
House vacation rentals in Annapolis
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Top-rated house rentals in Annapolis
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Popular amenities for Annapolis house rentals
House rentals with a pool

Bay Breeze Retreat
Fabulous views of Chesapeake Bay, pool was great, deer everywhere, house was spacious with three living areas. Would definitely stay there again.

Gorgeous, waterfront home - Perfect for Families.
Clare and Chris could not be nicer and easier to work with. My family/friends have been getting together since 1994 and have been to many great Airbnb's and VRBO's. My group could not stop telling me how great of a week we had. The primary features that were import to us which the house scored big are as follows: It has a dock (we arrived via boat), The kitchen is big, laid out for many "Cooks", The kitchen was open to the dining room table, The dining room table is open to the sitting areas, The pool was clean and inviting, The fire pit with seasoned firewood was a big hit for our group, All the beds were comfortable, The bedrooms were large and comfortable, The baths were clean, modern & large and The location to "What to do in Cambridge" is only 7-10 miles away. We made prearrangements: Richardson Maritime Museum to have a guided tour with David Williams on Friday and Spocott Windmill with George Radcliff. Both of these tours were fascinating. Our weekend was 5-Stars.

Large Home with Pool & 7 bedrooms; sleeps 21
This home was the perfect place to celebrate my daughter’s graduation! We had family travel in from several states, and everyone felt comfortable and truly enjoyed the spacious layout. It was a bit too chilly to use the pool, but I’m already looking forward to booking this home again. I’ll definitely be a repeat renter!

Waterfront Farmhouse Meets Modern Luxury
The house is beautiful and worked well for our family. The host was very helpful and responded quickly to any questions we had. The grounds are lovely and very peaceful. Pictures don’t do this property justice.

South River Beach Front House
I stayed here the week of my wedding and it was absolutely perfect! From waking up each morning to have coffee on the dock with my pups and husband, to the beautiful views from each room in the house, we truly had a lovely time and chose the right Airbnb for such a special week in our lives.

Gunpowder Retreat
This house was perfect for our stay in MD. Our family of six was very comfortable here and our kids loved the pool and spa. The house is clean, cute and very cozy. Tanya was very quick to respond and great to work with!

5 BEDR, Inground Pool+Billiard Table, Close To D.C
This place is fantastic for a stay. Daniel is super communicative and quick to respond. Plus, the pool is impeccably clean.

The Little Gypsy BoHome
Wonderful place - pictures do not do it justice. Home is spotless and beautifully furnished! We had a great time relaxing on our babymoon. Lots of great restaurants close by and so much to do at the house you never have to leave. Really appreciated the details such as the coloring station and ample beach towels. Hope to stay again in the future!
House rentals with free parking

Annapolis USNA Cottage Waterfront Pier Cozy Escape
Very quiet location but not far from amenities. The home had an attention to detail that not all air bnbs do (for example enough towel hooks for everyone staying!) as well as basic cooking amenities

Wright's Cottage- Pet's Welcome & EV Charging
Danielle’s place was the perfect spot for a short getaway. While it’s on the smaller side, it was comfortable and worked out great for two people and our two dogs. We didn’t spend a ton of time indoors, but we loved relaxing by the outdoor fireplace in the evenings, such a nice touch! It’s about a 20-minute drive to downtown Annapolis, offering the best of both worlds: close to the city, but a peaceful escape from the hustle and bustle.

Peaceful Waterfront Home in Annapolis 3BR 2BA.
Gwen’s peaceful waterfront retreat was truly just that—peaceful and relaxing! From the moment we arrived, we felt welcomed and at home. Gwen was a gracious and responsive host, making sure everything was perfect for our stay. The property was filled with thoughtful touches and amenities that made our visit incredibly comfortable: a charming gazebo dining area, outdoor kitchen, a coffee bar, fresh flowers (such a lovely touch!), and more. The beds and bedding were comfortable, ensuring a great night’s sleep. The neighborhood is beautiful and quiet, with access to a private beach area that made the whole experience feel extra special. The highlight of our stay was undoubtedly the incredible dock experience—sitting right on the water, surrounded by nature, with comfortable chairs perfectly placed to enjoy morning coffee, afternoon sun, or stunning sunsets. Highly recommend for anyone looking to unwind in a serene waterfront setting!

Chesapeake Paradise Lite 4-5 Br 3 Ba Vacation Home
This air b&b is in a beautiful setting with plenty to do (kayaking, hot tub, fire pits, bird watching, etc). It's also very centrally located so we could easily get to more populated areas in no time. The most stunning part of the house is the master suite in my opinion which is on the upper level (the upper level is shared with another apartment, but you don't really hear the air b&b tenants of this suite and it's completely separate with a separate entrance). Stunning views from both the master bedroom and the bath tub in the master suite! The downstairs is also quite lovely with two regular bedrooms, one small bedroom, and a sun room that has a pull out couch (we didn't use it). It's a lovely house to entertain in. It has personal photographs to the owner downstairs that speak to the family's history. The owner is communicative. The overall experience was quite lovely. We'd be happy to return.

Waterfront, Dog-friendly, Hot Tub, Peleton
We had the most amazing weekend. All of Kimberly’s recommendations were right on the money, and we were so impressed by the cleanliness, comfort and beauty of the home! Watching the sunrise over the water every morning from the front porch was heavenly!

Rachel's BnB
Above & beyond! The home was in a great spot with an excellent price. Tim was extremely accommodating with our requests and communication was perfect. The refrigerator was stocked with eggs and butter. The cupboards were stocked with staples and all the supplies we needed - toilet soap, shampoo, Kleenex, paper towels, bath towels, snacks, granola bars, etc. We would highly recommend this Airbnb to anyone and would use again. Thank you!

Downtown Annapolis Home
We booked Laura’s property 2 years in advance for Commissioning Week. Throughout the 2 years she answered our questions quickly and effectively. The house had room for 2 parents, 2 grandparents, and 1 sibling. Basement area is nice and private. The house looked just like the pictures. The driveway is hard to get out of during busy times, as it is on a roundabout. However, it was easily walkable to the stadium in less than 13 mins (perfect for graduation/commissioning week, as you have to pay for parking if you want to take the shuttle from the stadium to the yard). It is also walkable along West St, where all the shops and restaurants are. The furthest restaurant is 1 mile away, but there are many spots that are closer. It’s about 1.2 miles from Gate 1. You can take the free downtown shuttle that goes along West St if you don’t want to walk all the way. Overall a great place to stay when visiting a Midshipman or celebrating graduation!

Welcome to Heron House! Annapolis Waterfront Oasis
Very peaceful surroundings, you are out on a point overlooking the bay, with lots of outside space to relax in the mornings to enjoy your morning tea/coffee. I loved having the real fireplace and enjoyed an evening fire on the more chillier evenings. Felt at home and comfy.
Family-friendly house rentals

West Annapolis SuperHost!
Perfect location if you’re in Annapolis for a game or just to visit the city. Christopher’s house was the perfect location and distance from everything in the city. Also, very spacious and nice house perfect for me and my 4 other friends.

Luxury Townhouse. Roof Deck. Patios & Parking
A gorgeous gem in the center of everything! Ally’s place is clean, comfortable, and beautifully decorated. We cooked several meals in the well-stocked kitchen, enjoyed time on the sunny patio, and walked to many amazing restaurants and shops. There were lots of thoughtful details - from the umbrella that helped out in a sudden rain storm to the labels on the light switches. Truly a gorgeous property in a prime location!

Secluded acre near BWI and Baltimore
What a beautiful little spot of heaven at the end of the long driveway nicely tucked back with orioles, bunnies and even two kitties running around outside, inside is the so quaint and comfy and clean. The view out the windows gave peace and the fireflies at night were so cool. Stanley went above and beyond to be accommodating on our trip and his place is top notch. 10/10 would stay again

The Oxford House
This place is nicely furnished and the kitchen/dining area are very well supplied. We always enjoy our time in Oxford and the surrounding area and Suzanne Marie's place made it very comfortable. Walkable to the market, coffee shop, ice cream shop and 2 restaurants.

Sunny, private apartment in historic neighborhood
This is a great place. Its sunny, easy to access, parking was great. The bed was very comfy. We had a good stay.

BWI, Baltimore, Annapolis, DC, USNA - entire house
Craig is a great host. Very proactive and responsive in his communication. His place was perfect for our group. Overall a great stay. Would definitely stay there again.

Spacious relaxing home by DC, CP, woods & lake
We've stayed at Kopal's quite a few times - very peaceful neighborhood, very close to Lake Artemisia, which is lovely for walking, also very close to College Park. Great location. The house is always very clean, well-equipped and Kopal is so responsive.

Chesapeake Waterfront-Kayaks-Crab-Fish-FirePit-Spa
This was a beautiful waterfront home! This home was well equipped with everything you may need! The host was available if we needed anything! Would definitely recommend!
Quick stats about house rentals in Annapolis
Total rentals
390 properties
Total number of reviews
14K reviews
Family-friendly rentals
340 properties are a good fit for families
Pet-friendly rentals
130 properties allow pets
Rentals with dedicated workspaces
230 properties have a dedicated workspace
Wifi availability
390 properties include access to wifi
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- Nationals Park
- The White House
- Betterton Beach
- National Mall
- Georgetown University
- Hampden
- Oriole Park at Camden Yards
- National Museum of African American History and Culture
- Smithsonian National Museum of Natural History
- District Wharf
- M&T Bank Stadium
- Sandy Point State Park
- Arlington National Cemetery
- Washington Monument
- Georgetown Waterfront Park
- Patterson Park
- National Air and Space Museum
- Great Falls Park
- National Harbor
- Smithsonian American Art Museum
- Meridian Hill Park
- Lincoln Park
- Congressional Country Club
- Crystal Beach Manor, Earleville, MD