
Family-friendly holiday rentals in St. Michaels
Find and book unique family-friendly homes on Airbnb
Quick stats about holiday rentals that are family-friendly in St. Michaels

Total holiday rentals
Explore 20 holiday rentals in St. Michaels

Nightly prices starting at
St. Michaels holiday rentals start at $351 AUD per night before taxes and fees

Verified guest reviews
Over 2,420 verified reviews to help you choose

Pet-friendly accommodation
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of St. Michaels holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across St. Michaels rentals

4.9 Average rating
St. Michaels stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated family-friendly rentals in St. Michaels
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

Hideaway on the Bay: Waterfront Vintage A Frame
The Hideaway on the Bay is a waterfront A frame where you can disconnect from the things that can wait so you can connect with the people who matter most. A place where kids fall in love with nature, and where old friends make new memories. The house is a 2 bed 1 bath 1974 flat top A Frame that sits on two acres on the outskirts of Lusby, MD—and a low traffic hour(ish) drive from the DMV. Enjoy the indoor fireplace, outdoor fire pit, swinging chairs, kayaks, canoe, fish, and catch crabs --

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

Private Waterfront Home W/ Hot Tub, Dock & Kayaks
Soak in the waterfront hot tub or sit around the waterfront fire pit in this one story completely renovated house w/ 3 bedrooms and 2 full bath. One master bedroom with private bathroom and one bathroom for the rest of the house. Tv in each room and expansive views of the Chester River. There are tons of outdoor activities to do from fishing, kayaking, paddle boarding and biking. This is a gorgeous piece of property on Maryland’s eastern shore. Great crab houses and restaurants minutes away.

Soul Oasis - home on the Chesapeake Bay
Listen to the waves of the Chesapeake Bay from the trex deck. There are 2 private community beaches in the neighborhood where you can find fossils and sharks teeth. A great place to relax and unwind. You will hear the sounds of all kinds of birds, see lots of very tiny frogs in spring and summer and maybe some deer around the house! You can also expect to see/hear aircraft from Pax River Base fly overhead! Book your stay today and let the magic of the woods and water wash away your cares.

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.

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)

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.

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.

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.

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.

SM's Premier Rental Heated Pool (closes 10/27)
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.

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
Popular amenities for St. Michaels family-friendly rentals
Family-friendly home rentals with a hot tub

Cozy Cottage, Hot Tub, BlockToBeach, 1hr to DC

Cozy 3-bedroom home w/ Hot tub & firepit

Waterfront Cottage@ChesapeakeParadise Hot Tub/Dogs

Waterfront, Dog-friendly, Hot Tub, Gas Fireplaces

Peaceful Historic House Near Water, with Hot Tub!

Iconic Chesapeake. Unparalleled Luxury.

Harbor View Haven | Waterfront w/ Hot Tub + Dock!

River Refresh - Waterfront with Spa on Placid Bay
Family- and pet-friendly home rentals

Waterfront Getaway with Dock

Premier St Michaels Cottage- In Town Location

High St. Art Gallery Suite

Relaxing Water Views - Mill Creek Cottage

Annapolis Area Waterside Retreat

Gorgeous, Waterfront Home Is Perfect for Families!

Annapolis Garden Suite

Waterfront home, private dock
Family-friendly home rentals with a pool

Waterfront, 3 Beaches, Dock + Kayaks, Potomac

Bay Breeze Retreat

*Brand New | Modern Farmhouse | Lux 4 BR | Near DC

Rosses Chance Guest House

Coastal Waterfront 1 Bedroom Cottage

Serenity Bay-PrivPool-HotTub-AskAbout2NightStays!

The Little Gypsy BoHome

Historic Rousby Hall, Waterfront, Pool, Beach
When is the best time to visit St. Michaels?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $365 AUD | $372 AUD | $410 AUD | $498 AUD | $489 AUD | $459 AUD | $434 AUD | $425 AUD | $425 AUD | $424 AUD | $437 AUD | $399 AUD |
| Avg. temp | 3°C | 4°C | 8°C | 14°C | 19°C | 24°C | 26°C | 25°C | 22°C | 16°C | 10°C | 5°C |
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- M&T Bank Stadium
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- National Mall
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- Walter E Washington Convention Center
- Nationals Park
- Baltimore Convention Center
- FedExField
- Johns Hopkins University
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- Federal Hill Park
- Arlington National Cemetery
- Capital One Arena
- National Museum of African American History and Culture
- The Anthem
- Washington Monument
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- Howard University
- Smithsonian National Zoological Park
- National Harbor
- Dover Motor Speedway





