15 Best Annapolis Apartments on Holiday Lettings - Vacation rentals

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19 Vacation rentals

(15) Excellent 

25

Cottage rental in Annapolis

Maryland / Annapolis

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
Half a block to walk to the Naval Academy Stadium and minutes away from stunning Annapolis town center. This adorable little cottage has lots of sleeping and great outdoor space. Sun Porch & Plenty of parking. A perfect place to relax and enjoy Annapolis, the pro …see more

from $350 / night

$2100 / week

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from $350 / night

16

Annapolis Vacation apartment rental

Maryland / Annapolis

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Air conditioning
Known as the “Athens of America,” Annapolis is a city abundant with history and culture. This former capital of the United States has a little something for every interest and taste, whether you're a history buff, a sports enthusiast, or someone simply looking for a pe …see more

from $175 / night

$1225 / week

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from $175 / night

17

Annapolis Vacation home rental

Maryland / Annapolis

3 7 2 nights min

  • 3 bedrooms
  • Sleeps 7
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
We bought and renovated this rowhouse in 2007 for a second home for friends and family to stay when they visited and it eventually evolved into one of the most popular rental properties in all of Historic Annapolis. A former " Home of the Week" in the Capital Gazette it …see more

from $299 / night

$2300 / week

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Responds fast!
avg. 3 hours 34 minutes

from $299 / night

10

Vacation private room in Annapolis

Maryland / Annapolis

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Air conditioning
Our home is a 5 bedroom quality built home. This room is an office converted in to an extra bedroom space for guests to enjoy. It is located on the main level just inside the main entrance. It had double french doors which lock for privacy. Its a clean and cozy space an …see more

from $60 / night

$414 / week

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from $60 / night

(2) Excellent 

15

Vacation home in Annapolis

Maryland / Annapolis

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
Walk to the city docks and naval academy in this new (2014) luxury townhouse. The king bedroom suite also has a pullout twin bed for parents with small children. Enjoy the grand piano or relax by the gas fireplace. Cookout on the sunny patio. Visit local pubs and r …see more

from $450 / night

$3150 / week

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Responds fast!
avg. 2 hours 31 minutes

from $450 / night

(1) Good 

26

Vacation home in Annapolis

Maryland / Annapolis

3 9 2 nights min

  • 3 bedrooms
  • Sleeps 9
  • 2 nights min
  • Child friendly
  • Air conditioning
Come stay in this beautiful 3-bedroom, 3.5-bathroom single-family home on Oyster Creek – You’ll be able to enjoy fantastic views of the Chesapeake Bay from almost every single room! There’s enough room for 9 guests to comfortably sleep here, so it’s a great size for a f …see more

from $350 / night

$2100 - $5600 / week

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from $350 / night

7

Vacation apartment in Annapolis

Maryland / Annapolis

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Ask about pets
This is the newly renovated 780 sf studio unit that is on the ground floor of a main house that is similarly titled and on the same property. Striking and dramatic 8700 - 9000 sf contemporary, new loft style renovation of the main house with exposed structure and mecha …see more

from $300 / night

$1100 / week

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from $300 / night

(3) Excellent 

24

Vacation home rental

Maryland / Annapolis

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
  • Air conditioning
The Perfect House for a Navy Football Game Weekend!! This is a beautiful historic property within walking distance of downtown Annapolis and the Navy-Marine Corps Stadium. With six bedrooms (two queen beds, three fulls and two twins) the house could comfortably sleep …see more

from $750 / night

$5000 - $7000 / week

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from $750 / night

4

Vacation apartment in Annapolis

Maryland / Annapolis

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Child friendly
  • Air conditioning
My place is good for couples, solo adventurers, and business (URL HIDDEN) school just down the street , Great location for naval academy parents for parents day etc. A gourmet kitchen if you prefer to cook your own meals or cook your fish you have caught on your fishing …see more

from $250 / night

$1750 / week

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from $250 / night

(1)  

7

Vacation home in Annapolis

Maryland / Annapolis

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
  • Car not necessary
  • Ask about pets
Shellback house is a three bedroom, one and 1/2 bath historic townhouse in the heart of Downtown Annapolis with a private garden. The house has views of Ego Alley (Annapolis Waterfront) from the front stoop and the master bedroom. BOOK NOW FOR 2015 LEGISLATIVE SESSION …see more

from $450 / night

$3900 / week

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from $450 / night

(1) Excellent 

51

Annapolis Vacation home rental

Maryland / Annapolis

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Nearest beach 6 mi
  • Child friendly
  • Car not necessary
This City-inspected vintage cottage in Upper Eastport, located on a cul de sac, is a short walk to the Historic Harbor & just blocks from Spa Creek. History, waterfront, rooftop restaurants, wine bars, sailing, kayaking and more. We have everything here in Annapolis - U …see more

from $250 / night

$999 - $1139 / week

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from $250 / night

15

Vacation apartment in Annapolis

Maryland / Annapolis

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Car not necessary
  • Air conditioning
  • Private garden
Best location in Eastport ,We restored this lovely victorian house over the past sixteen years. The upstairs is modern and has all the great amenities that a renovated building provides. anderson windows to keep the place warm and toasty. Seperate heating/air conditioni …see more

from $180 / night

$2600 - $2950 / week

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from $180 / night

5

Annapolis Vacation yacht rental

Maryland / Annapolis

4 10 2 nights min

  • 4 bedrooms
  • Sleeps 10
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
PROTECTED WATERS, GREAT ANCHORAGES... …gorgeous natural scenery, unique towns and villages, and a forgiving bottom make the Chesapeake an excellent choice for sailors, novice and expert alike. Historic Annapolis, the crown jewel of the Mid-Atlantic, is the best sailing …see more

from $1250 / night

$8750 / week

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from $1250 / night

(3) Very Good 

30

Vacation home rental

Maryland / Annapolis

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Ask about pets
Our beautifully-appointed home pays homage to the Colonial Period. It comfortably sleeps eight guests with four bedrooms and 2.5 baths. It boasts elegant dining and living rooms. Enjoy the quiet street and an easy stroll to downtown Annapolis. We have taken great …see more

from $426 / night

$2500 - $3236 / week

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from $426 / night

24

Vacation home in Annapolis

Maryland / Annapolis

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Ask about children
  • Air conditioning
HOUSE This fully renovated, circa 1890 ,Victorian house is located in the middle of the Eastport peninsula . The house is within walking distance, or a three minute taxi ride, to downtown historic Annapolis and the US Naval Academy, as well as shopping, several marin …see more

from $375 / night

$2400 / week

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from $375 / night

21

Vacation home rental

Maryland / Annapolis

5 11 4 nights min

  • 5 bedrooms
  • Sleeps 11
  • 4 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Your family will thank you for choosing this Severn River Waterfront Retreat for Vacation! From the moment you enter this 5 bedroom home you will appreciate the spectacular views of the Severn River. Four of the five bedrooms view the Severn River, so your family will …see more

from $550 / night

$3200 / week

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from $550 / night

23

Vacation home in Annapolis

Maryland / Annapolis

3 8 5 nights min

  • 3 bedrooms
  • Sleeps 8
  • 5 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Walk to historic City Dock, waterfront restaurants, U.S. Naval Academy. Open, sunny floor plan ideal for entertaining. Craftsman style 3 BRM + den + office + front porch swing + screened back porch + game room + ample parking. Well-furnished. Sleeps 6-8 comfortably or u …see more

from $300 / night

$2000 / week

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from $300 / night

24

Vacation townhouse in Annapolis

Maryland / Annapolis

4 10 2 nights min

  • 4 bedrooms
  • Sleeps 10
  • 2 nights min
  • Child friendly
Our home is in a very nice, safe neighborhood (two blocks to firehouse and 2 blocks to police station) within walking distance to historic downtown Annapolis. It is also less than a block to the Navy football stadium and easily walkable to grocery store, pharmacy, liqu …see more

from $495 / night

$3000 / week

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from $495 / night

26

Vacation villa in Annapolis

Maryland / Annapolis

5 20 2 nights min

  • 5 bedrooms
  • Sleeps 20
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Child friendly
Comfort & Style: Enjoy stunning Chesapeake Bay Views, Beach, Pier, Boat Slips, Park, Water Access, Fire Pit, Patio Heater and more! Charming cottage & detached studio/game room (both upgraded in 2013) offer gourmet kitchen with new stainless steel appliances, a second …see more

from $695 / night

$3000 - $3840 / week

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from $695 / night

1