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Annapolis Vacation Rentals

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Recommended Vacation Rentals in Annapolis

Find your perfect vacation rental in Annapolis: from $162 per night

House Annapolis
-35%
Jan 4 - Jan 11
Free cancellation
House ∙ 12 guests ∙ 5 bedrooms

241 m² House

Annapolis, Anne Arundel County, Maryland, United States
$703$458
per night
$703$458
per night
View deal
House Annapolis
-50%
Dec 5 - Dec 12
House ∙ 6 guests ∙ 3 bedrooms

130 m² House

Annapolis, Anne Arundel County, Maryland, United States
$807$402
per night
Excellent(75 ratings)
$807$402
per night
View deal
House Annapolis
House ∙ 12 guests ∙ 5 bedrooms

House

Annapolis, Anne Arundel County, Maryland, United States
from $596
per night
Outstanding(53 ratings)
from $596
per night
View deal
House Annapolis
House ∙ 10 guests ∙ 5 bedrooms

311 m² House

Annapolis, Anne Arundel County, Maryland, United States
from $1,062
per night
Outstanding(66 ratings)
from $1,062
per night
View deal
House Annapolis
House ∙ 12 guests ∙ 5 bedrooms

House

Annapolis, Anne Arundel County, Maryland, United States
from $361
per night
Excellent(3 ratings)
from $361
per night
View deal
House Annapolis
House ∙ 12 guests ∙ 5 bedrooms

House

Annapolis, Anne Arundel County, Maryland, United States
from $1,153
per night
Outstanding(9 ratings)
from $1,153
per night
View deal
House Annapolis
House ∙ 10 guests ∙ 3 bedrooms

187 m² House

Annapolis, Anne Arundel County, Maryland, United States
from $413
per night
Outstanding(21 ratings)
from $413
per night
View deal
House Annapolis
House ∙ 10 guests ∙ 4 bedrooms

House

Annapolis, Anne Arundel County, Maryland, United States
from $842
per night
Outstanding(3 ratings)
from $842
per night
View deal
House Annapolis
House ∙ 6 guests ∙ 3 bedrooms

House

Annapolis, Anne Arundel County, Maryland, United States
from $683
per night
Outstanding(8 ratings)
from $683
per night
View deal
House Annapolis
House ∙ 14 guests ∙ 6 bedrooms

House

Annapolis, Anne Arundel County, Maryland, United States
from $845
per night
Outstanding(42 ratings)
from $845
per night
View deal
House Annapolis
House ∙ 18 guests ∙ 8 bedrooms

520 m² House

Annapolis, Anne Arundel County, Maryland, United States
from $1,475
per night
Outstanding(36 ratings)
from $1,475
per night
View deal
Apartment Annapolis
Apartment ∙ 4 guests ∙ 2 bedrooms

Apartment

Annapolis, Anne Arundel County, Maryland, United States
from $160
per night
Outstanding(11 ratings)
from $160
per night
View deal
House Annapolis
House ∙ 10 guests ∙ 5 bedrooms

325 m² House

Annapolis, Anne Arundel County, Maryland, United States
from $856
per night
Outstanding(79 ratings)
from $856
per night
View deal
Cottage Annapolis
Cottage ∙ 4 guests ∙ 2 bedrooms

Cottage

Annapolis, Anne Arundel County, Maryland, United States
from $305
per night
Outstanding(2 ratings)
from $305
per night
View deal
House Annapolis
House ∙ 10 guests ∙ 4 bedrooms

214 m² House

Annapolis, Anne Arundel County, Maryland, United States
from $718
per night
Outstanding(145 ratings)
from $718
per night
View deal

Best vacation rentals with a balcony

House  Annapolis
Mar 6 - Mar 13
-47%
$1,879
$990 per night
House ∙ 12 guests ∙ 3 bedrooms
Annapolis, Anne Arundel County, Maryland, United States
Free cancellation
Balcony
View deal
House  Annapolis
Nov 1 - Nov 8
-67%
$2,410
$797 per night
House ∙ 8 guests ∙ 3 bedrooms
Annapolis, Anne Arundel County, Maryland, United States
Free cancellation
Balcony
View deal
House  Annapolis
Dec 15 - Dec 22
-30%
$856
$596 per night
House ∙ 19 guests ∙ 5 bedrooms
Annapolis, Anne Arundel County, Maryland, United States
Free cancellation
Balcony
View deal
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Vacation rentals with a fireplace

House  Annapolis
Mar 15 - Mar 22
-54%
$1,656
$767 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
Outstanding(108 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Free cancellation
Fireplace
View deal
House  Annapolis
Nov 16 - Nov 23
-37%
$1,023
$647 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding(2 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Fireplace
View deal
House  Annapolis
Dec 2 - Dec 9
-45%
$1,194
$656 per night
House ∙ 10 guests ∙ 4 bedrooms
4.9
Outstanding(71 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Fireplace
View deal
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Apartments with a balcony or patio

House  Annapolis
Dec 2 - Dec 9
-55%
$1,348
$605 per night
House ∙ 6 guests ∙ 3 bedrooms
Annapolis, Anne Arundel County, Maryland, United States
Balcony/Patio
View deal
House  Annapolis
Oct 31 - Nov 7
-38%
$2,467
$1,536 per night
House ∙ 6 guests ∙ 3 bedrooms
4.8
Outstanding(27 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Free cancellation
Balcony/Patio
View deal
House  Annapolis
Nov 1 - Nov 8
-45%
$2,668
$1,456 per night
House ∙ 10 guests ∙ 5 bedrooms
Annapolis, Anne Arundel County, Maryland, United States
Free cancellation
Balcony/Patio
View deal
See all offers

Best Vacation Home Deals in Annapolis

Save up to 57%

House Annapolis
Dec 1 - Dec 8
-57%
$979
$424 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
Outstanding(1 rating)
Annapolis, Anne Arundel County, Maryland, United States
View deal

Book a welcoming vacation home from $162 per night by exploring the 1,301 properties being offered in Annapolis. All of the accommodations from our partner websites are directly compared on our website so you can save up to 49%.

Budget-friendly Rentals in Annapolis

Find Fantastic yet Inexpensive Rentals

House Annapolis
from $1,854 per night
House ∙ 15 guests ∙ 6 bedrooms
5.0
Outstanding(31 ratings)
Annapolis, Anne Arundel County, Maryland, United States
View deal
House Annapolis
from $851 per night
House ∙ 8 guests ∙ 4 bedrooms
4.9
Outstanding(57 ratings)
Annapolis, Anne Arundel County, Maryland, United States
View deal
House Annapolis
from $277 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding(7 ratings)
Annapolis, Anne Arundel County, Maryland, United States
View deal

Top-Rated Offers and Accommodations in Annapolis

Book Vacation Rentals with the Highest User Rating

House Annapolis
from $624 per night
House ∙ 6 guests ∙ 4 bedrooms
4.9
Outstanding(70 ratings)
Annapolis, Anne Arundel County, Maryland, United States
View deal
House Annapolis
from $414 per night
House ∙ 8 guests ∙ 3 bedrooms
4.8
Outstanding(24 ratings)
Annapolis, Anne Arundel County, Maryland, United States
View deal
House Annapolis
from $696 per night
House ∙ 14 guests ∙ 4 bedrooms
5.0
Outstanding(3 ratings)
Annapolis, Anne Arundel County, Maryland, United States
View deal

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Popular Rental Amenities in Annapolis

  • Pool (205)
  • Pet-friendly (466)
  • WiFi (1,247)
  • Kitchen (906)
  • Air conditioning (1,255)
  • TV (1,176)
  • Washing machine (650)
  • Parking (86)
  • Balcony/patio (462)
  • Dishwasher (501)
  • Grill (364)
  • Microwave (939)

Many users pay a closer look at the vacation rentals with a pool. A few of the properties have one in this destination. Additionally, more hotel room provide a pool than condo. Most of the hotel room with pools in Annapolis accommodate 11 guests and have an average cost of $531 per night. Among these accommodations, 59 of them are situated within 2 kilometres of water.

Dive into the past with an Annapolis vacation rental

Whether they’re colonial cottages or modern condos, vacation rentals in Annapolis are close to the action of this historic yet bustling modern city. With all the comforts of home combined with exciting things to see and do, this scenic area of Maryland will have you returning again and again.

Where are the unique attractions in Annapolis?

Sailing and other excursions

Annapolis is known for its sailing and other water activities on the Chesapeake Bay, and there’s always something to see near the harbor, such as the US Naval Academy Museum. There are many tours in the area, on water and on land, including Colonial Tours of Annapolis, Pirate Adventures on the Chesapeake (great for kids), and Segs in the City.

Information about vacation rentals in Annapolis

🏡 Vacation rentals available 1,301 rentals
💳 Possible discounts up to 49%
🌙 Nightly prices starting at $162
⭐ Popular amenities Pool, Pets allowed and Internet
🐾 Pet friendly homes 461 homes
🏊 Vacation rentals with pools 203 homes
2 reviews
Annapolis vacation rentals have an average rating of 5/5 on 2 reviews left by travelers.

Frequently Asked Questions

What is the typical availability of vacation rentals in Annapolis?

We found 1,301 vacation homes in Annapolis available for your next trip.

What are the most popular vacation home amenities in Annapolis?

When looking to book a vacation home in Annapolis, the most requested amenities include Pool, Pets allowed, and Internet.

Are there pet-friendly vacation rentals in Annapolis?

If you're travelling with a dog, over 35% of vacation rentals in Annapolis are pet-friendly.

What's the best month to book a vacation rental in Annapolis?

When booking a vacation rental in Annapolis, remember that the rainiest months are usually January and May, with September often being the sunniest.

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