Family-friendly holiday rentals in Talbot County

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Top-rated family-friendly rentals in Talbot County

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

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Top guest favourite

A modern living area features a light-colored sofa adorned with a teal throw blanket. A round wooden table accompanied by metal chairs is positioned nearby. A decorative mirror and an abstract painting are displayed on the wall, while a stone fireplace adds a subtle touch of warmth.

Flat in Stevensville

Boutique by the Bay

Completely renovated and exquisitely decorated, this one bedroom apartment has a private entrance from the main house and features a modern farmhouse vibe. Fully equipped kitchen with new glass top stove, large walk-in shower and queen sleeper sofa make this perfect for a couple or family. Located 9 miles south of the Bay Bridge, off of Route 8 on Kent Point Road ,this location is convenient for weddings at the Chesapeake Bay Beach Club or Swan Cove. Access to large in-ground pool included.

4.97 out of 5 average rating, 312 reviews

Top guest favourite

A modern guesthouse features a peaked roof and large windows, set against a vibrant sunset sky. The surrounding landscape includes wild grasses and a paved pathway, suggesting a serene connection to nature.

Cottage in St. Michaels

La Casita on Harris Creek, St. Michaels

La Casita on Harris Creek is an architecturally unique guest house situated on a private 40-acre farm in the heart of the Chesapeake Bay, 5 min by car to Saint Michaels, MD. The guesthouse, adjacent to the owner's main farm house, features an upstairs loft, open plan first floor TV/WiFi, full bath/shower, galley kitchen/ cook top stove, microwave, stainless refrigerator, microwave, stainless refrigerator. An adjacent private pool is available for guests. TALBOT COUNTY LICENSE NUMBER STRN 26-39

4.98 out of 5 average rating, 200 reviews

Guest favourite

A bright living area features a yellow sofa and an oversized ottoman, set against a backdrop of large glass doors overlooking the river. Natural light floods the space, highlighting the modern design and comfortable furnishings. A dining table is also visible, along with a seating area by the window.

Home in Preston

River House on the Choptank

Welcome to the River House! Stay in our renovated home on the Choptank River of MD's Eastern Shore, with your own low-tide beach and magnificent sunsets. We offer a peaceful location and thoughtful detail, creating a memorable getaway for a relaxing weekend or remote work location. Enjoy a day on the river with our paddle board or 2 kayaks, and end the day around the firepit. In cool weather, cozy up next to the fireplace. Also, visit nearby towns--St. Michaels, Easton, Oxford, and Chestertown.

4.93 out of 5 average rating, 126 reviews

Top guest favourite

The living room features a chandelier, a decorative mirror above the fireplace, and a cozy seating area with two armchairs and a chaise lounge. A colorful area rug covers the floor, while a small table and lamp provide additional lighting.

Home in St. Michaels

Historic Berkeley Hall in the heart of town

Berkeley hall is centrally located in historic Saint Michaels. Park your car and walk to everything! Great shops, restaurants and 3 blocks to the water. First floor includes a high ceiling parlor that connects to a lovely side porch and large kitchen. There is a mahogany staircase that takes you to the 2nd floor that has 2 master suites. One has a king bed the other has a queen bed w/ ladder to loft which is best for kids -has a twin size futon sofa bed. Perfect home for a romantic getaway.

4.96 out of 5 average rating, 217 reviews

Guest favourite

An aerial view captures the expansive property, featuring a large home surrounded by lush green lawns and mature trees. A heated in-ground pool is visible in the backyard, adjacent to a serene water body, with an expansive landscape enhancing the tranquil setting.

Cabin in St. Michaels

True St. Michaels 6 Acre Waterfront w/heated pool

TREMEZZO STAY - Spencer Creek Cabin Our properties are owned, managed, and hosted by us. We deliver personally hosted luxury rentals in St. Michaels, MD. We also own Tilghman Island Inn, a waterfront destination specializing in group retreats, weddings, and private events. If you do not see availability for your dates or are looking to sleep more than 8 please visit our additional exclusive listings! Punch Point (sleeps 10) Chesapeake Mansion (sleeps 12) Ranch at Royal Oak (sleeps 12)

4.99 out of 5 average rating, 124 reviews

Top guest favourite

The exterior entrance of a converted corn crib features natural wood siding and a gabled roof. Large double doors framed by lantern-style lights open into a welcoming space, complemented by potted plants on either side. Lush green trees and a gravel path are visible in the surrounding landscape.

Guest house in Easton

Chill in The Crib! Easton, Maryland

Welcome to Maryland's Eastern Shore and your own private space in a converted corn crib, complete with the comforts of home. The space includes a vaulted ceiling, queen-sized Casper® mattress, quality linens, heat & AC, wireless Internet, a coffee counter, stocked bar fridge, full bath w/ shower (includes quality bath supplies), and a private entrance. Our space is permitted for ONLY TWO INDIVIDUALS (No children under 8 years of age.), and please limit your visit to one vehicle only.

4.99 out of 5 average rating, 657 reviews

Top guest favourite

An aerial view captures a sprawling, waterfront property surrounded by lush greenery. The modern home sits prominently on a well-manicured lawn, leading to a serene bay. The driveway winds through tall trees, with clear blue water visible in the background.

Home in Cambridge

Osprey's Retreat Waterfront w/ private beach/dock

Enjoy a weekend escape or extended vacation for up to 6 guests at this freshly renovated gem located on LeCompte Bay . Beautiful waterfront property with a private sandy beach, located just 5 minutes outside of town with plenty of outside activities including a dock and fire pit. Super clean & comfortable, modern home & furnishings featuring a first floor premier, well appointed kitchen. This home is provided with everything you need for a fun, relaxing get-a-way on the Bay.

4.97 out of 5 average rating, 115 reviews

Guest favourite

A vibrant navy sofa decorated with red and white cushions sits in front of a glossy black coffee table. A geometric rug covers the wooden flooring, while a decorative plant and a luminous wall create a welcoming atmosphere. A series of signs indicating local towns provide a charming touch.

Flat in St. Michaels

Charming Apt. in St. Michaels

Welcome to Lucky Duck II! Enjoy a renovated, two-story private apartment in the heart of St. Michaels, located on Talbot Street in the historic 1850s McMillan House. Our cozy British-inspired retreat sleeps 4 with a private queen bedroom and full bath upstairs, plus a sleeper sofa and half bath downstairs. Enjoy a kitchenette, bar area, free WiFi & YouTube TV. Best of all, you're steps from the Miles River, restaurants, shops, museums & everything St. Michaels has to offer!

4.96 out of 5 average rating, 100 reviews

Top guest favourite

A bright yellow building features large blue shutters and a welcoming entrance. A sign is placed outside, and vibrant flowers border the steps. In the background, another structure is visible, along with flags proudly displayed.

Flat in St. Michaels

Blue Crab Lodge

Welcome to your charming and cozy short-term rental above the heart of St. Michaels' vibrant community! Nestled right above the delightful aroma of freshly brewed coffee, this unique and inviting space offers the perfect blend of comfort and convenience. Stepping outside, you'll find yourself in the heart of St. Michaels' quaint streets. The rental's prime location provides easy access to the town's boutique shops, waterfront promenades, and a diverse array of restaurants.

4.98 out of 5 average rating, 160 reviews

Top guest favourite

The image captures a serene evening scene by the pool with a view of the setting sun over the water. Sunlight filters through trees, creating a warm glow. Poolside lounge chairs are visible, along with a clear pool reflecting the colorful sky.

Guest house in Stevensville

Waterfront-View of Bay from your Bed

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

4.99 out of 5 average rating, 363 reviews

Top guest favourite

A serene waterfront scene is framed by a sprawling tree. Boats are moored along the docks, with calm water reflecting the sky. Quaint buildings line the shore, and a bench is positioned on the grass, inviting quiet contemplation of the picturesque surroundings.

Cottage in St. Michaels

The Little Anchor Cottage, St. Michaels, MD

Welcome to the Little Anchor cottage in St. Michaels, Maryland! The cottage was built in late 1880s and is located in the charming Historic District, where you can enjoy the convenience of walking one block to the downtown shops and restaurants on S. Talbot street. And for another 5 to 15 minute walk, you can reach more waterfront dining on St. Michaels Harbor with its boat slips, boat ramps, the Chesapeake Bay Maritime Museum, Muskrat Park and Hollis Park.

4.97 out of 5 average rating, 301 reviews

Top guest favourite

An aerial view captures a spacious home set on a wooded parcel adjacent to a serene body of water. The exterior features a large swimming pool surrounded by decking, with a manicured lawn and tall trees creating a natural boundary.

Home in Cambridge

Gorgeous, Waterfront Home Is Perfect for Families!

Looking for a large, beautiful house for a big family get-away? Casey's Porch is the place to go. Come and see for yourself. Bring your extended Family. Bring your friends. Enjoy the pool. Kayaks and paddle boards and bikes await you at this beautiful home on Hudson Creek. Fish from the dock. Pull crabs from the creek. Walk down quiet country lanes. Sit around the fire pit. So many fun, outdoor things to do. Casey's Porch has it all.

4.96 out of 5 average rating, 140 reviews