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Annapolis Vacation Rentals

Find 951 available offers from 8 partners
Annapolis
Anytime
Guests
Annapolis
Anytime
Guests

Choose the perfect vacation rental

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

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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Vacation rentals with Wi-Fi

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

House  Annapolis
Aug 17 - Aug 24
$804 per night
House ∙ 10 guests ∙ 3 bedrooms

House in Annapolis with Grill, Patio & Yard

5.0
Outstanding (30 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Internet
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House  Annapolis
Aug 3 - Aug 10
$464 per night
House ∙ 2 guests ∙ 1 bedroom

House in Annapolis with Yard

4.9
Outstanding (21 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Internet
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House  Annapolis
Aug 17 - Aug 24
-8%
$634
$586 per night
House ∙ 6 guests ∙ 3 bedrooms

Family Friendly Vacation Home in Annapolis with English Garden

4.8
Outstanding (75 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Internet
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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
Aug 3 - Aug 10
$357 per night
House ∙ 5 guests ∙ 3 bedrooms

House in Arundel On The Bay with Grill

5.0
Outstanding (28 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Air conditioning
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Apartment  Annapolis
Aug 10 - Aug 17
-8%
$318
$293 per night
Apartment ∙ 4 guests ∙ 1 bedroom

Apartment in Annapolis with Patio & Yard

5.0
Outstanding (127 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Air conditioning
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Apartment  Annapolis
Jul 26 - Aug 2
-4%
$344
$331 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Lovely Rental Apartment in Annapolis with Free Parking

5.0
Outstanding (219 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Air conditioning
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Vacation rentals with a fireplace

Get warm and cozy on cold winter nights in Annapolis by booking a vacation home with a fireplace.

Apartment  Annapolis
Aug 10 - Aug 17
-11%
$367
$327 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Rental Apartment in Annapolis with Yard & Patio

4.8
Outstanding (34 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Fireplace
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House  Annapolis
Aug 10 - Aug 17
$896 per night
House ∙ 8 guests ∙ 3 bedrooms

Vacation Home in Annapolis with Yard, Grill & Patio

5.0
Outstanding (83 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Fireplace
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House  Annapolis
Aug 17 - Aug 24
-6%
$918
$861 per night
House ∙ 10 guests ∙ 4 bedrooms

Vacation Home in Annapolis with Patio & Yard

5.0
Outstanding (68 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Fireplace
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Best Vacation Home Deals in Annapolis

Save up to 15%

Condo Annapolis
Aug 10 - Aug 17
-15%
$338
$287 per night
Condo ∙ 4 guests ∙ 1 bedroom

Beautiful Condo in Annapolis with Free Parking + Water View

4.9
Outstanding (149 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Aug 17 - Aug 24
-12%
$483
$428 per night
House ∙ 6 guests ∙ 2 bedrooms

House in Annapolis with Patio, Yard & Grill

5.0
Outstanding (84 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Aug 17 - Aug 24
-4%
$795
$765 per night
House ∙ 10 guests ∙ 4 bedrooms

House in Annapolis with Grill, Patio & Yard

5.0
Outstanding (171 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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Book a welcoming vacation home from $182 per night by exploring the 951 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 54%.

Recommended Vacation Rentals in Annapolis

Find your perfect vacation rental in Annapolis: from $182 per night

House Annapolis
Mar 2 - Mar 9
$786 per night
House ∙ 6 guests ∙ 3 bedrooms

Entire House in Annapolis with Front Garden + Great Views

5.0
Outstanding (2 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Aug 17 - Aug 24
$1,181 per night
House ∙ 10 guests ∙ 5 bedrooms

House in Annapolis with Grill & Patio

5.0
Outstanding (95 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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Boat Annapolis
Aug 17 - Aug 24
$619 per night
Boat ∙ 4 guests ∙ 2 bedrooms

Lovely Boat in Annapolis with Patio

5.0
Outstanding (108 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Aug 24 - Aug 31
$561 per night
House ∙ 6 guests ∙ 3 bedrooms

Wonderful Vacation Home in Annapolis with Patio, Grill & Yard

5.0
Outstanding (180 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Aug 10 - Aug 17
$529 per night
House ∙ 5 guests ∙ 2 bedrooms

Nice House in Annapolis with Grill & Patio

5.0
Outstanding (172 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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Condo Annapolis
Aug 17 - Aug 24
-20%
$489
$393 per night
Condo ∙ 6 guests ∙ 3 bedrooms

Condo in Annapolis with Patio & Yard + City Views

4.9
Outstanding (292 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Aug 17 - Aug 24
$472 per night
House ∙ 4 guests ∙ 2 bedrooms

Vacation Home in Annapolis with Grill & Yard + Water View

5.0
Outstanding (116 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Jul 26 - Aug 2
$719 per night
House ∙ 6 guests ∙ 3 bedrooms

House in Annapolis

5.0
Outstanding (6 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Aug 17 - Aug 24
$927 per night
House ∙ 6 guests ∙ 3 bedrooms

Beautiful House in Naval Academy with Grill, Yard & Patio

4.9
Outstanding (60 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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Budget-friendly Rentals in Annapolis

Find Fantastic yet Inexpensive Rentals

House Annapolis
Aug 17 - Aug 24
$685 per night
House ∙ 8 guests ∙ 3 bedrooms

Vacation Home in Annapolis with Grill, Patio & Yard + Peek-A-Boo View

5.0
Outstanding (29 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Aug 24 - Aug 31
$888 per night
House ∙ 8 guests ∙ 3 bedrooms

House in Annapolis with Yard & Patio

5.0
Outstanding (7 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Aug 3 - Aug 10
$1,302 per night
House ∙ 12 guests ∙ 6 bedrooms

House in Annapolis with Grill, Yard & Patio

5.0
Outstanding (82 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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Top-Rated Offers and Accommodations in Annapolis

Book Vacation Rentals with the Highest User Rating

House Annapolis
Aug 24 - Aug 31
$538 per night
House ∙ 5 guests ∙ 2 bedrooms

House in Annapolis with Patio

4.9
Outstanding (61 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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Apartment Annapolis
Aug 3 - Aug 10
$353 per night
Apartment ∙ 4 guests ∙ 1 bedroom

Apartment in Naval Academy with Yard & Patio

5.0
Outstanding (30 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Aug 3 - Aug 10
$303 per night
House ∙ 4 guests ∙ 1 bedroom

House in Annapolis

5.0
Outstanding (8 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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Popular Rental Amenities in Annapolis

  • Pool (205)
  • Pet-friendly (219)
  • WiFi (938)
  • Kitchen (611)
  • Air conditioning (955)
  • TV (888)
  • Washing machine (621)
  • Parking (62)
  • Balcony/patio (424)
  • Dishwasher (467)
  • Grill (345)
  • Microwave (683)

Many users pay a closer look at the vacation rentals with a pool. More than a fifth 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 10 guests and have an average cost of $529 per night. Among these accommodations, 65 of them are situated within 2 kilometres of water.

The Weather in Annapolis

max.
Min.

-1°
13 days 13
max.
Min.

11 days 11
max.
Min.
12°
11 days 11
max.
Min.
18°
11 days 11
max.
Min.
23°
15°
13 days 13
max.
Min.
28°
20°
11 days 11
max.
Min.
30°
23°
13 days 13
max.
Min.
29°
22°
9 days 9
max.
Min.
26°
19°
8 days 8
max.
Min.
20°
12°
8 days 8
max.
Min.
13°
8 days 8
max.
Min.
10°
12 days 12
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

The above is a climate diagram for Annapolis. In the next 6 months, July will have higher average temperatures. However, temperatures can go lower than -1° in Annapolis in January. September is the driest month.

7-Day Weather Forecast in Annapolis

Sun., 25 Feb.

0%

3 h

12 km/h

Mon., 26 Feb.
15°
10°

0%

4 h

8 km/h

Tue., 27 Feb.
15°
14°

15%

0 h

27 km/h

Wed., 28 Feb.
17°
15°

10%

0 h

30 km/h

Thu., 29 Feb.

10%

3 h

29 km/h

Fri., 1 Mar.

0%

6 h

8 km/h

Sat., 2 Mar.

10%

6 h

14 km/h

Accommodations for your vacation in Annapolis

Vacationers who are hoping to find house rental in Annapolis can find many options to choose from, as they are the most prevalent accommodation type in this destination. Additionally, the median size of vacation homes in Annapolis is 217 m² and they cost, on average, $1,092 per night. Furthermore, this specific type of residence is great for large groups, as the majority of house rental can welcome groups of 9. Vacationers interested in something other than house rental can also compare many apartment rental, which are the second most popular property type in Annapolis. These properties cost $475 per night on average and have an average size of 93 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 951 rentals
💳 Possible discounts up to 54%
🌙 Nightly prices starting at $182
⭐ Popular amenities Pool, Pets allowed and Internet
🐾 Pet friendly homes 208 homes
🏊 Vacation rentals with pools 205 homes

Frequently Asked Questions

What is the typical availability of vacation rentals in Annapolis?

We found 951 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 22% 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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