Annapolis Apartment Rentals & Vacation Rentals - 6 Rentals Available

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Annapolis Home
4 BR / 3.5 BA / Sleeps 8 4 8 3 night min stay
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 3.5 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
"Steps from Eastport marinas and great restaurants, this house was perfect for a get- together of 8 people. Property is well- maintained, cool on one of the hottest days/nights of the summer, and has plenty of parking. Owner is really helpful & easy..."
- Liz Hintz Worsham, Heathsville, Virginia USA
(1) Excellent (1 review)
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Annapolis Home
2 BR / 1 BA / Sleeps 6 2 6 Min stay varies
Home / 2 Bedrooms / Sleeps 6
2 bedrooms 1 bathroom Sleeps 6
High Speed Internet • Dishwasher • Microwave
"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..."
- Barbara Marchese, West Chester, PA
(1) Excellent (1 review)
1 / 17

Annapolis Home
5 BR / 2.5 BA / Sleeps 10 5 10 3 night min stay
Home / 5 Bedrooms / Sleeps 10
5 bedrooms 2.5 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
"The pictures DO NOT DO this home justice. This weekend was nothing short of a chapter from a picturesque page of a Mark Twain novel. From driving through the narrow roads of the neighborhood as kids play along side the street. I saw tire swings hang from..."
- Nubia Newsome, Los Angeles, CA
(2) Excellent (2 reviews)
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Kent Island Home - 8.5 mi away
4 BR / 2.5 BA / Sleeps 10 4 10 2 night min stay
Home / 4 Bedrooms / Sleeps 10
4 bedrooms 2.5 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
"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 house..."
- Carol Adkins, Salisbury, Maryland
(4) Excellent (4 reviews)
1 / 35

Kent Island Home - 12.8 mi away
4 BR / 3.5 BA / Sleeps 10 4 10 2 night min stay
Home / 4 Bedrooms / Sleeps 10
4 bedrooms 3.5 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
"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 adults..."
- Laura Schwarz, Hanover, PA
(13) Excellent (13 reviews)
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Kent Island Home - 14.0 mi away
4 BR / 3 BA / Sleeps 12 4 12 2 night min stay
Home / 4 Bedrooms / Sleeps 12
4 bedrooms 3 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
"I rented this property for my sisters and their families during my wedding and it was fantastic. The owners were very easy to work with and the home was every it was advertised to be. My entire family was overwhelmed by the the home and it's beautiful..."
- Grant Weston, Austin, Texas
(4) Excellent (4 reviews)
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St Michaels Home - 14.9 mi away
3 BR / 3.5 BA / Sleeps 8 3 8 Min stay varies
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 3.5 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
"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..."
- Kim Triplett Beck, York Haven, PA
(4) Excellent (4 reviews)
1 / 34

Centreville Home - 19.3 mi away
4 BR / 2 BA / Sleeps 8 4 8 Min stay varies
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
"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 much information about the..."
- Dee Keller, Pennsburg, Pennsylvania
(23) Excellent (23 reviews)

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.


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.


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.


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.


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.