
Condo vacation rentals in Annapolis
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Top-rated condo rentals in Annapolis
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Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Annapolis condo rentals
Weekly condo rentals

Chic Condo w/ Balcony in the Heart of Annapolis!
We found the location of this air bnb to downtown great! We walked everywhere! The apartment was quiet and felt nice and bright and spacious. We loved the garage parking and the ease of getting in and out of the property. We did have an issue when we arrived to the apartment. It took about 45 mins to get ahold of the bnb contact but when they did respond they addressed the issue as quickly as was possible. While it wasn’t the best start of our trip, they went out of their way to compensate us for our lost time spent the first day which we really appreciated. We understand things happen and the way they handled the issue would make me comfortable to use their bnb again. Overall a great place to stay in Annapolis!

Crystal City Boutique Flats / Free Parking 101
Kristen and Laurence were great and very helpful. I was in an unexpected bind and needed a place to stay very last minute. I was able to reserve and get into the apartment with no problem. I was very grateful for their assistance! Crystal City Metro is about a half mile walk and I took it everyday to work. There are a few restaurants on the route, when you do not feel like cooking. They did great remodeling the apartment - it was clean and has a very comfortable king size bed. The few neighbors I ran into were very nice and the building was quiet. Thank you for a great stay!

Historic Federal hills urban lifestyle
Loved staying here for a quick trip! Exteremly walkable and convenient, I definitely recommend!

Downtown Bethesda | 2 Bedrooms + Parking
This was our first time in Bethesda. The condo was perfect for our family’s needs. It was spacious, squeaky clean, and well stocked with essentials. Not only was there easy access to the Metro and DC, we were pleasantly surprised by the vibrancy of downtown Bethesda. Leslie was a fantastic host—she was friendly and super responsive with detailed instructions for check in and recommendations for restaurants in the neighborhood. We would definitely stay there again!

Comfortable 1 Bedroom Condo
Sean’s place was great, I felt right at home. The apartment was exactly how it looked in pictures, he provided every time you could think of and the neighborhood was quiet. i definitely would stay again.

Sunny studio condo in heart of DC
Beautiful place to stay , close to everything , nice area, nice apt , very attentive host .

Chic 2-bedroom condo in the heart of Shaw.
Perfect location and very comfortable for our marathon weekend!

Parkside Retreat Brand New 3-bedroom condo
Having stayed at this property before, the most as usual was great and very responsive and respectful to our needs. The host was very warm and accommodating to our last minute changes. We will definitely will be booking this property again due to amenities and warmth of the host to make our stay enjoyable. Thank you for such a great stay.
Pet-friendly condo rentals

New Downtown Annapolis Condo With Free Parking
Ellen’s place was clean, quiet , comfortable and very well appointed . It felt like home away from home . Ellen was extremely responsive and helpful during the entire booking time. Would definitely recommend this lovely home and hope to come back again soon .

Penthouse, Free Parking, Rooftop + Close to Sights
We took my parents on their first to DC. It was also their first time staying at an Air B&B. The 3 floor (including rooftop patio) penthouse was beautiful and the view was amazing! You can see the Capitol and the Washington Monument from the picture windows and the view is even more spectacular from the rooftop. Rayna was very helpful and communicative, giving us tips on good places to see the Cherry Blossoms and find nice restaurants. NoMa Gallumet Metro station was within walking (or bus) distance for us, but not for my parents (in their 80s), but it was within easy Uber distance. Parking around the back of the building was easy and off street. I loved the modern layout of the penthouse. It is a 3 story walk up. Then, once inside, the bedroom suite, kitchen, dining area, and living room are on the main floor with another bedroom suite (glam bathroom) on the lower floor. We felt very comfortable and at home during our stay and would definitely seek to stay here again.

Spacious Bloomingdale 1BR; garage parking included
Allans place is a 10/10 stay in the Shaw DC area. Clean and comfortable, the host was always responsive and understanding with everything I asked him. The parking is also very convenient and accessible if you have a vehicle. Easy to understand lock and spacious apartment indeed. Very pleased!

Trendy retreat in Bloomingdale with free parking
Pros - clean - big -comfy - well equipped kitchen -self checkin - private free parking - coffee, tea, water and sweets were provided - filtered tap water too Cons: - not very close by metro (20 min) Overall: very good place to stay for couple of days

Hill East BnB - Modern Style and Comfort 3BR/3BA
George was a great host and his place was very nice. Quiet neighborhood and convenient location.

Sunny, New 2BR w/ 65" TV, Firepit, Patio & Parking
Christopher is a great host. He responded immediately to my messages. His place was perfect for our needs. The kitchen was fully equipped and the beds were the most comfortable of any AirBnB I've stayed in. We will return when we visit Washington D.C. again.

Spacious 2-bedroom apartment with loft
Our family of four (one five year old, one seven year old, and two parents) wanted to spend the week of February break touring Washington DC, and this was the perfect unit for us! Commuting to and from the city via public transportation was especially easy.

Entire 2 Bedroom/ 2 Bathroom unit (Heart of SHAW)
Four of us stayed for the weekend. Plenty of room and possibility the cleanest Airbnb I’ve ever booked. The pictures don’t do it justice. The deck is an added bonus. We enjoyed our coffee out there each morning. Came for a show and all the sights so we didn’t explore the neighborhood but walked to brunch after checking out and wished we had more time in Shaw. We would definitely book this place again if we get an opportunity to return. The 2 flights of stairs are the only deterrent if you are someone who has a problem climbing them.
Condo rentals with a pool

1 BR National Harbor near D.C.
Great place, super close to Gaylord where our conference was held. Lots of places to shop and eat within walking distance!

Waterfront Baltimore 2 Bedroom 2 bathroom Apt
The house look just like the pictures wonder view from the roof, and it was relatively clean… I have no complaints. It’s a nice place if you wanna stay near Baltimore Harbor. A+

Beautiful 1 BR Suite at Wyndham National Harbor!
It was a great place to stay for a conference at the Gaylord. Very quick walk, maybe 4 minutes from the convention center. I also was upgraded to a 3 bedroom suite with a balcony. Very cool and spacious.

Wyndham National Harbor- 1 bdrm
Great place, enjoyed the stay while attending a professional conference at nearby convention center.

National Harbor 2bdrm condo near DC, Gaylord, MGM
Wonderful experience! The accommodations were just as described, well kept and comfortable, and the location was perfect. Thanks to Janee as well for answering all my questions and making for a seamless process!

National Harbor, 2 BR Dlx Suite
Christina facilitated an easy and smooth booking and stay experience, it was greatly appreciated! The place was exactly what we needed.

GREAT LOCATION ON SPA CREEK
We’ve stayed here for a few years now. His place is always clean and quiet. Beautiful location and very comfortable.

1st Floor Condo in Annapolis
There are a lot of great restaurants and it’s very quaint in the downtown area. We had a wonderful mini vacation visiting our son.
Quick stats about condo rentals in Annapolis
Total rentals
30 properties
Nightly prices starting at
$57 CAD before taxes and fees
Total number of reviews
2.2K reviews
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
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- Nationals Park
- Lincoln Park
- Patterson Park
- National Mall
- Hampden
- Arlington National Cemetery
- Georgetown University
- Sandy Point State Park
- M&T Bank Stadium
- National Air and Space Museum
- Columbia Country Club
- National Museum of African American History and Culture
- Washington Monument
- Great Falls Park
- American African Museum
- Idlewilde Restoration Project
- The Pentagon
- Gerry Boyle Park
- National Harbor
- Leesylvania State Park
- Georgetown Waterfront Park
- Cove Point Beach
- Six Flags America
- Lake Presidential Golf Club