Discover a selection of 500 vacation rentals in Annapolis, MD 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 swimming pools and private pools. Prices start at $130 per night, and houses and boats are popular options for a stay in Annapolis. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Annapolis
Destination guide

Historic Annapolis will entice you

The area's history and live music are just a few of the reasons to vacation in Annapolis. Renowned for its university setting, shopping and restaurants, this city welcomes all visitors. Arundel Mills Mall and Maryland Live Casino are just a couple of the must-sees in the area. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Things to do

Activities and attractions in and around Annapolis

Are you searching for things to do while you're in town? Venture out of your cozy vacation rental and check out everything that makes Annapolis a one-of-a-kind vacation spot. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Six Flags America (16 mi / 25.7 km)
  • Queenstown Harbor Golf Club (17.4 mi / 28 km)
  • Bingo World (18.4 mi / 29.6 km)
  • St. Michaels Winery (19.9 mi / 32.1 km)
  • Chesapeake Beach Water Park (19.9 mi / 32.1 km)
  • Laurel Park (20.3 mi / 32.7 km)
Natural features

Exploring the natural landscape of Annapolis

Whether you're an active traveler or just want to appreciate the scenery, Annapolis is a great place to get out in nature. Here are some of the area’s most enchanting features, all within 30 miles (48.2 km) of the city center:

  • Maryland Quiet Waters Park (2.8 mi / 4.4 km)
  • Sandy Point State Park (5.4 mi / 8.8 km)
  • Chesapeake Bay Environmental Center (14.3 mi / 23.1 km)
  • BWI Trail (20.5 mi / 33 km)
  • Greenbelt Park (21.6 mi / 34.8 km)
  • Ellen O. Moyer Nature Park at Back Creek (0.1 mi / 0.1 km)
How to get there

Transportation to and around Annapolis

Fly into Baltimore Washington Intl. Airport (BWI), the closest airport, located 16.8 mi (27 km) from the city center. If you can't find a flight that's convenient for your trip, you might consider flying into Ronald Reagan Washington National Airport (DCA), which is 30.8 mi (49.6 km) away.

What are the top vacation rentals in or near Annapolis?

Whether you want a cozy escape for you and your honey or someplace spacious to fit friends and family, you'll find some top vacation rentals in and around Annapolis. Here are a couple to get you inspired:

  • Take advantage of amenities including children's toys and golf at "Perfect - 100+ 5 - Star Reviews Great View". Situated around 55 miles from Annapolis, this unique option has 3 bedrooms and good guest reviews.
  • Another appealing choice is "Brand New Renovation In Historic District With 2 Parking Spots", which is around 1 mile from Annapolis. Offering 2 bedrooms, an iron and ironing board and off-street parking options, 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 Annapolis vacation rental for you.

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

For a completely different vacation experience, book one of Vrbo's tiny house rentals in Annapolis. A word of warning though — after you've lived the tiny house life, the urge to move into one of these pocket-sized digs will be tough to resist!

  • Unwind and recharge your batteries at "Annapolis Waterfront "tiny House" In Garden Setting". Located in Parole, internet services and a fridge are just two of the amenities included here.
  • Alternatively, get comfy at "A Serene Tiny Home Experience". Located in Parole, this tiny gem comes with off-street parking options and lowered locks.

Can I find log cabins to rent in or near Annapolis?

Yes, you can! From rustic retreats to lavish escapes, you'll find a great range of log cabins to rent in or near Annapolis. If you're seeking adventure, you'll love these options:

  • "Stunning Views From Waterfront Log Cabin With Fireplace On The Chesapeake Bay": This is the perfect base to try some of the fun outdoor activities offered in this region, including water skiing and sailing.
  • "Gorgeous 1840 Log Cabin - Downtown": Stay in and enjoy the quiet atmosphere or have a go at some of the thrilling activities nearby, including sledding and golf. The choice is all yours around here.

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

Forget about those household chores — weekends were made for having fun. Settle into one of these weekend getaways in and around Annapolis and take advantage of all the fantastic things to do close by:

  • Get away from it all at "Charming Historic Home Just Steps From Main Street", which is around 0.1 miles to the southeast of Annapolis. There's lots of nature and adventure on your doorstep here. Go fishing and cycling or just explore the sights of Fell's Point Visitor Center and Baltimore Cruise Terminal.
  • "Gorgeous Annapolis Getaway - Walk Everywhere" is another great property to consider. Around 1 mile southwest of Annapolis, use it as a base to do a little windsurfing or kayaking. Homewood Museum and 14 Fleet Street also have to be on your to-do list if you stay here.

Can I find studio apartments for rent in and around Annapolis?

Enjoy a taste of the culture and vibe of Annapolis from the privacy and comfort of a studio apartment. Whether you'd like to take time out on your own or have some fun with pals, you'll find the ideal studio apartment for rent in and around Annapolis:

  • Wake up, explore and then do it all over again at "Fabulous, Historic One Bedroom Capitol Hill Apartment With Off Street Parking". This vacation rental is a terrific base for seeing the sights and features amenities including a stovetop and an iron and ironing board.
  • Another popular choice is "Stunning, Stylish Flat, Cool Neighborhood Close To Everything". Make use of a fridge, a washing machine and other conveniences during your getaway.

With the cash you save on your studio apartment, you can afford to see even more of Annapolis. Cultural sights like Adventure Theatre and Basilica of the Assumption of the Blessed Virgin Mary will help you better understand the character of this destination.

Can I find short term rentals in or near Annapolis?

Just because you only have one or two days to spare doesn't mean you need to spend it in a boring hotel. Get away but still have the home comforts you love at one of these short-term rentals in or around Annapolis:

  • Close to the center of Annapolis, "Peaceful Cambridge Home On Jenkins Creek" is perfect for a quick break. While you're around, be sure to visit well-known attractions like Annapolis Bowl and Eisenhower Golf Course.
  • Sleep, relax and explore from "Charming Historic Home Just Steps From Main Street", another excellent option. Walden Golf Club and Crofton Bowl should be on your itinerary when it's time to sightsee.

What are the best romantic weekend getaways in or near Annapolis?

Nothing says "I love you" like a romantic weekend together. If you're longing to spend a couple of relaxing nights away with your other half, we've got some romantic getaways in and around Annapolis that will sweep you off your feet:

  • Sneak off on Friday for a few passionate nights at "Brand New Renovation In Historic District With 2 Parking Spots". Around 1 mile from Annapolis, this place comes with plenty of nice touches, including beauty services and a fireplace.
  • Otherwise, spend a few magical days enjoying each other's company at "Water Front Retreat - Sunrise And Sunset Water Views", around 20 miles from Annapolis. Beauty services and a fireplace will help ramp up the romance.

Are there mansions for rent in or near Annapolis?

We've got some superb mansions for rent in and near Annapolis. If you're chasing somewhere with plenty of space as well as a large serve of wow factor, these architectural stunners will tick your boxes:

  • Character, style and charm — "Chesapeake Mansion - New Pool/12" has it all in abundance. Approximately 18 miles southeast of Annapolis and offering a firepit and a fireplace, this showstopper is tough to beat.
  • Alternatively, score some serious Brownie points and stay a week or two at "Victorian Mansion - Mt. Vernon". It's located 25 miles to the north of Annapolis and comes with a separate dining area, a restaurant dining guide and more.

What are the best large group vacation rentals in or near Annapolis?

Big groups mean a whole lot of fun. They also mean finding someplace that'll easily fit your entire squad. Check out our large group vacation rentals in or around Annapolis and get your favorite people together under the same roof:

  • A nice range of amenities including a nearby waterfront and a water view make "Ultraclean Waterfront Home Annapolis Area" a group favorite. This generous property has 5 bedrooms and sleeps up to 12 guests. From the center of Annapolis, it's around 7 miles away to the north.
  • Nothing is more important than hanging out with loved ones, and "Washington Dc Suburb With Quite Neighborhood Just A Stones Throw From Everything" makes it easy to do that. Located around 25 miles to the west of Annapolis, as many as 12 guests can stay in this vacation rental which has 5 bedrooms. A garden and a kitchen are among the many amenities here.

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

Of all the conveniences a vacation rental can have, a pool promises the most fun. Browse these houses for rent with a pool in or near Annapolis and spend your days splashing around. Just remember to take your unicorn floatie:

  • Make yourself comfortable at "Gorgeous Row House 4 Bedroom With 2 Parking Walk To Metro And Dc Monuments", where your top priority will be relaxing by the pool. Amenities including a fridge and coffee and tea making facilities help make this getaway a guest favorite.
  • "Annapolis Waterfront "tiny House" In Garden Setting" is the kind of place you go to get away from it all and make the most of your surroundings, starting with its pool. A fridge and a living room are also on hand to make your visit comfortable and convenient.

Not sure how to pack your suitcase for your Annapolis escape? This enticing destination has a humid subtropical climate. In summer, expect average temperatures of between 70 ºF and 85 ºF. Browse our selection of Annapolis vacation rentals by using the search bar at the top of the page. Simply adjust the filters to get more ideas about where to stay.