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Family-friendly vacation rentals in Saint Michaels

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Top-rated family-friendly rentals in Saint Michaels

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

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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 Saint Michaels

4.86 out of 5 average rating, 125 reviews

Premier St Michaels Cottage- In Town Location

The truly special and restored historic Thomas Blades house is centrally located in the Town of St. Michaels on a quiet st. Shops, restaurants, museums and the Town park with its magnificent water views are steps away. It is a 2 bedroom 1.5 bath cottage with a large paneled family room and a large screened porch. Ideal for a small family or two couples, or a romantic getaway for two. Rate varies by day of the week and season. Discounts for stays of a week or more, or for "last minute" bookings.

Top guest favorite

A well-lit living area features a black piano along one wall, with a wooden cabinet displaying books and decorations nearby. A fireplace is set within a white brick surround, and a flat-screen TV is mounted above. Comfortable seating is arranged for relaxation.

Guest suite in Arnold

4.96 out of 5 average rating, 672 reviews

Old Bay Bungalow

This in-law apartment located in the lower level of my occupied home is just moments outside of Annapolis, mere blocks from the Magothy River. I enjoy inviting guests into the space, and take pride in treating new friends like family. Come rest your weary bones in your private retreat with its own separate entrance, relaxing sunporch, and stocked kitchenette. Reach into the fridge and enjoy cold soda or a local beer on me! Sit around our fireplace and relax. Settle into the Old Bay Bungalow!

Top guest favorite

A serene waterfront view reveals calm water framed by lush green trees. A small private dock is visible, featuring an orange kayak resting at the edge. The scene conveys tranquility, inviting relaxation amidst nature.

Guest suite in Chestertown

4.99 out of 5 average rating, 226 reviews

Beautiful Waterfront Chestertown Getaway

Lovely three room waterfront guest suite conveniently located less than 10 minutes from historic Chestertown and Washington College. Beautiful views of our tidal creek, full kitchen, wooded lot, quiet neighborhood, bird watching, kayaking, great biking & running options. Friendly pets (indoor cats and dogs who can share the yard with us and our dog) are welcome. We donate 5% of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice.

The exterior of a charming yellow house is featured, with a white railing enclosing a screened-in porch. Four wicker chairs are positioned on the porch, complemented by blue shutters on windows. A gated entrance provides access to the front yard, surrounded by greenery.

4.96 out of 5 average rating, 215 reviews

The Oxford House

Enjoy water views from the backyard or visit with friends on the screened in porch. The light and airy, 3bd, 2bath house is a short walk to Oxford’s best restaurants and favorite ice-cream shop. You can find the best beach in oxford only 75 yards from our front door or take the Ferry to the neighboring town of Saint Michaels, Maryland. You will love the scenic views and historical charm of this little town, the Oxford house has a central location allowing you to walk or bike to everything.

The interior of the cottage features a vaulted wooden ceiling with beams, creating an open atmosphere. A spacious sectional sofa faces a wood-burning stove. The kitchen is equipped with modern appliances, while light streams through large windows draped in sheer curtains.

Guesthouse in National Harbor

4.93 out of 5 average rating, 741 reviews

Urban Cottage,MD minutes from DC/National Harbor

Come and enjoy our spacious detached cottage,lounge on your private back deck overlooking private parkland forests. A real urban escape in an excellent location! Just a few blocks away from the MGM Resort / Casino, National Harbor, and shopping. Across the river from historic Alexandria and 10-minutes from Washington,DC. Great for a solo adventure,couples,and friends (up to 4 guests). Enjoy the seasonal steam house and personal wood-burning stove if you book in the cold months.

Top guest favorite

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 Saint Michaels

4.98 out of 5 average rating, 102 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.

A serene waterfront scene is captured at sunset, displaying calm water reflecting soft hues of orange and blue. Silhouettes of trees line the shore, while gentle ripples can be seen across the surface, creating a peaceful atmosphere.

Apartment in Deale

4.91 out of 5 average rating, 621 reviews

Romantic Wtrfrnt Flat+Solarium@Chesapeake Paradise

Gift yourself this private, secluded second floor Flat & Solarium Bedroom. Best hideaway to rest, bond, restore, create, or work. A breezy, country-like setting provides space to escape the city hustle! Nearby scenic drives & groceries, or venture to Annapolis TJ/WF or historic walks. Fully relax with pier, kayaks, swings, fire pit, starry nights, sun-drenched loungers, cozy up with books/movies & luxuriate in the deep soaking tub or European shower.

Top guest favorite

A light-filled entryway features two comfortable armchairs beside a small round table adorned with a flower vase. Natural light filters through the large windows, revealing a view of blooming pink flowers outside. The space is complemented by a stylish door with a modern light fixture.

Apartment in Solomons

4.99 out of 5 average rating, 293 reviews

Walk to famous Tiki Bar on Solomons Island!

Cute studio apartment on charming Solomons Island. Walking distance to restaurants, live music, boat and kayak rentals. The kitchen has a full sized refrigerator, microwave, toaster, two burner hot plate and coffee maker. We provide all bedding and bath towels for two people. Enjoy your coffee ( provided) or wine on the deck in the fenced in side yard. One well-behaved pet is welcome. Please make sure you pay the pet fee.

Top guest favorite

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.

5 out of 5 average rating, 141 reviews

Historic Rousby Hall, Waterfront, Pool, Beach

Rousby Hall is located on the Patuxent River, outside of Solomons Island with a view of the river's opening to the Chesapeake Bay. The 16-acre property is adjacent to our very private conservation area that borders our 300-foot private beach. The year-round property has a pier, and in-ground pool (May-October) with amazing river views. Also hosts weddings+events up to 100 guests (additional event fee applies).

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 Saint Michaels

4.99 out of 5 average rating, 113 reviews

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 rental experiences in St. Michaels, MD. 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)

A welcoming cottage sign is prominently displayed at the entrance, showcasing the name 'Wittman Cottage' along with the address. Lush greenery and colorful flowers surround the sign, adding a natural touch to the inviting atmosphere. The screened porch is visible in the background.

Cottage in Wittman

4.89 out of 5 average rating, 165 reviews

"Wittman Cottage"

Wittman Cottage is located on a beautiful stretch of waterfront views. It is a very nice vacation spot for the family. You can relax and watch the beautiful sunsets from our very large screened porch, or drive to shop and dine in St. Michael's and visit the Maritime Museum which is only 7 miles away..

Vacation rentals for every style

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Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Saint Michaels family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A modern living space is depicted, featuring a sleek dining table with comfortable chairs and a well-equipped kitchen in the background. Natural light enters through large windows, illuminating the neutral-toned decor. A cozy seating area includes a stylish sofa that complements the room's aesthetic.

Apartment in Northwest Washington

3.67 out of 5 average rating, 3 reviews

Washington 2 Bedroom Apt Near U.S. Capitol.

A screened porch features a hanging bench swing with cushions in shades of blue and nautical motifs. A small chair stands nearby, adorned with a decorative pillow. Tall curtains frame the space, providing a relaxed and inviting atmosphere surrounded by greenery.

Cottage in Annapolis

4.86 out of 5 average rating, 108 reviews

Nautical Vibe Walk 2 Harbor Pubs USNA

Top guest favorite

A pet feeding station is set on a textured mat, featuring two stainless-steel bowls. A colorful pet toy stands playfully beside the bowls, and a glass jar labeled with treats is positioned nearby. Light fills the space, enhancing the warm wood flooring.

Townhouse in Canton

4.96 out of 5 average rating, 528 reviews

Parkfront Hot Tub Haven for Families & Pets

Top guest favorite

An outdoor pool area features a large swimming pool alongside a hot tub. A gentle waterfall flows, creating a calming atmosphere. Lounge chairs are arranged nearby under shaded structures. The surrounding buildings reflect evening light against a twilight sky.

Condo in National Harbor

4.82 out of 5 average rating, 28 reviews

Wyndham National Harbor- 1 bdrm

A large, two-story home with a welcoming front porch is set amidst a spacious green lawn. The house features a grey exterior with white trim and multiple windows, surrounded by trees and landscaping, creating a peaceful and private atmosphere.

4.88 out of 5 average rating, 172 reviews

Large Home with Pool & 7 bedrooms; sleeps 21

A well-maintained inground pool can be seen surrounded by a spacious deck featuring lounge chairs and shaded seating areas. Lush greenery and trees create a natural backdrop, enhancing the outdoor space’s tranquility with direct views of the water.

Apartment in Arnold

4.96 out of 5 average rating, 175 reviews

Celebrate Summer by Your Private Pool

Top guest favorite

An aerial view captures the expansive waterfront estate surrounded by lush greenery and a tranquil waterway. The pier extends towards the water, while the house is set back from the banks. Nearby structures include docks and quaint homes along the shoreline.

4.99 out of 5 average rating, 146 reviews

Chesapeake Waterfront-Kayaks-Crab-Fish-FirePit-Spa

Two kayaks are positioned on a grassy area by the water, reflecting a sunset sky filled with warm hues. A wooden pier extends into the lake, framed by bare trees, offering a serene view of the calm water surface.

Bungalow in Deale

4.85 out of 5 average rating, 394 reviews

Cozy waterfront getaway on the Bay

Family- and pet-friendly home rentals

The charming exterior of a historic cottage is depicted, featuring a welcoming front porch and an American flag. Lush green landscaping with flowers adds a touch of color, while a stone pathway leads to the entrance. The house is set against a backdrop of trees.

Cottage in Rock Hall

4.88 out of 5 average rating, 128 reviews

Cottage with Modern Updates - Walk to Waterfront!

A cozy living area features a comfortable sofa and two green armchairs, with a decorative rug beneath. Large bifold glass doors open to a lush garden. Natural light fills the space, which is adorned with potted plants and a vibrant piece of wall art.

Apartment in NoMa

4.87 out of 5 average rating, 670 reviews

Union Market Garden Apartment

Top guest favorite

A row of charming brick townhouses is presented, each with distinct colors and architectural details. A well-kept front yard features low-maintenance landscaping, with a small table set in the outdoor area. The street is lined with trees, enhancing the neighborhood's appeal.

Apartment in Capitol Hill

4.99 out of 5 average rating, 239 reviews

Capitol Hill-1BR basement apt-Free parking

A bright living area features stylish seating arrangements with two blue sofas and a central ottoman. A wall-mounted television is positioned beneath decorative shelving. An open kitchen space is visible, showcasing modern bar stools and a dining area bathed in natural light from a nearby window.

Condo in Annapolis

4.94 out of 5 average rating, 398 reviews

Brand New Reno in Historic Dist w 2 Parking spots

The exterior of a single-story cottage is framed by lush greenery and mature trees. A white picket fence encloses the front yard, which features a small lawn and a decorative tree. Gravel pathways lead to the front entrance, with a shaded area beside the house.

Cottage in Deale

4.9 out of 5 average rating, 167 reviews

Rockhold Creek Cottage

A welcoming living space features a modern sectional sofa adorned with patterned pillows and a sleek coffee table. Nearby, a dining area with a round table and chairs is complemented by natural light from a window. A stainless steel refrigerator and decorative artwork enhance the ambiance.

Apartment in Silver Spring

4.92 out of 5 average rating, 444 reviews

Escape to a Sunny Apartment in a Quiet D.C. Suburb

Top guest favorite

The image captures a serene waterfront scene, showcasing a long wooden dock extending into the calm river. Lush greenery lines the riverbank, while a clear blue sky with scattered clouds provides a picturesque backdrop. The tranquil water reflects the surrounding landscape.

Apartment in Lexington Park

4.97 out of 5 average rating, 571 reviews

Historic St. Mary's City, MD

The studio apartment features exposed brick walls, enhancing its character. A spacious bed with a vibrant orange coverlet is positioned beside two bedside lamps. A large area rug adds color, while a television is visible across from the bed, complemented by an additional couch and decorative plants.

Apartment in Upper Fells Point

4.86 out of 5 average rating, 867 reviews

Stay in a Former Fells Point Bar! - Private Studio

Family-friendly home rentals with a pool

Top guest favorite

A large, clear swimming pool is surrounded by a well-maintained patio. A diving board is positioned at the edge, with a brick wall and lush greenery in the background. Sunlight reflects off the water's surface, enhancing the inviting atmosphere.

Home in Chestertown

5 out of 5 average rating, 24 reviews

Chestertown Watson Family Farm

A cozy living area is seen featuring a light-colored sofa and two accent chairs. A wooden coffee table holds decorative items, while a large piece of abstract wall art adds visual interest. Soft light filters through two windows, enhancing the neutral color palette.

Apartment in Foggy Bottom

4.81 out of 5 average rating, 585 reviews

#3 Foggy Bottom/Georgetown Apartment

A refreshing saltwater pool is framed by comfortable lounge chairs in vibrant red and blue. A large grassy area is visible beyond the pool, leading to serene waterfront views under a clear blue sky, complemented by a tree providing shade.

Home in Queenstown

4.81 out of 5 average rating, 157 reviews

Bay Breeze Retreat

Top guest favorite

A fenced-in pool area is surrounded by lush greenery, with tall plants and trees creating a natural backdrop. The pool features calm blue waters, and a small paved pathway leads toward it. A black chair is positioned near the entrance of the pool gate.

Guest suite in Catonsville

4.94 out of 5 average rating, 527 reviews

Rollingside: Two-Room Guest Suite

Top guest favorite

An outdoor hot tub features a sleek design with built-in jets, illuminated by soft purple lighting. The surrounding area is draped with white curtains, creating a secluded atmosphere. Seasonal use is indicated, adding a touch of relaxation to the outdoor space.

Place to stay in Annapolis

4.94 out of 5 average rating, 121 reviews

Chesapeake Bay View 3BR/2BA Duplex*Hot Tub*

Top guest favorite

A stately, historic home with a welcoming front porch is framed by manicured lawns and blooming flowers. A brick pathway leads to the entrance, illuminated by soft outdoor lighting. The exterior showcases a blend of traditional architecture and well-kept details against a twilight sky.

Home in Cambridge

5 out of 5 average rating, 17 reviews

Turtle's Nest - Hist. Cambridge

Top guest favorite

A cozy living area features large bay windows providing ample natural light. A sectional sofa and patterned rug add comfort, while a modern coffee table sits in the center. A flat-screen TV and entertainment unit complete the space, enhancing its inviting design.

Townhouse in Logan Circle

5 out of 5 average rating, 110 reviews

Charming 3BR Rowhouse in Shaw/Bloomingdale

A cozy bedroom features original exposed brick walls and a large window allowing natural light. The spacious bed is dressed in soft linens, complemented by matching decorative pillows. Two bedside lamps provide gentle illumination, and a wooden accent above the bed showcases a symbolic design.

Apartment in Dupont Circle

4.94 out of 5 average rating, 387 reviews

Dupont West 3: Charming Studio

Quick stats about vacation rentals that are family-friendly in Saint Michaels

Total rentals
20 properties
Nightly prices starting at
ﺩ.ﺇ918 before taxes and fees
Total number of reviews
2K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi

Destinations to explore