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Vacation Rentals in Annapolis, Maryland

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about Annapolis

Annapolis, Maryland Vacation Rentals and Tourism

With so many reasons to visit Annapolis, Maryland, vacation rentals in Annapolis are a perfect choice for a vacation home base for exploring the city. Annapolis vacation apartment rentals offer access to the nation’s capitol and great sights while they also give you a tranquil vacation home, condo or cottage near the Chesapeake Bay.

Annapolis, MD, rentals are near the Naval Academy, historic Annapolis architecture and landmarks, and lots of opportunities for boating here in the sailing capital. Step back in history in London Town or at the Annapolis Maritime Museum. A variety of tours will guide you through Annapolis by boat or carriage or on your own Segway. While vacationing in Annapolis, you’re just 30 miles from the monuments and museums in Washington, DC. With so much to see and do, be sure to take time to relax near your Annapolis rental and go kayaking, fishing or crabbing. Annapolis vacation rentals are near waterfront restaurants, pubs and cafés, and Annapolis is home to great shopping.

Annapolis vacation rentals are about 30 miles from Baltimore, MD, and Baltimore Washington International Airport. Come, explore the vibrant, historic town of Annapolis, Maryland, for yourself!

Annapolis Vacation Rental Deals

Annapolis is a cultural hub filled with theaters, historic sites, museums, art galleries, play halls, and outdoor attractions. Stay in one of our money saving Annapolis vacation rentals and fully enjoy everything that makes Annapolis such a special place to visit. Save money with our always discounted rates and find great Annapolis last minute deals. With such affordable Annapolis accommodations you will get the best value out of your trip here. So what are you waiting for? Plan to come to Annapolis for your next vacation and enjoy a home away from home.

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Check out more areas which feature homes, villas, cabins, cottages, or condos.

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* Nightly rates and average rates per bedroom are based on actual rates in this area. Learn More .

The Yellow Cottage
Annapolis Cottage Rental Picture
  • bedrooms 2
  • community
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 6
  • baths 1
  • rates (USD) $200 - $225 /nt
 
 
 
 
 

16 reviews write a review

Annapolis Waterfront South River Chesapeake Bay
Annapolis House Rental Picture
  • bedrooms 3
  • community Sylvan Shores
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 3
  • rates (USD) $300 - $350 /nt
    $2,000 - $2,400 /wk
 
 
 
 
 

29 reviews write a review

The Waterside Cottage on Harness Creek
Annapolis Cottage Rental Picture
  • bedrooms 2
  • community
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $175 - $275 /nt
    $1,250 - $1,550 /wk
    $2,500 - $5,000 /mth
 
 
 
 
 

8 reviews write a review

Annapolis - Large Private Contemporary
Annapolis House Rental Picture
  • bedrooms 5
  • community Woodlore
  • rental type House
  • sleeps 12
  • baths
  • rates (USD) $450 - $700 /nt
    $2,800 - $3,500 /wk
 
 
 
 
 

1 reviews write a review

Eastport Artists House
Annapolis House Rental Picture
  • bedrooms 3
  • community neighborhood
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $350 - $450 /nt
    $2,200 - $3,200 /wk
 
 
 
 
 

2 reviews write a review

Taylor House of Annapolis/Taylor Ave
Annapolis House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $300 - $600 /nt
    $1,050 - $3,000 /wk
    $3,500 - $4,500 /mth
 
 
 
 
 

1 reviews write a review

Peaceful 3BR House on Oyster Creek w/ Amazing Views of the Chesapeake Bay
Annapolis House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 9
  • baths
  • rates (USD) $350 - $1,200 /nt
    $1,750 - $6,000 /wk
    $7,500 - $25,714 /mth
 
 
 
 
 

2 reviews write a review

Charming Historic Home Just Steps from Main St! Beautifully Renovated!
Annapolis House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $450 /nt
    $2,800 /wk
    $6,000 /mth
 
 
 
 
 

18 reviews write a review

Beautiful Renovation in Historic District
Annapolis House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $425 - $500 /nt
    $2,400 /wk
    $4,500 /mth
 
 
 
 
 

9 reviews write a review

One block from City Dock, Main st, Naval Academy!! Newly remodeled!!!
Annapolis House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $450 /nt
    $2,450 /wk
 
 
 
 
 

6 reviews write a review

Beautiful Annapolis Getaway - Walk Everywhere!
Annapolis House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $350 - $400 /nt
 
 
 
 
 

26 reviews write a review

Luxurious Historic Home in the Heart of Downtown Annapolis!
Annapolis House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 9
  • baths
  • rates (USD)
 
 
 
 
 

61 reviews write a review

Amazing Waterfront in Annapolis, easy walk to Navy Stadium & Downtown
Annapolis House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 14
  • baths 4
  • rates (USD) $850 /nt
 
 
 
 
 

22 reviews write a review

Eastport Artist Accommodations House and/or Apartment
Annapolis House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $350 /nt
    $2,200 /wk
 
 
 
 
 

4 reviews write a review

Stunning Downtown Home Steps From the Academy!
Annapolis House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 9
  • baths 4
  • rates (USD) $875 - $1,000 /nt
    $5,800 /wk
    $14,250 /mth
 
 
 
 
 

17 reviews write a review

**Special Winter Offers!!! Quiet, Relaxing Waterfront Suisse Chalet with Dock
Annapolis Chalet Rental Picture
  • bedrooms 3
  • rental type Chalet
  • owner badgeowner badge
  • sleeps 10
  • baths
  • rates (USD)
 
 
 
 
 

7 reviews write a review