Annapolis Vacation Rentals

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Vacation Rentals in Annapolis

Fridge, microwave, oven, stovetop
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

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.
$1,041 nightly
The price is $1,186
Dec 8 - Dec 9
Total with taxes and fees
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
Fridge, microwave, oven, stovetop
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

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
Fridge, microwave, oven, stovetop
Spacious Modern Annapolis Retreat, Near Downtown, Firepit + Bar, Sleeps 12

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

2.0 star property
Cape Saint Claire
$528 nightly
The price is $602
Dec 15 - Dec 16
Total with taxes and fees
Spacious Modern Annapolis Retreat, Near Downtown, Firepit + Bar, Sleeps 12
Marina
Charming brick home with patio, WiFi, AC, & W/D - walk to everything

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
Terrace/patio
Historic Annapolis Home 1.5 blocks from center of town.

Historic Annapolis Home 1.5 blocks from center of town.

Historic District
9.8 out of 10, Exceptional, (44)
"Great location in DTA! Short walk to bars restaurants and USNA! "
United States
Liz D.
Historic Annapolis Home 1.5 blocks from center of town.
Interior
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis

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
Fridge, microwave, oven, stovetop
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

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

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.
Terrace/patio
Holiday Promo: Get 10% Off Holiday Stays

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

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.
Microwave, oven, stovetop, dishwasher
Walk to the stadium! - Lighthouse on Glenwood

Walk to the stadium! - Lighthouse on Glenwood

Annapolis
10.0 out of 10, Exceptional, (5)
$285 nightly
The price is $325
Dec 7 - Dec 8
Total with taxes and fees
Walk to the stadium! - Lighthouse on Glenwood
Terrace/patio
Annapolis Condominium in the heart of the historic center

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
Outdoor pool
Beautiful Condo - Water View Near City Dock

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
Fridge, microwave, oven, stovetop
Charming Historic Townhouse Steps From USNA

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
Fridge, microwave, oven, stovetop
Stunning, Large Historic Annapolis Home, Steps to Downtown, Private Driveway!

Stunning, Large Historic Annapolis Home, Steps to Downtown, Private Driveway!

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!
Fridge, microwave, oven, stovetop
Downtwn Stylish 3BR/2BA with Exclusive Parking in Annapolis-USNA Stadium

Downtwn Stylish 3BR/2BA with Exclusive Parking in Annapolis-USNA Stadium

Historic District
9.0 out of 10, Wonderful, (12)
"We were in Annapolis for a quick weekend trip. The house had everything we needed."
United States
Heather B.
Downtwn Stylish 3BR/2BA with Exclusive Parking in Annapolis-USNA Stadium
Outdoor spa tub
Bay View Studio Apartment

Bay View Studio Apartment

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
Exterior
PERFECT LOCATION in the heart of history

PERFECT LOCATION in the heart of history

Historic District
10.0 out of 10, Exceptional, (214)
"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
Smart TV
Waterfront 2-Bedroom Condo on Spa Creek

Waterfront 2-Bedroom Condo on Spa Creek

Eastport
10.0 out of 10, Exceptional, (11)
"Great location and condo was in perfect condition. Thank you again. Looking forward to staying here again. "
United States
Tim F.
Waterfront 2-Bedroom Condo on Spa Creek
Marina
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

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!
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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Rooms are in the different buildings so we needed to check in to find out where we were staying. Parking is difficult so we chose to pay for valet. Loved the location and it was convenient for Midnight Madness shopping and to great restaurants."
Carolyn Alexandra 1-night trip
Posted 19 hours ago
Historic Inns of Annapolis

Find out more about Annapolis

Everything you need to know about Annapolis vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Annapolis vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Annapolis vacation 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 low season months. For more hustle and bustle, you may prefer to visit Annapolis in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $325 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Annapolis rentals

At Expedia, we put the best Annapolis vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Annapolis?

Yes, there are vacation rentals in Annapolis near Annapolis Maritime Museum, or you can choose a secluded option if you're looking for extra privacy while you relax. Tourists who visit Annapolis speak highly of the college campus and array of shops. While you're in the area, you can also enjoy the top-notch restaurants and marina.

What's the top vacation rental in Annapolis?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: Visitors like this Annapolis vacation home rental. It offers a balcony, a garden, and a barbecue grill 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 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 vacation rentals will I find in Annapolis?

Expedia has 382 vacation 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 vacation rentals like in Annapolis?

Vacation rentals are privately owned properties you can stay in for a short or long stay in Annapolis. Vacation rentals offer amenities such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for families.