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Annapolis Vacation Rentals

Find 968 available offers from 11 partners
Annapolis
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Annapolis
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Popular Filters to find the Perfect Rental in Annapolis

2 Adults
1 Bedroom
4 Adults
Pets allowed
Pool
House
Internet

Apartments with a balcony or patio

House  Annapolis
Sept 17 - Sept 24
$846 per night
House ∙ 10 guests ∙ 4 bedrooms

Fully Equipped House with BBQ & Terrace | Nature View

5.0
Outstanding (26 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Balcony/Patio
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House  Annapolis
Sept 17 - Sept 24
$739 per night
House ∙ 10 guests ∙ 4 bedrooms

Fully Equipped Nice House with Terrace & Yard | City View | Dogs Allowed

4.5
Excellent (4 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Balcony/Patio
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House  Annapolis
Sept 17 - Sept 24
$748 per night
House ∙ 5 guests ∙ 3 bedrooms

House with Patio & Garden | City View

5.0
Outstanding (38 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Balcony/Patio
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Vacation rentals and apartments with air conditioning

House  Annapolis
Sept 17 - Sept 24
-8%
$795
$734 per night
House ∙ 14 guests ∙ 4 bedrooms

Vacation Home with Grill, Garden & Patio | Nature View

4.8
Outstanding (59 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Air conditioning
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House  Annapolis
Sept 17 - Sept 24
$750 per night
House ∙ 8 guests ∙ 3 bedrooms

House with Patio, Yard & Barbeque

4.8
Outstanding (23 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Air conditioning
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House  Annapolis
Sept 17 - Sept 24
$688 per night
House ∙ 6 guests ∙ 2 bedrooms

Family-Friendly Vacation Home with Terrace & Yard | City View | Perfect for Remote Work

5.0
Outstanding (76 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Air conditioning
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Vacation rentals with Wi-Fi

House  Annapolis
Sept 17 - Sept 24
$1,147 per night
House ∙ 10 guests ∙ 3 bedrooms

House with Garden, Barbecue & Patio | City View | Suitable for Remote Work

5.0
Outstanding (42 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Internet
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House  Annapolis
Sept 17 - Sept 24
$1,329 per night
House ∙ 10 guests ∙ 5 bedrooms

House with Grill, Terrace & Yard | Nature View | Perfect for Remote Work

4.8
Outstanding (47 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Internet
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House  Annapolis
Sept 17 - Sept 24
$1,003 per night
House ∙ 9 guests ∙ 3 bedrooms

Fully Equipped Pleasant Vacation Home for Vacation Getaway with Barbeque & Patio | City View

5.0
Outstanding (15 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Internet
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Best Vacation Home Deals in Annapolis

Save up to 63%

Apartment Annapolis
Sept 17 - Sept 24
-8%
$316
$291 per night
Apartment ∙ 5 guests ∙ 2 bedrooms

Rental Apartment with Yard, Grill & Patio | Suitable for Remote Work

5.0
Outstanding (16 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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Apartment Annapolis
Sept 17 - Sept 24
-16%
$475
$401 per night
Apartment ∙ 4 guests ∙ 1 bedroom

Children-Friendly Wonderful Apartment with BBQ, Yard & Terrace | Next to the Beach

5.0
Outstanding (44 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Aug 18 - Aug 25
-63%
$1,759
$659 per night
House ∙ 10 guests ∙ 4 bedrooms

Vacation Home with Grill, Garden & Jacuzzi

4.9
Outstanding (49 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Free cancellation
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Book a welcoming vacation home from $263 per night by exploring the 968 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 77%.

Recommended Vacation Rentals in Annapolis

Find your perfect vacation rental in Annapolis: from $263 per night

House Annapolis
Sept 17 - Sept 24
$840 per night
House ∙ 5 guests ∙ 2 bedrooms

House with BBQ & Patio | City View

4.9
Outstanding (12 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Sept 17 - Sept 24
$1,109 per night
House ∙ 6 guests ∙ 3 bedrooms

Fully Equipped House with Garden, Patio & Grill | Nature View | Suitable for Remote Work | Pets Allowed

4.9
Outstanding (5 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Dec 2 - Dec 9
-59%
$2,968
$1,209 per night
House ∙ 10 guests ∙ 5 bedrooms

House with Patio & Grill | Water View

5.0
Outstanding (2 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Free cancellation
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House Annapolis
Sept 17 - Sept 24
-52%
$1,759
$836 per night
House ∙ 10 guests ∙ 4 bedrooms

Fully Equipped Charming House with Barbecue, Yard & Hot Tub | Good for Workation | Pets Are Welcome

4.9
Outstanding (49 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Sept 17 - Sept 24
$478 per night
House ∙ 4 guests ∙ 2 bedrooms

Vacation Home for Relaxing Getaway with Grill & Garden | Nature View

5.0
Outstanding (110 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Sept 17 - Sept 24
$868 per night
House ∙ 6 guests ∙ 2 bedrooms

House with Patio & Barbeque | City View

5.0
Outstanding (40 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Sept 17 - Sept 24
-16%
$937
$791 per night
House ∙ 8 guests ∙ 3 bedrooms

House with Terrace, Garden & Private Pool

5.0
Outstanding (52 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Sept 17 - Sept 24
$711 per night
House ∙ 8 guests ∙ 3 bedrooms

Vacation Home with BBQ & Patio | City View

4.9
Outstanding (17 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Sept 17 - Sept 24
$379 per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation Home with Patio & BBQ

5.0
Outstanding (36 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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Budget-friendly Rentals in Annapolis

Find Fantastic yet Inexpensive Rentals

House Annapolis
Sept 17 - Sept 24
-8%
$1,069
$987 per night
House ∙ 8 guests ∙ 4 bedrooms

Child-Friendly House with Private Pool, Patio & Grill | Nature View | Pets Are Welcome

5.0
Outstanding (99 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Jan 4 - Jan 11
-39%
$1,328
$809 per night
House ∙ 10 guests ∙ 4 bedrooms

Child-Friendly Beautiful Vacation Home with Grill & Pool | Water View

Annapolis, Anne Arundel County, Maryland, United States
Free cancellation
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Cottage Annapolis
Sept 17 - Sept 24
-4%
$1,477
$1,418 per night
Cottage ∙ 6 guests ∙ 4 bedrooms

Cottage with Terrace, Private Pool & Barbecue | Nature View

5.0
Outstanding (58 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
from $916 per night
House ∙ 19 guests ∙ 5 bedrooms

Fully Equipped Vacation Home for Perfect Getaway with Garden, Patio & Barbeque | Lake View | Pets Allowed

5.0
Outstanding (19 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
from $698 per night
House ∙ 9 guests ∙ 3 bedrooms

Child-Friendly Vacation Home with Terrace, Grill & Yard | Nature View | Perfect for Remote Work | Pet-Friendly

5.0
Outstanding (6 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
Sept 17 - Sept 24
$769 per night
House ∙ 8 guests ∙ 3 bedrooms

Children-Friendly House with Yard & Terrace | Good for Workation

5.0
Outstanding (3 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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Popular Rental Amenities in Annapolis

  • Pool (193)
  • Pet-friendly (229)
  • WiFi (935)
  • Kitchen (605)
  • Air conditioning (923)
  • TV (883)
  • Washing machine (642)
  • Parking (65)
  • Balcony/patio (419)
  • Dishwasher (466)
  • Grill (343)
  • Microwave (673)

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 11 guests and have an average cost of $558 per night. Among these accommodations, 63 of them are situated within 2 kilometres of water.

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.

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 968 rentals
💳 Possible discounts up to 77%
🌙 Nightly prices starting at $263
⭐ Popular amenities Pool, Pets allowed and Internet
🐾 Pet friendly homes 235 homes
🏊 Vacation rentals with pools 194 homes
1 reviews
Annapolis vacation rentals have an average rating of 5/5 on 1 reviews left by travelers.

Frequently Asked Questions

What is the typical availability of vacation rentals in Annapolis?

We found 968 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 24% 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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