Choose from 409 vacation rentals located in Annapolis, Maryland. Top filters in Annapolis include Air conditioner, Internet / Wifi, and Kitchen or Kitchenette. Prices range from $77 to $2,994 per night. Our most popular vacation rental types near Annapolis are Hotel and RV.

Top vacation rentals in Annapolis

Terrace/patio
4.8
Outstanding(265 Reviews)
Annapolis Condominium in the heart of the historic center
Apartment
 in Annapolis
6 guests · 3 bedrooms · 2 baths
Garden · Kitchen or Kitchenette · Air conditioner

Looking for a Apartment in Annapolis, this Apartment for $337 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

$$$$
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Living room
4.5
Excellent(1,193 Reviews)
Graduate by Hilton Annapolis
Hotel
 in Annapolis
4star
1 king bed
Pets allowed · Kitchen or Kitchenette · Air conditioner
Most favorited

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

$$$$
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Other
4.1
Excellent(197 Reviews)
The Westin Annapolis
Hotel
 in Annapolis
4star
2 full beds
Pool · Pets allowed · Air conditioner

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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Restaurant/places to eat, Food close-up, Food, Breakfast
4.1
Excellent(297 Reviews)
Inn on Main Annapolis
Bed and Breakfast
 in Annapolis
1 queen bed
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 air conditioning in Annapolis

Exterior
5.0
Outstanding(198 Reviews)
Stunning Waterfront Cottage with Breathtaking Views!
House
 in Annapolis
6 guests · 2 bedrooms · 1 bath
Garden · Pool · Kitchen or 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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Property grounds
4.8
Outstanding(242 Reviews)
Renovated Historic Home located downtown with parking - Walk everywhere !
House
 in Annapolis
6 guests · 4 bedrooms · 2 baths
Garden · Pets allowed · Kitchen or 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 building
4.1
Excellent(576 Reviews)
Historic Inns of Annapolis
Hotel
 in Annapolis
3star
1 full bed
Pets allowed · Kitchen or Kitchenette · Air conditioner

Looking for a Hotel in Annapolis, this Hotel for $178 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(33 Reviews)
Flag House Inn
Inn
 in Annapolis
2 single beds, 1 king bed
Air conditioner · Internet / Wifi · Parking

This Inn for $175 in Annapolis, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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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-$2,994. The average price for rentals in Annapolis is $449 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?

  • Air conditioner
  • Internet / Wifi
  • Kitchen or Kitchenette

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