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Vacation Rentals & Apartments in Annapolis

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85 apartments

Annapolis Crows Nest Cottage: Chesapeake Bay View

Annapolis villa

5 bedrooms / 3 bathrooms / sleeps 21

Price per night from

$468

C/ean & Cozy

Annapolis private room

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$70

Annapolis Area Waterfront Home

Annapolis house

5 bedrooms / 4 bathrooms / sleeps 11

Price per night from

$557

Excellent Location in Downtown Annapolis- walk to everything !

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 41 minutes

Price per night from

$338

2. Private 20 acre waterfront estate - studio apt

Annapolis apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$356

Charming and Spacious Annapolis Victorian

Annapolis house

6 bedrooms / 5 bathrooms / sleeps 12

Responds fast! avg. 17 minutes

Price per night from

$870

Location,location,location,walk to city dock,free

Annapolis apartment

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$297

Walk to Shops/Eateries Charming Cottage. Dogs Wel.

Annapolis house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$296

Charming Eastport Home

Annapolis house

3 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$356

Annapolis House w/ Patio in Bay Ridge Maryland!

Annapolis house

3 bedrooms / 4 bathrooms / sleeps 6

Responds fast! avg. 4 minutes

Price per night from

$668

Charming Artists Home in Eastport/Annapolis

Annapolis house

3 bedrooms / 4 bathrooms / sleeps 6

Price per night from

$444

Perfect Annapolis with Lots of Parking & Hot Tub

Annapolis townhouse

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$587

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

$499

Your Eastport Annapolis Haven!

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 16 minutes

Price per night from

$500

810 Annapolis House

Annapolis condo

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$351

Downtown Annapolis Home, Walk to Navy Stadium

Annapolis townhouse

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 4 minutes

Price per night from

$136

Annapolis Home w/ Bay Views - Near Naval Academy!

Annapolis house

5 bedrooms / 3 bathrooms / sleeps 11

Responds fast! avg. 4 minutes

Price per night from

$775

Stunning Home in the Heart of Downtown Annapolis

Annapolis house

3 bedrooms / 5 bathrooms / sleeps 11

Price per night from

$824

The Heart of Historic Cool in Annapolis

Annapolis house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$1,185

Cozy Home in Historic Annapolis with Parking

Annapolis house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$236

Charming Annapolis Waterview home

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$574

Charming Annapolis Home w/ Yard - 5 Mins to Dwtn!

Annapolis house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 4 minutes

Price per night from

$304

Charming Townhouse - Steps to City Dock and USNA

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$533

*BOOK NOW* Beautiful Cottage in historic Annapolis

Annapolis cottage

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 23 minutes

Price per night from

$376

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

Annapolis condo

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$303

NEW! Charming Condo w/ Pool Access by Severn River

Annapolis condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 4 minutes

Price per night from

$135

Great rentals within 20 miles that match your search

Little Boat in Annapolis!

Edgewater boathouse

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$142

Love Point Luxury Waterfront in Stevensville

Stevensville house

3 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$1,646

Panoramic Views of Herrington Harbour on the Bay.

North Beach house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$592

Beautiful Home in Nice Community with up to 7 bedrooms

Severn house

4 bedrooms / 4 bathrooms / sleeps 14

Responds fast! avg. 19 minutes

Price per night from

$569

BEULAH Residence (Bedroom 4)

Glen Burnie guest house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$119

Small Boat in Annapolis!

Edgewater boathouse

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$143

Renovated Luxury Waterview House

North Beach house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$356

BEULAH Residence (Bedroom 3)

Glen Burnie guest house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$119

2 Bedroom Condo minutes away from DC & VA

Largo condo

2 bedrooms / 3 bathrooms / sleeps 4

Price per night from

$190

Upscale House/12 MINUTES FROM DC

Bowie house

5 bedrooms / 3 bathrooms / sleeps 16

Price per night from

$581

Metromax Lovely Private Studio!

Gambrills apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$71

Wellspring Manor & Spa

Largo house

5 bedrooms / 8 bathrooms / sleeps 10

Price per night from

$1,937

Viewing 38 of 85
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
Walk to Shops/Eateries Charming Cottage. Dogs Wel.
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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