Kid-friendly holiday rentals in Talbot County

Find and book unique kid-friendly rentals on Airbnb

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Popular amenities for Talbot County kid-friendly rentals

Child-friendly house rentals

Guest favourite
Home in Newcomb
4.98 out of 5 average rating, 53 reviews

Saint Michaels Waterfront Home

KaleighRating, 5 stars3 weeks ago
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.
Guest favourite
Home in Stevensville
4.93 out of 5 average rating, 225 reviews

Relax on Kent Island in 3 Bedroom Home w/Waterview

AmandaRating, 5 stars1 week ago
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.
Guest favourite
Home in Preston
4.95 out of 5 average rating, 98 reviews

River House on the Choptank

SandyRating, 5 stars2 weeks ago
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!
Guest favourite
Home in Cambridge
4.86 out of 5 average rating, 63 reviews

High St. Art Gallery Suite

NadineRating, 5 stars1 month ago
My husband and I had a nice peaceful retreat from city life. Kristin’s cute place was just what we needed. Highly recommend!
Guest favourite
Home in Cambridge
4.97 out of 5 average rating, 115 reviews

Gorgeous, waterfront home - Perfect for Families.

DavidRating, 5 stars2 weeks ago
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.
Guest favourite
Home in Stevensville
4.97 out of 5 average rating, 115 reviews

The Kent Island House

KendallRating, 5 stars1 month ago
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!
Top Guest favourite
Home in Chester
5 out of 5 average rating, 39 reviews

*Waterfront Sunset Bayview* sleeps 6

KellyRating, 5 stars1 week ago
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)
Top Guest favourite
Home in Cambridge
4.95 out of 5 average rating, 237 reviews

Great Historic Cambridge Home With Parking!

RachelRating, 5 stars2 weeks ago
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

Guest favourite
Apartment in Trappe
4.75 out of 5 average rating, 8 reviews

ALL INCLUDED- Chic Move in Ready

PeterRating, 5 stars6 months ago
Convenient for working on a boat in Oxford. Less expensive than staying in Oxford.
Top Guest favourite
Apartment in Saint Michaels
5 out of 5 average rating, 43 reviews

Saint Michaels Luxury Get Away

VaughanRating, 5 stars1 week ago
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!
Apartment in Cambridge
5 out of 5 average rating, 12 reviews

SUPER WATER-VIEW 1 BEDROOM APT/CAMBRIDGE MARYLAND

AmandaRating, 5 stars1 week ago
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!
Top Guest favourite
Apartment in Saint Michaels
4.97 out of 5 average rating, 90 reviews

Blue Crab Lodge

RhondaRating, 5 stars1 week ago
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.
Guest favourite
Apartment in Annapolis
4.94 out of 5 average rating, 17 reviews

Crow’s Nest Cottage - Down Under: Chesapeake Bay

RickRating, 5 stars3 months ago
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.
Guest favourite
Apartment in Cambridge
4.85 out of 5 average rating, 20 reviews

Cozy 3rd Floor Apartment in Historic West End

JudithRating, 5 stars4 months ago
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!!
Guest favourite
Apartment in Wye Mills
4.77 out of 5 average rating, 66 reviews

⋘ Lakeside Apartment ⋙| Private+Cozy Setting |

TimRating, 5 stars1 week ago
Host was responsive, rental was as pictures with no surprises and clean upon arrival. Would stay there again
Superhost
Apartment in Cambridge
4.9 out of 5 average rating, 130 reviews

Little Slice of Cambridge. 2 bedroom, pet friendly

JoanRating, 5 stars1 week ago
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.

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