Annapolis Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Holiday Rentals in Annapolis

Holiday Home in Historic District

10.0 out of 10, Exceptional, (33)
"Our stay was AMAZING! Perfect location, plenty of space! Will definitely book again when we have a larger group like we did for PPW! "
United States
Charolene P.
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Holiday Home in Cape Saint Claire

10.0 out of 10, Exceptional, (39)
"Fabulous place. We’ll be booking again next year. "
United States
Steve R.
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Holiday Home in Historic District

9.4 out of 10, Exceptional, (18)
"Our group had a great time! This house was super convenient location and easily walkable to Main Street. Thank you!"
United States
Kerry G.
The price is NZ$2,065
includes taxes & fees
2 Dec - 3 Dec
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Holiday Home in Historic District

10.0 out of 10, Exceptional, (124)
"This house is in a wonderful location relative to town and the Naval Academy. The house is lovely and was very comfortable for all 6 of us. Clean, spacious, and great bedding. The garden is beautiful. Arranging for parking on the street was great."
United States
cara
Charming garden row home, easy 4 block walk to the heart of Annapolis.

Holiday Home in Historic District

10.0 out of 10, Exceptional, (41)
"Perfect location and parking was a big bonus!"
United States
Angela H.
Location is perfect and a big bonus we have our own parking at the home!

Holiday Home in Eastport

10.0 out of 10, Exceptional, (125)
"We had a great stay! The house was adorable and the pool was awesome!"
United States
Kathleen J.
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

Holiday Home in Annapolis

7.0 out of 10, Good, (6)
"Very beautiful, uniquely designed home on the water. There were 2 bedrooms on the first floor making in it easy for our elderly quests. The main suite was great for our young adults to stay in together with 2 kings, sectional and multiple love sacs. Plenty of seating throughout the home both inside and out. "
United States
Kristin W.
Luxury Waterfront Executive Family Home Annapolis with All Amenities

Condo in Eastport

9.6 out of 10, Exceptional, (153)
"Clean, quiet, and very close to both downtown and Eastport restaurants."
United States
mickey p.
Beautiful Condo - Water View Near City Dock

Apartment in Annapolis

9.4 out of 10, Exceptional, (34)
"Very communicative host and the in apartment sauna and jacuzzi tub really helped us relax. A great stay overall!"
United States
George H.
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis

Holiday Home in Historic District

10.0 out of 10, Exceptional, (213)
"Perfect location! Ample room for our family of five.. can’t wait to return. "
United States
Christine A.
PERFECT LOCATION in the heart of history

Holiday Home in Murray Hill

2.5 star property
10.0 out of 10, Exceptional, (34)
"Absolutely perfect! Will stay again!!"
United States
Brian
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

Holiday Home in Annapolis

2.0 star property
The price is NZ$967
includes taxes & fees
10 Dec - 11 Dec
Fabulous 5-bedroom house with AC in charming Annapolis

Holiday Home in Historic District

10.0 out of 10, Exceptional, (34)
"We had an excellent stay with iTrip Annapolis! Location was 10/10. Walking distance to the main circle with tons of bars, restaurants, and shops. House was clean, comfortable, and well cared for."
United States
Taylor H.
Early Black Friday: Get 10% Off Holiday Stays

Cottage in Cape Saint Claire

10.0 out of 10, Exceptional, (100)
"Another fabulous stay at the Firefly Cottage "
United States
Debbie Y.
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, Holiday fun.

Condo in Historic District

9.8 out of 10, Exceptional, (290)
"Great stay! Easy check in, great location."
United States
Erin W.
Annapolis Condominium in the heart of the historic center

Holiday Home in Historic District

9.8 out of 10, Exceptional, (30)
"Great location "
United States
Jessica J.
Stunning, Large Historic Annapolis Home, Steps to Downtown, Private Driveway!

Apartment in Annapolis

10.0 out of 10, Exceptional, (57)
"This was our 2nd time staying here and we absolutely love it! Already booked us for another trip here! The view, property, and experience was amazing! "
United States
Jacqueline T.
Bay View Studio Apartment

Holiday Home in Historic District

10.0 out of 10, Exceptional, (240)
"We had a wonderful time staying at this property! The location was just perfect, and the host was so responsive. We would love to stay here again!"
United States
Frances A.
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Holiday Home in Historic District

10.0 out of 10, Exceptional, (13)
"The location is perfect!"
United States
suzanne d.
The price is NZ$1,165
includes taxes & fees
2 Dec - 3 Dec
Fisher House: Steps From USNA + Covered Parking!

Cottage in Hillsmere

10.0 out of 10, Exceptional, (170)
"Love the decor, the comfort and vibe of the place. Wish I had stayed longer! "
United States
Lauren m.
The Yellow Cottage on Harness Creek
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.

Black Friday Sale

Save up to 40% on select hotels
Save an average of 15% on thousands of hotels when you're signed in

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, 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 NZ$967 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.