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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.

Annapolis things to do

 

Pirate Adventures On the Chesapeake

Amazing! I was worried based on some pictures that my kids (6 and 7) would be too old but it was the perfect age. Flint was our crew member and he was so...read more

 

Schooner Woodwind

So glad we did this! My fiance and I decided to do the two hour trip and it was perfect. The captain and crew were attentive, funny, but not overbearing....read more

 

Key Bridge Boathouse

I bought a "trial season pass" through Groupon which gave me unlimited access to this location for April thru June. Those months ended up being kind of...read more

 

Annapolis Canoe & Kayak

What a great way to get onto the water! Annapolis Canoe and Kayak got us situated in our tandem kayak and we were off exploring Spa Creek in no time....read more

 

Rams Head On Stage

I think this would actually be a 3.5 star, but I'll give it 4 because of the live music, and that is always a plus.. Went to RH-On-Stage for a show for the...read more

 

Quiet Waters Park

I've gone to Quiet Waters a number of times, but mainly because it's convenient. It gets pretty crowded on the weekends sometimes. The park is very dog...read more

 

Terrapin Adventures

WONDERFUL experience!!! Far exceeded our expectations. Got more than our money's worth with the 4-hour Terrapin Challenge (zip line, ropes challenge, giant...read more

 

Annapolis Pottery

It's huge! that's what she said. I was rushed through the store because it was going to storm and I still had to make it back to the car without an...read more

 

49 West Coffeehouse, Winebar & Gallery

Last week, my husband and I decided to take our dog to Annapolis for a nice little walk around the water and a light lunch outside. Upon arrival, we...read more

 

Kayak Annapolis

Got a living social deal as a gift and booked for a Monday in august before it expires at the end of the month. It's only says in ONE spot on the website...read more

 

Maryland State House

If you're in Annapolis definitely stop by the State House for a self guided tour*. Although the State House is small, it is very nicely maintained and most...read more

 

Bikram Yoga Annapolis

I have done Bikram yoga all around the world as well as other forms of yoga for many years. Mediocre is the best I can say of this studio. The instructor...read more

 

Jonas Green Park

Beautiful place to sit and chill while enjoying the awesome weather, view, and peacefulness. We brought crab and lobster rolls and ice cream and it was a...read more

 

Pigtails & Crewcuts

This location is so wonderfully accommodating to kids of all ages. The stylists listen to what the parents want for their child's haircut. We always have a...read more

 

Evolutions Body Clinic

Love this place. It's a small enough gym that it isn't intimidating, but large enough that it has everything you need. The locker rooms are more like a...read more

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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 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

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
 
 
 
 
 

3 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) $400 /nt
 
 
 
 
 

36 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) $475 /nt
    $3,000 /wk
    $5,000 /mth
 
 
 
 
 

61 reviews write a review

In The Heart of Annapolis!
Annapolis House Rental Picture
  • bedrooms 1
  • rental type House
  • owner badgeowner badge
  • sleeps 5
  • baths 2
  • rates (USD) $275 - $425 /nt
    $1,500 - $2,900 /wk
 
 
 
 
 

7 reviews write a review

Labor Day Avail - New Listing! Neat & Clean 1BR Apartment in Historic Annapolis w/Wifi - Prime Location, Walking Distance to Downtown & the United States Naval Academy!
Annapolis Apartment Rental Picture
  • bedrooms 1
  • rental type Apartment
  • sleeps 2
  • baths 1
  • rates (USD) $160 - $250 /nt
    $960 - $1,500 /wk
    $4,800 - $7,500 /mth
 
 
 
 
 

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
 
 
 
 
 

21 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

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) $775 - $1,000 /nt
    $4,800 - $5,800 /wk
    $14,250 /mth
 
 
 
 
 

17 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 10
  • baths 3
  • rates (USD) $450 /nt
    $2,450 /wk
 
 
 
 
 

8 reviews write a review

Heart of Downtown Renovated Home - Historic Annapolis - Parking- Walk Everywhere
Annapolis House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $700 - $1,107 /nt
    $4,550 - $7,750 /wk
 
 
 
 
 

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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) $150 - $1,200 /nt
    $1,050 - $6,000 /wk
    $4,500 - $36,000 /mth
 
 
 
 
 

3 reviews write a review

Beautiful Catamaran With 4 Bedrooms And Private Baths
Annapolis Boat Rental Picture
  • bedrooms 4
  • rental type Boat
  • sleeps 10
  • baths 4
  • rates (USD) $350 - $800 /nt
    $3,200 /wk
    $11,000 /mth
 
 
 
 
 

1 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
 
 
 
 
 

26 reviews write a review

Available for PowerBoat Show! Across from Downtown Marriott!
Annapolis House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $325 - $400 /nt
 
 
 
 
 

13 reviews write a review

Charming Cottage Near Navy Marine Corp Stadium in Annapolis
Annapolis Cottage Rental Picture
  • bedrooms 1
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $165 /nt
    $1,000 /wk
    $2,100 /mth
 
 
 
 
 

24 reviews write a review

Wonderful Eastport home - walk to downtown. Great deck!
Annapolis House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $450 - $600 /nt
    $2,600 - $2,800 /wk
    $6,500 - $8,000 /mth
 
 
 
 
 

32 reviews write a review

Gorgeous-Historic Annap USNA Commissioning Week Available Due to Cancellation!
Annapolis House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $450 - $850 /nt
    $3,000 - $4,600 /wk
    $7,500 - $12,000 /mth
 
 
 
 
 

2 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

Beautiful Home In Heart of Eastport
Annapolis House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $425 /nt
    $2,400 /wk
    $4,200 /mth
 
 
 
 
 

3 reviews write a review

Comfortable Timber Frame deep waterfront home in Annapolis close to USNA
Annapolis House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $225 - $607 /nt
    $1,100 - $1,725 /wk
    $4,100 - $4,750 /mth
 
 
 
 
 

17 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
 
 
 
 
 

5 reviews write a review

Charming Vintage Cottage.Walk to pubs,shops. Free Pkg
Annapolis Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $225 - $300 /nt
    $990 - $999 /wk
    $2,250 /mth
 
 
 
 
 

47 reviews write a review

Largest Fully Refurbished Rental Home in the Historic District
Annapolis House Rental Picture
  • bedrooms 7
  • rental type House
  • owner badgeowner badge
  • sleeps 14
  • baths
  • rates (USD)
 
 
 
 
 

5 reviews write a review

Renovated Historic Home Located Downtown -Walk Everywhere!
Annapolis House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $295 - $395 /nt
    $2,100 /wk
    $4,000 /mth
 
 
 
 
 

47 reviews write a review