Family-friendly holiday rentals in Chester

Eric is an amazing host and person! Super friendly when it came to using the amenities and made us feel at home. Has great recommendations for food and local attractions. Beautiful property to walk around or just sit outside! Overall a 10/10 experience while staying at Eric’s home, couldn’t have asked for a better host for our weekend!

This house was absolutely central to all the activities we planned for our trip to Annapolis. Located in a wonderful neighborhood and a beautiful walk away from a tasty coffee shop!

We had an excellent stay! We were able to get a parking spot right out front before the post-work rush. The park across the street and neighborhood were very nice. It was a 20m walk to Fell’s Point and the grocery store and waterfront were a 10m walk. Brandon was a communicative and very thoughtful host. We would certainly stay here again!

Fantastic stay. Veronica was an excellent communicator from pre-booking to check-out. House was very nice, but the pool was exceptional. Home was as described. Thanks for a great weekend.

Our son was getting married and we needed a place that could host family members. Douglas's house fit that bill with lots of bedrooms. Unfortunately only two full baths, but we worked with it. The home is spacious and served our needs well. Douglas allowed us to host a family gathering the day after the wedding to celebrate father's day. The kids loved the pool and the beautiful large yard. Douglas was very responsive and easy to work with. Highly recommend for family stays!

We had a wonderful stay at Brenda’s place! The pool is amazing and the whole outdoor area is great. With the grill, chairs and tables, outdoor fire (two of them!) we had such a great weekend escape. Very quiet area, we didn’t see the hosts the whole time which made it feel private. They were so responsive and helpful all weekend. Wonderful stay and we will definitely be back!

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!

The ultimate Maryland water experience. Beautiful house with perfect amenities to enjoy the bay. With the dock, the view, the crabbing, the fishing, and the kayaking, you save time and money by having everything at your fingertips. The hot tub was wonderful even in summer. The house has everything you could want for a relaxing stay. We ate the crabs we caught every night for a week! Plenty to do and see in the area, too. Definitely want to return!

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.

Stayed here Memorial Day Weekend with my family of 4 and dog and had the most lovely time! The house is very clean and conveniently located to everything! Thomas was an excellent and communicative host. We will most certainly stay here again!

Stanley's place was a great for our two night stay. It is secluded and very private - the garden offers a private oasis and there's plenty of parking! We had four guests stay with tons of suitcases and space was not an issue. The house is older, but very clean. There are three bedrooms that can sleep 2 adults each. The bedroom off the living room is a little warmer than the rest of the house, just an fyi. The kitchen is well stocked with utensils, plates etc. Overall a great stay!

Exactly as pictured and described. Perfect stay and plenty of room. Beautiful back decks and yard. Great neighbors. Would stay again next time we are in the area.

We had an amazing stay at this property! The space was exactly as described. Ingrid was incredibly responsive and thoughtful, providing clear instructions and great local recommendations. The location was perfect—quiet, safe, and close to everything we needed. We’d absolutely stay here again and highly recommend it to anyone looking for a hassle-free and relaxing stay.

We had the most wonderful stay at this Airbnb! The home was absolutely perfect! Clean, cozy, and stocked with everything we could possibly need. Liz went above and beyond to make our trip special, even decorating for my boyfriend’s birthday and leaving us some sweet treats. It was such a thoughtful touch that really made us feel welcome. The fenced in backyard was a dream for our dog, and we loved how peaceful and private it felt. One of our favorite parts was how easy it was to walk downtown, just a short stroll to all the shops, restaurants, and waterfront. Truly a perfect weekend getaway spot. We would 100% stay here again!

A wonderful place to Get-away, have a working vacay, appreciate the outdoors. It's quiet and rests the eyes. Our family agreed that this home is like a ski chalet not on a mountain but rather in Miniature America Maryland on a river. Would love to return.

Jeremy was working to make sure the space was clean for us up until the time we arrived! was very kind and helpful, and provided ideas for things to do in the area!

Words can’t describe how incredible this home/property is! You have the option to just sit by the water or in the hammock watching the birds play and fish jump, or you can do one of the MANY activities Molly has provided for you. Kayaks, canoes, paddle boards, pickleball, yards games, pool activities, etc are all provided. The family room is all windows so it not only provides the most incredible breeze- it is great for enjoying all the sights even if you’re not outside in it. Inside there are tons of toys for kids- you do not have to bring a thing if you have kids. They have inside toys, outside toys, kids life jackets, goggles, water balloons, rafts, floaties, pack and play…. Molly and her family have thought of it ALL. We are already talking about coming back. Molly was the best host- responsive, helpful and inviting.

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

Calvin's place was exactly what we needed and much more. It was described accurately, yet exceeded expectations with tiny details. For example, there was not only coffee and tea available, but creamer in the fridge, too. We had a peaceful night sleep and a nice shower. I recommend this place to anyone needing a quiet space to work and stay in the area.

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.

This lovely house sits on a private lot with spectacular water views. The pool is pristine and was a perfect depth for both the children and the adults. in our group. There were 10 of us (three generations) and we had plenty of room to feel comfortable.

Dorie was fantastic. The space was really wonderful, quiet, and a great place to recharge.

The Pilot House on the Inn at Haven Harbour property was fantastic! For a family with kids this is the perfect amount of space to be able to spread out with two living spaces and 3 bedrooms. We loved having the outdoor dining space as well. The beds were all comfortable and having the kitchen fully equipped was a huge bonus. The location was probably our favorite aspect- just 2 minutes walking to the pool, the on site restaurant, the playground/beach area, etc. and just a 4 minute drive (15 minute walk) to the Rock Hall Main Street. Overall a great experience and stay!

The Woodland retreat is an amazing getaway! My sister and I were extremely happy to spend a weekend at the pool and can't wait to visit again soon!