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House Rentals in Annapolis

Find 888 available offers from 8 partners
Annapolis
Anytime
Guests

Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Accommodation types
Condo
House
Apartment
Distance to center
1 km
2 km
5 km
Rating
4.5+
4+
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

Save up to 76%

House Annapolis
Jan 19 - Jan 26
-76%
$414
$101 per night
House ∙ 8 guests ∙ 1 bedroom
Vacation Home in Arnold with Grill + Waterfront Views
4.9
Outstanding (7 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Details
Vrbo
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House Annapolis
Dec 1 - Dec 8
-59%
$904
$373 per night
House ∙ 15 guests ∙ 5 bedrooms
Entire House in Annapolis with Grill & Yard
5.0
Outstanding (7 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Details
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Cottage Annapolis
Dec 9 - Dec 16
-26%
$675
$500 per night
Cottage ∙ 10 guests ∙ 4 bedrooms
Cottage in Parole with Grill & Yard
4.9
Outstanding (59 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Details
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Discover a vacation home matching your expectations among the 888 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.

Top-Rated Rentals and Accommodations in Annapolis

Book Vacation Rental Offers with the Highest User Rating

Apartment Annapolis
Dec 2 - Dec 9
$168 per night
Apartment ∙ 4 guests ∙ 1 bedroom
Rental Apartment in Annapolis with Pool
4.6
Excellent (7 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Dec 2 - Dec 9
$232 per night
House ∙ 10 guests ∙ 3 bedrooms
House in Annapolis with Free Parking
5.0
Outstanding (6 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Details
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House Annapolis
Dec 1 - Dec 8
-66%
$703
$236 per night
House ∙ 10 guests ∙ 3 bedrooms
House in Edgewater with Private Balcony
5.0
Outstanding (5 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 $101 per night

House Annapolis
Nov 6 - Nov 13
-55%
$1,375
$619 per night
House ∙ 10 guests ∙ 4 bedrooms
Vacation Home in Annapolis with Free Parking
5.0
Outstanding (72 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Details
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Condo Annapolis
Dec 2 - Dec 9
-33%
$415
$279 per night
Condo ∙ 7 guests ∙ 2 bedrooms
Condo in Annapolis with Pool + Sweeping Views
5.0
Outstanding (3 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Details
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House Annapolis
Mar 2 - Mar 9
$200 per night
House ∙ 5 guests ∙ 3 bedrooms
House in Arundel On The Bay with Grill
5.0
Outstanding (24 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Details
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House Annapolis
Dec 3 - Dec 10
-60%
$548
$221 per night
House ∙ 5 guests ∙ 2 bedrooms
Vacation Home in Annapolis with Private Pool
5.0
Outstanding (105 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Dec 9 - Dec 16
-50%
$2,102
$1,049 per night
House ∙ 15 guests ∙ 6 bedrooms
Vacation Home in Edgewater with Grill & Yard + Expansive Views
5.0
Outstanding (2 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Aug 10 - Aug 17
-59%
$752
$308 per night
House ∙ 14 guests ∙ 4 bedrooms
House in Annapolis with Free Parking
4.9
Outstanding (23 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Oct 27 - Nov 3
$254 per night
House ∙ 7 guests ∙ 3 bedrooms
Vacation Home in Annapolis
5.0
Outstanding (11 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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Apartment Annapolis
Apr 6 - Apr 13
-57%
$333
$143 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Lovely Rental Apartment in Annapolis with Free Parking
5.0
Outstanding (203 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Oct 27 - Nov 3
-62%
$525
$202 per night
House ∙ 8 guests ∙ 3 bedrooms
House in Annapolis with Grill
5.0
Outstanding
Annapolis, Anne Arundel County, Maryland, United States
Details
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Budget-friendly Vacation Rentals in Annapolis

Find Fantastic yet Inexpensive Offers

House Annapolis
Mar 2 - Mar 9
-43%
$473
$270 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Annapolis with Screened-In Patio
4.9
Outstanding (9 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Jan 13 - Jan 20
-43%
$1,725
$989 per night
House ∙ 10 guests ∙ 5 bedrooms
Vacation Home in Annapolis with Outdoor Pool + Lake Views
5.0
Outstanding (5 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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Condo Annapolis
Jul 20 - Jul 27
$152 per night
Condo ∙ 4 guests ∙ 1 bedroom
Beautiful Condo in Annapolis with Free Parking + Water View
4.8
Outstanding (143 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  Annapolis
Jan 6 - Jan 13
-30%
$896
$629 per night
House ∙ 18 guests ∙ 6 bedrooms
Nice House in Annapolis with Private Parking
5.0
Outstanding (1 rating)
Annapolis, Anne Arundel County, Maryland, United States
Internet
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House  Annapolis
Mar 2 - Mar 9
-17%
$448
$370 per night
House ∙ 10 guests ∙ 5 bedrooms
Vacation Home in Annapolis with Yard & Grill
4.9
Outstanding (156 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Internet
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House  Annapolis
Mar 2 - Mar 9
$420 per night
House ∙ 13 guests ∙ 4 bedrooms
House in Arundel On The Bay with Yard & Grill + Water Views
4.8
Outstanding (43 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  Annapolis
Dec 9 - Dec 16
$362 per night
House ∙ 12 guests ∙ 6 bedrooms
Wonderful House in Annapolis with Free Parking
Annapolis, Anne Arundel County, Maryland, United States
Kitchen
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House  Annapolis
Jan 5 - Jan 12
$125 per night
House ∙ 4 guests ∙ 2 bedrooms
Vacation Home in Annapolis with Grill
4.9
Outstanding (24 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Kitchen
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House  Annapolis
Mar 2 - Mar 9
-37%
$500
$316 per night
House ∙ 6 guests ∙ 2 bedrooms
House in Annapolis with Private Patio
4.9
Outstanding (22 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  Annapolis
Dec 1 - Dec 8
-37%
$899
$568 per night
House ∙ 10 guests ∙ 5 bedrooms
House in Annapolis with Furnished Terrace
4.8
Outstanding (23 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Air conditioning
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Apartment  Annapolis
Mar 16 - Mar 23
-27%
$205
$150 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Private Apartment in Annapolis
5.0
Outstanding (7 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Air conditioning
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House  Annapolis
May 4 - May 11
-17%
$359
$300 per night
House ∙ 10 guests ∙ 4 bedrooms
Pleasant Vacation Home in Annapolis with Grill & Yard
4.7
Excellent (43 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Air conditioning
Details
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Popular Rental Amenities in Annapolis

  • Pet-friendly (180)
  • Pool (211)
  • WiFi (891)
  • TV (827)
  • Parking (58)
  • Air conditioning (875)
  • Kitchen (573)
  • Balcony/patio (160)
  • Washing machine (583)
  • Fireplace (274)
  • Fishing (220)
  • Hot tub (44)

Filters are provided so you can tailor your search and find a great property in Annapolis. In Annapolis, 179 properties include "Pets allowed". Consequently, if you bring your pet everywhere, use the Pets allowed filter to compare these properties. Plan your vacation in advance if you need a fenced-in backyard or you want a rental providing a crib. There are just 62 listed properties with "Fenced" and 136 accommodations with "Crib."

Price and Availability Index in Annapolis

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Vacation Rental Price Information in Annapolis

The price graph will give you the nightly price average for the upcoming months of the year. Annapolis is more expensive in May (5/18 - 5/25), where prices are on average $1,211 a night. The week with the lowest average prices is in January (1/13 - 1/20).

Rental availability information in Annapolis

This graph shows the vacation rental availability rate for the next twelve months. Be careful if you plan to go to Annapolis in August, as it comprises the busiest week of the next 12 months (8/31 - 9/7). October (10/28 - 11/4) has got the highest percentage of available rentals.

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

Wed, 27 Sep
69°
62°

10%

3 h

11 mi/h

Thu, 28 Sep
71°
62°

15%

5 h

10 mi/h

Fri, 29 Sep
73°
64°

15%

0 h

11 mi/h

Sat, 30 Sep
75°
62°

0%

10 h

9 mi/h

Sun, 1 Oct
77°
64°

0%

11 h

5 mi/h

Mon, 2 Oct
75°
64°

0%

11 h

5 mi/h

Tue, 3 Oct
71°
62°

10%

11 h

9 mi/h

Accommodations for your vacation in Annapolis

340 among the 888 listed properties in Annapolis are house rental. They account for more than two-thirds of the accommodation types in this destination (77.63%). Additionally, the standard size of house rental in Annapolis is 229 m² with an average price of $827 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 $349 per night on average and have an average size of 101 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 available 888 homes
💳 Possible discounts up to 94%
🌙 Nightly prices starting at $101
⭐ Popular amenities Pets allowed, Pool and Internet
🐾 Pet friendly homes 172 homes
🏊 Vacation rentals with pools 211 homes

Frequently Asked Questions

What is the nightly price for a vacation home in Annapolis?

The average accommodation in Annapolis is priced at $101 per night. If you would like to stay in a house rental, the average price is $827 per night. A apartment rental Annapolis will cost on average $349 per night.

How many vacation rentals are available to book in Annapolis?

There are 888 vacation rentals from 7 providers in Annapolis.

What are the most popular amenities for vacation rentals in Annapolis?

Most travelers search for Pool, Pets allowed, and Internet when booking a vacation rental in Annapolis.

How many vacation homes with pools are there in Annapolis?

There are 211 vacation rentals across 7 providers in Annapolis.

Are dogs allowed in vacation homes in Annapolis?

If traveling with a pet in Annapolis, 19% of vacation homes are pet-friendly.

What's the best time of year to travel to Annapolis?

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

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