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

Vacation rentals in Annapolis

Browse 1,009 available vacation homes and compared across 7 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+

  • Popular amenities

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

  • Other Services

    • 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 1,009 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

We use AI to generate the short summary in each offer below, check full description before booking.
House Annapolis
House ∙ 14 guests ∙ 6 bedrooms

Family-oriented beautiful vacation home with private pool, barbeque & patio | Perfect for remote work | Dogs allowed

Annapolis, Anne Arundel County, Maryland, United States
This house rental in Annapolis features a private heated pool, a fireplace, and space for 14, making it perfect for family getaways.
from $1,576
per night
Outstanding(39 ratings)
from $1,576
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 $231
per night
Outstanding(49 ratings)
from $231
per night
View deal
Apartment Annapolis
Apartment ∙ 4 guests ∙ 2 bedrooms

Holiday apartment with yard, 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 $230
per night
Outstanding(100 ratings)
from $230
per night
View deal
House Annapolis
House ∙ 20 guests ∙ 7 bedrooms

Vacation home with yard, terrace & barbeque | Perfect for remote work

Annapolis, Anne Arundel County, Maryland, United States
This Annapolis house rental offers a yard, balcony, and fireplace, making it perfect for family gatherings of up to 20 guests.
from $646
per night
Outstanding(14 ratings)
from $646
per night
View deal
House Annapolis
House ∙ 12 guests ∙ 4 bedrooms

House with terrace & barbeque

Annapolis, Anne Arundel County, Maryland, United States
This waterfront house rental in Annapolis features a kitchen, balcony, and parking, accommodating up to 12 guests and pets.
from $798
per night
Outstanding(1 rating)
from $798
per night
View deal
House Annapolis
House ∙ 9 guests ∙ 3 bedrooms

House with barbeque

Annapolis, Anne Arundel County, Maryland, United States
This Arundel on the Bay house rental accommodates 9, features a kitchen, parking, and welcomes pets for a memorable stay.
from $477
per night
from $477
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 $945
per night
Excellent(41 ratings)
from $945
per night
View deal
House Annapolis
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with terrace, garden & barbecue | Nature view

Annapolis, Anne Arundel County, Maryland, United States
This house rental in Anne Arundel County features a fireplace, kitchen, yard, balcony, and parking, accommodating up to 8 guests.
from $1,492
per night
Outstanding(25 ratings)
from $1,492
per night
View deal
House Annapolis
House ∙ 14 guests ∙ 4 bedrooms

Vacation home with garden, private pool & jacuzzi | Good for workation

Annapolis, Anne Arundel County, Maryland, United States
This house rental in Annapolis features a private pool, hot tub, and ample space for 14 guests, making it ideal for gatherings.
from $514
per night
Outstanding(24 ratings)
from $514
per night
View deal
House Annapolis
House ∙ 6 guests ∙ 4 bedrooms

Vacation home with 4 bedrooms for 6 persons

Annapolis, Anne Arundel County, Maryland, United States
This house rental in Annapolis offers a perfect retreat for 6, just minutes from waterfront attractions and local dining.
from $160
per night
from $160
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 $776
per night
Outstanding(20 ratings)
from $776
per night
View deal
House Annapolis
House ∙ 10 guests ∙ 5 bedrooms

House with yard, grill & hot tub

Annapolis, Anne Arundel County, Maryland, United States
This Annapolis house rental features a fireplace, hot tub, and balcony, perfect for families seeking a memorable getaway.
from $1,354
per night
Outstanding(25 ratings)
from $1,354
per night
View deal
House Annapolis
House ∙ 8 guests ∙ 3 bedrooms

Fully equipped house with barbeque, terrace & pool

Annapolis, Anne Arundel County, Maryland, United States
This waterfront house in Annapolis features a pool, fireplace, kitchen, and parking, accommodating up to 8 guests for a perfect getaway.
from $724
per night
Outstanding(154 ratings)
from $724
per night
View deal
House Annapolis
House ∙ 4 guests ∙ 2 bedrooms

Fully equipped beautiful vacation home with garden | City view

Annapolis, Anne Arundel County, Maryland, United States
This house rental in Annapolis features a kitchen, yard, and parking, perfect for a memorable getaway with friends or family.
from $369
per night
Excellent(2 ratings)
from $369
per night
View deal
House Annapolis
House ∙ 6 guests ∙ 2 bedrooms

Children-friendly house with garden, terrace & barbeque | City view | Perfect for remote work | Dogs allowed

Annapolis, Anne Arundel County, Maryland, United States
This family-friendly house rental in Riva features a kitchen, fireplace, and pet-friendly amenities, accommodating up to four guests.
from $375
per night
Outstanding(5 ratings)
from $375
per night
View deal

Dog-Friendly Vacation Rentals

We use AI to generate the short summary in each offer below, check full description before booking.
House Annapolis
from $441
per night
House ∙ 10 guests ∙ 4 bedrooms

Vacation home with BBQ

5.0
Outstanding(1 rating)
Annapolis, Anne Arundel County, Maryland, United States
Pet-friendly
View deal
House Annapolis
from $218
per night
House ∙ 6 guests ∙ 3 bedrooms

Fully equipped charming house with BBQ & yard | Perfect for remote work | Pets allowed

5.0
Outstanding(1 rating)
Annapolis, Anne Arundel County, Maryland, United States
Pet-friendly
View deal
House Annapolis
from $481
per night
House ∙ 12 guests ∙ 5 bedrooms

Vacation home with patio, garden & jacuzzi | Nature view

5.0
Outstanding(59 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Pet-friendly
View deal
See all offers

Vacation Rentals With Fireplaces

We use AI to generate the short summary in each offer below, check full description before booking.
House Annapolis
from $284
per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with terrace & barbeque

4.5
Excellent(33 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Fireplace
View deal
House Annapolis
from $425
per night
House ∙ 3 guests ∙ 3 bedrooms

Fully equipped house with terrace & grill

Annapolis, Anne Arundel County, Maryland, United States
Fireplace
View deal
House Annapolis
from $555
per night
House ∙ 8 guests ∙ 4 bedrooms

Family-friendly vacation home with yard, barbeque & hot tub | Nature view

5.0
Outstanding(1 rating)
Annapolis, Anne Arundel County, Maryland, United States
Fireplace
View deal
See all offers

Vacation Houses With Pools

We use AI to generate the short summary in each offer below, check full description before booking.
House Annapolis
from $802
per night
House ∙ 15 guests ∙ 5 bedrooms

Children-friendly nice vacation home with patio, barbeque & private pool | City view | Suitable for remote work

3.9
Good(12 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Pool
View deal
House Annapolis
from $1,203
per night
House ∙ 8 guests ∙ 4 bedrooms

Fully equipped nice vacation home with sauna, patio & private pool | Nature view

4.9
Outstanding(5 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Pool
View deal
Condo Annapolis
from $175
per night
Condo ∙ 4 guests ∙ 1 bedroom

Family-friendly charming condo with private pool & patio | Nature view | Good for workation

4.8
Outstanding(199 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Pool
View deal
See all offers

Budget-friendly rental options

Enjoy affordable vacation rentals in Annapolis offering exceptional value for money

House Annapolis
from $266
per night
House ∙ 10 guests ∙ 5 bedrooms

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

4.9
Outstanding(211 ratings)
Annapolis, Anne Arundel County, Maryland, United States
View deal
House Annapolis
from $980
per night
House ∙ 10 guests ∙ 4 bedrooms

House with yard, grill & terrace | Perfect for remote work

4.8
Outstanding(44 ratings)
Annapolis, Anne Arundel County, Maryland, United States
View deal
Cabin Annapolis
from $173
per night
Cabin ∙ 4 guests ∙ 1 bedroom

Cottage with patio & garden

5.0
Outstanding(305 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 $499
per night
House ∙ 8 guests ∙ 4 bedrooms

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

5.0
Outstanding(101 ratings)
Annapolis, Anne Arundel County, Maryland, United States
View deal
House Annapolis
from $288
per night
House ∙ 8 guests ∙ 3 bedrooms

Vacation home with yard

4.8
Outstanding(40 ratings)
Annapolis, Anne Arundel County, Maryland, United States
View deal
House Annapolis
from $713
per night
House ∙ 6 guests ∙ 3 bedrooms

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

5.0
Outstanding(32 ratings)
Annapolis, Anne Arundel County, Maryland, United States
View deal

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Verified reviews

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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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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 (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, $514. 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 1,009 rentals
🌙 Nightly prices starting at $37
⭐ Popular amenities Pets allowed, Pool and Internet
🐾 Pet friendly homes 440 homes
🏊 Vacation rentals with pools 210 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 $37 per night. Nightly prices for house rentals are $870 on average. Apartment rentals in Annapolis cost $388 per night on average.

How many vacation rentals are available for booking in Annapolis?

Currently there are 1,009 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 210 vacation rentals from 7 providers in Annapolis.

Are dogs allowed in vacation homes in Annapolis?

Sure, there are 440 vacation rentals in Annapolis that allow pets , with an average price of $514 per night.

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