Family-friendly holiday rentals in St. Michaels

4.97 out of 5 average rating, 197 reviews

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

KitchenFamilyRiver

4.95 out of 5 average rating, 308 reviews

A serene waterfront scene is captured at dusk, featuring a dock illuminated by soft lighting. A swing sits beneath a large tree, providing a peaceful spot to relax while overlooking the calm water.

Home in Grasonville

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.

KitchenIndoor spacesWalkability

4.96 out of 5 average rating, 215 reviews

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.

KitchenIndoor spacesView

A spacious backyard features a circular fire pit surrounded by Adirondack chairs. A picnic table sits to one side, and a hot tub is partially shielded by evergreen trees and a wooden fence, providing a serene outdoor retreat.

4.94 out of 5 average rating, 186 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.

FamilyIndoor spacesCheck-in

4.99 out of 5 average rating, 655 reviews

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.

Guesthouse 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.

KitchenFamilyNearby

A covered deck area features a large black dining table surrounded by striped chairs. A ceiling fan is present above. Scenic views of the water and shoreline are framed by tall trees, creating a serene outdoor dining space.

4.99 out of 5 average rating, 223 reviews

Sunset Breezes - quiet waterfront retreat

Enjoy well equipped waterfront home styled after historic lighthouses. Relax in the hammock by the water under the pines; Enjoy smores by the fire pit. Wood included. Free use of 4 kayaks, 2 paddleboards, and a 3 person canoe. Yard games include corn hole, croquet, & bocce. Dine on the deck while enjoying beautiful sunsets. Bring your cameras for local wildlife. NEW Fun & Fitness Barn: sauna, golf simulator, free weights, game space and more. Ask about access code and hours.

KitchenIndoor spacesBiking

Apartment in St. Michaels

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.

4.97 out of 5 average rating, 158 reviews

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.

KitchenFamilyGetting around

5.0 out of 5 average rating, 211 reviews

Home in Shady Side

Iconic Chesapeake. Unparalleled Luxury.

Summer at The Cottage at Silver Water is effortless and indulgent. A sweeping waterfront lawn leads to a private shoreline for swimming, kayaking, and long days in the sun. Evenings bring golden skies, spectacular sunsets, and fires by the water’s edge. Inside, the cottage is beautifully designed with luxurious bedding, curated art, and thoughtful amenities that make every stay relaxed, refined, and unforgettable. See why all our guests only have a 5-Star experience.

Indoor spacesFamilyNearby

Guesthouse in Stevensville

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.

4.99 out of 5 average rating, 360 reviews

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.

KitchenIndoor spacesBreakfast

4.97 out of 5 average rating, 297 reviews

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.

KitchenFamilyHeating

4.97 out of 5 average rating, 115 reviews

A charming blue cottage is depicted with a gabled roof and white columns framing the entrance. Lush green bushes line the pathway, providing an inviting approach. Clear blue skies and tall trees are visible in the background, enhancing the peaceful setting.

Home in St. Michaels

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.

KitchenFamilyCheck-in

5.0 out of 5 average rating, 125 reviews

A charming cottage is visible beside a clear pool, surrounded by well-maintained green lawns. Two shaded umbrellas stand over cushioned lounge chairs by the water's edge, creating a comfortable outdoor space for relaxation. The inviting pool reflects the bright sky, enhancing the serene atmosphere.

Cottage in Easton

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

Indoor spacesFamilyAccuracy

Popular amenities for St. Michaels family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

5.0 out of 5 average rating, 325 reviews

The outdoor area features a circular pool surrounded by colorful lounge chairs in yellow, blue, and white. Umbrellas in red and blue provide shade over a dining table with red chairs. Towering trees frame the view of the expansive waterfront beyond.

Home in Kent Narrows

Chester Riverfront At Kent Narrows

FamilyIndoor spacesDecor

Superhost

A scenic waterfront view is captured, featuring a spacious green yard with a double swing and a hammock situated under a tall tree. Calm waters reflect the sky, creating a serene atmosphere. Lush greenery lines the shore, enhancing the peaceful setting.

4.88 out of 5 average rating, 141 reviews

Waterfront Oasis! Hot tub! 2+ acres - Sleeps 8

FamilyKitchenGetting around

5.0 out of 5 average rating, 185 reviews

A comfortable living area is framed by large windows showcasing a vibrant sunset over the water. Soft furnishings include two chairs with decorative pillows and a coffee table. Plants are positioned thoughtfully, enhancing the serene atmosphere.

Home in North Beach

Waterfront, Dog-friendly, Hot Tub, Gas Fireplaces

Indoor spacesFamilyPets

4.94 out of 5 average rating, 196 reviews

A tranquil beach scene presents soft sand leading to calm water, framed by an open sky dotted with clouds. A weathered log rests on the shoreline, while distant rocky formations add interest to the horizon.

Cottage in St. Leonard

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

KitchenFamilyValue

4.97 out of 5 average rating, 103 reviews

A bright and open living space features large windows that provide views of the river. A long dining table is accompanied by upholstered chairs. A modern kitchen counter with stools is visible, along with a chandelier overhead and a cozy fireplace on one side.

Home in St. Leonard

Blue Pearl-Luxury estate with private dock/jacuzzi

FamilyKitchenParks

4.96 out of 5 average rating, 134 reviews

Home in Colonial Beach

River Refresh - Waterfront with Spa on Placid Bay

Indoor spacesFamilyNearby

4.98 out of 5 average rating, 190 reviews

A cozy living area features two brown leather sofas, a patterned rug, and a soft ottoman. A reading nook is created with a gray chair draped in a yellow blanket. Natural light streams in through a large window, with plants and bookshelves enhancing the space.

Home in Chestertown

Cozy 3-bedroom home w/ Hot tub & firepit

Indoor spacesFamilyAmenities

4.99 out of 5 average rating, 112 reviews

A sandy beachfront scene features a log cabin surrounded by lush greenery. A well-maintained lawn leads to a gently sloping beach, where the calm waters meet the shore. Multiple seating areas, including lounge chairs, are visible along the edge of the water.

Cabin in Lusby

Bayfront Walk-Out Beach Home | Sunrise & Fire Pit

FamilyIndoor spacesCheck-in

Family- and pet-friendly home rentals

4.87 out of 5 average rating, 141 reviews

A classic historic cottage features white siding and a steeply pitched roof. An American flag hangs from the front door, which is framed by a small porch and decorative elements. Lush greenery and a white picket fence enhance the welcoming facade.

Home in St. Michaels

Premier St Michaels Cottage- In Town Location

KitchenIndoor spacesDecor

4.92 out of 5 average rating, 265 reviews

The vintage A-frame home is nestled amongst trees, featuring a deck with a canopy in the foreground. A stone path leads to the entrance, where large windows allow for ample natural light. The surrounding landscape is adorned with greenery and decorative plants.

Cabin in Lusby

Hideaway on the Bay: Waterfront Vintage A Frame

FamilyIndoor spacesHiking

A bright and inviting room features two pink armchairs with a small table between them, set against a backdrop of light walls and hardwood flooring. An elegant chandelier hangs from the ceiling, while a vintage-style dresser and a decorative fireplace enhance the space's charm.

4.89 out of 5 average rating, 114 reviews

High St. Art Gallery Suite

KitchenFamilyCheck-in

4.95 out of 5 average rating, 105 reviews

The charming exterior of a waterfront cottage, featuring a white picket fence and a welcoming front deck. Large windows allow for natural light, while vibrant surroundings enhance the coastal feel. The front porch is partially shaded by lush greenery, inviting relaxation and enjoyment of the outdoors.

Cottage in North Beach

Cozy Waterfront Cottage - Pet Friendly

KitchenIndoor spacesPets

4.97 out of 5 average rating, 470 reviews

A spacious living area features large windows that allow natural light to fill the space, showcasing views of the surrounding greenery. Comfortable seating is arranged around a low table, with a television mounted on the wall, and decorative shelves filled with various items.

Cottage in Annapolis

Relaxing Water Views - Mill Creek Cottage

Indoor spacesKitchenTV

4.94 out of 5 average rating, 104 reviews

Lush green grass leads to the waterfront, where the calm water reflects the surroundings. Two white Adirondack chairs sit invitingly under the shade of tall trees, providing a serene spot for relaxation. A wooden dock extends into the water, enhancing the picturesque setting.

Home in Neavitt

Waterfront, Dog friendly, St Michaels home

Indoor spacesKitchenBreakfast

4.97 out of 5 average rating, 130 reviews

The outdoor area features a spacious concrete saltwater pool surrounded by lounge chairs and tables. The house showcases a light-colored façade with multiple entrances, large windows, and umbrellas providing shade, all set against a backdrop of lush greenery.

Home in Stevensville

Beautiful Kent Island Getaway with Pool

Indoor spacesFamilyNearby

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.

4.96 out of 5 average rating, 139 reviews

Gorgeous, Waterfront Home Is Perfect for Families!

Indoor spacesKitchenNearby

Family-friendly home rentals with a pool

5.0 out of 5 average rating, 224 reviews

An aerial view captures the waterfront cottage situated on the South River. The property is surrounded by water and greenery, featuring a manicured lawn with a patio area. A private dock is visible, leading from the house to the water, alongside a pool nestled within the landscaping.

Guesthouse in Annapolis

Coastal Waterfront 1 Bedroom Cottage

Indoor spacesKitchenGetting around

4.99 out of 5 average rating, 175 reviews

The historic home features a charming exterior with a mix of white clapboard and dark shingles. An inviting porch is framed by green shutters and surrounded by well-maintained landscaping. A gravel driveway leads to the front entrance, enhancing the property’s welcoming appeal.

Home in Lusby

Historic Rousby Hall, Waterfront, Pool, Beach

FamilyKitchenQuiet

4.99 out of 5 average rating, 117 reviews

A red barn-style building is positioned on a lush green lawn, surrounded by trees and residential structures. A porch is visible on the upper level, and a colorful wheel mural decorates the front. A gravel path leads to the entrance.

Guesthouse in Cambridge

The Loft at Sailor's Retreat. Waterfront Apartment

KitchenFamilyQuiet

Apartment in Stevensville

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.

4.97 out of 5 average rating, 312 reviews

Boutique by the Bay

FamilyIndoor spacesQuiet

4.82 out of 5 average rating, 171 reviews

A winding stone pathway leads through a vast green lawn towards the shimmering waters of the eastern Chesapeake Bay. Two comfortable lounge chairs are positioned at the water's edge, offering a serene view of the horizon under a soft blue sky.

Home in Queenstown

Bay Breeze Retreat

FamilyIndoor spacesParking

4.99 out of 5 average rating, 143 reviews

A cozy living area features a spacious sectional couch adorned with patterned cushions. A wooden coffee table sits centrally, with a decorative rug beneath. A brick fireplace is present, flanked by windows allowing natural light, and a green door leads to the exterior.

Guesthouse in Cambridge

Rosses Chance Guest House

Indoor spacesKitchenSleep quality

4.98 out of 5 average rating, 158 reviews

A spacious bedroom features a large wooden bed with a light comforter and decorative pillows. Two leather benches are positioned at the foot of the bed. Natural light fills the room through large windows adorned with wooden shades, and a ceiling fan adds to the comfort.

Home in Montross

Waterfront, 3 Beaches, Dock + Kayaks, Potomac

Indoor spacesKitchenLong stay