Choose from 392 vacation rentals located in Annapolis, Maryland. Top filters in Annapolis include Internet / Wifi, Air conditioner, and Kitchen / Kitchenette. Prices range from $77 to $2,679 per night. Our most popular vacation rental types near Annapolis are Hotel and RV.

Top vacation rentals in Annapolis

One of the most photographed homes downtown
4.8
Outstanding(227 Reviews)
House
 in Annapolis
Renovated Historic Home located downtown with parking - Walk everywhere !
6 guests · 3 bedrooms · 2 baths
Garden · Pets allowed · Kitchen / Kitchenette

Are you ready to indulge in a relaxing getaway? Our House in Annapolis has everything you need for a rejuvenating stay. Treat yourself to Renovated Historic Home located downtown with parking - Walk everywhere !'s exceptional amenities, such as Air conditioner, Dishwasher and Fireplace.

$$$$
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Property grounds
4.8
Outstanding(240 Reviews)
Condo
 in Annapolis
Annapolis Condominium in the heart of the historic center
6 guests · 3 bedrooms · 2 baths
Garden · Kitchen / Kitchenette · Air conditioner

Looking for a Condo in Annapolis, this Condo for $273 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

$$$$
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Property view
4.5
Excellent(1,388 Reviews)
Hotel
 in Annapolis
4star
Graduate Annapolis
Pets allowed · Air conditioner · Internet / Wifi

Soak up the beauty of Annapolis in our Hotel, Graduate Annapolis. With a range of amenities such as Air conditioner, Internet / Wifi and Laundry, you'll feel right at home.

$$$$
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Property view
4.1
Excellent(283 Reviews)
Bed and Breakfast
 in Annapolis
Inn on Main Annapolis
Pets allowed · Air conditioner · Internet / Wifi

Experience the best of Annapolis with this Bed and Breakfast available for $178. This property is equipped with amenities including Air conditioner, Internet / Wifi and Pets allowed, and more.

$$$$
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Vacation rentals with internet & wifi in Annapolis

Living Room
5.0
Outstanding(178 Reviews)
House
 in Annapolis
Stunning Waterfront Cottage with Breathtaking Views!
6 guests · 2 bedrooms · 1 bath
Garden · Pool · Kitchen / Kitchenette

Looking for the perfect place to call home during your trip to Annapolis? This House offers a comfort and style with top-notch amenities, including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Historic 19 East
5.0
Outstanding(175 Reviews)
House
 in Annapolis
PERFECT LOCATION in the heart of history
8 guests · 3 bedrooms · 3 baths
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Experience the best of Annapolis with this House available for $333. This property is equipped with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Gourmet kitchen
5.0
Outstanding(162 Reviews)
House
 in Annapolis
Charming Historic Annapolis Home With Two Off-street Parking Places!
8 guests · 3 bedrooms · 3 baths
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Looking for a memorable stay in Annapolis? Our House might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more during your stay.

$$$$
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Property view
4.3
Excellent(188 Reviews)
Hotel
 in Annapolis
4star
Annapolis Waterfront Hotel, Autograph Collection
Pets allowed · Air conditioner · Internet / Wifi

Looking for the perfect place to call home during your trip to Annapolis? This Hotel offers a comfort and style with top-notch amenities, including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
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city photo
Annapolis

Annapolis travel guide

Let us help you plan your perfect Annapolis vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Annapolis, and more.

Frequently asked questions

What is the price range for rentals in Annapolis?

Vacation rentals in Annapolis have a price range between $77-$2,679. The average price for rentals in Annapolis is $376 per night.

What do I need to know before visiting Annapolis, MD?

Before visiting Annapolis, MD, there are several important things to know:

  • The city's climate is humid and subtropical, and temperatures can vary drastically throughout the year
  • The city is the capital of Maryland and is home to the United States Naval Academy
  • The main mode of transportation in the city is by car or boat

Some of the popular attractions in the city are the Maryland State House, the United States Naval Academy, and the Maryland Science Center.

What are the top things to do in Annapolis, MD?

Annapolis, MD, is a great destination for anyone looking for a fun and educational experience. Here are some of the top things to do in Annapolis:

  • Visit the United States Naval Academy
  • Explore the Historic Annapolis Museum
  • Stroll the streets of the Historic District
  • Enjoy the outdoors at Sandy Point State Park

From exploring the history of the city to enjoying the great outdoors, there is something for everyone to do in Annapolis. Whether you're looking for a relaxing day or an adventure, Annapolis has something for you.

Where is Annapolis, MD?

Annapolis, MD is located in the state of Maryland, on the Chesapeake Bay. It is the state capital and the county seat of Anne Arundel County. The city is home to the United States Naval Academy, St. John's College, and the historic district of Annapolis.

What are the popular shopping destinations in Annapolis, MD?

Annapolis, MD has a variety of popular shopping destinations. Here are a few of the most popular:

  • Westfield Annapolis Mall
  • Historic Downtown Annapolis
  • Annapolis Towne Centre

These are great places to find unique souvenirs, clothing, and more!

Is Annapolis, MD safe to travel to?

Annapolis, MD is a safe place to travel to. Here are some reasons why:

  • Low crime rate
  • Highly rated police and fire departments
  • Plenty of tourist attractions

What is the culture like in Annapolis, MD?

Annapolis, MD is a city that is rich in culture and history. The atmosphere of the city is unique and the people of Annapolis are proud of their hometown. Here are 5 bullet points about the culture in Annapolis:

  • The city is home to a vibrant art and music scene, with many galleries and live music venues.
  • Annapolis is known for its diverse range of restaurants that feature cuisine from around the world.
  • The city is home to the United States Naval Academy, which has a strong presence in the community.
  • Annapolis is a sailing hub and hosts many sailing events, regattas, and races.
  • The city celebrates its history and culture through a variety of festivals and parades throughout the year.

Where can I find affordable accommodation in Annapolis, MD?

Annapolis, MD has a variety of affordable accommodations for all budgets. Here are a few of the most popular options:

  • The Annapolis Inn: a boutique hotel located in the heart of downtown Annapolis.
  • The Governor Calvert: a historic bed and breakfast located in the historic district.
  • The Loews Annapolis Hotel: a luxurious hotel with spacious rooms and stunning views of the Chesapeake Bay.
  • The Westin Annapolis: a modern hotel with a rooftop pool and spa.

No matter what your budget is, Annapolis, MD has a variety of affordable accommodations to fit your needs.

How can I get around in Annapolis, MD?

There are a number of ways to explore the city of Annapolis, MD:

  • Driving – There is a roadway system that stretches through the city.
  • Walking – The downtown area of Annapolis is walk-able and is a great way to explore the city.
  • Public Transit – Local bus routes serve the city and surrounding area.

What are the must-visit tourist attractions in Annapolis, MD?

Annapolis, MD is a popular tourist destination, with plenty of attractions to explore. Here are just a few of the must-visit attractions in Annapolis:

  • United States Naval Academy
  • Historic Annapolis
  • William Paca House & Garden
  • Maryland State House

Whether you're interested in history, architecture, or simply want to explore the city, Annapolis has something for everyone. Don't miss out on these amazing attractions!

What are the most popular vacation rental amenities in Annapolis?

  • Internet / Wifi
  • Air conditioner
  • Kitchen / Kitchenette

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