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Family-friendly holiday rentals in Baileys Crossroads

Find and book unique family-friendly homes on Airbnb

Quick stats about holiday rentals that are family-friendly in Baileys Crossroads

  • Total holiday rentals

    Explore 40 holiday rentals in Baileys Crossroads

  • Nightly prices starting at

    Baileys Crossroads holiday rentals start at $77 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,500 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    40 of Baileys Crossroads holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Baileys Crossroads rentals

  • 4.8 Average rating

    Baileys Crossroads stays are highly rated by guests – averaging 4.8 out of 5!

Top-rated family-friendly rentals in Baileys Crossroads

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

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Top guest favourite
A spacious bedroom features a wooden ceiling and walls, accentuated by natural light from large windows. A single bed is draped in a deep blue coverlet, paired with a plush chair and leafy plants. A vibrant piece of wall art adds a pop of color to the serene space.
Farm stay in Accokeek
4.97 out of 5 average rating, 184 reviews

Frolic Fields: A Woodsy 14 Acre Homestead w/ Sheep

Easily escape to the woods on a 14 acre homestead that's only 20 miles from DC. Surrounded by the forest with amazing views, designed by artists, this secluded hideaway is a celebration of Nature and Art. Recharge amongst these ancient trees and all the singing critters that soundtrack the night. Enjoy a fire, frolic in the fields, read on a hammock, strum a guitar, and feel the pressure of modern life melt away. Explore the many bucolic trails nearby. Perfect for retreats and workshops.

Guest favourite
The open living area features a comfortable gray sofa with decorative pillows, a wooden coffee table, and a dining area with bar stools at a kitchen counter. Natural light enters through the window, highlighting the clean, modern design and artwork on the walls.
Apartment in Penrose
4.88 out of 5 average rating, 334 reviews

Newly Renovated 1BR Condo Sleeps 4 - Unit 4

Completely renovated, stylishly furnished condo unit in Arlington, VA just one stoplight from Washington DC, the Pentagon, Clarendon, Crystal City and National Airport. Spacious unit with free cable TV, secure Internet/Wi-Fi, FREE reserved parking in private lot, in-unit Washer/Dryer, Full Kitchen. Steps away from public transit buses that route to multiple Orange/Blue/Silver line Metro trains. Comfortably accommodates the traveling professional, those on vacation and is even kid friendly.

Top guest favourite
A comfortable living room features rich brown leather sofas arranged around a small coffee table with a marble top. A dark wooden bookshelf displays various decor items and books, while a potted plant adds a touch of greenery to the space.
Guest suite in Alexandria
4.97 out of 5 average rating, 210 reviews

Oasis near DC-1king+1studio queen BR,yard, parking

Families visiting Washington, D.C. love to stay with us. Our location is just a twenty-minute drive from all major attractions. A plaza and bus station just a short walk away, providing numerous dining options and groceries. 3.4 miles to the metro station. This pravite and spacious 1,600 sf basement apartment features a separate entrance, dedicated free parking, and inviting outdoor living areas. It offers a cozy retreat that feels like your own. The hosts quietly reside on the two upper levels.

Top guest favourite
The interior features a cozy living area with wooden accents and a rug centered beneath a table and chairs. An air conditioning unit is mounted above the space. A staircase leads to a lofted sleeping area, while large windows provide views of surrounding greenery.
Tiny home in Falls Church
4.98 out of 5 average rating, 188 reviews

Log Out

Our project to make use of leftover logs turned into a tiny house! Cozy Log Cabin looking out on almost an acre of nature but just minutes from all the DC sites. Perfect for a single escape, a romantic getaway, a small family/group gathering, or a serene remote work location. 1/4 mile to bus and 1.5 miles to DC metro, plenty of free parking. We live in a log home next door - so happy to provide advice on sites/restaurants and directions. No-SMOKING of any kind , NO pets and NO parties allowed.

Top guest favourite
Guest suite in Arlington
4.98 out of 5 average rating, 115 reviews

"The NEST" Studio Apartment in Arlington

Welcome to The Nest – a cozy and bright studio above the garage with a private entrance. It features a queen bed, full kitchen, bath, living area, in-unit washer/dryer, and clever hidden storage. Enjoy ample street parking, with a private driveway available on request. Whether you’re visiting for a weekend getaway or an extended retreat, The Nest offers a warm and inviting escape. Modern, clean, and full of thoughtful touches, it’s the perfect place to relax, recharge, and feel right at home.

Top guest favourite
A spacious living area is highlighted by a large flat-screen television and a comfortable blue couch adorned with red accent pillows. A dining island with high-backed chairs is visible, leading to a bright kitchen equipped with modern appliances and ample cabinetry.
Guest house in Alexandria
4.97 out of 5 average rating, 110 reviews

NoVA guest house

One bedroom guest house, with spacious living area, full kitchen, large dining island, and one full bathroom. Convenient to Washington DC and Old Town Alexandria, Virgnia. Quiet, wooded neighborhood, enjoy your own little house on a beautifully landscaped 1/2 acre lot. Private outdoor sitting area and fully stocked kitchen. All folks are welcome to stay in our comfortable retreat, close-in to the city, yet feels like the country! Lots of amenities in this newly built cottage - come visit!

Top guest favourite
A cozy bedroom features a spacious bed with decorative pillows and a soft blanket. A wooden table and chair are positioned nearby, along with a TV mounted on the wall. Natural light enters through a window covered by a dark curtain, adding warmth to the room.
Guest house in Falls Church
4.97 out of 5 average rating, 227 reviews

Beautiful New Apartment Surrounded by Nature

Beautiful, private detached studio apartment surrounded by a 3.5 acre park. Spacious light filled home away from home with a queen and single bed and available air mattress. Washer dryer in unit. Full private bath and kitchen with built in 2 burner induction burner, oven, microwave, coffee maker, hot pot, rice cooker and kitchen essentials. Walk to metro or take the bus from the corner. Bars, restaurants, grocery and other shopping and entertainment in walking distance or quick metro to DC.

Guest favourite
A bright living room features a comfortable seating area with a sectional sofa and decorative pillows. A television is mounted above a cozy brick fireplace. Bar stools are arranged at a unique table, and large windows allow natural light to fill the space.
Home in Alexandria
4.96 out of 5 average rating, 107 reviews

Shanti (Peace) Home & Garden

The Shanti Home & Garden is a beautiful, cozy gem tucked in a leafy neighborhood. You will be pleasantly surprised at how peaceful it is, despite being conveniently close (15-25 minutes) to the major attractions across Washington DC, Arlington, Alexandria, and National Harbor. Restaurants, cafes, stores, gyms, trails, grocery, bus stops, and Capital Bikeshare are within walking distance. It is perfect for your getaway, family/friends vacation, staycation, business trip, and remote working.

Top guest favourite
The living room features a modern design with hardwood flooring and large windows. A cozy seating arrangement includes two soft armchairs, a sofa, and a round coffee table, centered on a multi-colored area rug. A decorative fireplace and a small TV add character to the space.
Home in Alexandria
4.97 out of 5 average rating, 126 reviews

Modern 3BR/2BA.Free Parking.Comfort & Convenience!

Say hello to your new home-away experience in Northern Virginia. You open the door to something vibrant, yet relaxing and cozy. Sparkling clean, modern furnishings make this one level house your perfect home base for vacation/remote work, or relocating. Free WiFi . Free parking. Minutes to I 395-495. Just 7 miles to DC attractions and historic Alexandria, this brick house is in a quiet neighborhood, surrounded by nature parks. A clean modern oasis you’ll love. Look no further!

Top guest favourite
Guest suite in Alexandria
4.95 out of 5 average rating, 308 reviews

Private Waterfront Suite Near DC & NOVA

Welcome to our private waterfront suite in Alexandria right near DC. Enjoy a complementary coffee or tea from your cozy room and outdoor patio with stunning water views. Our independent entrance suite features a private bathroom, fridge, microwave, coffee machine, desk & a queen-sized bed. Just a short drive from downtown DC & NOVA attractions, this is the perfect place for business or pleasure. Check-in is contactless and a breeze. Book now for a relaxing retreat!

Top guest favourite
Home in Barcroft
4.98 out of 5 average rating, 196 reviews

Family & Pet-Friendly Stay with Playground Near DC

Welcome to our renovated ranch-style single-family home, perfect for families, groups, and pets. This 5BR, 2BA retreat features a cozy, fully equipped interior and a game area with air hockey, ping pong, and pool. Outside, enjoy a large unfenced backyard with a playground for kids and pets. Just minutes from Washington, DC, Arlington, Alexandria, it’s the ideal home base — combining comfort, fun, and easy access to the area’s top attractions.

Guest favourite
A spacious bedroom is presented with a large bed covered in a patterned quilt. A wooden desk and chair are positioned near a window, allowing natural light to brighten the room. Two windows provide ventilation, and the polished wooden floor adds warmth.
Guest suite in Glencarlyn
4.89 out of 5 average rating, 152 reviews

A private suite & parking

You get everything you see in the pictures, a private suite ready to welcome a last-minute reservation. If you need to check in early or check out late, the host will try to accommodate you when possible. A $70 extra fee applies for a guest who wants to use the second bedroom. It is currently used to keep bedding and linen. It remains locked. The host will always knock or text before entering the living room on the first floor.

Popular amenities for Baileys Crossroads family-friendly rentals

When is the best time to visit Baileys Crossroads?

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