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House Rentals in Annapolis

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Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Accommodation types
House
Apartment
Condo
Distance to center
Max. 1 km
Max. 2 km
Max. 5 km
Rating
Outstanding: 4.5+
Very Good: 4+
Good: 3.5+

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.

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Best Vacation Home Deals in Annapolis

House Annapolis
Nov 4 - Nov 11
-47%
$500
$266 per night
House ∙ 7 guests ∙ 3 bedrooms
House in Annapolis with Yard & Grill
4.9
"Excellent" (24 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Oct 20 - Oct 27
-99%
$665
$4 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Annapolis
4.7
"Outstanding" (6 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Nov 3 - Nov 10
-60%
$1,131
$457 per night
House ∙ 10 guests ∙ 5 bedrooms
House in Annapolis with Free Parking
5.0
"Excellent" (21 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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Discover a vacation home matching your expectations among the 859 great options from more than 7 providers in Annapolis. By comparing these properties, HomeToGo features the best deals as well as the highest rated properties in Annapolis.

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Top-Rated Rentals and Accommodations in Annapolis

House Annapolis
Dec 23 - Dec 30
$220 per night
House ∙ 4 guests ∙ 2 bedrooms
Vacation Home in Annapolis with Grill & Yard + Water View
5.0
"Excellent" (107 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Dec 30 - Jan 6
$508 per night
House ∙ 6 guests ∙ 3 bedrooms
Beautiful House in Naval Academy with Grill & Yard
4.9
"Excellent" (43 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Jul 22 - Jul 29
$200 per night
House ∙ 5 guests ∙ 3 bedrooms
House in Arundel On The Bay with Grill
5.0
"Excellent" (19 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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Recommended Vacation Rentals in Annapolis

Find your perfect vacation rental in Annapolis: from $140 per night

House Annapolis
Mar 16 - Mar 23
-40%
$1,052
$434 per night
House ∙ 4 guests ∙ 5 bedrooms
House in Annapolis with Furnished Terrace
5.0
"Excellent" (7 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Dec 9 - Dec 16
-25%
$585
$418 per night
House ∙ 10 guests ∙ 3 bedrooms
Vacation Home in Annapolis with Private Parking
5.0
"Excellent" (24 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Dec 30 - Jan 6
$495 per night
House ∙ 6 guests ∙ 4 bedrooms
Pleasant Vacation Home in Arundel On The Bay with Yard & Grill
4.8
"Excellent" (27 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Dec 1 - Dec 8
-52%
$878
$431 per night
House ∙ 10 guests ∙ 4 bedrooms
House in Annapolis with Free Parking
5.0
"Excellent" (28 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Jun 6 - Jun 13
$950 per night
House ∙ 10 guests ∙ 5 bedrooms
Vacation Home in Annapolis
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Sep 16 - Sep 23
-22%
$310
$243 per night
House ∙ 7 guests ∙ 3 bedrooms
Vacation Home in Annapolis
5.0
"Excellent" (2 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Dec 30 - Jan 6
$400 per night
House ∙ 6 guests ∙ 2 bedrooms
Nice Vacation Home in Annapolis with Pool, Grill & Yard + Waterfront Views
5.0
"Excellent" (218 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Nov 4 - Nov 11
-31%
$1,230
$850 per night
House ∙ 14 guests ∙ 5 bedrooms
House in Annapolis with Private Patio
5.0
"Excellent" (54 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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Apartment Annapolis
May 1 - May 8
-16%
$195
$176 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Rental Apartment in Annapolis with Yard
4.7
"Outstanding" (28 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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Budget-friendly Vacation Rentals in Annapolis

House Annapolis
Apr 22 - Apr 29
-23%
$782
$600 per night
House ∙ 12 guests ∙ 5 bedrooms
Charming Vacation Home in Annapolis with Grill & Yard
5.0
"Excellent" (31 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Jun 6 - Jun 13
$950 per night
House ∙ 10 guests ∙ 5 bedrooms
Vacation Home in Annapolis
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Nov 4 - Nov 11
-55%
$440
$200 per night
House ∙ 6 guests ∙ 3 bedrooms
Wonderful Vacation Home in Annapolis with Grill & Yard
5.0
"Excellent" (153 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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Vacation rentals with Wi-Fi

Stay connected while traveling and book a Annapolis accommodation with high-speed internet.

House Internet Annapolis
Dec 9 - Dec 16
-60%
$554
$221 per night
House ∙ 5 guests ∙ 2 bedrooms
Vacation Home in Annapolis with Private Pool
5.0
"Excellent" (109 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Internet
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House Internet Annapolis
Dec 9 - Dec 16
-43%
$973
$559 per night
House ∙ 10 guests ∙ 4 bedrooms
Vacation Home in Annapolis with Second-Floor Balcony
5.0
"Excellent" (33 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Internet
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House Internet Annapolis
Apr 4 - Apr 11
$419 per night
House ∙ 8 guests ∙ 3 bedrooms
Lovely House in Annapolis with Yard
5.0
"Excellent" (40 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Internet
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Apartments and vacation rentals with a kitchen

Cook up a feast on your next vacation and book a Annapolis rental with full kitchen.

House Kitchen Annapolis
Dec 9 - Dec 16
-44%
$614
$342 per night
House ∙ 4 guests ∙ 3 bedrooms
Nice House in Annapolis with Outdoor Fireplace
4.9
"Excellent" (7 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Kitchen
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House Kitchen Annapolis
Apr 4 - Apr 11
$298 per night
House ∙ 8 guests ∙ 4 bedrooms
Whole Vacation Home in Annapolis
Annapolis, Anne Arundel County, Maryland, United States
Kitchen
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Condo Kitchen Annapolis
Dec 2 - Dec 9
$140 per night
Condo ∙ 4 guests ∙ 1 bedroom
Beautiful Condo in Annapolis with Free Parking + Water View
4.8
"Excellent" (114 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Kitchen
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Vacation rentals and apartments with air conditioning

Keep cool during your trip to Annapolis and book a vacation rental with air conditioning.

House Air conditioning Annapolis
Dec 30 - Jan 6
$309 per night
House ∙ 5 guests ∙ 2 bedrooms
House in Annapolis + Water Views
5.0
"Excellent" (95 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Air conditioning
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House Air conditioning Annapolis
Dec 30 - Jan 6
$370 per night
House ∙ 10 guests ∙ 5 bedrooms
Vacation Home in Annapolis with Yard & Grill
4.9
"Excellent" (148 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Air conditioning
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House Air conditioning Annapolis
Mar 16 - Mar 23
-37%
$421
$264 per night
House ∙ 8 guests ∙ 4 bedrooms
Vacation Home in Annapolis with Indoor Fireplace
5.0
"Excellent" (2 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Air conditioning
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Popular Rental Amenities in Annapolis

  • Internet (1,069)
  • Air conditioning (1,013)
  • TV (971)
  • No smoking (844)
  • Microwave (831)
  • Kitchen (743)
  • No pets (660)
  • Washer (604)
  • Dishwasher (550)
  • Grill (481)
  • Yard (390)
  • Fireplace (353)

The Weather in Annapolis

max.
Min.
43°
30°
13 days 13
max.
Min.
45°
32°
11 days 11
max.
Min.
54°
37°
11 days 11
max.
Min.
64°
48°
11 days 11
max.
Min.
73°
59°
13 days 13
max.
Min.
82°
68°
11 days 11
max.
Min.
86°
73°
13 days 13
max.
Min.
84°
72°
9 days 9
max.
Min.
79°
66°
8 days 8
max.
Min.
68°
54°
8 days 8
max.
Min.
55°
41°
8 days 8
max.
Min.
50°
37°
12 days 12
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

Check out our climate diagram to find the perfect month for your vacation. In July maximum temperatures go higher than 86°. However, temperatures can go lower than 30° in Annapolis in January. The rainiest month is January while the driest month is September.

7-Day Weather Forecast in Annapolis

Sat, 1 Apr
73°
62°

15%

2 h

20 mi/h

Sun, 2 Apr
53°
37°

5%

10 h

10 mi/h

Mon, 3 Apr
66°
44°

0%

10 h

13 mi/h

Tue, 4 Apr
64°
53°

0%

10 h

7 mi/h

Wed, 5 Apr
68°
57°

15%

5 h

9 mi/h

Thu, 6 Apr
62°
55°

15%

0 h

8 mi/h

Fri, 7 Apr
53°
44°

10%

0 h

9 mi/h

Accommodations for your vacation in Annapolis

502 among the 859 listed properties in Annapolis are house rental. They account for more than two-thirds of the accommodation types in this destination (79.06%). Additionally, the standard size of house rental in Annapolis is 218 m² with an average price of $877 a night. Moreover, most house rental in this destination can host 8 guests, which makes it a wonderful vacation spot for large groups. If you are interested in a different accommodation type, you may want to have a look at apartment rental, which are the second most typical accommodation option in Annapolis. These accommodations cost $341 per night on average and have an average size of 87 m².
What are the best places to discover the arts and culture of Annapolis?

Art, history, and culture

From its earliest days, Annapolis has been known as the “Athens of America” for its cultural, social and intellectual activities. Your vacation rental in Annapolis will be close to many artistic and cultural offerings, such as Historic London Town and Gardens, where you can explore 23 acres of history, archeology, and beautiful flora.

Experience performances by the Annapolis Shakespeare Company, Ballet Theatre of Maryland, or the Annapolis Symphony Orchestra. If visual art is your cup of tea, there are 25 fine art galleries downtown alone, as well as the Elizabeth Myers Mitchell Gallery, a museum that is open daily and has free admission.

What are the best nightlife spots in Annapolis?

Music and other nightlife

Much of historic Annapolis is walkable. Across the street from the visitors center, in the Arts District, is Rams Head On Stage, a delightful bar/restaurant/concert venue with a healthy offering of music or comedy almost every night. There’s an active music scene in Annapolis, with dozens of local bands calling the area home. See them perform in pubs, bars, and restaurants all over the city, such as Armadillo's Bar and Grill and Castlebay Irish Pub.

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 859 properties
💳 Possible discounts up to 60%
🌙 Nightly prices starting at $140
⭐ Popular amenities Internet, Air conditioning and TV
🐾 Pet friendly accommodations 246 properties
🏊 Vacation rentals with pools 269 properties

Frequently Asked Questions

What is the average price per night for a vacation rental in Annapolis?

The average accommodation in Annapolis is priced at $140 per night. If you would like to stay in a house rental, the average price is $877 per night. A apartment rental Annapolis will cost on average $341 per night.

How many vacation homes are available for booking in Annapolis?

Currently there are 859 vacation rentals in Annapolis to choose from and book for your next trip.

What amenities are most popular for vacation homes in Annapolis?

If you're looking to book a vacation rental in Annapolis, others search for accommodation with Internet, Air conditioning and TV.

How many vacation rentals with a pool are there in Annapolis?

There are 269 vacation rentals across 7 providers in Annapolis.

Are dogs allowed in vacation homes in Annapolis?

Yes, there are 246 vacation homes in Annapolis that allow dogs , with an average rate of $561 per night.

What's the best month to travel to Annapolis?

The warmest months in Annapolis are July and August, with temperatures around 86 °F. The coldest months in Annapolis are January and February, with 30 °F on average.

We list offers from thousands of providers, including:

Booking.com Vacation Rentals in Annapolis TripAdvisor Vacation Rentals in Annapolis Vrbo Vacation Rentals in Annapolis VacationRentals.com Vacation Rentals in Annapolis HouseTrip Vacation Rentals in Annapolis FlipKey Vacation Rentals in Annapolis Homestay.com Vacation Rentals in Annapolis Only-apartments Vacation Rentals in Annapolis Interhome Vacation Rentals in Annapolis Novasol Vacation Rentals in Annapolis HomeEscape Vacation Rentals in Annapolis

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