
Kid-friendly vacation rentals in Dorchester County
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Top-rated kid-friendly rentals in Dorchester County
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Popular amenities for Dorchester County kid-friendly rentals
Kid-friendly house rentals

Spacious Lakefront Cottage w/ Private Pier
Awesome place and looked like the pictures. Crabbing was easy and kayaks were a lot of fun. Don’t use the elevator

Family Retreat - Private Pool, 4 Bedroom, Fire Pit
Wow. The pictures don't do this place justice -- at all. What an extraordinary layout, especially for larger groups who all enjoy a bit of personal space and quiet. There are nooks and spots for everyone and everything, from the awesome pool area to the endless spots to sit and read a book or enjoy some coffee. And Ann! What a gem. She bent over backwards to answer questions and make us feel at home, even providing us with special coffee and food recommendations. I've been using Airbnb for a while now -- and Ann is the #1 host I've ever come across. I mean...she's a joy. Her place, of course, is amazing and you'd be a fool not to stay! 10 Stars!

Peace Point - Waterfront, Secluded, Home w/hot tub
I don’t know if I can express how much I loved our stay at Rich and Yumi’s place. The property is very beautiful, private and very peaceful. We enjoyed fishing and taking in all of the sights and sounds of nature surrounding us. The fire pit area and hot tub were very nice additions to the property. The house was very clean and comfortable. The house was very well stocked. Rich and Yumi pay great attention to detail. We were greeted by a nice welcome basket and card to welcome us. After departing we realized that my daughter had forgotten a few items. Rich was very responsive and helpful in locating the items and arranging to ship them to us. I absolutely fell in love with this place and definitely plan to return in the future. Thank you very much Rich and Yumi for sharing your amazing property with us!

Beachfront Chesapeake Bay Retreat
We enjoyed our stay in Maggie & James’s quaint and cozy home. The area was quiet and like something out of a book with all the locals and marina and restaurant. Our teens enjoyed playing board games from their childhood even though there were games there for their age group. We were gifted a beautiful loaf of sourdough bread from our hosts. So very thoughtful! If you plan to stay there be sure to check the weather and high tide schedule due to coastal flooding. You’re between the sound and the marshes and low roads can get covered with water. If you’re arriving at night it can be difficult to see where the road ends and the marshy area begins. We enjoyed our stay and our teens want to return when we can have more time sitting out on the beach by the water which is just a few steps from their home.

Rumbley Retreat
Came down for a duck hunting trip! The place was perfect! Very clean and cozy! Hope the owner was very attentive and quick to respond with any questions! If in the area again I will definitely book again!

Pet-Friendly Cottage – Ideal for Summer Getaways!
The Waterman has beautiful views, is very quiet and has well clean, appointed rooms. The beds were extremely comfortable.

Our Bay House-Your Home Away from Home!
I had a great stay at Edna's! It was a wonderful place to rest after long work days. Edna asked what temperature we wanted the place and we chose 70 degrees. One of the bedrooms got much warmer than that, and one of the bedrooms was much colder than the target temperature. I know the thermostat was new to them, but that is my only small complaint. Everything else was excellent!

Great Historic Cambridge Home With Parking!
What a gem! My daughters and I loved our week spent here. The home is a true beauty with all the charm of a seaside getaway. All of the amenities truly made it feel like home, and the kitchen is amazing! Everything was streamlined and easy, the host was wonderfully responsive, and the home had such a friendly, warm, relaxing feel to it. It was such a terrific experience through and through, I would highly recommend taking full advantage of this beaut!
Kid-friendly apartment rentals

ALL INCLUDED- Chic Move in Ready
Convenient for working on a boat in Oxford. Less expensive than staying in Oxford.

The Grove Studio
Never rented an Airbnb before. Was amazed how easy it was, the place was perfect for my needs. Al was responsive when I contacted him, always kind and courteous. Decided to rent another one of his locations after my time at this one ended. Looking forward to it. Place was clean, accessible, private, easy to reach and I truly enjoyed myself. Will recommend his rentals to family and friends.

2nd floor studio apartment
I enjoyed my stay here while attending a conference at the Hyatt Regency. It was quiet, clean, and convenient. The hosts were very responsive and accommodating. Highly recommend!

Cozy apartment in Dorchester County
The Edgar's were warm & welcoming! It's a lovely secluded property. They treated us like longtime friends!

Cozy 3rd Floor Apartment in Historic West End
We actually ended up staying at another property of Mary’s because of a boiler issue at the original place. Mary got in touch immediately & offered an upgrade for the price of our original stay. She made sure we got everything we needed, sending over supplies & solving an issue with the tv. A super responsive host and we much appreciated that! The place we ended up at was right on the Choptank River with gorgeous views and even ducks to feed!!! (Mary supplied the duck food!) A great, relaxing stay!!

Historic St. Mary's City, MD
The location was beautiful and the home was very cozy. Sitting on the screened porch, reading and enjoying the view of the yard and water was good for the soul. It was very quiet and we had all the amenities we needed.

Morning Light Apartment
Such a cozy place to stay with all of the necessary amenities. We had a wonderful weekend and would absolutely come back again!

Eden Farm: Private Studio Minutes from Salisbury
Our stay was lovely! The property is quiet and peaceful. The apartment is right above the roosters so we could hear them crow every morning, but it didn't bother us. The parking is a bit of a walk from the apartment, but everything was clearly labeled and easy to find. The kitchen had basic pots and pans, plates and bowls, and utensils. But did not have things like cooking oil, salt/pepper, etc. It didn't hinder our stay, but these are mentioned in the listing, so it was noted. Overall, we enjoyed our stay!
Kid-friendly condo rentals

A Kozy Waterfront Condo
The photos are mirror images of the condo. The kitchen and bath are amply supplied with all the items needed, even to prepare meals if you choose. Accessibility features are a bonus when traveling with an individual with mobility issues. Locally, Portside Seafood was a welcome surprise with a delicious menu. It was the perfect place for my sister and me to have some downtime and recharge. Thank you for sharing your beautiful home.

The Drinking Gourd: Stunning Cambridge Penthouse
Great place for a quick weekend away. Clean, quiet, but close to downtown area.

The Station House: Upscale Condo in Cambridge, MD
Loved our stay here in this cute private apartment. Parking was easy. Neighborhood was adorable, lots of restaurants and the marina all super close by. Downtown Cambridge is pretty quiet, so still very peaceful despite being close to everything. The only thing to note is that there is an historic government building nearby that chimes it's bell every hour. If you are s light sleeper, bring earplugs.

Beautiful 2-Bedroom Loft in Historic Cambridge
The perfect place to stay in downtown Cambridge! You step right out the front door to all the shops and restaurants. Beautiful space with all the amenities you could need. Jennifer has thought of everything! Wonderful and responsive host. We will definitely be back for another stay!

Cozy Oxford Getaway
Our visit is always wonderful not only for the lovely setting and convenience of being in town, but for the gracious hospitality. Not only are Chris and Kate welcoming and attend to any needs, their staff at the Oxford Market are also marvelous folks. The cottage is a great fit for my elderly parents as it is all on one floor. The location is perfect as you can walk to many delightful places. My Dad enjoyed getting the newspaper and homemade muffins each morning. Just perfect! Thank you! Katie Dodds
Destinations to explore
- Rentals with a fireplace Dorchester County
- Rentals with lake access Dorchester County
- Rentals with a kayak Dorchester County
- Rentals with breakfast Dorchester County
- Rentals with a fire pit Dorchester County
- Apartment rentals Dorchester County
- Rentals with a washer and dryer Dorchester County
- Rentals with a patio Dorchester County
- Rentals with a hot tub Dorchester County
- Rentals with outdoor seating Dorchester County
- House rentals Dorchester County
- Pet-friendly rentals Dorchester County
- Rentals with beach access Dorchester County
- Waterfront rentals Dorchester County
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- Rentals with pools Dorchester County
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- Sandy Point State Park
- Six Flags America
- Heritage Shores
- Maryland Renaissance Festival
- Gerry Boyle Park
- Idlewilde Restoration Project
- Quiet Waters Park
- Guard Shore
- Ragged Point Beach
- Quiet Waters Dog Beach
- Sparrows Beach
- Matapeake Clubhouse and Beach
- Plantation Lakes Golf and Country Club
- Saint Jerome Beach
- Langford Sand
- Severn Beach
- Flounder Pavilion Beach Front - Sandy Point State Park
- Lake Presidential Golf Club
- Piney Point Beach
- Lane Beach
- Brownies Beach
- Chesapeake Beach Water Park
- Rose Haven Memorial Park
- Triton Beach