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Vacation Rentals & Apartments in Annapolis

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107 apartments

2. Private 20 acre waterfront estate - studio apt

Annapolis apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$331

Charming and Spacious Annapolis Victorian

Annapolis house

6 bedrooms / 5 bathrooms / sleeps 12

Responds fast! avg. 1 hour 37 minutes

Price per night from

$843

Perfect Annapolis with Lots of Parking & Hot Tub

Annapolis townhouse

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$781

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

$478

Stunning Home in the Heart of Downtown Annapolis

Annapolis house

3 bedrooms / 5 bathrooms / sleeps 11

Price per night from

$987

The Heart of Historic Cool in Annapolis

Annapolis house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$1,103

Cozy Home in Historic Annapolis with Parking

Annapolis house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 30 minutes

Price per night from

$200

Charming Annapolis Waterview home

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$786

The Fleet's Inn just steps from the Waterfront in this modern Historic home

Annapolis house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 25 minutes

Price per night from

$405

Historic Union Row House in Downtown Annapolis & Parking

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 25 minutes

Price per night from

$402

New! Waterfront luxury barn with private pier

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 2 hours 25 minutes

Price per night from

$379

Seashell in the City 2 parking spots and Walkable to Main Street!

Annapolis house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 25 minutes

Price per night from

$195

Take your Leave of Absence around gorgeous gardens with a private driveway

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 2 hours 25 minutes

Price per night from

$402

Duke's Den Downtown home with 2 PARKING spots!

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 14

Responds fast! avg. 2 hours 25 minutes

Price per night from

$417

Hanover House across from USNA Gate 3 with Parking Pass!

Annapolis house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 25 minutes

Price per night from

$350

The Pet Friendly Lofted Port on 2nd Floor

Annapolis apartment

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 2 hours 25 minutes

Price per night from

$251

1 Block to Naval Academy with Chapel Views with off-site parking!

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 2 hours 25 minutes

Price per night from

$417

Hang just 2 blocks from Navy Stadium all on 1 floor

Annapolis house

3 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 2 hours 25 minutes

Price per night from

$366

Beautiful Downtown Annapolis home with Parking Pass

Annapolis house

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 2 hours 25 minutes

Price per night from

$195

Comfort & Luxury near downtown, mall, coffee shops and more

Annapolis apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$191

Marine's Gate across Gate 1 - Family's Tribute to Heroic Marine

Annapolis house

3 bedrooms / 4 bathrooms / sleeps 6

Responds fast! avg. 2 hours 25 minutes

Price per night from

$419

Two Master Suites in this renovated Bayview Charmer!

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 11

Responds fast! avg. 2 hours 25 minutes

Price per night from

$382

Waterfront Cottage by the Bay all one level in waterfront community

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 25 minutes

Price per night from

$351

Waterfront Coastal home just minutes to Annapolis

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 2 hours 25 minutes

Price per night from

$398

Historic Carriage House in the center of town with parking

Annapolis house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 25 minutes

Price per night from

$343

PARKING at Randall House in Downtown Annapolis

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 11

Responds fast! avg. 2 hours 25 minutes

Price per night from

$411

3 PARKING SPOTS at this Lux Downtown Red Door Gem

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 2 hours 25 minutes

Price per night from

$382

Chill in Mellow Yellow with PARKING!

Annapolis cottage

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 25 minutes

Price per night from

$165

Serene waterfront sunsets in this sprawling Annapolis home

Annapolis house

5 bedrooms / 2 bathrooms / sleeps 12

Responds fast! avg. 2 hours 25 minutes

Price per night from

$637

Naval Academy Themed at the Gates with PARKING!

Annapolis house

4 bedrooms / 2 bathrooms / sleeps 11

Responds fast! avg. 2 hours 25 minutes

Price per night from

$629

Take it Easy in Eastport steps from the Water with street Parking

Annapolis house

2 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 2 hours 25 minutes

Price per night from

$393

Cozy Downtown Annapolis Apartment

Annapolis apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$243

Sleep over in cute Annapolis condo with parking!

Annapolis condo

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 25 minutes

Price per night from

$240

Admiral's Retreat - close to Navy Stadium with Parking!

Annapolis house

4 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 2 hours 25 minutes

Price per night from

$370

West Annapolis Cottage

Annapolis house

6 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$899

Newly-managed Eastport Gem - Walk to Downtown & USNA

Annapolis house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 25 minutes

Price per night from

$400

Gorgeous Deep in the Heart of Annapolis; PARKING for days!

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 6

Responds fast! avg. 2 hours 25 minutes

Price per night from

$393

Gorgeous renovated home "Around the corner" from everything!

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 25 minutes

Price per night from

$402

Viewing 38 of 107
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

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