
Kid-friendly holiday rentals in Talbot County
Find and book unique kid-friendly rentals on Airbnb
Top-rated kid-friendly rentals in Talbot County
Guests agree: These kid-friendly rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Talbot County kid-friendly rentals
Child-friendly house rentals

Saint Michaels Waterfront Home
Beautiful location and home to spend over Memorial Day weekend. The house had everything we needed and was a comfortable stay. Brandon was very nice and accommodating.

Relax on Kent Island in 3 Bedroom Home w/Waterview
Quiet neighborhood, very close to our venue. We enjoyed the comforts of the home and our host was extremely helpful before during and after our stay.

River House on the Choptank
The house was perfect for us. We were in town for grandson's graduation and needed extra space and this definitely delivered. The property was amazing. Even though we couldn't physically enjoy much outside activities due to the rain we did get to enjoy beautiful views of the river from the large picture windows. Steven was always quick to respond to messages which was much appreciated!

High St. Art Gallery Suite
My husband and I had a nice peaceful retreat from city life. Kristin’s cute place was just what we needed. Highly recommend!

Gorgeous, waterfront home - Perfect for Families.
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.

The Kent Island House
Our stay here was great. Clean space with awesome views. The sleeping situation was funky but perfect for our friend's wedding weekend. We hope to come back!

*Waterfront Sunset Bayview* sleeps 6
The perfect mom and teen boy getaway! The house is on the water with gorgeous sunsets and super clean! My boys attempted fishing daily even without any luck. Altho we didn't kayak because of the choppy water, its great location (there's a ladder at the private pier or a public launch a few yards away) We cooked and ate in a few nights and also enjoyed a local spot on the water (The Narrows). The neighborhood was quiet, relaxing and peaceful. We enjoyed a visit to the Chesapeake Environmental center (abt a 12 min drive) which was a hidden treasure. The Chesapeake Outdoors (recommended by our host Jeremiah) was a great find for bait and info from the locals. Morning coffee on the patio and evening sunsets on the pier were some of my favorites, along with the spacious open floor plan (yet privacy with bedrooms). Jeremiah was super responsive and kind! We'll be back to kayak, fish more, enjoy the hot tub coming soon, the serenity and gorgeous sunsets! (maybe we'll even bring dad -LOL)

Great Historic Cambridge Home With Parking!
Cambridge is so cute and this house was perfect for our stay! Walkable to lots of little shops and restaurants, very friendly neighbors, and an immensely cute and comfortable home.
Kid-Friendly apartment rentals

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

Saint Michaels Luxury Get Away
Best place to stay in St Michaels! Pristine and right in the heart of the town. Walkable to everything. We loved every bit of our stay. Michelle was easy to communicate with and allowed us to check in early. We arrived to a bottle of champagne and thoughtful snacks and treats. Incredibly comfortable and newly renovated. Highly recommend. Will be staying here again next time we’re in the area!

SUPER WATER-VIEW 1 BEDROOM APT/CAMBRIDGE MARYLAND
Larry's place was perfect. We were able to book with him last minute for the Eagleman and he was able to accommodate our needs. It was a pleasure to meet Larry and have him give us a tour of the home. He was a great host. Would recommend to anyone!

Blue Crab Lodge
Brian, we really enjoyed our stay even though it w has only one night. We celebrated my sister’s birthday and the walkable location was perfect. Thanks.

Crow’s Nest Cottage - Down Under: Chesapeake Bay
I cannot say enough about Paul! Proactive, great recommendations and an all-around fantastic fellow! My children, two dogs, and I had a wonderful time and would come back in a heartbeat! The place itself is immaculate and has a gorgeous view of the Chesapeake Bay. Minutes from the Naval Academy and an easy ride to the Greenbelt metro so we could catch a DC United game in the city.

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!!

⋘ Lakeside Apartment ⋙| Private+Cozy Setting |
Host was responsive, rental was as pictures with no surprises and clean upon arrival. Would stay there again

Little Slice of Cambridge. 2 bedroom, pet friendly
We rented A Little Slice of Cambridge because of the Iron Man competition held that weekend. It was convenient to the venue...and allowed to walk to the competition and nearby restaurants. Pamela was a wonderful host...communicating easily. The rental was well stocked with toiletries, dishes, pots and pans and extras. The house was comfy and the beds comfortable. An enjoyable stay...unfortunately, we weren't able to stay for more sightseeing...although I did walk down to the Lighthouse and beautiful wharf.
Destinations to explore
- Rentals with a patio Talbot County
- Rentals with a fire pit Talbot County
- Rentals with a fireplace Talbot County
- Rentals with pools Talbot County
- Rentals with outdoor seating Talbot County
- Beachfront rentals Talbot County
- Rentals with a washing machine and dryer Talbot County
- Rentals with breakfast Talbot County
- House rentals Talbot County
- Rentals with lake access Talbot County
- Rentals with a kayak Talbot County
- Apartment rentals Talbot County
- Rentals with beach access Talbot County
- Pet-friendly rentals Talbot County
- Rentals with a hot tub Talbot County
- Waterfront rentals Talbot County
- Kid-friendly rentals Maryland
- Kid-friendly rentals United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Nationals Park
- The White House
- Betterton Beach
- National Mall
- Oriole Park at Camden Yards
- National Museum of African American History and Culture
- Hampden
- District Wharf
- Smithsonian National Museum of Natural History
- M&T Bank Stadium
- Sandy Point State Park
- Washington Monument
- Patterson Park
- National Air and Space Museum
- National Harbor
- Smithsonian American Art Museum
- Lincoln Park
- Meridian Hill Park
- Quiet Waters Park
- Crystal Beach Manor, Earleville, MD
- Maryland Renaissance Festival
- Flounder Pavilion Beach Front - Sandy Point State Park
- Library of Congress
- Heritage Shores