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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Guest favorite

A serene waterfront view showcases the Chesapeake Bay, stretching towards the horizon under a clear sky. The shoreline features wooden docks and gentle waves, while quaint homes are seen along the sandy beach. Green trees provide shade in the foreground.

Home in Saint Leonard

4.9 out of 5 average rating, 130 reviews

Perfect Bay and Beach Getaway one hour from DC!

Our waterfront home with sweeping views of the Chesapeake Bay is close to beaches, the Flag Harbor Marina, Solomon's Island, Flag Pond Nature Preserve and Calvert Cliffs State Park. You’ll love the spectacular sunrises/sunsets over the Bay, diving ospreys and eagles, and exploring the bay by kayak, canoe, or paddle board. Our house is great for families (with kids), groups, and well-mannered dogs. New in 2023: we will be replaced the upstairs HVAC system, baby proofing, and fall 2023 paint

Guest favorite

A living room features a fold-out couch adorned with colorful throw pillows. A wooden desk with books and a lamp is positioned nearby, while a vibrant rug adds warmth to the space. Natural light filters through a window, and a green lamp provides ambient lighting.

Bungalow in Silver Spring

4.92 out of 5 average rating, 178 reviews

Astoundingly Charming Bungalow, Bells & Whistles!

This unique property offers its guests the best of both worlds: a single-family house with a large, fenced dog-friendly backyard and a multi-car driveway, within walking distance of the Silver Spring and Takoma Park Metro Stations as well as all the shops, restaurants, bars, and theaters of downtown Silver Spring, MD. Hop on the Metro to play in DC and come back to a comfortable home with a full kitchen, off-street parking, outdoor space, and neighbors who are the friendliest of people.

Top guest favorite

A bright kitchen and dining area is revealed, featuring a table with two chairs positioned beneath a window. The space includes light wood flooring, a kitchenette with modern appliances, and various seating options. Natural light filters in through a partially covered window.

Home in Fruitland

4.97 out of 5 average rating, 129 reviews

Amazingly convenient yet secluded.

Our place has views; the yard has beautiful shade trees that set the mood for deep relaxation. One can walk to Walmart, Denny's, Hampton Inn Suites, Ruby Tuesdays and many other business's in minutes. Ocean City is about a 35minute drive. Salisbury University is a five minute drive. UMES is a 13 minute drive.This home is ideally located. A retired teacher on one side is your closest neighbor; on the other property is a caregiver. Needless to say this is a very safe place; enjoy.

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, 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.

Guest favorite

The exterior of the cottage features a welcoming yellow facade, complemented by a manicured lawn with shrubs and mulch. A wooden deck with white columns provides entry to the front door, which is flanked by large windows. An American flag hangs proudly to the left.

Cottage in Colonial Beach

4.93 out of 5 average rating, 169 reviews

Bayside Cottage- In the Town with views

Welcome to Bayside Cottage, a newly renovated beach cottage in the very charming (Town of Colonial Beach), Virginia! The cottage boasts 3 bedrooms and 2 full baths and is centrally located in town. Walk across the property to Bayside Marina, where you can watch the sun go down on the rooftop deck with a drink in hand (contact host for instructions) Bayside Cottage was recently fully renovated and is best suited for groups of 6.

Top guest favorite

A park scene is visible, featuring a playground with colorful slides and climbing structures framed by several green trees. People are seen enjoying the space, with some pushing strollers on the grassy area. The setting appears to be family-friendly and inviting.

Townhouse in Federal Hill - Montgomery

4.96 out of 5 average rating, 196 reviews

Fed Hill & Inner Harbor / BEST Location & Reviews!

Walk to EVERYTHING! Steps to the Inner Harbor, museums, restaurants, stadiums, & parks. Charm City Circulator & Water Taxi nearby for access to the entire city! Bright home in Historic Federal Hill. Live like a local in an upscale setting! Quiet, comfortable 2 bedroom home perfect for families Preference for booking age to be 25 or older. Baltimore is thriving & evolving, see for yourself how beautiful the area is year round!

Guest favorite

The bathroom features a clean layout with a white tiled shower surrounded by glass. A modern sink and vanity with a dark wood finish are complemented by a large mirror above. A small plant adds a touch of greenery to the space, while art pieces adorn the wall.

Condo in Bethesda

4.89 out of 5 average rating, 189 reviews

Bright 2br w amazing loc and view

850 sq ft 2 bedroom 1 bathroom condo in great downtown Bethesda location. Corner unit with windows everywhere making for great light, energy, and views. Balcony overlooking one of the main Bethesda squares. Close to metro and walkable to more restaurants and bars than you can possibly try. Tandem parking for two cars. New flooring as of June 2023. This condo will exceed your expectations.

Guest favorite

A spacious living room features a coffered ceiling and hardwood flooring. Natural light enters from large windows draped with sheer curtains. A round coffee table sits at the center, complemented by a patterned area rug. A decorative mirror and a small plant enhance the inviting atmosphere.

Townhouse in Northwest Washington

4.92 out of 5 average rating, 154 reviews

Spacious Family Retreat in Tranquil Neighborhood

Our home is one of the largest homes in the neighborhood. It is beautifully decorated for your enjoyment. Our large family room will make you feel like you are at home. House is 2,700 sq ft. The house is a close 2.5 miles from the well-known National Zoo. Also, 0.7 miles to the METRO station that has a direct route to the National Mall - a perfect tourist destination.

Guest favorite

Villa in Annapolis

4.84 out of 5 average rating, 112 reviews

Crow's Nest Cottage: Chesapeake Bay View*HOT TUB*

Escape to Serenity: Chesapeake Bay Oasis Experience the ultimate Chesapeake Bay retreat - stunning 6-bedroom, 3-bath water-view villa, perfectly suited for family reunions & special gatherings. Enjoy breathtaking bay views, steps from the water's edge, with gated 240’ pier, sandy beach, protected swim area, picnic tables, BBQ grills & children's playground. .

Top guest favorite

A decorative welcome sign hangs on the door, featuring a serene beach scene with two adirondack chairs. The sign is framed by an oval glass design, enhancing a cheerful first impression for guests entering the home.

Home in Lusby

4.99 out of 5 average rating, 295 reviews

Cove Point Beach Cabin

My place is close to shopping, restaurants and dining in Lusby and Solomons Island, the Chesapeake Bay, and family-friendly activities. You’ll love my place because of the comfy beds, the coziness, and the views. My place is good for couples, solo adventurers, business travelers, and families (with kids). No pets allowed.

Top guest favorite

A bright common room features a comfortable white sofa paired with a glass coffee table. A small wooden table with a floral arrangement is positioned nearby. A map adorns the wall, and a kitchenette area includes a toaster and coffee setup, providing convenience for guests.

Guest suite in Annapolis

4.95 out of 5 average rating, 193 reviews

Cozy Naptown Perch

Perfectly Placed Perch in Murray Hill neighborhood. 1 mile to USNA stadium; 1 mile to historic downtown. Walk to local restaurants, in town events. Few blocks to water access. 2 bedroom upstairs suite recently renovated. Common room has sofa, table and chairs, coffee/ tea set up. Patio, fire pit available to guests.

Guest favorite

Cottage in Deale

4.9 out of 5 average rating, 165 reviews

Rockhold Creek Cottage

The Perfect rock fishing and crabbing cottage in Deale, Maryland right on Rockhold Creek, with docks and spectacular views! The waterfowl are mesmerizing to watch. Just 1/2 block from Happy Harbor and Fishing Charters! No need to make that drive at 4am, you can stay the night before and after for maximum enjoyment!