This is another educational spot for families along with the Thurgood Marshall Memorial. Even the Starbucks at the Annapolis Inn holds history. It resides in an 18th century tavern visited by George Washington.

Transit

Annapolis is tucked between the nation's capital and Baltimore, Maryland, with easy access to D.C.'s two airports as well as Baltimore's. To get to Annapolis, you'll most likely need a car, but once there, the town is very walkable and parking is extremely limited and expensive. Park your car at your Annapolis vacation rental and walk or bike into town. That way you don't have to worry about navigating the congested, narrow streets or paying the daily parking fee, which is often well over twenty dollars a vehicle.

Climate

Annapolis enjoys ample breezes because of its location on the water. This seaside spot also keeps it from frigid winter temperatures. The average temperature in January and February is in the 40s, with summers in the upper 80s.

Events

Spring is the most beautiful time to visit, if it's possible to choose just one season. With bountiful blooms everywhere and the beginning of the sailing season, it's a popular time to stroll the quaint town and harbor. Spring also brings the Southern Maryland Celtic Festival, and with the beginning of sailing season in April, you can catch the weekly Wednesday Night Sailboat Races. August is the perfect time to taste what all the fuss is about Maryland Blue Crabs at the Annapolis Rotary's Crab Feast. The social year comes to a close with the delightful Eastport Yacht Club Lights Parade. Christmas is also a beautiful time in this historic village.

Shopping

Annapolis has a thriving arts scene with dozens of galleries filled with the works of local artisans. Historic Annapolis is the section of town leading down to the harbor that features converted row homes on Main Street that are brimming with sailing souvenirs and nautical-themed décor. But you don't have to love the water to enjoy the many bistros, galleries, and boutiques in this area. While you're treasure hunting, you can also follow the self-guided Annapolis Walking Tour.

An Annapolis vacation rental is an ideal way to enjoy this charming area. The homes and cottages embrace the historic character and marry it with all the modern amenities you'd expect on vacation. The area places you within easy access of a number of historic sites and cultural opportunities, not to mention the pageantry of the Naval Academy formations.   

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