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Vacation Rentals & Apartments in Annapolis

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Vacation Rentals & Apartments in Annapolis

About Annapolis

78 apartments

Annapolis Crows Nest Cottage: Chesapeake Bay View

Annapolis villa

5 bedrooms / 3 bathrooms / sleeps 20

Price per night from

$696

1 / 26

Charming Annapolis home with stunning water views

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 11

Price per night from

$500

1 / 55

C/ean & Cozy

Annapolis room

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$59

1 / 10

2. Private 20 acre waterfront estate - studio apt

Annapolis apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$298

1 / 7

Annapolis Area Waterfront Home

Annapolis house

5 bedrooms / 4 bathrooms / sleeps 11

Price per night from

$551

1 / 21

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

Annapolis apartment

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$180

1 / 15

Excellent Location in Downtown Annapolis- walk to everything !

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 2 hours 21 minutes

Price per night from

$299

1 / 17

Walk to Shops/Eateries Charming Cottage. Dogs Wel.

Annapolis house

3 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 1 hour 49 minutes

Price per night from

$251

1 / 52

Charming and Spacious Annapolis Victorian

Annapolis house

6 bedrooms / 5 bathrooms / sleeps 12

Responds fast! avg. 1 hour 34 minutes

Price per night from

$741

1 / 19

Annapolis Townhome w/Deck by Nature Trails & River

Annapolis house

1 bedroom / 2 bathrooms / sleeps 4

Responds fast! avg. 28 minutes

Price per night from

$89

1 / 24

Charming Artists Home in Eastport/Annapolis

Annapolis house

3 bedrooms / 4 bathrooms / sleeps 6

Price per night from

$375

1 / 24

Perfect Annapolis with Lots of Parking & Hot Tub

Annapolis townhouse

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$495

1 / 4

Charming Eastport Home

Annapolis house

3 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$250

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NEW! Annapolis House in Bay Ridge Maryland!

Annapolis house

3 bedrooms / 4 bathrooms / sleeps 6

Responds fast! avg. 22 minutes

Price per night from

$449

1 / 31

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, decor

Price per night from

$426

1 / 30

The Yellow House- Gorgeous Southern Colonial

Annapolis house

6 bedrooms / 6 bathrooms / sleeps 14

Responds fast! avg. 1 hour 30 minutes

Price per night from

$996

1 / 43

Annapolis Condo Near River - Walk to Dwtn!

Annapolis apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 22 minutes

Price per night from

$196

1 / 24

NEW! Charming Annapolis Home w/ Yard-5 Mins to DT!

Annapolis house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 22 minutes

Price per night from

$319

1 / 24

3BR Annapolis Home on Oyster Creek w/Amazing Views

Annapolis house

3 bedrooms / 4 bathrooms / sleeps 9

Responds fast! avg. 22 minutes

Price per night from

$350

1 / 26

Charming Townhouse - Steps to City Dock and USNA

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$450

1 / 7

Charming Home close to historic district

Annapolis house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 59 minutes

Price per night from

$250

1 / 31

*BOOK NOW* Beautiful Cottage in historic Annapolis

Annapolis cottage

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 3 minutes

Price per night from

$350

1 / 25

Great rentals within 20 miles that match your search

Bay Cottage

Rock Hall house

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 3 hours 15 minutes

Price per night from

$251

1 / 8

Panoramic Views of Herrington Harbour on the Bay.

North Beach house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$501

1 / 11

DOLCE VIDA AT Kent Island- 4 bedrooms House for rent-SLEEPS 10-12

Chester house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$751

1 / 32

Location Location! St Michaels-- In Town Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

“Crabtastic Great Escape” This cottage is the perfect great escape. Conveniently located in the middle of quaint St Michael's close to the harbor, restaurants, and shops. The property is clean and well-maintained with beautiful landscaping. The buildin

Responds fast! avg. 3 hours 32 minutes

Price per night from

$151

1 / 27

Premier Cottage in St. Michaels- In Town Location!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 hours 32 minutes

Price per night from

$151

1 / 24

Clean & Spacious

Cape Saint Claire house

4 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$348

1 / 12

Upscale House/12 MINUTES FROM DC

Bowie house

5 bedrooms / 3 bathrooms / sleeps 16

Price per night from

$487

1 / 33

Best sunrise in St. Michaels....Broadview Bay House

St. Michaels house

6 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$596

1 / 24

Harris Cove Cottages LLC

St. Michaels cottage

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$201

1 / 12

Wellspring Manor & Spa

Largo house

5 bedrooms / 8 bathrooms / sleeps 10

Price per night from

$1,637

1 / 6

Price per night from

$301

1 / 12

Lochhaven house for rent

Edgewater house

3 bedrooms / 1 bathroom / sleeps 2

Price per night from

$100

1 / 4

St. Michaels award-winning waterfront BayCottage, pool, docks, sundeck, grounds

St. Michaels villa

6 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 1 hour 1 minutes

Price per night from

$840

1 / 38

Luxury vacation condominum with private beach

Chester house

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$437

1 / 35

KI Golf House-A PAR for the Course & Mile to Beach

Kent Island house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$601

1 / 17

Kent Island Beach House II:Chesapeake Bay Fisherman's Village at Kentmorr Marina

Stevensville house

4 bedrooms / 2 bathrooms / sleeps 12

Price per night from

$646

1 / 9
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About Annapolis

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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.

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