Take a Step Back in Time in Annapolis Rentals

Annapolis rentals place any water-loving traveler in the middle of the "Sailing Capital" in Maryland. Warm-weather visitors love sailing, fishing and competing in annual contests, enjoying the perfect mix of both the convenience of city living and the freedom of waterfront locations.

Stay in Annapolis Rentals for Summer Vacations


For an economical choice in accommodations, nothing tops Annapolis, MD rentals. Many families choose to spend the entire summer in this city, and staying in Annapolis apartment rentals allows for an affordable extended stay as well as a place to call "home" for a season. Consider reserving a group of rentals for large groups and extended family members for a memorable summer trip together too.

Tour the Town near Annapolis, MD Rentals


History buffs already know that Annapolis rentals place you in the middle of a rich collection of historical buildings and homes. Taking a tour will show you the homes of all four Maryland natives who signed the Declaration of Independence, as well as several other notable examples of 18th-century architecture.

Annapolis, MD rentals may be some of these historical buildings or located very near to them. Of course, Annapolis apartment rentals also place you and your loved ones within walking distance to every place of interest you may want to visit during your stay.

Enjoy the Convenience of Annapolis Apartment Rentals


Whether you live in the countryside or another city, you’re sure to appreciate the Annapolis rentals found within the city limits here. You can enjoy the surrounding theaters, musical events, museums and art galleries all year round near Annapolis, MD rentals. Many travelers also enjoy reserving Annapolis apartment rentals for a quick holiday weekend stay near the historical celebrations found in and around town for Christmas and July 4th.

Expand your search for Maryland vacation rentals by considering these options: lodging in Chesapeake Bay or Ocean City rentals.

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Annapolis: Houses, Cottages & More(148)

148 Results
2 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 10
#968476
(27)
2 - 4 night minimum stay
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 15
#223105
(16)
2 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
#951256
(42)
2 - 5 night minimum stay
  • 5 BR,
  • 3 BA,
  • Sleeps 21
#390303vb
(47)
2 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 14
#241350
(24)
2 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 9
#173289
(61)
2 night minimum stay
  • 3 BR,
  • 2 BA,
  • 2 HF BA,
  • Sleeps 10
#989211
(6)
2 - 5 night minimum stay
  • 3 BR,
  • 3 BA,
  • 2 HF BA,
  • Sleeps 9
#345765
(17)
2 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
#461541vb
(32)
4 night minimum stay
  • 5 BR,
  • 2 BA,
  • 2 HF BA,
  • Sleeps 11
#360959
(11)
3 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
#346388
(9)
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
#58142vb
(48)
2 - 4 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
#432131vb
(36)
2 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 10
#602963vb
7 night minimum stay
  • 5 BR,
  • 5 BA,
  • Sleeps 15
#974540
(11)
4 night minimum stay
  • 6 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 15
#283672
(50)
1 - 3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 7
#3589066
(3)
3 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
#116553
(13)
  • 7 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 14
#313972vb
(5)
2 - 3 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
#283626vb
2 Reviews
2 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
#900086
(17)
3 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
#319055
(32)
2 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 12
#379081
(28)
3 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
#60381vb
1 Review
3 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 10
#274348
(11)
3 night minimum stay
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
#248720
  • 4 BR,
  • 4 BA,
  • Sleeps 12
#561848vb
4 - 7 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 11
#487066vb
  • 4 BR,
  • Sleeps 10
#373566vb
2 Reviews
2 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
#458610vb
(21)
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