Annapolis Holiday Rentals from €378: Search Short-Term Rentals

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Our top choices for Annapolis holiday rentals

1. Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA

Historic District

Brian L.

includes taxes & fees

31 Aug - 1 Sept

A kitchen with a wooden countertop, a stove, and a refrigerator.

2. 18th Cent. Charm in Historic Downtown Annapolis

Historic District

Maureens B.

includes taxes & fees

11 Sept - 12 Sept

A kitchen counter with a marble top, a striped basket, a tissue box, and a potted plant.

3. Dean Street's Lower Deck House!

Historic District

Nathaniel R.

includes taxes & fees

31 Aug - 1 Sept

A lobby with a reception desk, a blue sofa, a plant, and a door leading outside.

4. New Downtown Annapolis Condo With Free Parking

Historic District

Darby F.

includes taxes & fees

31 Aug - 1 Sept

A modern lobby with a blue sofa, two framed abstract paintings, a potted plant, and a marble floor.

5. Upscale Condo in Annapolis w/Private Parking

Historic District

Scott P.

includes taxes & fees

8 Sept - 9 Sept

A wooden dock extending into a calm body of water with boats docked at the end.

6. Cozy 2br home w/ parking in downtown Annapolis

Historic District

Mary G.

includes taxes & fees

9 Sept - 10 Sept

A swimming pool with a waterfall feature surrounded by lush greenery.

7. Waterfront Oasis of Annapolis Star

Annapolis

Thomas

includes taxes & fees

1 Sept - 2 Sept

A modern kitchen with wooden cabinets, stainless steel appliances, and a large island.

8. Luxe Row Home Steps to USNA Gate 3!

Historic District

Christine A.

includes taxes & fees

30 Aug - 31 Aug

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Top Annapolis Hotel Reviews

Hilton Garden Inn Annapolis

10/10 Excellent

"None."

SpringHill Suites by Marriott Annapolis

8/10 Good

"The property, including the room, was clean. The staff was friendly and attentive. Breakfast was okay (continental) and staff will accommodate if needed for dietary restrictions. The dining area is small but does have tables with seats/high chairs to sit. There are two computers, a laundry room, ice room, and an exercise room. Based on a window peep, there is a disabled accessible pool/jaccuzi, but it was closed for maintenance during our stay and reopened on our check-out day so we didn't get to use it. One of the issues we experienced was getting a parking citation everyday even though we paid at check-in. The desk clerk assured we wouldn't be towed and the company would be notified by email regarding the error, but it still was frustrating. Parking is $9.50/day via third party scan code or text to pay through a website. The second issue was our microwave did not work properly but we used the common one downstairs. The final issue was our mini-fridge was loud if not closed a certain way yet, it did work to keep our items cold. The location is quiet and felt safe. You have to use your key card to enter the lobby after 12am. Overall, we would choose to book this hotel again if available in the future."

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good

"The location of the hotel was awesome along with our balcony view. However you should not have to pay an additional $50 per day to park your car especially since the garage up the street is Therefore the guests are getting pentalized to park at the hotel . Additionally the front desk women were rude and condescending"

Find out more about Annapolis

Everything you need to know about Annapolis holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Annapolis holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Annapolis holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Annapolis holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Annapolis. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Annapolis holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Annapolis holiday rentals we have selected for you start as low as €378 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Annapolis rentals

At Expedia, we put the best Annapolis holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Annapolis rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Annapolis holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Annapolis. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.

What are some of the best holiday rentals that Annapolis has to offer?

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: This highly rated holiday home rental in Annapolis is located near the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. Some other top choices in Annapolis are Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! and Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably.

How many holiday rentals will I find in Annapolis?

Expedia has 378 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 The Colonial Players. 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.

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Check prices for these dates

Our top choices for Annapolis holiday rentals

1. Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA