Annapolis vacation rentals

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Booking Insights
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Best Annapolis vacation rentals

Charming cottage with parking. Easy walk to downtown. - Annapolis - Living room
Charming cottage with parking. Easy walk to downtown.
Annapolis, MD
9.9Wonderful(42)
House
Free Wi-Fi
$449+
Check availability
Spectacular Location Two Bedroom State Circle Apartment - Annapolis - Kitchen
Spectacular Location Two Bedroom State Circle Apartment
Downtown
9.3Wonderful(28)
Apartment
Free Wi-Fi
$547+
Check availability
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking! - Annapolis - Balcony
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Annapolis, MD
9.8Wonderful(92)
House
Free Wi-Fi
Pool
$521+
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2-story downtown home with enclosed yard, deck, firepit, gas grill & fireplace - Annapolis - Living room
2-story downtown home with enclosed yard, deck, firepit, gas grill & fireplace
Annapolis, MD
9.7Wonderful(23)
House
$466+
Check availability
Walk to the stadium, downtown, West St - close to everything - Annapolis - Living room
Walk to the stadium, downtown, West St - close to everything
Annapolis, MD
10Wonderful(4)
House
Parking
Free Wi-Fi
$266+
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Charming Historic Townhouse Steps From Usna - Annapolis - Living room
Charming Historic Townhouse Steps From Usna
Downtown
10Wonderful(28)
House
Free Wi-Fi
$359+
Check availability
New Downtown Annapolis Condo With Free Parking - Annapolis - Living room
New Downtown Annapolis Condo With Free Parking
Annapolis, MD
10Wonderful(31)
Condo
Free Wi-Fi
$368+
Check availability
Studio Apartment in Downtown Annapolis - Annapolis - Bedroom
Studio Apartment in Downtown Annapolis
Annapolis, MD
10Wonderful(4)
Apartment
$287+
Check availability
Charming Renovated Historic Home Downtown wparking - Annapolis - Dining room
Charming Renovated Historic Home Downtown wparking
Annapolis, MD
9.6Wonderful(65)
House
Free Wi-Fi
$589+
Check availability
NEW Charming Historic Home .75mile to Navy Stadium, 1mile to USNA and Downtown - Annapolis - Living room
NEW Charming Historic Home .75mile to Navy Stadium, 1mile to USNA and Downtown
Annapolis, MD
9.7Wonderful(7)
House
Free Wi-Fi
$485+
Check availability
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids - Annapolis - Bedroom
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Annapolis, MD
10Wonderful(44)
Apartment
$463+
Check availability
2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free - Annapolis - Patio
2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free
Annapolis, MD
9.8Wonderful(13)
House
$1,109+
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Beautifully Renovated Historic District Home - Annapolis - Dining room
Beautifully Renovated Historic District Home
Downtown
9.8Wonderful(21)
House
Free Wi-Fi
$830+
Check availability
Waterfront Oasis in Eastport-Easy Walk to Downtown - Annapolis - Living room
Waterfront Oasis in Eastport-Easy Walk to Downtown
Annapolis, MD
9.8Wonderful(41)
House
Free Wi-Fi
$1,012+
Check availability
Sailor's Retreat! Perfect home for the getaway weekend. Best location! - Annapolis - Patio
Sailor's Retreat! Perfect home for the getaway weekend. Best location!
Annapolis, MD
9.8Wonderful(12)
House
Free Wi-Fi
$547+
Check availability
Coastal Edgewater Home with Private Hot Tub! - Annapolis
Coastal Edgewater Home with Private Hot Tub!
Annapolis, MD
8.8Very good(10)
House
Free Wi-Fi
$410+
Check availability
Booking Insights

KAYAK’s insights for vacation rentals in Annapolis

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Annapolis with confidence.

What is the cheapest day of the week to book a vacation rental in Annapolis?

Friday offers the lowest rates in Annapolis, with an average nightly price of $149. The highest prices are found on Sunday, with average rates at $635.

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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

February
July
$473
$316
Cheapest month to stay with an average 85% drop in price.
Most expensive month to stay with an average 66% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Annapolis vacation rental deals

  • Pool and pet friendly are the most popular vacation rental property amenities in Annapolis
  • Vacation rentals in Annapolis are around 62% more expensive than hotels on average. Search here to compare prices for all accommodation types in Annapolis.
  • The best vacation rental properties in Annapolis are Charming Historic Townhouse Steps From Usna (10.0, 28 reviews), New Downtown Annapolis Condo With Free Parking (10.0, 31), and Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids (10.0, 44), based on ratings and reviews from real travelers.
  • If you’re looking for a cheap vacation rental in Annapolis, you should consider visiting during the low season. The cheapest vacation homes in Annapolis can be found in February and January.
  • The cheapest night for renting a vacation home in Annapolis is Friday. In contrast, the most expensive is Sunday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Annapolis for 14 days.

FAQs when booking a vacation home in Annapolis

  • What types of vacation rentals are available in Annapolis?

    There are loads of different property types that you can make your vacation home in Annapolis. You’ll find apartments, condos, cottages, houses, homestays, hotels, houseboats and villas.

  • What are some of the most-loved vacation rentals available in Annapolis?

    If you’re looking for something special, the vacation rental most loved by KAYAK users is Candlewood Suites Annapolis By IHG.

  • Are there any pet-friendly vacation rentals in Annapolis?

    There are a number of dog and pet-friendly Annapolis vacation rentals, with around 6% allowing you to bring your pet along with you.

  • How much is a vacation rental in Annapolis for this weekend?

    In the last 72 hours, users have found Annapolis vacation rentals for this weekend for as low as $324 per night. Search here for similar prices

  • How can I find vacation rentals near me in Annapolis?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

Where to stay in Annapolis?

Our map will help you find the perfect place to stay in Annapolis by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Annapolis