A historic town street at dusk with a prominent church dome, brick buildings, and a yellow fire hydrant.

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Annapolis holiday rentals

A hot tub area with a covered patio, outdoor seating, and a view of the surrounding landscape.

1. Idyllic Pasadena Retreat With Garden + Hot Tub!

Idyllic Pasadena Retreat With Garden + Hot Tub!
3.0 star property
Green Haven
The price is ฿7,487
฿16,226 total
includes taxes & fees
22 Oct - 23 Oct
Idyllic Pasadena Retreat With Garden + Hot Tub!
Room

2. Wyatt's Saloon Guest House 2

Wyatt's Saloon Guest House 2
2.0 star property
Fells Point
The price is ฿11,112
฿18,769 total
includes taxes & fees
12 Nov - 13 Nov
Wyatt's Saloon Guest House 2
A balcony with wicker chairs and a small table, adorned with string lights.

3. 1-BD Home near Stadiums Free Parking

1-BD Home near Stadiums Free Parking
3.0 star property
Pigtown
6.2 out of 10, (12 reviews)
"Conveniently located walking distance from the stadiums and restaurants but the apartment definitely needs some work. Minimal furnishings and there are quite a few things that need to be repaired/ replaced."
United States
Patricia
The price is ฿6,016
฿7,069 total
includes taxes & fees
25 Oct - 26 Oct
1-BD Home near Stadiums Free Parking
A brick building with a storefront, outdoor seating, and a crosswalk.

4. Entire Unit-5min to M&TBank Camden Yards

Entire Unit-5min to M&TBank Camden Yards
3.0 star property
Hollins Market
4.0 out of 10, (1 review)
"Not enough characters to submitt what I really wanna say. But will not refer to any1. ONLY GOOD THING IS THAT IT WAS CLOSE TO WERE WE ACTUALLY NEEDED TO BE"
United States
Shanna
The price is ฿9,359
฿15,007 total
includes taxes & fees
21 Oct - 22 Oct
Entire Unit-5min to M&TBank Camden Yards
A house with a deck, a fire pit, and blue Adirondack chairs.

5. Lakefront Home Firepit BWI Marleycreek River

Lakefront Home Firepit BWI Marleycreek River
3.0 star property
Marley
The price is ฿10,562
฿12,507 total
includes taxes & fees
21 Oct - 22 Oct
Lakefront Home Firepit BWI Marleycreek River
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Annapolis Hotel Reviews

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"Great location, hotel super clean and good restaraunt . Short walking distance to great shopping and many more bars and restaraunts"
Robin 1-night trip
Posted 8 hours ago
Annapolis Waterfront Hotel, Autograph Collection

Find out more about Annapolis

Search for holiday rentals in Annapolis on Expedia! You can easily find your home rentals, villas, holiday apartments in Annapolis using one of the methods below:

  • View our selection of featured holiday rentals in Annapolis
  • Use the map to find apartments and other holiday homes in the Annapolis neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Annapolis while they last

Look no further and take a look at our great range of rental properties in Annapolis!

Frequently asked questions

Are there holiday rentals in Annapolis?

Yes, there are holiday rentals in Annapolis close to Maryland Hall for Creative Arts, or you can select a more secluded option if you're looking for a relaxing stay. Tourists who visit Annapolis speak highly of the university campus and array of shops. While you're in the area, you can also enjoy the top-notch restaurants and marina.

How many holiday rentals will I find in Annapolis?

Expedia has 381 holiday rentals for your stay in Annapolis.

What can I see and do in Annapolis?

Enjoy the outdoors at Maryland Quiet Waters Park and Bay Ridge Beach, or simply take in cultural attractions like Annapolis Maritime Museum and Hammond-Harwood House. While here, Maryland State House and William Paca House are other places worth a visit.

What are holiday rentals like in Annapolis?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Annapolis. Holiday rentals offer amenities like kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you to travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for a family trip or a small group gathering.