Search 105,200+ Vacation Rentals

Annapolis Apartments & Vacation Rentals - 3 Rentals Available

Payment Protection
To book this vacation rental you need to pay through the Vacation Home Rentals website. We can’t protect your payment if you don’t pay through us. Learn more

3 Vacation rentals

(2)

1 / 29

Annapolis House

  • 2
  • 6
  • 2 nights min
  • Child friendly
  • Air conditioning
“We found the house to be very conveniently located in the historic district; we walked to all sites and there are many restaurants and shops close by. The only time we moved our car was to make a grocery store run. The photos tell the story well. The...”
- Review left on 05/16/2016

$250

Excellent (2 reviews)

Book

from $250 / night

(1)

1 / 19

Annapolis Cottage

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

$285

Excellent (1 reviews)

Inquire

from $285 / night

(1)

1 / 24

Annapolis House

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

$850

Very Good (1 reviews)

Inquire

from $850 / night

Your search has been expanded 29.9 miles to include more rentals

(3)

1 / 17

Kent Island House - 8.7 miles away

  • 4
  • 10
  • Min stay varies
  • Nearest beach 0 mi
  • Child friendly
  • Air conditioning
“The Kent Island Golf House was the perfect answer for lodging during our daughters wedding weekend at Kent Manor Inn. We arrived on Friday, Donna and Bob met us there and gave a complete tour of the home and explained how to use everything. The...”
- Review left on 07/15/2014

$425

Excellent (3 reviews)

Book

from $425 / night

(13)

1 / 35

Chester House - 12.7 miles away

  • 4
  • 10
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Child friendly
“We stayed at the condo on Kent Island in late June 2016. The view is spectacular, the condo is spacious and the simple stylish decor is comfortable with abundant seating and space. Ten adults in our party stayed in the condo for 3 nights. Eight...”
- Review left on 06/30/2016

$440

Excellent (13 reviews)

Inquire

from $440 / night

(1)

1 / 24

Churchton House - 13.3 miles away

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

$169

Excellent (1 reviews)

Inquire

from $169 / night

(5)

1 / 11

Claiborne House - 15.2 miles away

  • 3
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“The pictures do not do this house justice. It is a very big, open, airy home. It is advertised as 3 bedrooms, but really there are 4. The decks allow you to see the water no matter where you are on them. The 3 bedrooms each have sliding glass...”
- Review left on 04/08/2014

$275

Excellent (5 reviews)

Inquire

from $275 / night

1 / 22

Maryland House - 16.4 miles away

  • 6
  • 2 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly

from $146 / night

1 / 26

Maryland House - 16.4 miles away

  • 8
  • 2 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly

from $203 / night

(21)

1 / 34

Centreville House - 19 miles away

  • 4
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“We definitely enjoyed this house. So many interesting conversation pieces, and more books than you could possibly read on a vacation......all subjects. We especially enjoyed reading the book Alan had written himself....so much information about the...”
- Review left on 10/04/2016

$350

Excellent (21 reviews)

Book

from $350 / night

(10)

1 / 24

Royal Oak Cottage - 23.5 miles away

  • 3
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
“I rented the cottage with some friends for a New Years getaway. The house is wonderful, located on a small street quite off the main road. The property is beautiful, and the house is open with a ton of windows to enjoy the amazing creek view and...”
- Review left on 01/10/2013

$100

Excellent (10 reviews)

Book

from $100 / night

(8)

1 / 14

Washington DC Apartment - 28.3 miles away

  • 1
  • 6
  • 1 night min
  • Child friendly
  • Car not necessary
  • Air conditioning

$238

Excellent (8 reviews)

Inquire

from $238 / night

(9)

1 / 17

Washington DC Townhouse - 28.9 miles away

  • 3
  • 10
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
“Wonderful room or more like apartment. Everything we needed was right there. This was located in a beautiful area with unique shops and restaurants. We took a bus to the Metro and trained all over D.C. So much to do! Would go back again when we...”
- Review left on 04/11/2012

$210

Very Good (9 reviews)

Inquire

from $210 / night

(8)

1 / 24

Washington DC Apartment - 29.1 miles away

  • 2
  • 6
  • Min stay varies
  • Child friendly
  • Air conditioning
“The apartment had all the amenities you needed for a comfortable stay: Full Kitchen w/ granite tops, queen size bed, air conditioning, FREE Wi-Fi. The location was great, we were less than 1.5 blocks from the Metrorail station. The area we stayed...”
- Review left on 07/22/2014

$229

Very Good (8 reviews)

Book

from $229 / night

1 / 5

Washington DC Apartment - 29.5 miles away

  • 1
  • 4
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$199

Book

from $199 / night

1 / 6

Washington DC Apartment - 29.5 miles away

  • 2
  • 6
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$289

Book

from $289 / night

(2)

1 / 64

Washington DC Apartment - 29.9 miles away

  • 1
  • 6
  • Min stay varies
  • Nearest beach 197 mi
  • Child friendly
  • Car not necessary

$100

Excellent (2 reviews)

Book

from $100 / 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.   

Read More