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

Vacation rentals in Annapolis

Browse 999 available vacation homes and compared across 12 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+

  • 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 999 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
This house rental in Annapolis features a fireplace, parking, and space for nine, perfect for an unforgettable getaway.
from $253
per night
Outstanding(7 ratings)
from $253
per night
View deal
House Annapolis
House ∙ 8 guests ∙ 4 bedrooms

Fully equipped charming house with patio & BBQ | City view | Good for workation

Annapolis, Anne Arundel County, Maryland, United States
This Annapolis house rental features a fireplace and kitchen, accommodating up to 8 guests for a memorable getaway.
from $405
per night
Outstanding(36 ratings)
from $405
per night
View deal
House Annapolis
House ∙ 15 guests ∙ 6 bedrooms

House with grill, patio & garden | Nature view

Annapolis, Anne Arundel County, Maryland, United States
This house rental in Annapolis accommodates 15, featuring a kitchen, fireplace, yard, and parking, perfect for family gatherings.
from $1,242
per night
Outstanding(31 ratings)
from $1,242
per night
View deal
House Annapolis
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with garden & patio

Annapolis, Anne Arundel County, Maryland, United States
This house rental in Annapolis features a kitchen and yard, perfect for six guests seeking a memorable getaway.
from $310
per night
Outstanding(78 ratings)
from $310
per night
View deal
House Annapolis
House ∙ 14 guests ∙ 6 bedrooms

Vacation home with garden, terrace & grill

Annapolis, Anne Arundel County, Maryland, United States
This Annapolis house rental features a fireplace, kitchen, yard, balcony, and parking, welcoming up to 14 guests for a memorable stay.
from $563
per night
Outstanding(53 ratings)
from $563
per night
View deal
House Annapolis
House ∙ 5 guests ∙ 3 bedrooms

House with barbeque

Annapolis, Anne Arundel County, Maryland, United States
This house rental in Arundel on the Bay offers a kitchen and parking, perfect for a getaway with up to five guests.
from $215
per night
Outstanding(44 ratings)
from $215
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
This waterfront apartment in Annapolis features a private heated pool, fireplace, and kitchen, perfect for family getaways.
from $240
per night
Outstanding(99 ratings)
from $240
per night
View deal
House Annapolis
House ∙ 10 guests ∙ 5 bedrooms

Fully equipped vacation home with barbeque, terrace & yard | City view

Annapolis, Anne Arundel County, Maryland, United States
This Annapolis house rental accommodates 10, featuring a kitchen and a yard perfect for gatherings and outdoor relaxation.
from $154
per night
Outstanding(192 ratings)
from $154
per night
View deal
House Annapolis
House ∙ 18 guests ∙ 5 bedrooms

Fully equipped vacation home with terrace, yard & BBQ | Lake view | Suitable for remote work

Annapolis, Anne Arundel County, Maryland, United States
This waterfront house rental in Annapolis Neck features a kitchen, fireplace, yard, and balcony with direct beach access.
from $640
per night
Excellent(31 ratings)
from $640
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
This Annapolis house rental features a fireplace, kitchen, yard, balcony, and parking, accommodating up to 10 guests.
from $905
per night
Outstanding(49 ratings)
from $905
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 $343
per night
Outstanding(89 ratings)
from $343
per night
View deal
House Annapolis
House ∙ 6 guests ∙ 3 bedrooms

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

Annapolis, Anne Arundel County, Maryland, United States
This house rental near the Naval Academy features a kitchen, yard, and parking, perfect for family gatherings of up to six.
from $420
per night
Outstanding(75 ratings)
from $420
per night
View deal
House Annapolis
House ∙ 8 guests ∙ 3 bedrooms

Vacation home with grill, terrace & garden | City view | Perfect for remote work

Annapolis, Anne Arundel County, Maryland, United States
This house rental in Annapolis features a yard, fireplace, and kitchen, accommodating up to 8 guests and welcoming pets.
from $392
per night
Outstanding(124 ratings)
from $392
per night
View deal
House Annapolis
House ∙ 4 guests ∙ 2 bedrooms

Vacation home with garden, private pool & terrace | Nature view

Annapolis, Anne Arundel County, Maryland, United States
This house rental in Parole features a private pool, spa, and a yard, perfect for a family getaway with pets welcome.
from $211
per night
Outstanding(23 ratings)
from $211
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 $313
per night
Outstanding(34 ratings)
from $313
per night
View deal

Vacation Rentals With Fireplaces

House Annapolis
from $428
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 $568
per night
House ∙ 7 guests ∙ 3 bedrooms

Fully equipped big vacation home with patio & grill | City view | Good for workation

5.0
Outstanding(128 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Fireplace
View deal
House Annapolis
from $287
per night
House ∙ 5 guests ∙ 2 bedrooms

House with yard & terrace

4.8
Outstanding(80 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Fireplace
View deal
See all offers

Vacation rentals and apartments with air conditioning

House Annapolis
from $614
per night
House ∙ 12 guests ∙ 4 bedrooms

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

5.0
Outstanding(70 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Air conditioning
View deal
House Annapolis
from $667
per night
House ∙ 12 guests ∙ 4 bedrooms

Children-friendly pleasant house with hot tub, BBQ & terrace | City view

4.9
Outstanding(40 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Air conditioning
View deal
House Annapolis
from $403
per night
House ∙ 7 guests ∙ 3 bedrooms

House with yard, patio & barbeque

5.0
Outstanding(7 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Air conditioning
View deal
See all offers

Vacation houses with Balconies or Patios

House Annapolis
from $402
per night
House ∙ 8 guests ∙ 3 bedrooms

Vacation home with garden, grill & patio | Nature view

5.0
Outstanding(48 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Balcony/Patio
View deal
House Annapolis
from $275
per night
House ∙ 6 guests ∙ 2 bedrooms

Vacation home with yard, patio & grill | City view | Good for workation

5.0
Outstanding(72 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Balcony/Patio
View deal
House Annapolis
from $270
per night
House ∙ 6 guests ∙ 3 bedrooms

House with yard, patio & barbeque | City view | Good for workation

5.0
Outstanding(30 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Balcony/Patio
View deal
See all offers

Budget-friendly rental options

Enjoy affordable vacation rentals in Annapolis offering exceptional value for money

House Annapolis
from $1,398
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
View deal
House Annapolis
from $431
per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with patio, barbecue & yard | City view

4.9
Outstanding(50 ratings)
Annapolis, Anne Arundel County, Maryland, United States
View deal
House Annapolis
from $429
per night
House ∙ 10 guests ∙ 3 bedrooms

Children-friendly house with pool, patio & barbeque | Good for workation | Pets allowed

5.0
Outstanding(13 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

Condo Annapolis
from $101
per night
Condo ∙ 4 guests ∙ 1 bedroom

Family-friendly charming condo with private pool & patio

4.8
Outstanding(176 ratings)
Annapolis, Anne Arundel County, Maryland, United States
View deal
Apartment Annapolis
from $200
per night
Apartment ∙ 4 guests ∙ 1 bedroom

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

5.0
Outstanding(80 ratings)
Annapolis, Anne Arundel County, Maryland, United States
View deal
House Annapolis
from $373
per night
House ∙ 8 guests ∙ 3 bedrooms

House with terrace & barbecue

4.9
Outstanding(66 ratings)
Annapolis, Anne Arundel County, Maryland, United States
View deal

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Verified reviews

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

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Spend your budget exactly as planned by comparing thousands of providers.

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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, $438. 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 999 rentals
🌙 Nightly prices starting at $133
⭐ Popular amenities Pets allowed, Pool and Internet
🐾 Pet friendly homes 422 homes
🏊 Vacation rentals with pools 213 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 $133 per night. Nightly prices for house rentals are $814 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 999 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 213 vacation rentals from 12 providers in Annapolis.

Are dogs allowed in vacation homes in Annapolis?

Sure, there are 422 vacation rentals in Annapolis that allow pets , with an average price of $438 per night.

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