Kid-friendly holiday rentals in Madison Heights

Find and book unique family-friendly rentals on Airbnb

Top-rated family-friendly rentals in Madison Heights

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

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Guest favourite

Home in Wintergreen Resort

4.96 out of 5 average rating, 105 reviews

Peaceful 3-BR Mountain home w/Fireplace + Hot tub

Charming 3-bedroom mountain retreat at the top of Wintergreen Resort. Peaceful and private location. Relax in front of the gas fireplace, soak in the hot tub, or sit on the deck and enjoy the views. Spend your day hiking a nearby trail and enjoy visiting local restaurants, breweries, and wineries. Kitchen is fully stocked and there is a new gas grill on deck. Kids will love the upstairs twin bedroom, complete with a play area with books & toys. Separate den with TV and workspace on lower level

Guest favourite

Home in Afton

4.99 out of 5 average rating, 154 reviews

Clean family-friendly 5br for wine country getaway

Come to Sunnyside! A new 5 bedroom home with game room, hot tub, and space for 12 people on 4 acres on a private farm road. Just off the infamous Route 151, or "Brew Ridge Trail", you are RIGHT in the middle of the action: 7 minutes to 10 wineries / breweries, 5 minutes to the nearest family farm or golf course, 10 minutes to Skyline Drive with PLENTY of places to hike, and 25 minutes to skiing at Wintergreen. You are surrounded by jaw-dropping mountain views/sunsets that surprise every guest.

Guest favourite

Home in Charlottesville

4.99 out of 5 average rating, 143 reviews

Belleview Retreat | 5 Bedroom Home Near Downtown

Charming 5 bedroom house in Charlottesville located just 1.6 miles from downtown. The Rivanna River Trail is only a five minute walk away. Amazing shopping and dining is close by. The house comes with two kayaks and two bikes for your enjoyment! Use this space as your starting point for vineyard/brewery tours. Whether you're visiting the area for a weekend getaway, a wedding, graduation, UVA event, or anything else, the Belleview Retreat is the perfect place to stay to experience our area!

Top guest favourite

Home in Madison Heights

4.95 out of 5 average rating, 19 reviews

Sleeps 20 | Family-friendly | Near DT LYH & LU

Enjoy the convenience of staying in both of these beautiful homes that are right next door! Enough space to sleep up to 20 people! This is a perfect situation for large groups who are trying to gather together but still have your own space. Between the two homes, The Madison and Golden Jewel, there are 6 bedrooms and 5 bathrooms. Located on a safe, quiet street. Both homes have large backyards with fire pits and decks. Golden Jewel has a great basement that's ideal for creating memories!

Guest favourite

Home in Goodview

4.98 out of 5 average rating, 282 reviews

Lakehome with HotTub Fireplace Theater & Game Room

HUGE 4/3 LAKEFRONT wildlife viewing RETREAT sitting on over 2 acres overlooking beautiful SML. This home is ideal for family gatherings. Large dock with deep, clean water in a quiet cove perfect for swimming and excellent fishing. We provide kayaks, paddle boat, canoe, paddle board. Our SPACIOUS home provides lots of fun for the whole family Indoor fun includes Movie theater, pool table, air hockey, foosball, video games and kids play room.Just outside is a hot tub, firepit, b-ball & more!

Superhost

Home in Huddleston

4.91 out of 5 average rating, 132 reviews

$198 Lakefront Home Dockw/Lift HotTub Kayaks Bikes

Lakefront House...7 beds. Secluded w/Big Yard 1.68 Acres. Most Desirable and Cleanest Water Location on SML. Best fishing area. HotTub. Amazing Views. No steps entrance. Gentle lot w/ paved walkway to lake. Dock w/Boat Lift, Firepit w/Wood, 4 Kayaks/LifeVests, Bikes w/Helmets, Screened Porch. Deck. Gas Grill. Activities for kids. Near Marina w/Boat Rentals. Near State Park w/Hiking. Family/Older Folks/Kids/Pets. Lots of Parking. Near Lynchburg/Roanoke. May-August Special Mon. nights $198

Superhost

Home in Charlottesville

4.86 out of 5 average rating, 129 reviews

Close to UVA/Downtown - for Large Groups

Specious house in one of the nicest neighborhoods in Charlottesville close to Stonefield Shopping Center, Whole Foods and Trader Joe's and 5 min drive from UVA and Downtown. You can enjoy the gorgeous view from all floors. The house has a lot of space for large groups and includes DeLonghi Espresso Machine, K-Cup and Regular Coffee Makers, Air Hockey, Oculus VR, Netflix, HBO Max, Disney Plus, Hulu, ESPN+, Prime Video and 245+ channels. The house is well equipped for families with kids.

Superhost

Apartment in Moneta

4.81 out of 5 average rating, 148 reviews

5/23-5/25 AVAIL Bernards Landing BEST 2B-Next2POOL

⭐️NEW REMODEL -2024⭐️ BERNARDS VACATION PROPERTIES -BOOKBERNARDS-Voted as one of the “BEST PLACES TO STAY” at Smith Mountain Lake- January issue of Laker Magazine IF OUR DATES ARE BOOKED PLEASE SEE OUR OTHER PROPERTIES BEST LOCATION 2 BEDROOM AND VIEWS AT BERNARDS NEW RESTAURANT IN THE RESORT OPEN YEAR ROUND-NAPOLI BY THE LAKE ⭐️5G FAST WIFI⭐️ NEW KING BED-UPGRADED MATTRESS WE NOW HAVE KAYAKS, RACKET BALL, PICKLE BALL, TENNIS RACKETS & BALLS, AND MORE FUN FOR GUESTS TO USE!

Top guest favourite

Cottage in Huddleston

4.97 out of 5 average rating, 140 reviews

Peaceful 3 bedroom cottage near SML State Park

The enormous screened porch is where you will want to relax and enjoy the views. 3/4 mile to SML State Park(beach, hiking, biking, boat ramp), 4 miles to Parkway Marina, 1/2 mile to Mariners Landing Golf Course. Plenty of parking for multiple vehicles and a loop driveway if you’re towing boats. 2 queen and 2 twin beds. Fully equipped kitchen, cozy living room with smart TV and fireplace, 400Mbps WiFi. Separate sunroom for gaming or teleworking. Well behaved owners with dogs welcome.

Guest favourite

Cabin in Afton

4.97 out of 5 average rating, 204 reviews

Inn at the Woods: Updated Cabin w/Mountain Views

Fall in love with the charm of this recently updated ‘Hansel & Gretel’ style cabin located on Castle Rock Mountain. This cabin has 3 bedrooms + a loft, with a total of 4 queen beds. Hike and explore the 20+ acres or relax on the large multi-tiered deck and fire-pit area while soaking in the mountain sunsets. Enjoy nearby dining, breweries, or wineries, the historical town of Charlottesville, or spa, golf, tennis, and skiing at the Wintergreen Resort - both just a short drive away.

Guest favourite

Apartment in Wintergreen Resort

4.94 out of 5 average rating, 133 reviews

BlueRidge Getaway- Dog Friendly

Relax and enjoy spectacular top-floor mountain views from the deck. This recently renovated unit is at the top of the mountain close to many hiking trails. Visit the Wintergreen village, with its restaurants and shops, with a 5 minute drive or an easy hike through the woods. You also have access to Rhodes Farm and Chestnut Hills pool. This condo is convenient to Devils Backbone, Bold Rock, and the litany of other breweries, cideries, distilleries, and restaurants. Dogs welcome!

Superhost

Cottage in Afton

4.79 out of 5 average rating, 675 reviews

Cottage on Wine/Brew Trail!

Cottage right in the center of all the wineries, breweries, distilleries, cideries, Shenandoah National Park, hiking, App.Trail, Blue Ridge Pkwy, Wintergreen Resort.Pets welcome for an added fee ($40). Located on 151 -"alcohol alley". Literally seconds to Blue Mountain Brewery or Flying Fox Vineyard & a minute or two drive to Veritas, Cardinal Point, Afton Mt, Silverback, Valley Rd and more! Fiber internet, disinfected--couldn't ask for a better spot!