10 Vacation Rentals In Annapolis, Maryland - Updated 2022


The historic city of Annapolis is located in Maryland, USA. This city is best known for the United States sailboats show and its historic Maryland statehouse. Thanks to the United States sailboat show, Annapolis has grown to be a popular tourist destination. There are also other amenities which makes Annapolis preferable such as, naval academy, Banneker Douglass museum and the bricked streets which are lined with classy shops, boutiques, hotels restaurants, and cafes. If you choose Annapolis as your destination, to make your stay better, check out these affordable vacation rentals in Annapolis, Maryland. Book the one that suits you best, as you will not be disappointed.

1. Condominium in the heart of the historic city (from USD 265)

At an affordable price, you can secure this three-bedroom home located in the historic town centre of Annapolis downtown. This apartment is located on the main street close to several amenities including restaurants, shops and coffee bars. For maximum comfort during your stay, the apartment is packed with one queen bed with very comfortable mattress in the bedrooms, a fully equipped kitchen with granite countertops and stainless appliances, stereo and 42-inch flat screen in the living room, and a private bathroom with a walking-shower and a water closet. Come with your old family and enjoy the Annapolis water, sites, live music entertainments and piano bars.

Annapolis Condominium in the heart of the historic center
204 reviews  Wifi Available
condo 6 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 6
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 14 days before check-in.

Top guest reviews
Amenities & Room:
great apartment is very comfortable
there is one more set of stairs inside the front door
The outside temp was warm so returning to the condo
there are 4 flights of stairs to climb to get there
The condo is spacious clean and very comfortable; and the rooftop deck is the icing on the cake
It was exactly as described and
the place is spacious clean
quiet and can easily accommodate 6 persons
Christina was a quick communicator and made the check in and out processes more than simple
the Christina was very attentive to our emails
Christina is an absolute gem of a person/rental owner/host; communication with her and the check-in process was seamless and worry-free
Stairs and absence of private parking was not an issue for us but may need to be taken in consideration by some Communication with the owner was easy and cordial Thanks Christina for the great e...
We arrived after dark and the owner prepped the place by turning on the lights Very nice after traveling all day Comfortable space and temperature
Great place to stay for a visit to Annapolis everything in walking distance
got everything you need if you want to cook and is also close to main street restaurants if you don't
Very conveniently situated close to Main street
This was an ideal location for a "stay-cation"
As locals to the area
Read more reviews

2. A bright and cosy home near everything (from USD 275)

While you are here, you should enjoy this beautiful two-bedroom home located at the heart of Annapolis only five minutes away from several amenities including shops, bars, restaurants and hotels. If you book this accommodation you should expect it to have modern in house amenities such as a cable TV, air conditioning, fire extinguisher and a music system. If you are in Annapolis for football games, couple getaways or family getaway this is the place you should rather be. Towels, linen and toiletries are also provided by the host.

Come enjoy Historic Annapolis!
91 reviews  Wifi Available
House 5 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 5
Minimum Nights: 1
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
The beds were extremely comfortable and the kitchen modern and well stocked
The kitchen is well-equiped and the beds were very comfortable
The house was great Plenty of room and the beds were comfortable
All you could ask for - a little home away from home
The additional charges should be transparent when agreeing to the rental
The property was sparkling clean
It was very clean and had everything we needed
The unit was also very clean
This was important as parking was very limited and once parked we were hesitant to move the car House very clean and comfortable for 4 adults and one teen
well appointed and exceeded our expectations
Love this property and will definitely be returning for more trips in the future
and I fell in love with the City Accommodations
The Hosts quickly answered any?all questions both beforehand and throughout our stay Highly recommend this property and look forward to returning
Loved the character & charm affiliated with this quaint home
Easy walk to good restaurants
House is beautifully kept and in a great neighborhood a few minutes walk to downtown yet
Ego Alley (walking distance) perfect for leisurlely people and boat watching from sidewalk cafes
25 Steps to the Naval Academy and 2 short blocks to the MarketPlace City Dock and Shopping
It was a great location with easy access to downtown and the Naval Academy
Read more reviews

3. Charming home in the historic District (from USD 264)

This is a very clean, spacious and charming accommodation located in a very safe and quiet residential street at the heart of Annapolis. If you book this accommodation, you will be within a walking distance to shops, restaurants, coffee shops, pubs and few blocks away from United States Naval Academy and Main Street. The accommodation features two bedrooms and has the capability to accommodate up to six guests. The most important in-house features include comfy beds, private bathroom, a study table, large dining room, fully equipped kitchen; washer, dryer, free WIFI, flat-screen TV, coffee maker, iron box, and polished wooden floorboards to offer warmth. This accommodation is perfect for family and friends’ getaways.

Charming Row House in Historic District
Annapolis, Maryland, United States
456 reviews  Wifi Available
Entire home 3 Beds 6 Guests 2 Bedrooms 1 Bathroom

Accommodates: 6

Top guest reviews
Amenities & Room:
the beds were super comfy and we had everything we needed
the entire space was very comfortable especially the beds
comfy beds coffee and a nice bottle of wine was there on my arrival
the bedrooms were comfortable and we found the space perfect for our two kids
very clean and comfortable
very clean and comfortable
ami and sean’s place was spotless gorgeous and incredibly convenient
clean beautifully decorated and well-stocked
ami & sean were great hosts the house was clean cozy and comfortable
the hosts are very hospitable and welcoming
hosts were very helpful and engaged
they were so helpful and quick to respond
would 100% stay again the hosts was very helpful and kind
our hosts provided everything we needed and made our stay really nice
awesome location and wonderful house
great location quiet but very walkable
the location was amazing very short walking distance to main street and nice neighborhood
right in the middle of annapolis and easy to walk everywhere
very nice place and location is within walking distance to the center of town
Read more reviews

4. Spacious loft at the centre of the city (from USD 160)

Looking for the best accommodation in Annapolis? Then this luxurious apartment should be your first and maybe only option. It is located only five minutes from the town centre of Annapolis close to several amenities including shops, pubs and restaurants. The accommodation features important amenities such as comfy beds, a sofa bed, unlimited internet access and a kitchen which is fully equipped with a fridge, microwave, sink, oven, dishwasher and coffee maker, flat-screen TV and hangers. This accommodation is highly preferred by guests because they offer the best customer care services and the place is of high hygiene. Come enjoy!

Step Out to Main Street From a Chic Loft
Annapolis, Maryland, United States
714 reviews Superhost  Wifi Available
Entire loft 1 Bed 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
nice view of the capitol dome from the living room window
bed was comfortable and all amenities well appointed
it was incredibly clean and comfortable
it was very clean and matt is very accommodating
stylish fun and clean
the place was spotless and very nicely appointed inside
sparkling clean super cute
matt is an awesome host
matt was great host and simple to check-in/checkout
) matt was a great host and very accommodating
matt was responsive provide clear instructions was accommodating of our request to drop our bags early
the entire check-in process was so simple and matt was very friendly
great location for walking to everything
perfect location and a great place
perfect location and wonderful loft
great location for easy access to downtown annapolis
we loved being walking distance from everything
Read more reviews

5. Unique apartment on Main Street (from USD 135)

Come and experience an unforgettable holiday in Annapolis by booking this unique apartment located in downtown Main Street. Its location gives easy access to restaurants, pubs, shops and all that Annapolis has to offer. This accommodation is spacious enough for up to six guests and it is furnished with modern amenities such as a cable TV, a comfy couch and air conditioning. As for your sleeping arrangements, all the bedroom have comfy beds, a dressing table and a wardrobe. For those who prefer preparing their own meals, the kitchen is fully equipped with a microwave, toaster, fridge and oven. If you are looking for the perfect holiday getaway experience look no more. This is the place to be.

Modern Apartment over the Heart of Main Street!
Annapolis, Maryland, United States
457 reviews Superhost  Wifi Available
Entire rental unit 2 Beds 6 Guests 2 Bedrooms 1 Bathroom

Accommodates: 6

Top guest reviews
Amenities & Room:
the beds were super comfortable
comfortable bed and with earplugs just in case slept great every night
two comfortable bedrooms nice sitting room and a kitchenette
we had a heater on (the apartment was pretty chilly) and the tv at the same time
the place was beautiful and the beds were very comfortable
clean and spacious space
clean and spacious 2 bedroom
place was super clean and spectacular
the unit was really clean updated and set up well
apartment very clean with extremely comfortable beds
helpful and nice host
matt was an amazing host
matt was an awesome host
restaurant staff was very friendly and respectful of our privacy
nice touches from the host matt
great location on main st
we loved the location it was close to everything
great location easy access to downtown
the location was excellent with everything in walking distance
great location right in the middle of everything
Read more reviews

6. Renovated historic home in Annapolis

Come and unwind in this three-bedroom home located the heart of downtown Annapolis. The first thing you will love about this accommodation is its strategic position near a historic church, the Main Street, Annapolis City Dock, and Gate #1 of USNA. By booking this accommodation, you will be able to enjoy their facilities including the wood floor, tin copper ceiling, block counters, comfortable dining table, outdoor grill and queen-size beds. This home can comfortably accommodate up to six guests and you can request for an additional queen air mattress. Come enjoy the charm of this historic home in downtown Annapolis. This accommodation is ideal for team bonding, larger groups and wedding parties.

Renovated Historic Home located downtown with parking - Walk everywhere !
208 reviews  Wifi Available
House 6 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 6
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
Parking was an ease with the pass provided
we had everything we needed in the well-stocked kitchen
The property is well appointed with comfortable modern conveniences in an older home
We had a comfortable 4 night stay for 4 adults in historic Annapolis
Very cozy & comfortable home Highly recommend
The home was very clean and Meghan (property manager)
Very comfortable & nicely furnished- had everything that I needed Clean & Megan
The property manager was very accessible and lovely (as indicated through her helpful texts in response to our queries)
The house had everything we needed and the five of us (all adults) were very comfortable
was so helpful and gracious
Perfect location Very responsive and helpful home owner
left me some helpful tips about the CVS basically being a "mini mart" - very good salads there
We had the best vacation
We had high hopes but were disappointed
Great location: just around corner from neighborhood park walk to town and to
but the times we did eat at the house
Perfect location that is indeed walking distance from DTA and USNA Quaint street with really nice neighbors too
I have never slept better
Upstairs bath a little small but not a deal breaker
Read more reviews

7. Newly renovated apartment in downtown Annapolis (from USD 218)

Now that you have decided that Annapolis will be your vacation destination, come and enjoy this newly renovated apartment located at the heart of Annapolis. It is located within the walking distance of some of the best shops, pubs, and restaurants in Annapolis. Thanks to its spacious nature, the accommodation can comfortably accommodate up to four guests. For maximum comfort during your stay, the accommodation features a queen bed, fresh sheets and towels, a fully packed kitchen with utensils, a microwave, a fridge, and a dishwasher. As for your entertainment, the living room is equipped with a convertible futon, flat-screen TV, free WIFI, front porch, central heating, and air conditioner. This apartment is ideal for long-stay family getaways. You won’t be disappointed.

Pet Friendly, walk Downtown Annapolis w/ full kitchen washer/dryer...
65 reviews  Wifi Available
Apartment 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
The railcar layout of the place with one room leading to the next was odd
I think it was because of the holiday
Plenty of room for a dad and three kids
The kitchen was equipped with table settings a coffeemaker and some other basics
but the rooms suited our needs for planning and preparing our day trips
Very pleasantly decorated Very clean and walking distance to everything
Highly recommend Very clean and comfortable Washer and dryer come in handy
Very clean recently updated and fully equipped
Walking distance to everything clean comfortable and overall neat little place
Very clean comfortable and excellent communication
The unit was clean didn't lack for anything and easily sleeps 4 though with one rather small bath it would be tight for that many Spoke with the owner who is a very nice guy he immediately fi...
Clean well maintained and comfortable
the owner was very easy to work with and everything we needed was available
Parking pass was awesome to have We are in love with Annapolis and excited to continue visiting for the next 4 years
shops ice cream pet-friendly 40 minute boat ride Naval Academy
Short walk to Annapolis Parking is not a problem at all
Most sights within walking distance Big plus
a sea of white uniforms walking all around
We really liked that it was just a short walk to Main street
The location was ideal for visiting my daughter during her plebe summer parent weekend
Read more reviews

8. Great location and easy access (from USD 167)

This is one of the best accommodations that you can find in Annapolis. Given its demand, only a minimum of two nights booking is processed here. This gorgeous apartment offers the modern amenities such as a big and spacious living room with a very comfy pull-out couch, a flat-screen TV, a queen-size bed and another TV in the bedroom. For those who like cooking, the kitchen is fully equipped with everything you may need including a microwave, stove, family-sized fridge, and Keurig. For a small family getaway, you won’t be disappointed.

Legislative Session Available
23 reviews  Wifi Available
Apartment 3 Guests 1 Bedroom 1 Bathroom

Accommodates: 3
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 14 days before check-in.

Top guest reviews
Amenities & Room:
Got to our stay late; no trouble getting in Bed nearly filled the room but was comfortable and welcome after nine hours on the road
King George Pied-a-Terre is a wonderful apartment in a historic row house
Plenty of room for our stuff and a nice family/sitting room
We were perfectly located with almost immediate access to everything we needed or wanted to do
Apartment was clean and cozy Loved
The apartment we had was wonderful Updated kitchenette with modern appliances
the unit is functional clean and in a great location
Julann was very responsive to all our pre-trip questions
so we love the whole historical atmosphere
This is a great location with really easy access to Gate 1 and DTA Julann was very responsive and helpful throughout our stay
It is in the perfect location for a visit to downtown Annapolis and surrounding area
Very convenient to walk to USNA Gate 1 from here Beautiful view of the Chapel Dome Host
It is within walking distance of USNA and the inner harbor restaurants bars and shops
Perfect spot for Academy events or a visit to annapolis Easy walk to restaurants and shopping Comfy accomdations
King George Street is busy during the day but otherwise fairly quiet and convenient to downtown Annapolis Would gladly stay there again
Read more reviews

9. Luxurious accommodation with stunning views

This lovely house is a newly renovated excellent apartment strategically located in the historic district of Annapolis just less than five minutes’ walk from away from the naval academy. Given its spacious nature, this accommodation is capable of hosting up to nine guests. The home consists of a living room which is furnished with a dining table for six, two sofa beds and LED TV. You will also have access to the kitchen which is fully equipped with a microwave, oven, toaster and a fridge. As for your sleeping arrangement, all the three bedrooms have queen beds and LED TV. Booking this accommodation will place you in a very ideal location for everything which Annapolis has to offer including museums, pubs, shopping, and restaurants which are all a short walk away and its free from late night bars and traffic noises.

Historic District - Two blocks to Main Street!
67 reviews
House 9 Guests 3 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
the kitchen has everything you need
All was easy to find and use
the parking garage is just around the corner We did miss the one off street parking space that use to come with the rental
The house will well appointed
The 6 of us loved this home - beautiful comfortable
The manager was very easy and the House was exactly as pictured
Great home in a convenient location Rooms and linens were very clean
Ms DePew was extremely helpful with our visit
This property is all that and more
Spent a long weekend with three generations to enjoy historic Annapolis
well supplied and amazing location
Beautiful home was spacious for our 6 guests
Beautiful property in a quiet location but close to everything
we loved walking around Annapolis shopping and eating
The house was close to everywhere
The house has lots of convienences towles sheets and walking distance to downtown shops
Charming and historic house in the heart of Annapolis
Read more reviews

10. Cozy home close to the city dock

For the perfect vacation experience in Annapolis, you should book this cosy apartment located in a gorgeous environment three minutes’ drive from the historic town centre. Given its spacious nature, the accommodation can easily accommodate up to three guests. It consists of a single bedroom, a living room, kitchen and a private bathroom. For maximum comfort, the guest is offered amenities including unlimited access to the internet and flat-screen TV. For those who prefer to prepare their own meals, the kitchen is a fully equipped kitchen with all basics like microwave, oven, toaster, unit sink and fridge. This place is ideal for business travellers, romantic couples, and solo adventurers. Come experience the charm.

Annapolis cozy place-close to the city dock!
Annapolis, Maryland, United States
96 reviews
Entire apartment 2 Beds 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
nathalie was very flexible and made sure that our stay was as comfortable and worry-free as possible
great location attentive host tv the size of a computer screen (in the bedroom not the living room)
we had a lovely stay in this apartment
we felt very relaxed welcomed (email hidden by airbnb) fy bed
it is clean and cozy
it was very clean and all went well
very clean quiet comfortable place
it was clean comfortable and quiet
nathalie place was clean quiet and bed was great
she was very responsive with any questions or concerns
nathalie was a wonderful host
our host was very easy to work with
the space is wonderful and she is a wonderful host
the host is super nice and is always on the line to answer our needs
very cute cozy apartment in a great location
it was a great location for the price
perfect location for the archives and downtown
great little place close to everything
great cozy place close to plenty of restaurants and the mall
Read more reviews

Explore Annapolis

Whether you are here for business or just for fun when you are Annapolis you are never out of options to stay. Check them out, book one and enjoy.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

Get Trip101 in your inbox

Unsubscribe in one click. See our privacy policy for more information on how we use your data

 Want to contribute as a Local Expert?
Explore Annapolis
Good things are meant to be shared!