Annapolis Vacation Rentals

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Vacation Rentals in Annapolis

Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis
Stay at this family-friendly vacation home in Annapolis. Enjoy free WiFi, onsite parking, and a garden. Popular attractions Annapolis City Dock and Westfield ...
4.9/5 Exceptional! (42 reviews)
Wonderful Property
"This property was just perfect. It was close to the beach and had all the amenities we could hope for. Communication with Winston was easy as well. We really enjoyed our stay."

Reviewed on Apr 26, 2022

Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis
Waterfront Oasis of Annapolis Blue
The price is $245 per night from May 17 to May 18
Stay at this vacation home in Annapolis. Enjoy an outdoor pool, WiFi, and onsite parking. Popular attractions Annapolis City Dock and Chesapeake Bay Bridge are ...
5/5 Exceptional! (7 reviews)
Amazing property!
"The location, property, and owners are all amazing. My husband and our 3 kids stayed here for 3 nights and had the best time. It is a great location to anywhere you want to go. The owners are fantastic and even brought us ponchos and umbrellas when a huge storm hit as we were headed to a soccer game. ..."

Reviewed on Oct 25, 2021

Waterfront Oasis of Annapolis Blue
Welcome Aboard the Back of the Moon
Stay at this houseboat in Annapolis. Enjoy WiFi, onsite parking, and a garden. Popular attractions Annapolis City Dock and Westfield Annapolis Mall are located ...
5/5 Exceptional! (3 reviews)
"Great stay out in Annapolis! Dean was easy to plan and communicate with as well as super helpful and welcoming when we arrived. We had plenty of space to move around and enjoy our time on the water. Sitting on the top deck and having access to kayaks made the weekend super enjoyable. We will be ..."

Reviewed on May 2, 2022

Welcome Aboard the Back of the Moon
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Cozy place close to the city dock
Stay at this apartment in Annapolis. Enjoy WiFi, onsite parking, and a balcony. Popular attractions Westfield Annapolis Mall and Annapolis City Dock are located ...
4.8/5 Exceptional! (19 reviews)
Great experience! Close to USNA and Annapolis Inner Harbor.
"Very easy process and Nathalia was very accommodating."

Reviewed on Apr 30, 2022

Cozy place close to the city dock
Anchor's Away in the Heart of Eastport!
The price is $169 per night from Jun 8 to Jun 9
Stay at this apartment in Annapolis. Enjoy free WiFi, onsite parking, and barbecue grills. Popular attractions Annapolis City Dock and Westfield Annapolis Mall ...
4.7/5 Exceptional! (9 reviews)
Perfect Place
"This beautiful efficiency apartment was perfect for our weekend visit with family who live just 3 blocks away. Everything was clean, comfortable, and well decorated!! We hope to stay there when we visit Annapolis again."

Reviewed on Mar 30, 2022

Anchor's Away in the Heart of Eastport!
Waterfront Oasis of Annapolis Gold
The price is $275 per night from May 19 to May 20
Stay at this vacation home in Annapolis. Enjoy an outdoor pool, WiFi, and onsite parking. Popular attractions Annapolis City Dock and Chesapeake Bay Bridge are ...
Waterfront Oasis of Annapolis Gold
Gorgeous Annapolis Getaway - Walk Everywhere, Parking & Private Backyard!
Stay at this family-friendly vacation home in Annapolis. Enjoy free WiFi, onsite parking, and a garden. Our guests praise the family amenities and the property ...
5/5 Exceptional! (69 reviews)
The house is beautiful and had everything we needed. Great location walking distance to downtown.
"We had an amazing stay! The house is beautiful and we loved all of the indoor and outdoor spaces. The house is really well appointed and has everything you need. We loved being walking distance to town. The neighborhood is very friendly and has lots of beautiful waterfront parks."

Reviewed on Apr 24, 2022

Gorgeous Annapolis Getaway - Walk Everywhere, Parking & Private Backyard!
Prime location in Downtown Annapolis - Nice quiet street yet close to it all!
Stay at this apartment in Annapolis. Enjoy WiFi, onsite parking, and a garden. Our guests praise the restaurant and the overall value in our reviews. Popular ...
4.7/5 Exceptional! (63 reviews)
Great place
"Enjoyed the place and would rent again."

Reviewed on Dec 13, 2021

Prime location in Downtown Annapolis - Nice quiet street yet close to it all!
Private coastal Guest Suite with pool. Minutes from Downtown Annapolis and USNA
The price is $175 per night from Jun 7 to Jun 8
Stay at this apartment in Annapolis. Enjoy free WiFi, an outdoor pool, and onsite parking. Popular attractions Chesapeake Bay Bridge and Annapolis City Dock ...
4.9/5 Exceptional! (18 reviews)
Quiet Getaway
"The suite was exactly as described and fit my needs perfectly: a couple days away from home with just enough amenities and comfort."

Reviewed on Mar 28, 2022

Private coastal Guest Suite with pool. Minutes from Downtown Annapolis and USNA
Beautiful Luxury 2 bedroom
Stay at this property in Annapolis. Enjoy WiFi, onsite parking, and a Smart TV. Popular attractions Westfield Annapolis Mall and Annapolis City Dock are located ...
Beautiful Luxury 2 bedroom
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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.

Other types of properties in Annapolis you may be interested in

Crowne Plaza Annapolis, an IHG Hotel

Crowne Plaza Annapolis, an IHG Hotel

3.5 out of 5
173 Jennifer Rd, Annapolis, MD, 21401
The price is $116 per night from May 29 to May 30
Crowne Plaza Annapolis, an IHG Hotel
Graduate Annapolis

Graduate Annapolis

4 out of 5
126 West St, Annapolis, MD, 21401
Fully refundableReserve now, pay when you stay
The price is $127 per night from Jun 13 to Jun 14
Graduate Annapolis
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.

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 months, such as . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year. is the cheapest month to visit, with the most expensive. 

Your chosen location, property type, and amenities will impact the cost of your trip, too. Right now, Annapolis vacation rentals range between $116 per night and $275 per night.

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. 

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