Holiday Rentals in Annapolis

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Holiday Rentals in Annapolis

Apartment in Annapolis

10.0 out of 10, Exceptional, (81)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is €368
includes taxes & fees
1 Dec - 2 Dec
Waterfront Oasis of Annapolis Star

Condo in Historic District

10.0 out of 10, Exceptional, (1)
"The host family was incredible to work with. Patient with details. Easy location walking distance to USNA and the stadium. "
United States
Jennifer H.
The price is €538
includes taxes & fees
18 Dec - 19 Dec
Upscale Condo in Annapolis

Holiday Home in Annapolis

10.0 out of 10, Exceptional, (6)
"The property provided the space I needed for my family. It is located in a cute neighborhood. The property was clean and the owner was very responsive to any questions that I had. I really enjoyed staying here."
United States
Kristina
The price is €489
includes taxes & fees
2 Dec - 3 Dec
Charming Pet-Friendly Stay - Near Bay & Beaches.

Holiday Home in Cape Saint Claire

9.8 out of 10, Exceptional, (11)
"Very nice home, location, close to our family and activities. Enjoyed our stay and would recommend to other renters looking for spaciousness and holiness that a hotel cannot provide! "
United States
Lisa S.
The price is €517
includes taxes & fees
9 Dec - 10 Dec
Neptune by the Water - Pet Friendly Fenced Yard

Holiday Home in Arundel on the Bay

9.8 out of 10, Exceptional, (11)
"Very clean - well equipped - perfect for our relaxing weekend."
United States
Chris J.
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Holiday Home in Admiral Heights

9.8 out of 10, Exceptional, (6)
"We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!"
United States
Tammy L.
The price is €489
includes taxes & fees
30 Nov - 1 Dec
Cute bungalow blocks to Stadium

Holiday Home in Homewood

9.8 out of 10, Exceptional, (8)
"This house was perfect for us! We love the ease of getting into town without having to drive and park in a parking garage. I would 10/10 recommend this house!"
United States
Elaina H.
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Holiday Home in Historic District

10.0 out of 10, Exceptional, (72)
"Great little house easy to walk to West St, Main St & the Yard (USNA). Has parking included which is nice. Great communication we owner. Will stay again. "
United States
Sheldon E.
The price is €275
includes taxes & fees
1 Dec - 2 Dec
Cozy 2br home w/ parking in downtown Annapolis

Holiday Home in Eastport

Cozy Private Suite in Eastport, Near USNA

Holiday Home in Annapolis

9.2 out of 10, Wonderful, (15)
"The property was well cleaned and communication with owner was excellent. Would stay again"
United States
Kristen
The price is €365
includes taxes & fees
27 Dec - 28 Dec
Wright's Cottage- Pet's Welcome & EV Charging

Holiday Home in Homewood

10.0 out of 10, Exceptional, (1)
"This house was a TEN! We booked it for family and friends to stay with us for a military retirement over homecoming weekend. The location was great. Perfect for walking to and from the stadium with kids. Easy few minutes drive or Uber to the Academy. The house was well equipped and perfect for a big group. The yard was amazing! Wish we’d planned on a family flag football game! Plenty of space in the kitchen and living room. Management was super responsive when we needed something or had a...
United States
Catherine S.
Stunning 4 BR Home - Walking Distance to Stadium

Apartment in Historic District

10.0 out of 10, Exceptional, (2)
"We had a great time—the location is fantastic and our dog loved the backyard! A great base to rest and recover between adventures in Annapolis. "
United States
Nathaniel R.
Dean Street's Lower Deck House!

Holiday Home in Historic District

10.0 out of 10, Exceptional, (5)
"Wonderful location. Easy walking to downtown restaurants, shops, city docks and USNA. Enjoyed spending time on front porch and swing.Comfortable beds and home like atmosphere.No need for a vehicle, but if you have one, parking garage is just a few blocks away. "
United States
Katie S.
Historic Row Home 1 Block from Gate 1 at USNA!

Holiday Home in Cape Saint Claire

10.0 out of 10, Exceptional, (3)
"This was a beautiful property and I would stay here again if we travel back to the area."
United States
Katherine D V.
Annapolis Baystone House

Holiday Home in Cape Saint Claire

2.0 star property
Spacious Modern Annapolis Retreat, Near Downtown, Firepit + Bar, Sleeps 12

Holiday Home in Historic District

10.0 out of 10, Exceptional, (13)
"The location is perfect!"
United States
suzanne d.
The price is €577
includes taxes & fees
1 Dec - 2 Dec
Fisher House: Steps From USNA + Covered Parking!

Holiday Home in Annapolis

2.0 star property
Modern Retreat w/ Fire Pit & Parking

Holiday Home in Eastport

2BR, 1BA Boutique Brick Beauty located in historic Eastport.

Holiday Home in Annapolis

10.0 out of 10, Exceptional, (5)
The price is €344
includes taxes & fees
30 Nov - 1 Dec
Walk to the stadium! - Lighthouse on Glenwood

Holiday Home in Annapolis

2.0 star property
10.0 out of 10, Exceptional, (4)
"Great house & great location! We will definitely be returning! Thank you Jessica!"
United States
Holly W.
Mins to DTA - King Beds - Parking
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

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 €470 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 Annapolis Maritime Museum, 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?

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!: This highly rated holiday home rental in Annapolis is located in the city centre, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games. Another good choice for your trip to Annapolis is Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably.

How many holiday rentals will I find in Annapolis?

Expedia has 385 holiday rentals for your stay in Annapolis.

What can I see and do in Annapolis?

Enjoy the outdoors at Spa Creek and Maryland Quiet Waters Park, or simply take in cultural attractions like Maryland Hall for Creative Arts and Annapolis Maritime Museum. While here, Thurgood Marshall Memorial and Maryland State 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.