Pet-friendly holiday rentals in Annapolis

We had a short but nice stay here! We really appreciated the quick responses and thorough explanations of everything. We also appreciated the cookies and couple of waters that we so desperately needed after such a long trip! The place itself is just how it looks in pics and isn’t too far away from the downtown area ☺️

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

Perfect home to stay for our daughters daughters wedding at the Chesapeake Bay Beach Club. Home was spacious , was warm decor. About a half mile walk to town, 1 mile Naval Academy. Beautiful quiet safe neighborhood. Master suite with large closet on first floor. Loved the little extras Megan offered with her home, they were very helpful ( chargers, snacks..) We will def be coming back to a future stay here. Highly recommend.

Everything was great! Would stay again.

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!

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!

Ashley was an excellent host! She was very clear about all the instructions from day one which was great. The place was clean, and the beds were cozy. It did take us a bit to figure out the sink, but she even gave excellent instructions on that. We had a lovely time, it was only a 8 min drive to The Melting pot where we had dinner, and another 10 maybe to get downtown! Lots of parking!

We were looking for a relaxing getaway, and saw an opening at this property. Booked for two weeks, and thoroughly enjoyed our stay… Very large property on the water.. fields and wooded, very quiet, very peaceful. A long dock with a great view of the bay. Supermarket nearby, a couple of very good restaurants. Richard had the house stocked with literally everything needed…. All we provided were groceries! Ducks, geese, herons, ospreys, egrets, songbirds, and several deer provided daily entertainment. Communication was excellent, responses just about instant. Got a chance to meet Mark, who provided some interesting history of this family property. To sum it up, highly recommend!!!

This is a great place to stay and tour the DC Metro area - provided you have a car. Most days it would take us 30 minutes to get to and from DC though if we hit rush-hour, it was as long as an hour. The space is tidy and great. My kids love the pool, though it was a little cold for me-they swam there every night. Jennifer is great to communicate if you have any needs she gets stuff done right away. Note that there is only one bathroom, which can be a pain if you have a full house of six people. The washer and dryer are small so it will take you longer if you’re used to a full size. She had all the cooking methods and appliances available. The theater room has Netflix and Amazon prime ready for you to watch a show. There is even a popcorn maker. We did not use the gym, but it was nice - comparable to a small hotel gym. Property is in the owner’s basement, so there is some sound from upstairs as identified in the listing. Host stays out of your way but is there if you need anything.

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.

We found Paul’s home very comfortable and accommodating. Paul was accessible when we reached out to him and he communicated well with us. It was a very nice location with a fantastic view of the bay, as we hoped for.

Heather's place was as described. Clean and neatly organised. The linens and towels were very clean. The facilities available were adequate. The kitchen is not a full kitchen but has enough for heating. We had left some medicines behind and Heather and her team spotted it, and communicated the same to us. In addition, they took the trouble to drop it off at the local FedEx office.

Jennifer’s place was wonderful! We had a great stay here, and it was in a nice part of town. Plenty of places to eat as well. The apartment was as described.

We absolutely loved our stay here! The space was the perfect getaway for us and our pup especially loved all the walks nearby the property! The space was clean and well-decorated and felt like a relaxing escape from the city. Martha was very responsive and gave great recommendations for places to eat and take hikes. She even provided treats for our pup, which he loved! We are definitely coming back soon!

Immaculate Airbnb, phenomenal location, great value for what it offers. Walkable to so much, 20 min drive to DC, we loved this Airbnb. Thanks to Jomeka for flawless communication. I would recommend this stay.

Modern airbnb in a great location. Very walkable and close to restaurants and grocery stores.

Sarah was a fantastic host and the home was perfect for us. Very convenient location, clean and with a number of unexpected conveniences that really made it feel like home. The little things really added up here (the decks of cards my family played games with, the expansive coffee setup, the extra super soft pillows on each bed). Thank you for the stay, Sarah!

The house is easy to find and has a great outdoor seating area. The house and linens were very clean and Sekai even provided fresh fruit upon arrival! The stocked Kurig pods were very handy and appreciated in the morning as well. From this location you have easy access to downtown Annapolis and all of its history. If you go the other way out of the neighborhood, you can browse the mall and TownCentre for all your other shopping needs. This is a pet friendly house that you would not know there had ever been a dog in there. Fortunately, ours was well behaved so you still won't know a pet was ever there! He enjoyed walking the large private yard.

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.

Nice comfortable apartment. Great quiet residential location with plenty of street parking and accessible to everything. Thank you for offering!

Perfect location as we walked to downtown easily. The backyard was beautifully landscaped, secure and so much fun for our pup to run around in. The house was clean and had everything we needed to complete our stay. We’ll definitely be back!

Ruby on the bay lives up to its name. Such beautiful surroundings - loved being on the deck hearing the wind in the pines. I was grateful to unplug! Excellent size for my sister, me and our fur bosses. Could have comfortably fit 2 - 3 more adults. Nikki was instantly responsive & informative. I would love to return.

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.

This is now one of my favorite places to stay at MD bayside! Definitely love it. It is just perfect fit to relax, and definitely have fun at the same time.