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Annapolis Vacation Rentals

Find 859 available offers from 7 partners
Annapolis
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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+
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 Annapolis

Save up to 55%

House Annapolis
Dec 23 - Dec 30
-55%
$761
$342 per night
House ∙ 5 guests ∙ 2 bedrooms
Vacation Home in Annapolis with Private Pool
5.0
"Excellent" (108 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Dec 23 - Dec 30
-36%
$889
$571 per night
House ∙ 8 guests ∙ 3 bedrooms
Vacation Home in Cape Saint Claire with Pool, Yard & Grill + Peaceful View
5.0
"Excellent" (44 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Jun 15 - Jun 22
-39%
$642
$390 per night
House ∙ 8 guests ∙ 2 bedrooms
Vacation Home in Mayo with Pool, Hot Tub & Grill + Panoramic View
4.7
"Outstanding" (47 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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Discover a rental that meets your criteria among the 859 fantastic options from 8 partner websites in Annapolis. Using HomeToGo's search feature you can instantly search and compare the offers of each listed rental to discover the best price and save up to 55%.

Top-Rated Offers and Accommodations in Annapolis

Book Vacation Rentals with the Highest User Rating

House Annapolis
$490 per night
House ∙ 12 guests ∙ 5 bedrooms
Vacation Home in Arundel On The Bay with Yard & Grill + Water Views
5.0
"Excellent" (71 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
$675 per night
House ∙ 7 guests ∙ 3 bedrooms
Lovely House in Annapolis with Free Parking
5.0
"Excellent" (11 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
$277 per night
House ∙ 4 guests ∙ 1 bedroom
House in Annapolis
5.0
"Excellent" (2 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 $136 per night

House Annapolis
Jan 6 - Jan 13
-35%
$772
$504 per night
House ∙ 5 guests ∙ 2 bedrooms
Vacation Home in Annapolis with Private Pool
5.0
"Excellent" (106 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Jul 15 - Jul 22
$226 per night
House ∙ 4 guests ∙ 2 bedrooms
Vacation Home in Annapolis with Grill
4.9
"Excellent" (22 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Oct 14 - Oct 21
$577 per night
House ∙ 8 guests ∙ 3 bedrooms
Vacation Home in Cape Saint Claire with Pool, Yard & Grill + Peaceful View
5.0
"Excellent" (43 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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Cottage Annapolis
$654 per night
Cottage ∙ 6 guests ∙ 3 bedrooms
Nice Cottage in Annapolis with Grill & Yard
5.0
"Excellent" (2 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
$1,166 per night
House ∙ 8 guests ∙ 4 bedrooms
Charming House in Parole with Private Pool + Panoramic Views
5.0
"Excellent" (98 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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Condo Annapolis
$617 per night
Condo ∙ 7 guests ∙ 2 bedrooms
Condo in Annapolis with Pool + Sweeping Views
5.0
"Excellent" (1 rating)
Annapolis, Anne Arundel County, Maryland, United States
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Cottage Annapolis
$400 per night
Cottage ∙ 7 guests ∙ 3 bedrooms
Cottage in Parole with Grill & Yard + Water Views
4.8
"Excellent" (20 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
$442 per night
House ∙ 7 guests ∙ 3 bedrooms
Vacation Home in Annapolis
5.0
"Excellent" (6 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
$372 per night
House ∙ 10 guests ∙ 4 bedrooms
House in Annapolis with Free Parking
5.0
"Excellent" (122 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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Budget-friendly Rentals in Annapolis

Find Fantastic yet Inexpensive Rentals

Apartment Annapolis
$264 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Rental Apartment in Parole with Private Patio + Water Views
5.0
"Excellent" (16 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
$902 per night
House ∙ 10 guests ∙ 4 bedrooms
Vacation Home in Annapolis with Outdoor Pool
4.7
"Outstanding" (7 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
$589 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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Vacation rentals and apartments with air conditioning

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

Condo Air conditioning Annapolis
$136 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
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House Air conditioning Annapolis
$333 per night
House ∙ 5 guests ∙ 3 bedrooms
House in Arundel On The Bay with Grill
5.0
"Excellent" (22 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Air conditioning Annapolis
$303 per night
House ∙ 8 guests ∙ 2 bedrooms
Vacation Home in Mayo with Pool, Hot Tub & Grill + Panoramic View
4.6
"Outstanding" (45 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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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
$261 per night
House ∙ 4 guests ∙ 2 bedrooms
Vacation Home in Parole with Pool, Yard & Grill
5.0
"Excellent" (4 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Kitchen Annapolis
$628 per night
House ∙ 10 guests ∙ 4 bedrooms
Vacation Home in Arundel On The Bay with Grill & Pool
5.0
"Excellent" (4 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Kitchen Annapolis
$445 per night
House ∙ 10 guests ∙ 3 bedrooms
House in Edgewater with Private Balcony
5.0
"Excellent" (3 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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Vacation homes and cottages with a garden

Looking for vacation homes with a little extra outdoor space? Check out these accommodations in Annapolis with private yards.

House Yard Annapolis
$803 per night
House ∙ 8 guests ∙ 4 bedrooms
Beautiful House in Cape Saint Claire with Yard & Grill + River Views
5.0
"Excellent" (26 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Yard Annapolis
$992 per night
House ∙ 10 guests ∙ 5 bedrooms
House in Annapolis with Furnished Terrace
4.9
"Excellent" (12 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Yard Annapolis
$835 per night
House ∙ 8 guests ∙ 3 bedrooms
Vacation Home in Selby-On-The-Bay with Grill & Yard + Water Views
5.0
"Excellent" (5 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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Popular Rental Amenities in Annapolis

  • Pool (206)
  • Pet-friendly (189)
  • WiFi (851)
  • Kitchen (533)
  • Air conditioning (835)
  • TV (787)
  • Washing machine (545)
  • Parking (58)
  • Balcony/patio (159)
  • Dishwasher (425)
  • Grill (339)
  • Microwave (646)

Travelers who are specifically searching for a pet-friendly vacation rental will find Annapolis convenient since many properties are pet-friendly there. Hotel room are the most pet-friendly type of accommodation in Annapolis. In addition, a night in a pet-friendly vacation rental there is, on average, $770. One-third of the pet-friendly rentals (32) are situated less than 2 kilometres away from the city centre.

The Weather in Annapolis

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Min.

-1°
13 days 13
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Min.

11 days 11
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Min.
12°
11 days 11
max.
Min.
18°
11 days 11
max.
Min.
23°
15°
13 days 13
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Min.
28°
20°
11 days 11
max.
Min.
30°
23°
13 days 13
max.
Min.
29°
22°
9 days 9
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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

Find the Annapolis climate diagram. July is the warmest month in Annapolis with average maximum temperatures of 30°. However, temperatures can go lower than -1° in Annapolis in January. September is the driest month.

7-Day Weather Forecast in Annapolis

Sun., 24 Sep.
21°
16°

15%

1 h

16 km/h

Mon., 25 Sep.
21°
17°

10%

6 h

12 km/h

Tue., 26 Sep.
22°
17°

10%

2 h

14 km/h

Wed., 27 Sep.
21°
17°

10%

3 h

19 km/h

Thu., 28 Sep.
22°
17°

15%

5 h

17 km/h

Fri., 29 Sep.
23°
18°

15%

0 h

18 km/h

Sat., 30 Sep.
24°
17°

0%

10 h

14 km/h

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 859 homes
💳 Possible discounts up to 55%
🌙 Nightly prices starting at $136
⭐ Popular amenities Pool, Pets allowed and Internet
🐾 Pet friendly homes 186 homes
🏊 Vacation rentals with pools 209 homes

Frequently Asked Questions

What is the typical price of a vacation home in Annapolis?

The starting price for House rental or Apartment rental in Annapolis is $136 per night.

What is the typical availability of House rental in Annapolis?

We found 859 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.

How many House rental and Apartment rental can I find in Annapolis?

Annapolis has 859 House rental and Apartment rental available to book.

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 visit Annapolis?

If you're looking for balmy weather, July and August are typically the hottest months in Annapolis with temperatures around 30 °C. January and February in Annapolis are the coldest, with -1 °C on average.

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