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 Saint Michaels
4.86 out of 5 average rating, 125 reviews

Premier St Michaels Cottage- In Town Location

Marissa & ChrisRating, 5 stars3 weeks ago
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!
Top Guest favourite
Home in Easton
5 out of 5 average rating, 16 reviews

Cozy 2BR Home near Idlewild Park

BethRating, 5 stars4 months ago
Lynda’s place was the perfect spot for our mother/daughter/dog weekend getaway to Easton. As my daughter said, staying at Lynda’s house was like “being in a big hug”. Everything was so clean and comfortable. Lynda provided us with all the comforts of home including lots of local goodies in the kitchen to eat and drink. She even bought a special dog treat and had water and food bowls and a dog blanket for the sofa for our pup. Not only was the house welcoming to our dog, but right across the street is a wonderful rail trail walking path which made dog walking a breeze. I highly recommend visiting Easton and staying at Lynda’s!
Guest favourite
Home in Oxford
4.96 out of 5 average rating, 214 reviews

The Oxford House

CatalinaRating, 5 stars1 week ago
My partner and I ran the Ironman 70.3 in Cambridge and stayed here for the weekend. The house had everything we needed and it was great for us to rest before and after the race. Would totally recommend staying here for vacation or a relaxing weekend!
Guest favourite
Home in Cambridge
4.97 out of 5 average rating, 116 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 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.
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, 91 reviews

Blue Crab Lodge

Lisa Rating, 5 stars1 day ago
This is a beautiful space in a great location! So homey and comfortable :)
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 Saint Michaels
4.91 out of 5 average rating, 58 reviews

The heart of St Michaels awaits.

LaurenRating, 5 stars1 month ago
AMAZING location! We loved being able to park the car and walk to the shops, brewery, winery, restaurants, farmers market and more! The place was peaceful which helped since we had a baby with us. We would definitely rent again if we were to go back!
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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