Discover a selection of 141 vacation rentals in Historic District, Annapolis that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including WiFi and parking. Prices start at $166 per night, and houses and condos are popular options for a stay in Historic District. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Historic District
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What are the top vacation rentals in or near Historic District?

Whatever you're looking for in a getaway, you'll find a rental property in or around Historic District that suits your style. Here are some of our favorites:

  • "Charming Historic Home Just Steps From Main Street" is popular with guests. Around 0.1 miles from Historic District, it has 3 bedrooms and loads of amenities to help you feel at home, including free toiletries and a fridge.
  • Another enticing choice is "Gorgeous Annapolis Getaway - Walk Everywhere", which is around 1 mile from Historic District. Featuring 3 bedrooms, a TV and a separate dining area, it has everything you need to keep you content and comfortable.

For even more great options, use the search bar at the top of the page to find the perfect Historic District vacation rental for you.

What are the best tiny house vacation rentals in or near Historic District?

Punching far above its weight when it comes to charm and character, a tiny house vacation rental in Historic District delivers big adventure. Unplug your laptop and turn your focus to outdoor fun at one of these neat little stays:

  • Expect a simpler way of living at "Annapolis Waterfront "tiny House" In Garden Setting". Amenities at this small wonder in Parole include air conditioning, WiFi and more.
  • "A Serene Tiny Home Experience" in Parole is another highly rated pick. A TV and internet services will help make your time here even more comfortable.

What are the top-rated vacation rentals for weekend getaways in or near Historic District?

Your Monday to Friday will be easier to get through if you've got something awesome lined up for the weekend. Give yourself something to look forward to by arranging a stay at one of these top weekend getaways in or near Historic District:

  • Book a few nights at "Charming Historic Annapolis Home With Two Off", around 1 mile to the east of Historic District, and you've got yourself the best kind of weekend escape. You'll have nature hotspots like Rocky Point Golf Course and Carrs Beach close by and amenities like an oven and shopping to make use of.
  • Also consider "Directly Across From Gate One And Steps From The Waterfront", which is around 1 mile east of Historic District. After a day of discovering nearby sights like Goddard Visitor Center and Top of the World Observation Level, relax in your rental and make use of a water park, a TV and more.

Can I find studio apartments for rent in and around Historic District?

Studio apartments are difficult to beat when it comes to location, convenience and affordability. Get cozy in one of these studio apartments for rent in or near Historic District and discover the vibrant local culture:

  • Make "Annapolis Waterfront "tiny House" In Garden Setting" your home for a few days or more. This sought-after vacation rental comes with amenities including heating and WiFi.
  • Alternatively, spend your escape at "Beautiful Condo - Water View Near City Dock", which comes with conveniences including free toiletries and an elevator.

When it's time to step foot outside your studio apartment and explore the highlights, there's lots to keep you amused around Historic District. Enjoy cultural attractions? Swing by ARTFX Gallery of Fine Crafts and Arts and Ballet Theater of Maryland.

Can I find short term rentals in or near Historic District?

Just because you only have one or two days off work doesn't mean you need to spend it in a bleak hotel room. Get away but still have the home comforts you need at one of these short-term rentals in or around Historic District:

  • "Perfect Weekend Getaway" is near the heart of Historic District, which means there are loads of things to see and do. Explore unique sights like U.S. Naval Academy and Maryland State House when you're not making the most of your cozy digs.
  • "Perfect Location In The Heart Of History" is another excellent option. We recommend adding William Paca House and Westfield Annapolis Mall to your must-do list when it's time to sightsee.

What are the best romantic weekend getaways in or near Historic District?

Forget about flowers and chocolates. Sometimes all you need is to get away for a weekend, just you and your sweetie. At Vrbo, we've got romantic getaways in and around Historic District that would make even Cupid envious. Here are some we think you'll adore:

  • Around 0.1 miles from Historic District, "Charming Historic Home Just Steps From Main Street" is a perfect place for adoring couples. A fireplace and shopping facilities are just some of the many amenities you'll find here.
  • Another option where you can enjoy a few magical days together is "Gorgeous Annapolis Getaway - Walk Everywhere". Located 1 mile from Historic District, beauty services and a fireplace add to the ambiance here.

What are the best houses for rent with a pool in or near Historic District?

Having access to a pool is always a plus when you're vacationing, especially if you're taking the kids. Stay and splash the days away at one of these houses with a pool in or near Historic District:

  • Pack your favorite swimsuit and stay at "Annapolis Waterfront "tiny House" In Garden Setting". Other amenities here include a kitchen and a toaster.
  • Alternatively, stay at "Fantastic House With Lots Of Parking In Downtown Annapolis" and spend your vacation poolside. A barbecue grill and a fenced yard are other things your crew will love about this vacation home.

What are the best large family vacation rentals in or near Historic District?

A family get-together should be one to remember. Whether you're planning some time away with the kids or a long-overdue family reunion, these large family vacation rentals in or near Historic District offer a home away from home with plenty of space for everyone:

  • Get everyone under the same roof at "Charming Historic Home Just Steps From Main Street", which has 3 bedrooms that sleep up to 8 guests. This getaway is around 0.1 miles to the east of Historic District and comes with amenities such as pet-friendly facilities and a stereo.
  • Another great choice is "Gorgeous Annapolis Getaway - Walk Everywhere". This large rental is 1 mile southwest of Historic District and comes with a toaster, a fenced yard and more. With 3 bedrooms accommodating up to 9 people, you won't need to leave anyone off your guest list.

If you're chasing family-friendly attractions in the area, you won't have far to go. Annapolis Bowl, Helen Avalynne Tawes Garden and 14 Fleet Street offer fun for all the gang.

Are there one-bedroom vacation rentals in or near Historic District?

Often located in sought-after positions due to their smaller size, a one-bedroom vacation rental is the perfect solution for one or two travelers. Here's a taste of Vrbo's range in or near Historic District:

  • Consider "Annapolis Waterfront "tiny House" In Garden Setting", a great centrally located one-bedroom vacation property. A garden and a kitchen are available to guests here.
  • Also within easy reach of all the delights of Historic District, "Beautiful Condo - Water View Near City Dock" is another popular one-bedroom option. After a day of exploring, come home and take advantage of a water view and a kitchen.

Can I find two-bedroom vacation rentals in or near Historic District?

It's easy to arrange a wonderful vacation with Vrbo. Whether you opt for a cozy cabin or a trendy apartment, you'll find amazing two-bedroom options in or near Historic District: Here are some of our personal faves:

  • With a swimming pool and a garden, "Stunning Waterfront Cottage With Breathtaking Views" has all you need for an excellent stay. Unpack your luggage and then get out and explore your surrounds.
  • "Spectacular Location: State Circle Apartment" is another popular two-bedroom property in the Historic District area. It comes loaded with amenities like a kitchen and an oven.