Annapolis Holiday Rentals

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Holiday Rentals in Annapolis

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

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

Charming garden row home, easy 4 block walk to the heart of Annapolis.

Historic District
10.0 out of 10, Exceptional, (125)
"Great location, very clean house, wonderful stay"
United States
Kathryn O.
Charming garden row home, easy 4 block walk to the heart of Annapolis.

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Historic District
9.4 out of 10, Exceptional, (19)
"Great place, excellent location!"
United States
Joseph C.
The price is AU$1,833
includes taxes & fees
8 Dec - 9 Dec
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

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

2.0 star property
Cape Saint Claire
The price is AU$828
includes taxes & fees
16 Dec - 17 Dec
Spacious Modern Annapolis Retreat, Near Downtown, Firepit + Bar, Sleeps 12

PERFECT LOCATION in the heart of history

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

Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis

Annapolis
9.4 out of 10, Exceptional, (36)
"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

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

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 Promo: Get 10% Off Holiday Stays

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.
Holiday Promo: Get 10% Off Holiday Stays

Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

2.5 star property
Murray Hill
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.

Walk to the stadium! - Lighthouse on Glenwood

Annapolis
10.0 out of 10, Exceptional, (5)
The price is AU$498
includes taxes & fees
4 Dec - 5 Dec
Walk to the stadium! - Lighthouse on Glenwood

Fabulous 5-bedroom house with AC in charming Annapolis

2.0 star property
Annapolis
10.0 out of 10, Exceptional, (1)
"Great location to walk to Navy game. Good space and great communication with property owner."
United States
Rebecca G.
The price is AU$665
includes taxes & fees
9 Dec - 10 Dec
Fabulous 5-bedroom house with AC in charming Annapolis

Charming brick home with patio, WiFi, AC, & W/D - walk to everything

Historic District
9.2 out of 10, Wonderful, (28)
"Didn’t really use the (small) kitchen because we were just steps from everything and all the restaurants. Impossible to beat the location. "
United States
Chris A.
Charming brick home with patio, WiFi, AC, & W/D - walk to everything

Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything

Historic District
9.8 out of 10, Exceptional, (30)
"Great location !"
United States
John E.
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything

Firefly Cottage at the Cape, Community beach, Hot tub, USNA vs Army game, pets

Cape Saint Claire
10.0 out of 10, Exceptional, (101)
"Another fabulous stay at the Firefly Cottage "
United States
Debbie Y.
Firefly Cottage at the Cape, Community beach, Hot tub, USNA vs Army game, pets

Annapolis Condominium in the heart of the historic center

Historic District
9.8 out of 10, Exceptional, (291)
"Great stay! Easy check in, great location."
United States
Erin W.
Annapolis Condominium in the heart of the historic center

Beautiful Condo - Water View Near City Dock

Eastport
9.6 out of 10, Exceptional, (154)
"Good location. 10 minute walk to city dock. Apartment was fine with no major issues. No problem finding parking within the parking area."
United States
Robert D.
Beautiful Condo - Water View Near City Dock

Charming Historic Townhouse Steps From USNA

Historic District
10.0 out of 10, Exceptional, (36)
"The location was perfect, and the home itself was clean, charming, and exactly what we needed for our stay. "
United States
Anna W.
Charming Historic Townhouse Steps From USNA

Walking distance to Navy Stadium! No cleaning fees!

West Annapolis
10.0 out of 10, Exceptional, (8)
"We had a great time in Annapolis and enjoyed our stay in this beautiful house! Short walk to the naval academy, football stadium, and house was immaculate and well stocked with everything we needed. Thank you for making our stay special!"
United States
Kristin N.
Walking distance to Navy Stadium! No cleaning fees!

Historic Annapolis Home 1.5 blocks from center of town.

Historic District
9.8 out of 10, Exceptional, (44)
"We had a fabulous stay on Charles Street. The location and layout of the house is great! I have already booked another stay in the spring at this rental. "
United States
Natalie W.
Historic Annapolis Home 1.5 blocks from center of town.

Location is perfect and a big bonus we have our own parking at the home!

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!
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, 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 favourite 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 depend 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 AU$498 per night. Entering your travel dates in the search wizard might find you 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?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: This highly rated holiday home rental in Annapolis offers a balcony, a garden and a BBQ to help you feel perfectly comfortable 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. Another good choice for your trip to Annapolis is Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!.

How many holiday rentals will I find in Annapolis?

Expedia has 382 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.