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

Vacation rentals in Annapolis

Browse 1,016 available vacation homes and compared across 9 trusted partners
Anytime
Guests
Anytime
Guests

  • Price per night

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

  • Accommodation types

    • Condo
    • House
    • Apartment

  • Distance to center

    • 1 mi
    • 2 mi
    • 3 mi

  • Rating

    • 4.5+
    • 4+

  • 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 1,016 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

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
This family-friendly house rental in Annapolis features a yard, balcony, and fireplace, making it perfect for your getaway.
from $306
per night
Excellent(82 ratings)
from $306
per night
View deal
House Annapolis
House ∙ 12 guests ∙ 6 bedrooms

Family-oriented spacious vacation home | City view | Perfect for remote work

Annapolis, Anne Arundel County, Maryland, United States
This house rental in Annapolis offers a kitchen, parking, and space for up to 12 guests, perfect for family gatherings.
from $982
per night
Outstanding(73 ratings)
from $982
per night
View deal
House Annapolis
House ∙ 6 guests ∙ 4 bedrooms

Fully equipped pleasant vacation home with garden, barbecue & terrace

Annapolis, Anne Arundel County, Maryland, United States
This waterfront house in Arundel on the Bay features a fireplace, kitchen, yard, balcony, and parking for a perfect getaway.
from $472
per night
Outstanding(29 ratings)
from $472
per night
View deal
Condo Annapolis
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with terrace & yard | City view

Annapolis, Anne Arundel County, Maryland, United States
This Annapolis condo features a kitchen and yard, perfect for a getaway with family or friends, accommodating up to six guests.
from $304
per night
Outstanding(342 ratings)
from $304
per night
View deal
Houseboat Annapolis
Houseboat ∙ 4 guests ∙ 2 bedrooms

Lovely boat with patio

Annapolis, Anne Arundel County, Maryland, United States
This Annapolis houseboat features a kitchen, waterfront balcony, and parking, perfect for a memorable getaway with friends.
from $355
per night
Outstanding(113 ratings)
from $355
per night
View deal
House Annapolis
House ∙ 6 guests ∙ 3 bedrooms

Family-oriented lovely vacation home with BBQ, terrace & yard | Nature view | Suitable for remote work

Annapolis, Anne Arundel County, Maryland, United States
This house rental in Annapolis features a cozy fireplace, a kitchen, and a yard, perfect for families and parking convenience.
from $263
per night
from $263
per night
View deal
House Annapolis
House ∙ 10 guests ∙ 3 bedrooms

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

Annapolis, Anne Arundel County, Maryland, United States
This waterfront house in Annapolis features a hot tub, fireplace, and yard, accommodating up to 10 guests for an unforgettable getaway.
from $345
per night
Outstanding(89 ratings)
from $345
per night
View deal
House Annapolis
House ∙ 6 guests ∙ 2 bedrooms

Family-friendly pleasant vacation home

Annapolis, Anne Arundel County, Maryland, United States
This house rental in Arundel on the Bay offers parking and accommodates up to 6 guests for a memorable family getaway.
from $231
per night
Outstanding(14 ratings)
from $231
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
This waterfront house rental in Annapolis Neck features a pool, fireplace, kitchen, and beach access for a perfect family getaway.
from $381
per night
Outstanding(36 ratings)
from $381
per night
View deal
House Annapolis
House ∙ 14 guests ∙ 5 bedrooms

Family-friendly house with grill, private pool & hot tub | Perfect for remote work | Dogs allowed

Annapolis, Anne Arundel County, Maryland, United States
This spacious house rental in Annapolis features a private pool, yard, and accommodates up to 14 guests, perfect for families.
from $1,095
per night
Outstanding(37 ratings)
from $1,095
per night
View deal
House Annapolis
House ∙ 6 guests ∙ 3 bedrooms

Fully equipped beautiful vacation home with patio & garden

Annapolis, Anne Arundel County, Maryland, United States
This house rental in Annapolis features a kitchen and yard, perfect for six guests seeking an ideal getaway.
from $379
per night
Outstanding(156 ratings)
from $379
per night
View deal
House Annapolis
House ∙ 10 guests ∙ 3 bedrooms

Children-friendly house with barbeque | Pets allowed

Annapolis, Anne Arundel County, Maryland, United States
This house rental in Annapolis features a pool, kitchen, and balcony, perfect for family gatherings with pets welcome!
from $458
per night
Outstanding(17 ratings)
from $458
per night
View deal
House Annapolis
House ∙ 8 guests ∙ 4 bedrooms

House with patio

Annapolis, Anne Arundel County, Maryland, United States
This Annapolis house rental features a kitchen and parking, perfect for accommodating up to 8 guests in a vibrant location.
from $371
per night
Outstanding(14 ratings)
from $371
per night
View deal
House Annapolis
House ∙ 10 guests ∙ 4 bedrooms

Child-friendly charming vacation home with grill, yard & patio

Annapolis, Anne Arundel County, Maryland, United States
This waterfront house rental in Annapolis features a kitchen, yard, balcony, and parking, perfect for family gatherings of 10.
from $553
per night
Outstanding(70 ratings)
from $553
per night
View deal
House Annapolis
House ∙ 18 guests ∙ 6 bedrooms

Family-friendly spacious house with garden, patio & hot tub | Good for workation | Dogs allowed

Annapolis, Anne Arundel County, Maryland, United States
This Annapolis house rental features a hot tub, yard, and fireplace, accommodating up to 18 guests with pet-friendly options.
from $990
per night
Outstanding(17 ratings)
from $990
per night
View deal

Vacation rentals and apartments with air conditioning

House Annapolis
from $859
per night
House ∙ 12 guests ∙ 6 bedrooms

House with patio, yard & barbeque | City view

5.0
Outstanding(84 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Air conditioning
View deal
House Annapolis
from $845
per night
House ∙ 6 guests ∙ 3 bedrooms

House with patio, barbecue & yard | Perfect for remote work

5.0
Outstanding(37 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Air conditioning
View deal
House Annapolis
from $418
per night
House ∙ 10 guests ∙ 4 bedrooms

Family-friendly house with barbeque, terrace & garden | Suitable for remote work | Pet-friendly

5.0
Outstanding(198 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Air conditioning
View deal
See all offers

Vacation houses with Balconies or Patios

House Annapolis
from $478
per night
House ∙ 6 guests ∙ 3 bedrooms

Children-friendly beautiful house with barbecue, yard & patio | City view | Good for workation

4.9
Outstanding(82 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Balcony/Patio
View deal
House Annapolis
from $1,012
per night
House ∙ 14 guests ∙ 4 bedrooms

Vacation home with garden, private pool & jacuzzi

5.0
Outstanding(22 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Balcony/Patio
View deal
Apartment Annapolis
from $96
per night
Apartment ∙ 2 guests ∙ 1 bedroom

Rental apartment with terrace

5.0
Outstanding(155 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Balcony/Patio
View deal
See all offers

Vacation homes and rentals with a yard

House Annapolis
from $283
per night
House ∙ 8 guests ∙ 3 bedrooms

Family-oriented spacious vacation home with yard, barbecue & terrace

4.6
Excellent(12 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Yard
View deal
House Annapolis
from $1,048
per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with terrace, garden & barbecue | Nature view

5.0
Outstanding(25 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Yard
View deal
House Annapolis
from $327
per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with garden & patio

4.9
Outstanding(80 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Yard
View deal
See all offers

Budget-friendly rental options

Enjoy affordable vacation rentals in Annapolis offering exceptional value for money

House Annapolis
from $281
per night
House ∙ 8 guests ∙ 3 bedrooms

Vacation home with yard

5.0
Outstanding(34 ratings)
Annapolis, Anne Arundel County, Maryland, United States
View deal
House Annapolis
from $893
per night
House ∙ 11 guests ∙ 4 bedrooms

Vacation home with patio | City view

4.9
Outstanding(97 ratings)
Annapolis, Anne Arundel County, Maryland, United States
View deal
House Annapolis
from $303
per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with garden, barbeque & terrace | City view

5.0
Outstanding(85 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 $749
per night
House ∙ 12 guests ∙ 4 bedrooms

Child-friendly house with patio & grill

5.0
Outstanding(33 ratings)
Annapolis, Anne Arundel County, Maryland, United States
View deal
House Annapolis
from $537
per night
House ∙ 10 guests ∙ 4 bedrooms

House with barbeque | City view | Good for workation

5.0
Outstanding(20 ratings)
Annapolis, Anne Arundel County, Maryland, United States
View deal
House Annapolis
from $731
per night
House ∙ 10 guests ∙ 3 bedrooms

Vacation home with barbecue

5.0
Outstanding(1 rating)
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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Popular Features & Amenities in Annapolis

  • Pet-friendly (423)
  • Pool (213)
  • WiFi (931)
  • TV (940)
  • Parking (61)
  • Air conditioning (988)
  • Kitchen (555)
  • Balcony/patio (407)
  • Washing machine (577)
  • Fireplace (359)
  • Fishing (147)
  • Hot tub (42)

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, $508. You can also search for pet-friendly rentals that are centrally located. In Annapolis, Nearly half 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 1,016 rentals
🌙 Nightly prices starting at $222
⭐ Popular amenities Pets allowed, Pool and Internet
🐾 Pet friendly homes 431 homes
🏊 Vacation rentals with pools 215 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 $222 per night. Nightly prices for house rentals are $903 on average. Apartment rentals in Annapolis cost $424 per night on average.

How many vacation rentals are available for booking in Annapolis?

Currently there are 1,016 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 215 vacation rentals from 9 providers in Annapolis.

Are dogs allowed in vacation homes in Annapolis?

Sure, there are 431 vacation rentals in Annapolis that allow pets , with an average price of $508 per night.

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