Vacation rentals in Annapolis - HomeToGo base64Hash Vacation rentals in Annapolis - HomeToGo

Vacation rentals in Annapolis

Browse 990 available vacation homes and compared across 13 trusted partners
Anytime
Guests
Anytime
Guests

  • Price per night

    • Up to $100
    • $100 - $199
    • From $200

  • Accommodation types

    • Condo
    • House
    • Apartment

  • Distance to center

    • 2 mi
    • 3 mi
    • Any

  • Rating

    • 4.5+
    • 4+

  • Booking Options

    • Instant Booking

  • Services

    • Pool
    • WiFi
    • TV
    • Parking
    • Air conditioning
    • Kitchen
    • Balcony/patio
    • Washing machine
    • Fireplace
    • Hot tub
    • Dishwasher
    • Microwave
    • Yard
    • Crib
    Show more

  • Accommodation type

    • Pet-friendly
    • No smoking
    • Wheelchair access
    • No pets

  • Activities

    • Fishing
    • Grill

Top 15 most Recommended Vacation Rentals in Annapolis

Discover your ideal Annapolis vacation rental with real-time comparisons of 990 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Annapolis
House ∙ 9 guests ∙ 5 bedrooms

Fully equipped house with grill

Annapolis, Anne Arundel County, Maryland, United States
from $240
per night
Outstanding(5 ratings)
from $240
per night
View deal
House Annapolis
House ∙ 12 guests ∙ 5 bedrooms

House with terrace

Annapolis, Anne Arundel County, Maryland, United States
from $152
per night
Very good(13 ratings)
from $152
per night
View deal
House Annapolis
House ∙ 8 guests ∙ 4 bedrooms

House with terrace & grill

Annapolis, Anne Arundel County, Maryland, United States
from $500
per night
Outstanding(58 ratings)
from $500
per night
View deal
House Annapolis
House ∙ 14 guests ∙ 6 bedrooms

Vacation home with garden, terrace & grill

Annapolis, Anne Arundel County, Maryland, United States
from $575
per night
Outstanding(53 ratings)
from $575
per night
View deal
Apartment Annapolis
Apartment ∙ 4 guests ∙ 2 bedrooms

Holiday apartment with barbecue & private pool | City view

Annapolis, Anne Arundel County, Maryland, United States
from $263
per night
Outstanding(98 ratings)
from $263
per night
View deal
House Annapolis
House ∙ 6 guests ∙ 3 bedrooms

Vacation home | Nature view

Annapolis, Anne Arundel County, Maryland, United States
from $353
per night
Outstanding(67 ratings)
from $353
per night
View deal
House Annapolis
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with barbeque, patio & pool | Good for workation

Annapolis, Anne Arundel County, Maryland, United States
from $183
per night
Outstanding(32 ratings)
from $183
per night
View deal
House Annapolis
House ∙ 12 guests ∙ 4 bedrooms

Children-friendly vacation home with terrace, BBQ & yard | City view | Perfect for remote work

Annapolis, Anne Arundel County, Maryland, United States
from $579
per night
Outstanding(70 ratings)
from $579
per night
View deal
House Annapolis
House ∙ 9 guests ∙ 3 bedrooms

Fully equipped lovely house with barbeque & terrace | City view

Annapolis, Anne Arundel County, Maryland, United States
from $464
per night
Outstanding(48 ratings)
from $464
per night
View deal
House Annapolis
House ∙ 10 guests ∙ 3 bedrooms

House with patio, grill & garden

Annapolis, Anne Arundel County, Maryland, United States
from $301
per night
Outstanding(5 ratings)
from $301
per night
View deal
House Annapolis
House ∙ 10 guests ∙ 5 bedrooms

Vacation home with BBQ, patio & yard | City view

Annapolis, Anne Arundel County, Maryland, United States
from $1,031
per night
Outstanding(47 ratings)
from $1,031
per night
View deal
House Annapolis
House ∙ 10 guests ∙ 4 bedrooms

Family-oriented pleasant vacation home with barbeque, yard & patio | Pets are welcome

Annapolis, Anne Arundel County, Maryland, United States
from $325
per night
Excellent(76 ratings)
from $325
per night
View deal
House Annapolis
House ∙ 8 guests ∙ 3 bedrooms

Children-friendly lovely house with grill, yard & patio | Perfect for remote work

Annapolis, Anne Arundel County, Maryland, United States
from $415
per night
Outstanding(11 ratings)
from $415
per night
View deal
House Annapolis
House ∙ 8 guests ∙ 3 bedrooms

Vacation home with terrace | City view

Annapolis, Anne Arundel County, Maryland, United States
from $376
per night
Outstanding(53 ratings)
from $376
per night
View deal
Apartment Annapolis
Apartment ∙ 4 guests ∙ 2 bedrooms

Rental apartment with patio, yard & barbecue | Good for workation

Annapolis, Anne Arundel County, Maryland, United States
from $132
per night
Outstanding(34 ratings)
from $132
per night
View deal

Vacation Rentals With Fireplaces

House Annapolis
from $436
per night
House ∙ 8 guests ∙ 4 bedrooms

Child-friendly house with barbecue

4.9
Outstanding(46 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Fireplace
View deal
House Annapolis
from $557
per night
House ∙ 8 guests ∙ 3 bedrooms

Vacation home with barbecue, yard & patio | City view

5.0
Outstanding(81 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Fireplace
View deal
House Annapolis
from $408
per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with patio | City view

5.0
Outstanding(54 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Fireplace
View deal
See all offers

Vacation rentals and apartments with air conditioning

Apartment Annapolis
from $280
per night
Apartment ∙ 8 guests ∙ 4 bedrooms

Fully equipped ample rental apartment

5.0
Outstanding(1 rating)
Annapolis, Anne Arundel County, Maryland, United States
Air conditioning
View deal
House Annapolis
from $454
per night
House ∙ 8 guests ∙ 4 bedrooms

Fully equipped charming vacation home with patio & garden

5.0
Outstanding(125 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Air conditioning
View deal
House Annapolis
from $1,151
per night
House ∙ 11 guests ∙ 5 bedrooms

House with yard, grill & hot tub

5.0
Outstanding(23 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Air conditioning
View deal
See all offers

Vacation rentals with a balcony

House Annapolis
from $545
per night
House ∙ 6 guests ∙ 3 bedrooms

Children-friendly nice vacation home with barbecue, jacuzzi & patio | Perfect for remote work | Pet-friendly

4.8
Outstanding(10 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Balcony
View deal
House Annapolis
from $906
per night
House ∙ 10 guests ∙ 5 bedrooms

Vacation home with terrace, BBQ & yard | City view | Suitable for remote work

4.8
Outstanding(17 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Balcony
View deal
House Annapolis
from $605
per night
House ∙ 10 guests ∙ 4 bedrooms

Fully equipped vacation home with barbeque, patio & yard | Perfect for remote work | Pet-friendly

5.0
Outstanding(2 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Balcony
View deal
See all offers

Budget-friendly rental options

Enjoy affordable vacation rentals in Annapolis offering exceptional value for money

House Annapolis
from $310
per night
House ∙ 8 guests ∙ 3 bedrooms

Family-oriented ample vacation home with garden, terrace & grill | City view | Pet-friendly

5.0
Outstanding(295 ratings)
Annapolis, Anne Arundel County, Maryland, United States
View deal
House Annapolis
from $424
per night
House ∙ 8 guests ∙ 4 bedrooms

Family-oriented nice house with garden, patio & BBQ | City view

5.0
Outstanding(95 ratings)
Annapolis, Anne Arundel County, Maryland, United States
View deal
House Annapolis
from $525
per night
House ∙ 8 guests ∙ 4 bedrooms

House with barbeque, terrace & yard | Suitable for remote work

4.8
Outstanding(22 ratings)
Annapolis, Anne Arundel County, Maryland, United States
View deal

Top-Rated Vacation rentals in Annapolis

Book the highest-rated Annapolis vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

House Annapolis
from $273
per night
House ∙ 6 guests ∙ 2 bedrooms

Children-friendly vacation home with yard & terrace | City view | Good for workation

5.0
Outstanding(91 ratings)
Annapolis, Anne Arundel County, Maryland, United States
View deal
House Annapolis
from $366
per night
House ∙ 10 guests ∙ 3 bedrooms

Fully equipped house with yard, grill & patio | City view | Perfect for remote work | Dogs allowed

4.8
Outstanding(89 ratings)
Annapolis, Anne Arundel County, Maryland, United States
View deal
Apartment Annapolis
from $198
per night
Apartment ∙ 4 guests ∙ 1 bedroom

Children-friendly lovely apartment with BBQ, garden & patio | Nature view | Close to the beach

5.0
Outstanding(75 ratings)
Annapolis, Anne Arundel County, Maryland, United States
View deal

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Trust in the quality and comfort of your stay with verified guest reviews.

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Find your dream stay

Find your dream stay

Explore 15 million+ rentals, the world’s biggest selection of vacation homes.

Popular Features & Amenities in Annapolis

  • Pet-friendly (389)
  • Pool (218)
  • WiFi (944)
  • TV (906)
  • Parking (67)
  • Air conditioning (955)
  • Kitchen (531)
  • Balcony/patio (443)
  • Washing machine (573)
  • Fireplace (357)
  • Fishing (145)
  • Hot tub (49)

In Annapolis, there are many options if you want to book a an accommodation that allows pets. Hotel room are the most pet-friendly accommodation type in Annapolis. Additionally, a night in a pet-friendly accommodation there is, on average, $428. You can also search for pet-friendly rentals that are centrally located. In Annapolis, One-third of the accommodations vacation rentals less than 2 miles away from the city center.

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 990 rentals
🌙 Nightly prices starting at $97
⭐ Popular amenities Pets allowed, Pool and Internet
🐾 Pet friendly homes 387 homes
🏊 Vacation rentals with pools 218 homes
4 reviews
Annapolis vacation rentals have an average rating of 5/5 on 4 reviews left by travelers.

Frequently Asked Questions

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

Prices for vacation rentals in Annapolis start from $97 per night. Nightly prices for house rentals are $744 on average. Apartment rentals in Annapolis cost $412 per night on average.

How many vacation rentals are available for booking in Annapolis?

Currently there are 990 vacation rentals available for booking for your upcoming vacation.

What amenities are most popular for vacation homes in Annapolis?

If you're looking to book a vacation rental in Annapolis, travelers search for vacation homes with these amenities: Pool, Pets allowed and Internet.

How many vacation rentals with pools are in Annapolis?

There are 218 vacation rentals from 13 providers in Annapolis.

Are dogs allowed in vacation homes in Annapolis?

Sure, there are 387 vacation rentals in Annapolis that allow pets , with an average price of $428 per night.

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