Kid-friendly holiday rentals in Talbot County

Find and book unique family-friendly rentals on Airbnb

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Popular amenities for Talbot County family-friendly rentals

Kid-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 Preston
4.95 out of 5 average rating, 98 reviews

River House on the Choptank

SandyRating, 5 stars3 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!
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 Chester
5 out of 5 average rating, 39 reviews

*Waterfront Sunset Bayview* sleeps 6

KellyRating, 5 stars2 weeks 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)
Guest favourite
Home in Cambridge
4.98 out of 5 average rating, 59 reviews

Small, peaceful getaway

LindseyRating, 5 starstoday
Our stay was really wonderful! Heather is a great host, responsive and friendly. Her home is super clean and nicely decorated, as well as spacious and private. We spent a day adventuring along the Blackwater River and this space was perfect to rest and recoup in. Would definitely return if we stay in Cambridge again and highly recommend!!

Family-friendly apartment rentals

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

ALL INCLUDED- Chic Move in Ready

PeterRating, 5 stars7 months ago
Convenient for working on a boat in Oxford. Less expensive than staying in Oxford.
Flat 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
Flat 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
Flat 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
Flat 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
Flat 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
Flat 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
Flat 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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