Pet-friendly holiday rentals in Annapolis

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.

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.

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.

Jared was timely with every response and very accommodating!

We had a great stay! The yard was perfect for our dog and playing with our grandson. There was plenty of water and the house met all our needs. The neighborhood was fantastic and we loved taking walks and seeing everyone else out walking their kids and dogs! Definitely will come back!!

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 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!

Natalie’s place was just like the pictures. Everything was clean and well stocked for our stay of 6 adults. The sunsets were beautiful from the dock and the kayaks were a definite bonus! We enjoyed time outside on the dock, deck, and in the hot tub! The beds were very comfortable and our stay was great!

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.

Nathan has a lovely home—it feels like stepping back in time into one of old Washington’s charming houses. Everything was spotless and well-maintained, and communication with Nathan was excellent. The location is convenient, about a 25-minute walk to Capitol Hill. While the surrounding area could be better—the streets were a bit dirty—it wasn’t a big deal and didn’t affect our overall experience. We had a wonderful time in Washington, and staying at this house was definitely part of it. Thank you, Nathan!

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.

Cute & spacious boho apartment. My family of 5 was very comfortable inside. Metro & restaurants were close by (5 min or less walk). Free parking pass was great. Currently there is a lot of construction happening in the parking garage and on the street but it wasn’t too loud and once you got used to the few streets that were closed it was easy to drive and walk around the neighborhood.

Martha's place is a lovely retreat. There is enough privacy between the main house and the guest house. The guest house is spacious and comfortable with a great screened in porch and access to the pool. It's in a quiet and peaceful area. I look forward to coming back again.

Thank you Kenny for the hospitality and the coffee! The place was perfect and we had no issues with our stay. We both enjoyed the area and will be back again when Kenny is available of course. Appreciate it!

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.

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.

He was a great host and the neighborhood was perfect for us with little kids ! We had a wonderful weekend away!

We were in town for night. Place was super clean and convenient. Walkable to restaurants but may want to opt for the car. Super convenient if you are attending a football game. Exactly as advertised and what we needed. Hosts were super responsive.

Can’t say enough good things about our stay! Beautiful place with everything we could possibly need. The kitchen was well stocked and our host had thought of everything! Clear instructions, great recommendations for local spots etc. And the huge backyard and deck was perfect for us and our pups. Very comfortable beds and pillows too! Finally, host communicated so well and was incredibly accommodating.

We really enjoyed staying at Carolyn’s place. The house was in a great location. The neighborhood was quiet but close to downtown and also to the highway. The house was very clean and well stocked with everything you could need including a very well stocked kitchen . We had to communicate with Carolyn and her team a couple of times and the response was so quick which was very much appreciated. We loved having the two living spaces to spread out a bit and having a big table with space for everyone to eat at was great. Thank you!

Keith’s water view cottage is so beautiful and peaceful. My husband and I had a lovely long weekend stay with our little dog. Even with the storms that passed through the bay we felt extremely safe and cozy throughout our stay. Keith was very responsive and flexible with checkin /checkout. Would definitely stay again!! Thanks Keith !

Beautiful setting. Very cozy house that was well appointed with everything that we needed for a longer stay. I was able to cook full meals in the kitchen with ease and my husband grilled one night. Other than that, there are local restaurants to enjoy as well. During the day my boys had fun fishing and being out on the water and the sunsets over the lake was definitely worth sticking around for. Unfortunately I had to work during the majority of our stay but I was able to do that seamlessly with the desk and reliable internet connection. Overall we had a great time at Miss Kitty’s Place and would love to stay there again someday.