Kid-friendly holiday rentals in Talbot County

Find and book unique family-friendly rentals on Airbnb

Top-rated family-friendly rentals in Talbot County

Guests agree: these family-friendly rentals are highly rated for location, cleanliness and more.

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Superhost

Home in Stevensville

4.93 out of 5 average rating, 215 reviews

Relax on Kent Island in 3 Bedroom Home w/Waterview

Enjoy your vacation in this Beautiful & Stylish 3 Bedroom Home with a view of the Chesapeake Bay from living room & kitchen! Perfect for Families & Wedding Groups. We are conveniently located to many areas/cities: Annapolis- 20 miles Baltimore- 45 Wash. DC- 50 Easton- 35 Enjoy a Self-Check-in to this Beautiful Home that is perfectly situated near all the local Kent Island Restaurants, Shops, Attractions. This is a Non-Smoking House. Also No Pets, Parties or Large Groups (11 max). Book Today!

Superhost

Cottage in Royal Oak

5 out of 5 average rating, 11 reviews

Newly Renovated Summer Paradise-Pool-Tennis-Garden

Our newly renovated garden cottage is nestled on an 18 acre waterfront private retreat with access to a swimming pool, gym, tennis court & private dock! The kitchen is fully-equipped with stainless steel appliances and laundry located in house. The cottage shares the grounds with a few other of our private cottages. Guests also have access to kayaks, fishing equipment, the fire pit, ice cream shop, library and more! Quiet and remote but very close to both Easton and Saint Michaels for a perfect

Superhost

Flat in Annapolis

4.94 out of 5 average rating, 17 reviews

Crow’s Nest Cottage - Down Under: Chesapeake Bay

Crow’s Nest Cottage - Down Under: 3BR/1BA garden-level duplex with fenced Zen garden, natural bamboo, water fountain, gas BBQ grill, brand new gourmet kitchen, sleeps 8. TV in all BR’s, steps to Chesapeake Bay waterfront. Sandy beach, protected swimming lagoon, park, bbq grills & picnic tables. Enjoy coastal Maryland’s beautiful flora & fauna. Nature lovers paradise, lower-level duplex (5 steps down) in waterfront community, access to pier, boat ramp, kayaks. Best vacation rental holiday home

Superhost

Flat in Cambridge

4.91 out of 5 average rating, 124 reviews

Little Slice of Cambridge. Newly listed, 2 bedroom

You’ll be staying right in the center of the Historic district, close enough to walk to town and enjoy shopping or some of the great restaurants. Just two blocks from the water, a short stroll to the lighthouse or down to the water front and enjoy the park. This newly listed 2 bedroom , pet- friendly apartment has everything you will need to explore the history, food and waterfowl found in this area. Park your boat here. We can’t wait for you to experience Cambridge and relax in the “West End”.

Superhost

Home in Stevensville

4.97 out of 5 average rating, 32 reviews

Carolina Cottage - 2 story, pet-free home

A home away from home! From the 2 car garage to the oversized deck, large master suite, and large yard, there is plenty of room for everyone to spread out and enjoy themselves. Take a walk to the neighborhood beach for some unbelievable sunsets, make a meal in the fully stocked kitchen, eat together at the large dining table, play board games, listen to the record player, play corn hole, or ride the bikes. Don't miss the many amazing restaurants! There is plenty to see and do on the Island.

Superhost

Home in Neavitt

4.96 out of 5 average rating, 84 reviews

Waterfront, Dog friendly, St Michaels home

Lovingly restored waterfront historic home just minutes from St. Michaels. Located in a quiet waterman's village, Seth's Landing provides tranquility and beautiful surroundings. Up for a little adventure? Bring your watercraft of choice - house has dock with two deepwater boatslips. Or bring your bikes - great area for biking! Or rent any of these from local business and have delivered to house. Great for couples and small families. Due to proximity to water, not good for young children.

Superhost

Home in Queenstown

4.81 out of 5 average rating, 156 reviews

Bay Breeze Retreat

Incredible private luxury retreat on the eastern Chesapeake Bay. Complete with every amenity- saltwater pool, firepit, multiple Smart TVs, sleeps 10 in comfort, premium memory foam mattresses in every room, fast Wi-Fi, 100' pier, huge front yard. Unbelievable views!!! Extensively renovated. Please note that no parties or disturbances will be tolerated. We require that guests respect our neighbors and serene community at all times. We explicitly do not allow bachelor or bachelorette parties.

Superhost

Home in Cambridge

4.94 out of 5 average rating, 133 reviews

Peaceful Historic House Near Water, with Hot Tub!

Peaceful 3 bedroom/1.5 bath Victorian house near the water. Located in Historic West End, this 1900 house has been recently renovated to accentuate its historic charm while delivering all the modern comforts. Just a short walk from Long Wharf Park, the Choptank River Lighthouse, and downtown Cambridge with great restaurants and shops. Amenities include air conditioning/heating, a hot tub, WIFI, a back deck and grill, front porch with rocking chairs, and a fire pit with Adirondack chairs.

Superhost

Cottage in Saint Michaels

4.82 out of 5 average rating, 38 reviews

Cottage #6 Wild Goose on the left of Main House

OPEN Year round. No6) Wild goose located to left of main house, consist of-full Kitchen, dining table, queen size bed all in a single room a Futon pulls out to bed. Only separate room is bathroom. Please call Jaimie upon arrival. No pets allowed! We no longer provide bed linens, Coffee, sugar or creams. or Towels. Boats are rentals! Bring waters we are on a well 1 Queen Bed 1 Futon . Basis Cottage setting All 7 cottages face Harris Creek, upper loft. 2 night min stay.

Superhost

Home in Saint Michaels

4.98 out of 5 average rating, 100 reviews

SM’s Premier Rental Heated Pool opens 4/11/2025

Harbor Hideaway's in- town location and now featuring a PRIVATE POOL is a rare find. Steps away from everything that SM's has to offer. HH is a 1940’s - 1 1/2 story cottage loaded with thoughtful amenities. Airy and appointed with modern/ comfortable furnishings, resort quality linens, a well stocked kitchen; this 2 bdrm /2 B cottage is sure to please! Perfect for 1 to 2 couples, girls' wknds, small family, or anyone just in need of a relaxing getaway.

Superhost

Cottage in Easton

5 out of 5 average rating, 102 reviews

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Cottage on Solitude Creek, Hot Tub (open), Fire Pit, Pool (Not Heated -closed Oct-June) Convenient to St. Michaels, Easton, Oxford - this beautiful cottage has a fully equipped kitchen, patio with private hot tub and gas grill. Waterfront. Host resides on property, but will give you your privacy. *PLEASE NOTE: property complies with zoning of Talbot County which enforces a 3-night minimum and 4 guest max. NO DOGS ALLOWED No Parties #STRN-23-51

Superhost

Cottage in Stevensville

4.95 out of 5 average rating, 156 reviews

Cottage on the Bay - Kent Island

Chesapeake Bay Waterfront home on Kent Island! Enjoy year round big sky and water views from the comfort of the screened porch & family room. Fish & crab from the pier or take a dip in the bay. Open concept living and rear bedroom/rec room are perfect for relaxing and having fun with family & friends. Close to popular wedding venues, local marinas & charter fishing boats, restaurants, Tiki bars, beaches, golfing, parks, & bike trails.