Pet-friendly holiday rentals in Cambridge

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.

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!!

Laurie’s place was just liked it is described. It’s located in a beautiful area and walkable to all the attractions in Annapolis Maryland. I would recommend it and I would stay there again if ever back in Annapolis! Thanks for wonderful stay!

We had a wonderful stay at this well-appointed, cozy, and impeccably clean home. From the moment we arrived, it was clear that every detail had been thoughtfully considered—from the comfortable furnishings to the fully stocked kitchen and fresh linens. The space felt warm and inviting - perfect for relaxing after a long day. Communication with the host was smooth and responsive, and check-in was a breeze. I would absolutely stay here again and highly recommend it to anyone looking for a peaceful and comfortable getaway.

One of the best places we have stayed! Nice and peaceful! We had the best time at Maria’s place.

Very nice house in a great walkable neighborhood. Host were very helpful and responsive.

This Airbnb was amazing!! Honestly even cuter in person compared to the photos! I would recommend this spot to anyone visiting the area!! 10/10 experience!

Truly amazing stay. Our hosts were so kind and proactive with anything we needed. The welcome booklet they made even had itineraries for anything you could possibly want to do. It was a historic home and it was beautifully and tastefully decorated to encourage comfort, relaxation, and family fun. We played almost every board game they had! My family and I created lasting memories that we will cherish forever.

The house was beautiful and clean. The lication was great! Too bad it rain during out stay so we couldn’t enjoy the pool and the backyard. Thank you!

Great deal and pet friendly! Responded when I needed something within seconds and answered any questions I had. Clean and beautiful! Thanks again!

We had such a wonderful stay! The house was beautiful, peaceful, and had everything we needed for a relaxing getaway. The layout was perfect for spending quality time together while still giving everyone space to unwind. Private beach access made it even more special—we made great memories, met some lovely neighbors, and even had a chance to paddle board and spot a stingray! Huge shout-out to Leigh, our amazing host—so thoughtful, responsive, and kind. We’re so grateful for the experience and would absolutely stay here again. Highly recommend!

Great location, close to Rehoboth Beach and good access to stores and restaurants. House was exactly as described, would recommend.

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.

Just spent Thanksgiving weekend at the Bugaboo. What a delightful house. I arrived late Wednesday night and quickly discovered there was no running water. With Thanksgiving being the next day, I assumed nothing could be done until Friday. However, much to my surprise, Rita and Elaine were right on it, knocking on the door early Thursday morning to let me know that water would be restored within hours. And it was! I was so impressed with the quick response and handling of the situation. Before checking out on Sunday, Elaine again visited and told me I didn’t have to rush to be out of the house at checkout time because no one was coming in that day. Again, pleasantly surprised and appreciative. The icing on the cake was that the host reimbursed me for one night’s stay because of the water situation even though I didn’t ask for it or expect it. I definitely plan to rent Bugaboo again. It’s clean, has nice furniture, a most comfortable bed, a great kitchen and a great location!

This was the perfect stay for me and my friends. We needed a place to relax and spend some time together. This place has lots of room and the balcony was such a great place to get some relaxing in and conversation with friends. Vitaliy was a gracious host and was very quick to answer any questions we had. The stores for shopping and groceries were close to his place. Even though the weather was not on our side , We highly recommend his place for an all around great vacation.

We really enjoyed our stay at Sara‘s condo. The location was convenient to a lot of activities, and we appreciated the shopping center within walking distance. Our dog also enjoyed his stay! Thank you for the friendly, welcoming touches such as the complementary waters and snack/coffee as well as the dog treats! We would stay here again :-)

Enjoyable getaway in Blackwater area. The cabin really felt off the grid, and I enjoyed the wide selection of movies and non-internet entertainment. The area is very buggy when we went in early June, I wasn't quite ready for that as Cambridge is not. I liked the feel and would recommend it for anyone looking for quiet and remote feeling, but not challenging to get to.

Perfect for our group for the weekend. Owners are very responsive and accommodating! Cozy and well kept house. Would book again!

My husband, dog, and I enjoyed a wonderful Thanksgiving break at this very nice and beautifully situated cottage! The views from the back deck and kitchen are as gorgeous as the listing photos suggest and, while the house is right next door to another one, we heard not a peep from the neighbors during our 5 days there. Everything was very attractive and well thought out - the kitchen was well appointed with everything we needed; the chairs, sofa, and bed were super comfy, the bathroom was clean and cheerful. Maxine was great host, answering all our questions quickly and helpfully. It's a 15-20 minute drive to downtown Cambridge, where we had nice dinners out in town at Blue Ruin and Bombay Social. We also took good day trips to Easton, St. Michaels, the Blackwater National Wildlife Refuge, and the impressive Harriet Tubman Underground Railroad Park and Visitor Center. The whole area is full of beauty and history, and this cottage was a great home base!

David and Wendy’s home was the perfect place for our family participating in and supporting the Cambridge Ironman with an easy walk to the course and to the Main Street. They went above and beyond accommodating our requests, since we were traveling with a two month old and a two year old. We were very comfortable and loved our evenings in the screened in porch and pool. We would love to stay at David and Wendy’s again.

Clare was super responsive, and got right back to me with recommendations for restaurants and answering any questions. The home was great for our party and we were able to walk downtown to restaurants and shops. Beds and pillows were very comfortable. Overall a great stay!

Beautiful, clean home ! Nice new appliances and comfortable stay !

A beautiful home in a great quiet location. This home has everything you need was a great stay. Ramona is a great host.

Although we had been to Maryland before on holidays, we hadn’t been to the Eastern Shore before and we loved the location and the incredibly friendly locals who made us feel very welcome. The pace of life suited us just fine as we’re rural folks too. Many happy memories made and special shout out to Jacob at the nearby Neck District Grill for feeding us so well!