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Annapolis Vacation Rentals

Find 829 available offers from 7 partners

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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.

Save up to 56%

Best Vacation Home Deals Annapolis

Aug. 5 - Aug. 12

-56%

~~$614~~

$268 per night

Apartment ∙ 4 guests ∙ 2 bedrooms

Rental Apartment in Annapolis with Pool

Annapolis, Anne Arundel County, Maryland, United States

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Discover a rental that meets your criteria among the 829 fantastic options from 7 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 56%.

Book Vacation Rentals with the Highest User Rating

Top-Rated Offers and Accommodations Annapolis

$195 per night

House ∙ 5 guests ∙ 2 bedrooms

House in Annapolis + Water Views

5.0

"Excellent" (95 ratings)

Annapolis, Anne Arundel County, Maryland, United States

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$714 per night

House ∙ 8 guests ∙ 4 bedrooms

House in Annapolis with Grill

5.0

"Excellent" (52 ratings)

Annapolis, Anne Arundel County, Maryland, United States

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$1,158 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

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Recommended Vacation Rentals Annapolis

Find your perfect vacation rental Annapolis: from $199 per night

$238 per night

Apartment ∙ 4 guests ∙ 2 bedrooms

Rental Apartment in Annapolis with Pool

Annapolis, Anne Arundel County, Maryland, United States

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$497 per night

House ∙ 12 guests ∙ 4 bedrooms

House in Annapolis

Annapolis, Anne Arundel County, Maryland, United States

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$667 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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$578 per night

House ∙ 10 guests ∙ 4 bedrooms

House in Edgewater with Grill + Exceptional Views

5.0

"Excellent" (13 ratings)

Annapolis, Anne Arundel County, Maryland, United States

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$982 per night

House ∙ 10 guests ∙ 5 bedrooms

House in Annapolis with Grill

5.0

"Excellent" (91 ratings)

Annapolis, Anne Arundel County, Maryland, United States

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$711 per night

House ∙ 8 guests ∙ 4 bedrooms

House in Annapolis with Grill

5.0

"Excellent" (52 ratings)

Annapolis, Anne Arundel County, Maryland, United States

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$233 per night

Apartment ∙ 4 guests ∙ 2 bedrooms

Lovely Rental Apartment in Annapolis with Free Parking

5.0

"Excellent" (171 ratings)

Annapolis, Anne Arundel County, Maryland, United States

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$568 per night

House ∙ 6 guests ∙ 2 bedrooms

House in Annapolis with Private Patio

4.7

"Outstanding" (6 ratings)

Annapolis, Anne Arundel County, Maryland, United States

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$200 per night

House ∙ 5 guests ∙ 2 bedrooms

House in Annapolis + Water Views

5.0

"Excellent" (95 ratings)

Annapolis, Anne Arundel County, Maryland, United States

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Find Fantastic yet Inexpensive Rentals

Budget-friendly Rentals Annapolis

Jul. 29 - Aug. 5

$901 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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Jul. 29 - Aug. 5

$464 per night

House ∙ 4 guests ∙ 2 bedrooms

Vacation Home in Annapolis with Grill & Yard + Water View

5.0

"Excellent" (108 ratings)

Annapolis, Anne Arundel County, Maryland, United States

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$146 per night

Condo ∙ 4 guests ∙ 1 bedroom

Beautiful Condo in Annapolis with Free Parking + Water View

4.8

"Excellent" (113 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.

$354 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

Internet

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$1,112 per night

House ∙ 10 guests ∙ 5 bedrooms

Vacation Home in Annapolis with Outdoor Pool + Lake Views

5.0

"Excellent" (2 ratings)

Annapolis, Anne Arundel County, Maryland, United States

Internet

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$859 per night

House ∙ 8 guests ∙ 3 bedrooms

House in Annapolis with Grill & Yard

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.

$592 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

Air conditioning

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$562 per night

House ∙ 8 guests ∙ 4 bedrooms

House in Annapolis with Free Parking

5.0

"Excellent" (13 ratings)

Annapolis, Anne Arundel County, Maryland, United States

Air conditioning

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$736 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

Air conditioning

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Cabins with a sauna

Relax and enjoy yourself in one of these Annapolis vacation rentals with saunas.

$1,637 per night

House ∙ 18 guests ∙ 6 bedrooms

Beautiful Vacation Home in Annapolis with Private Pool + Great Views

4.8

"Excellent" (19 ratings)

Annapolis, Anne Arundel County, Maryland, United States

Sauna

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$1,918 per night

House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Annapolis with Finnish Sauna

5.0

"Excellent" (14 ratings)

Annapolis, Anne Arundel County, Maryland, United States

Sauna

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$249 per night

Apartment ∙ 4 guests ∙ 1 bedroom

Pleasant Apartment in Annapolis with Private Sauna

5.0

"Excellent" (3 ratings)

Annapolis, Anne Arundel County, Maryland, United States

Sauna

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Popular Rental Amenities Annapolis

Internet (1,032)
Air conditioning (977)
TV (935)
No smoking (808)
Microwave (796)
Kitchen (710)
No pets (633)
Washer (572)
Dishwasher (539)
Grill (451)
Yard (388)
Fireplace (334)

Travelers who are specifically searching for a pet-friendly vacation rental will find Annapolis convenient since many properties are pet-friendly there. Hotel rooms are the most pet-friendly type of accommodation in Annapolis. In addition, a night in a pet-friendly vacation rental there is, on average, $746. More than half of the pet-friendly rentals (50) are situated less than 2 kilometres away from the city centre.

The Weather Annapolis

max. Min. 6° -1° 13 days 13	max. Min. 7° 0° 11 days 11	max. Min. 12° 3° 11 days 11	max. Min. 18° 9° 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° 5° 8 days 8	max. Min. 10° 3° 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 Annapolis with average maximum temperatures of 30°. However, temperatures can go lower than -1° Annapolis in January. September is the driest month.

7-Day Weather Forecast Annapolis

Fri., 24 Mar.

10°

7°

Sat., 25 Mar.

19°

7°

Sun., 26 Mar.

17°

8°

Mon., 27 Mar.

17°

10°

Tue., 28 Mar.

10°

6°

Wed., 29 Mar.

9°

4°

Thu., 30 Mar.

16°

5°

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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 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 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 Annapolis

🏡 Vacation rentals available	829 properties
💳 Discounts available	up to 56%
🌙 Price per night from	$153
⭐ Popular amenities	Internet, Air conditioning and TV
🐾 Pet friendly accommodation options	234 properties
🏊 Vacation rentals with pools	260 properties

Frequently Asked Questions

What is the typical price of a vacation home Annapolis?

The starting price for House rental or Apartment rentals Annapolis is $153 per night.

What is the typical availability of House rental Annapolis?

We found 829 vacation homes Annapolis available for your next trip.

What are the most popular vacation home amenities Annapolis?

When looking to book a vacation home Annapolis, the most requested amenities include Internet, Air conditioning, and TV.

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

Annapolis has 829 House rental and Apartment rentals available to book.

Are there pet-friendly vacation rentals Annapolis?

If you're travelling with a dog, over 21% of vacation rentals 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 Annapolis with temperatures around 30 °C. January and February Annapolis are the coldest, with -1 °C on average.

We list offers from thousands of providers, including:

Annapolis Vacation Rentals

Choose the perfect vacation rental

Dive into the past with an Annapolis vacation rental

Best Vacation Home Deals Annapolis

Top-Rated Offers and Accommodations Annapolis

Recommended Vacation Rentals Annapolis

Budget-friendly Rentals Annapolis

Vacation rentals with Wi-Fi

Vacation rentals and apartments with air conditioning

Cabins with a sauna

Popular Rental Amenities Annapolis

The Weather Annapolis

7-Day Weather Forecast Annapolis

Art, history, and culture

Music and other nightlife

Sailing and other excursions

Information about vacation rentals Annapolis

Frequently Asked Questions

What is the typical price of a vacation home Annapolis?

What is the typical availability of House rental Annapolis?

What are the most popular vacation home amenities Annapolis?

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

Are there pet-friendly vacation rentals Annapolis?

What's the best month to visit Annapolis?

Vacation Destinations Near Annapolis

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