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

Vacation rentals in Annapolis

Find 1,396 available house rentals from 14 partners
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Top 15 Recommended vacation rentals in Annapolis

Find your perfect vacation rental in Annapolis from just $107 per night!

House Annapolis
Sep 6 - Sep 13
House ∙ 19 guests ∙ 5 bedrooms

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

Annapolis, Anne Arundel County, Maryland, United States
$599
per night
Outstanding(34 ratings)
$599
per night
View deal
House Annapolis
Aug 2 - Aug 9
House ∙ 12 guests ∙ 5 bedrooms

House with terrace

Annapolis, Anne Arundel County, Maryland, United States
$272
per night
Outstanding(7 ratings)
$272
per night
View deal
House Annapolis
Sep 6 - Sep 13
House ∙ 10 guests ∙ 5 bedrooms

Vacation home with patio & garden | Nature view | Perfect for remote work

Annapolis, Anne Arundel County, Maryland, United States
$644
per night
Outstanding(28 ratings)
$644
per night
View deal
House Annapolis
Jun 21 - Jun 28
House ∙ 12 guests ∙ 6 bedrooms

House with patio, yard & barbeque | City view

Annapolis, Anne Arundel County, Maryland, United States
$675
per night
Outstanding(77 ratings)
$675
per night
View deal
House Annapolis
May 4 - May 11
House ∙ 14 guests ∙ 5 bedrooms

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

Annapolis, Anne Arundel County, Maryland, United States
$1,143
per night
Outstanding(17 ratings)
$1,143
per night
View deal
House Annapolis
Aug 16 - Aug 23
House ∙ 8 guests ∙ 5 bedrooms

Child-friendly charming house with yard, patio & grill | Perfect for remote work | Pet-friendly

Annapolis, Anne Arundel County, Maryland, United States
$244
per night
Outstanding(13 ratings)
$244
per night
View deal
House Annapolis
-36%
May 2 - May 9
House ∙ 10 guests ∙ 7 bedrooms

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

Annapolis, Anne Arundel County, Maryland, United States
$828$528
per night
Outstanding(54 ratings)
$828$528
per night
View deal
House Annapolis
Jul 5 - Jul 12
House ∙ 10 guests ∙ 5 bedrooms

Vacation home with BBQ, patio & yard | City view

Annapolis, Anne Arundel County, Maryland, United States
$949
per night
Outstanding(39 ratings)
$949
per night
View deal
House Annapolis
May 29 - Jun 5
House ∙ 14 guests ∙ 7 bedrooms

Family-friendly house with grill & garden | Perfect for remote work | Dogs allowed

Annapolis, Anne Arundel County, Maryland, United States
$500
per night
Outstanding(42 ratings)
$500
per night
View deal
House Annapolis
Jul 2 - Jul 9
House ∙ 12 guests ∙ 6 bedrooms

Fully equipped vacation home with private pool, patio & BBQ | Lake view

Annapolis, Anne Arundel County, Maryland, United States
$1,480
per night
Outstanding(18 ratings)
$1,480
per night
View deal
House Annapolis
Jun 14 - Jun 21
House ∙ 10 guests ∙ 5 bedrooms

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

Annapolis, Anne Arundel County, Maryland, United States
$418
per night
Outstanding(182 ratings)
$418
per night
View deal
House Annapolis
-50%
May 4 - May 11
House ∙ 8 guests ∙ 4 bedrooms

Fully equipped house with patio & BBQ

Annapolis, Anne Arundel County, Maryland, United States
$555$277
per night
Outstanding(8 ratings)
$555$277
per night
View deal
House Annapolis
-55%
Jun 14 - Jun 21
House ∙ 10 guests ∙ 6 bedrooms

House with terrace, yard & barbeque

Annapolis, Anne Arundel County, Maryland, United States
$1,305$583
per night
Outstanding(99 ratings)
$1,305$583
per night
View deal
House Annapolis
May 17 - May 24
House ∙ 6 guests ∙ 3 bedrooms

House with 3 rooms for 6 persons

Annapolis, Anne Arundel County, Maryland, United States
$600
per night
(4 ratings)
$600
per night
View deal
House Annapolis
Aug 16 - Aug 23
House ∙ 8 guests ∙ 4 bedrooms

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

Annapolis, Anne Arundel County, Maryland, United States
$345
per night
Outstanding(127 ratings)
$345
per night
View deal

Vacation rentals and apartments with air conditioning

House  Annapolis
May 5 - May 12
-64%
$555
$201
per night
House ∙ 8 guests ∙ 3 bedrooms

Family-oriented wonderful house with yard & barbeque | Pet-friendly

5.0
Outstanding(2 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Air conditioning
View deal
House  Annapolis
May 4 - May 11
-22%
$508
$395
per night
House ∙ 12 guests ∙ 5 bedrooms

Fully equipped house with patio, grill & garden | City view | Pets are welcome

4.9
Outstanding(18 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Air conditioning
View deal
Cottage  Annapolis
Apr 25 - May 2
$286
per night
Cottage ∙ 6 guests ∙ 4 bedrooms

Family-oriented cottage with BBQ, yard & patio | City view | Good for workation | Dogs allowed

4.9
Outstanding(36 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Air conditioning
View deal
See all offers

Vacation houses with Balconies or Patios

House  Annapolis
May 2 - May 9
-46%
$776
$423
per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with patio, barbecue & garden | City view

5.0
Outstanding(56 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Balcony/Patio
View deal
House  Annapolis
Aug 11 - Aug 18
$522
per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with barbecue, terrace & yard | City view

4.9
Outstanding(74 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Balcony/Patio
View deal
House  Annapolis
Jun 28 - Jul 5
$357
per night
House ∙ 7 guests ∙ 4 bedrooms

House with terrace, grill & garden | Nature view | Perfect for remote work

5.0
Outstanding(97 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Balcony/Patio
View deal
See all offers

Vacation rentals with a balcony

House  Annapolis
May 4 - May 11
-72%
$1,450
$401
per night
House ∙ 8 guests ∙ 4 bedrooms

House with grill

5.0
Outstanding
Annapolis, Anne Arundel County, Maryland, United States
Balcony
View deal
House  Annapolis
Jun 14 - Jun 21
$500
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(8 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Balcony
View deal
House  Annapolis
Aug 2 - Aug 9
$1,200
per night
House ∙ 7 guests ∙ 4 bedrooms

Family-oriented vacation home with patio, grill & garden | City view | Good for workation | Pets are welcome

5.0
Outstanding(18 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Balcony
View deal
See all offers

Best Vacation Home Deals in Annapolis

Save up to 51%

Apartment Annapolis
Feb 7 - Feb 14
-51%
$509
$248
per night
Apartment ∙ 6 guests ∙ 2 bedrooms

Child-friendly rental apartment with garden & terrace

4.9
Outstanding(124 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Free cancellation
View deal
House Annapolis
May 29 - Jun 5
-18%
$393
$321
per night
House ∙ 6 guests ∙ 3 bedrooms

Fully equipped house with terrace

5.0
Outstanding(10 ratings)
Annapolis, Anne Arundel County, Maryland, United States
View deal
House Annapolis
May 29 - Jun 5
-42%
$703
$407
per night
House ∙ 8 guests ∙ 3 bedrooms

House with garden, grill & patio | Nature view

5.0
Outstanding(16 ratings)
Annapolis, Anne Arundel County, Maryland, United States
View deal

Choose a welcoming rental from $107 per night by searching through the 1,396 properties featured in Annapolis. Using HomeToGo you can instantaneously compare the prices of each available property to discover the best price and save up to 51%.

Budget-friendly Vacation Rentals in Annapolis

Find Fantastic yet Inexpensive Offers

House Annapolis
Jun 9 - Jun 16
$490
per night
House ∙ 10 guests ∙ 4 bedrooms

Child-friendly vacation home with grill, garden & patio | City view

5.0
Outstanding(68 ratings)
Annapolis, Anne Arundel County, Maryland, United States
View deal
House Annapolis
Jun 14 - Jun 21
$309
per night
House ∙ 5 guests ∙ 2 bedrooms

House with terrace | City view

5.0
Outstanding(148 ratings)
Annapolis, Anne Arundel County, Maryland, United States
View deal
House Annapolis
Jul 12 - Jul 19
$487
per night
House ∙ 13 guests ∙ 6 bedrooms

Family-oriented house with terrace, yard & barbeque | Pets are welcome

5.0
Outstanding(4 ratings)
Annapolis, Anne Arundel County, Maryland, United States
View deal

Top-Rated Rentals and Accommodations in Annapolis

Book Vacation Rental Offers with the Highest User Rating

House Annapolis
Jul 2 - Jul 9
House ∙ 8 guests ∙ 3 bedrooms

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

Annapolis, Anne Arundel County, Maryland, United States
$257
per night
Outstanding(271 ratings)
$257
per night
View deal
House Annapolis
Aug 2 - Aug 9
House ∙ 8 guests ∙ 4 bedrooms

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

Annapolis, Anne Arundel County, Maryland, United States
$431
per night
Outstanding(86 ratings)
$431
per night
View deal
House Annapolis
May 29 - Jun 5
House ∙ 14 guests ∙ 5 bedrooms

House with jacuzzi, patio & yard | Nature view

Annapolis, Anne Arundel County, Maryland, United States
$402
per night
Outstanding(72 ratings)
$402
per night
View deal

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Popular Rental Amenities in Annapolis

  • Pet-friendly (490)
  • Pool (210)
  • WiFi (1,332)
  • TV (1,273)
  • Parking (90)
  • Air conditioning (1,371)
  • Kitchen (1,000)
  • Balcony/patio (476)
  • Washing machine (714)
  • Fireplace (516)
  • Fishing (313)
  • Hot tub (79)

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, $538. 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.

Price and Availability Index in Annapolis

Click on any bar to see price and availability information

Vacation Rental Price Information in Annapolis

This graph displays the average prices of vacation rentals and apartments located in Annapolis. The week with the highest average prices is in May (5/17 – 5/24). During this week, a nightly price on average will be $658. Vacation rental prices go down to $585 per night in April (4/19 – 4/26).

Rental availability information in Annapolis

Have a look at the above graph to see the average availability of vacation rentals in Annapolis. The busiest time to book a rental in Annapolis so far is in April (4/4 – 4/11), where only 12% rentals are available. July (7/19 – 7/26) has got the highest percentage of available rentals.

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.

What are the best places to discover the arts and culture of Annapolis?

Art, history, and culture

From its earliest days, Annapolis has been known as the “Athens of America” for its cultural, social and intellectual activities. Your vacation rental in Annapolis will be close to many artistic and cultural offerings, such as Historic London Town and Gardens, where you can explore 23 acres of history, archeology, and beautiful flora.

Experience performances by the Annapolis Shakespeare Company, Ballet Theatre of Maryland, or the Annapolis Symphony Orchestra. If visual art is your cup of tea, there are 25 fine art galleries downtown alone, as well as the Elizabeth Myers Mitchell Gallery, a museum that is open daily and has free admission.

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 1,396 rentals
💳 Possible discounts up to 51%
🌙 Nightly prices starting at $107
⭐ Popular amenities Pets allowed, Pool and Internet
🐾 Pet friendly homes 473 homes
🏊 Vacation rentals with pools 209 homes
116,956 reviews
Annapolis vacation rentals have an average rating of 4.7/5 on 116,956 reviews left by travelers.

Frequently Asked Questions

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

The average accommodation in Annapolis is priced at $107 per night. $815 is the average nightly price for house rentals in Annapolis. Apartment rentals in Annapolis cost on average $419 per night.

How many vacation homes are available to book in Annapolis?

There are currently 1,396 vacation rentals in Annapolis to browse and book for your upcoming trip.

What amenities are most popular for vacation rentals in Annapolis?

Travelers look for Pool, Pets allowed, and Internet when booking a vacation rental in Annapolis.

How many vacation rentals with pools are there in Annapolis?

Browse 209 vacation rentals available in Annapolis.

Are pets allowed in vacation homes in Annapolis?

Absolutely, currently there are 473 vacation rentals in Annapolis that allow dogs and the average nightly price is $538.

What's the best time to travel to Annapolis?

If you are booking a vacation rental in Annapolis, consider that rainy season is usually in January or May, with September often being the driest.

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