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Vacation Rentals & Apartments in Annapolis

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Price: high to low

Number of reviews

80 apartments

2. Private 20 acre waterfront estate - studio apt

Annapolis apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$343

Charming and Spacious Annapolis Victorian

Annapolis house

6 bedrooms / 5 bathrooms / sleeps 12

Responds fast! avg. 23 minutes

Price per night from

$856

Vintage Bungalow-cozy, walkable, free pkg.

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$485

Perfect Annapolis with Lots of Parking & Hot Tub

Annapolis townhouse

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$565

Beautiful Murray Hill Home (Annapolis)

Annapolis house

4 bedrooms / 3 bathrooms / sleeps 9

“Comfortable and secure in a great home - almost as good as at ho” The house is set is a terrific neighborhood of annapolis within easy walking distance to two small parks on the water and to town. We all found the house a delight - the design, decorating, furnishings are tasteful and match the age and the imagery of the house. It is well equipped with comfortable bedrooms, adequate bathrooms and linens, utensils and staple supplies. We certainly will attempt to stay at this house again if we ever return to annapolis.

Price per night from

$485

Stunning Home in the Heart of Downtown Annapolis

Annapolis house

3 bedrooms / 5 bathrooms / sleeps 11

Price per night from

$796

The Heart of Historic Cool in Annapolis

Annapolis house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$1,142

Cozy Home in Historic Annapolis with Parking

Annapolis house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 17 minutes

Price per night from

$85

Charming Annapolis Waterview home

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$798

Heart of Annapolis - 3 bedroom single home

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$314

Downtown Annapolis Condo w/ Free Parking + Coffee

Annapolis condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$216

Play at the beach minutes to downtown Annapolis

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 1 hour 16 minutes

Price per night from

$381

Beautifully furnished home close to Navy Stadium

Annapolis house

4 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 1 hour 16 minutes

Price per night from

$369

Luxury Home Walkable to Main Street w Parking!

Annapolis house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 16 minutes

Price per night from

$194

Stay in this newly-decorated gorgeous Downtown Annapolis home with parking!

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 14

Responds fast! avg. 1 hour 16 minutes

Price per night from

$416

Spend the night in Historic Downtown Annapolis

Annapolis house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 16 minutes

Price per night from

$381

New - Gorgeous downtown Annapolis home with parking for days!

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 1 hour 16 minutes

Price per night from

$392

New! Gorgeous renovated home "Around the corner" from everything!

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 16 minutes

Price per night from

$438

Newly Managed Guest Suite in Eastport

Annapolis apartment

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 1 hour 16 minutes

Price per night from

$251

Annapolis-themed home in Downtown Annapolis with Parking

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 16 minutes

Price per night from

$194

USNA-themed 3 Bedroom home off West Street with parking!

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 16 minutes

Price per night from

$394

Newly managed - quiet Annapolis home close to everything!

Annapolis house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 1 hour 16 minutes

Price per night from

$416

New! 1 Block to Naval Academy with Chapel Views!

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 1 hour 16 minutes

Price per night from

$414

Walkable to Downtown Annapolis

Annapolis house

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 1 hour 16 minutes

Price per night from

$194

Newly-renovated home in waterfront community available now!

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 11

Responds fast! avg. 1 hour 16 minutes

Price per night from

$381

New Waterfront Cottage on all one level in waterfront community

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 16 minutes

Price per night from

$425

Newly Managed Randall House in Downtown Annapolis

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 11

Responds fast! avg. 1 hour 16 minutes

Price per night from

$410

Lux Downtown Annapolis Home with 3 parking spots!

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 1 hour 16 minutes

Price per night from

$381

Chill in this Annapolis Cozy Cottage

Annapolis cottage

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 16 minutes

Price per night from

$170

New Downtown Annapolis waterview home available for Navy Events!

Annapolis house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 16 minutes

Price per night from

$573

Naval Academy Themed at the Gates with parking!

Annapolis house

4 bedrooms / 2 bathrooms / sleeps 11

Responds fast! avg. 1 hour 16 minutes

Price per night from

$610

Steps from the Waterfront in Eastport

Annapolis house

2 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 1 hour 16 minutes

Price per night from

$389

View of the Capital and Steps to Main Street

Annapolis house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 16 minutes

Price per night from

$385

Renovated Eastport Firehouse in Annapolis

Annapolis house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 16 minutes

Price per night from

$287

22 Fleet St. - Best Spot for Commissioning Week, Newly-Renovated & Historic!

Annapolis condo

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$302

Historic Charm! Walk to Annapolis Waterfront & Academy

Annapolis house

3 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 1 hour 16 minutes

Price per night from

$419

West Annapolis Hidden Gem

Annapolis apartment

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$113

Great rentals within 20 miles that match your search

Sandy Pines: Enjoy Harris Creek w/Pool and Boats

St. Michaels house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 34 minutes

Price per night from

$782

Viewing 38 of 80
rentals in Annapolis

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About Annapolis

Come to Annapolis to experience the best of old world style and Chesapeake Bay charm. This distinguished town, located on the salty bay, has provided visitors with the perfect Maryland vacation getaway for centuries. Visit the museums here and learn more about the early settlers of the area, the natural history and the wildlife that populate fragile Maryland ecosystems, and the important events in American history that took place here. Find a vacation rental, summer home, or bayside cottage overlooking the shoreline. Head downtown to experience Maryland's annual festivals celebrating regional music and the famous Maryland blue crab. Go antique and craft shopping in the heart of the city. Explore Annapolis museums and art galleries and spend some time on the emerald green golf courses around the Chesapeake Bay. At night, head downtown for world-class seafood and a live performance at a local theater.

Here are a few additional suggestions for your trip:

  • Visit the Maryland State House: Annapolis was America's first peacetime capitol, and the statehouse is the oldest still in legislative use.
  • Visit the US Naval Academy: Take a tour of the Naval Academy, one of the proud institutions of Annapolis.
  • Go on a pirate adventure: Take a real life pirate adventure on a ship in Annapolis Harbor. Pirate Adventures on the Chesapeake offers a full day of true buccaneering on an Annapolis boat, complete with face paint, pirate fashions, and a water cannon battle.
  • Experience Annapolis sailing: Nothing can compare with a real sailing adventure aboard an authentic Chesapeake Skipjack. Help man the sails, try your hand at Annapolis fishing and crabbing, or just relax on the deck and watch the harbor birds sail overhead.
  • Visit the William Paca Garden: This colonial garden offers peace, serenity, and history lessons along with guided tours.
  • Explore Quiet Waters Park: This 340 acre park just outside the city center offers more than six miles of trails perfect for strolling, jogging, or biking.

Thousands of visitors come to this area every year to enjoy long weekend getaways, family reunions, and beautiful wedding venues in Annapolis. If you're among them, find the perfect rental apartment in the heart of downtown, or a bayside condo near the harbor. While you're here, consider visiting a few other popular vacation destinations in Maryland like Arnold and Lake Shore.

Top Destination reviews

Beautiful Murray Hill Home (Annapolis)
wonderful homey feel

The house worked out great for 3 couples and one 3 year old. The 3 year old loved having his own room with a great selection of books and toys. Everyone else enjoed the feel of house. Roomy and a great location. We walked to downtown annapolis twice during our short weekend visit. Completely supplied with an assortment of food and anything you could think of. The homemade muffins and bottle of wine was a treat. I am a very critical person that expects alot.see more
Charming and Spacious Annapolis Victorian
Charming house in a great location! Perfect for larger group!

We just returned from our sailing weekend in Annapolis and had an amazing time staying at this lovely house for the weekend. The house was perfect for a larger group. The large deck out back and patio furniture were wonderful for grilling and eating dinner outside. (The outdoor giant Jenga was a hit!) We went with a group of various couples and a couple of our single friends and everyone had their own space. It never felt crowded. It's only about a 10 minute walk to the heart of downtown Annapolis to the restaurants and dock, and you're only about two blocks away from the free trolley that you can catch near the Westin hotel which will transport you directly to town if you don't feel like walking. The beds were all comfortable! Plenty of bathrooms and the kitchen is very nice, open and fully stocked with anything you need to cook and hang out with family and friends. The owner is very responsive and accommodating. It's a perfect location! We will certainly stay here again for our next Annapolis getaway. Our entire group really enjoyed it and found it to be a very comfortable place to call home for the weekend. They also had free wifi and speakers to plug in your ipod and stream pandora, etc..and have some great music while enjoying breakfast, hanging out, etc. Great place to stay! Thanks for everything!see more
Vintage Bungalow-cozy, walkable, free pkg.
Great place. My dog loved the yard. I loved the Porch

If you want a cozy place to relax this is the place. Yard was perfect for my dog to run around and I did not have to worry it was all fenced in. Love to grill so I was able to grill a couple a steaks and have a semi barbeque (little cold so the porch was perfect) by eating and entertaining on the Porch.see more

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