
Family-friendly holiday rentals in Highland County
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Highland County
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Highland County family-friendly rentals
Family-friendly home rentals with a hot tub

Secluded 3BR Log Cabin! Hot Tub! Waterfall! WIFI!
Awesome place, very cozy and private! Very roomy and spacious would highly recommend to anyone that is looking to stay in the area!

Cozy, family-friendly, mountain getaway!
We had a fantastic stay at Sylvia’s Airbnb! The space was much more spacious than the pictures suggested, and it had such a cozy atmosphere. The kitchen was well-equipped and perfect for cooking meals, and we really appreciated having laundry and a hot tub—both great bonuses after long days on the slopes. The location was super convenient, making it easy to get to Snowshoe. The only downside was that essential supplies like toilet paper, paper towels, and trash bags were limited. While Sylvia wasn’t able to restock them during our stay, she did reimburse us for what we purchased, which we appreciated. Overall, we had a great experience and would love to book again next winter!

Luxurious 2 Bdrm Family Style - Soaring Eagle 106
Great location and a perfect place for our family!

Comfortable, well kept, and convenient
Bill was hands down the best host I’ve ever had, super down to earth and just an all around great guy and host. We went snowboarding just about all week and had an absolute blast. I would recommend this place to my friends and family any day. Even though our vacation hit a few bumps Bill was extremely accommodating and helpful even though he didn’t have to be. Hoping to come back again next year if he’ll have us. 10/10 would recommend this stay.

Great Views AC Ski In Ski Out! Fireplace! Hot Tub
Stayed at this condo for few days, great location and wonderful view. Would definitely stay at this place again

Wilhelm's House- Mountain escape in VA
We visited for the weekend and had a wonderful stay. Peaceful, unique, clean - first words that come to mind when thinking of the Fenton Inn. Recommend making reservations in advance (when needed) for local dining as some of the breweries have limited seating availability due to COVID. Recommend Bold Rock for great food, views, and outdoor dining. We drove to Crabtree Falls for the day, great hike and drive along the Blue Ridge parkway which is just minutes from this location. Excited to see a couple black bear cubs!

Shays Landing #6: 4 BR, 4.5 Bath: Slope Side
We always visit Snowshoe the weekend before Christmas and have stayed at Summit. Our family has grown and we needed a bigger space. We booked this property and we all loved it. Lots of room to spread out, large kitchen for preparing meals and the location was perfect. We were able to walk to the village with a 2 year old toddler and had no problem. Powder monkey lift was out the front door. We will definitely book again for next year! Angela B

Newly Remodeled Snowcrest Condo
Anna’s place was the perfect size and location for 2 adults and 3 kids. The triple bunk beds are fun and cute. The place was fully stocked with everything we needed and more. The kids loved all the board games and the 2 hot tubs right outside our door! It was also super easy and convenient to walk down to the Soaring Eagle lift and get right on the slopes. Highly recommend!
Family- and pet-friendly home rentals

Eagle Annie's Cottage in Relaxing Highland County
Patti’s communication was great! There was nothing we needed to question her about after meeting her. Enjoyed our stay at Eagle Annie’s Cottage!

Peaceful 3 bdrm, a meadow, creek running through.
This place was tranquil & peaceful.

Warm Springs Mountain Cabin w/ Modern Style
Fantastic spot…we shall return.

Charming Getaway Cottage
Jennifer‘s place was exactly as described if not better. We reached out to her and brought our dog and the fenced in yard was an excellent addition to the trip. Jennifer was very responsive.

1720 High Ridge at Wintergreen Resort
Beautiful location with the daily sunrise over the blue ridge mountains is captivating. Kimberly who manages the property is the provides the best customer service I've ever had at Air B&B . (Got well over 100 nights in withAirB&B)

Breathtaking Views from The Ledges
house was very well stocked for an Airbnb (games, kitchen stuff, household items, etc), having an onsite firewood supply was amazing as was being within walking distance of some of the slopes. Vivian's instructions were very clear on the check in/check out procedure and everything was described accurately. Would stay here again!

Wintergreen Resort: Weeping Rock Retreat
From start to finish this was a terrific stay. This is about 1 hour from Liberty University which was the purpose of the trip. Plenty of walking trails right next to the house.

Cozy Creekside 2-bedroom home.
Very beautiful place and awesome host! The property is surrounded by a beautiful landscape & views of Mother Nature. Awesome host that was always responsive if we needed anything. Def would book again!
Family-friendly home rentals with a pool

Private Studio Apt Retreat
Brad’s place was very spacious and just what we were looking for! I would definitely recommend for a single traveler or couple. Looking forward to our next trip there.

Walk to Market/Slopes!
What a gem to find. My stay was comfortable, relaxing and perfect for me. This is on my return list. Thank you.

Eight Minute Walk to Everything
beautiful mountain top and away from the hustle and bustle. The place was very clean and peaceful, but the oven temp was a little off other then taht the place was perfect.

The Bear Dance Cabin at Wintergreen Resort
I’d argue that this is one of the best places to stay in Wintergreen. The cabin itself is perfect. We are a young family and it was comfortable, clean, and had everything we needed. The location is also perfect. It is very close to all the attractions on the resort. Clay was a great host as well. The perfect amount of communication; engaged without being intrusive. I would recommend this place to anyone who wants to be sure their trip is easy and successful!

Blue Ridge Bliss - For family & friends to enjoy!
We loved our stay at this condo in Wintergreen. The condo was beautifully furnished. Very clean. And the views from the balcony are unbelievable. Since it was spring, it was very quiet which we enjoyed. The mountains were so lush and green. The host responded to any questions within minutes. Check out was a breeze. We will be booking again!

Cabin on Penmerryl Farm - (2-Night Minimum Stay)
My family and I truly enjoyed our stay. My husband took our kids (ages 10 and 7) fishing on the property, which they absolutely loved. We spent time swimming in the pool and hiking the beautiful surroundings. We also visited the nearby Virginia Safari Park and Natural Bridge Park—both were wonderful day trips. The host was fantastic, and the property was peaceful and relaxing. We’d love to come back!

Cozy, clean, quiet mountain condo- King bed
John and Ritta were amazing to work with and so helpful. We found their cozy condo after a trip fell through. We were so glad to have found this amazing place in close proximity to hiking spots, good food, wineries and breweries. We will definitely be back.

Mntn View Hot Tub Pool Table Pool Tennis Golf
A wonderful property nestled in the Wintergreen Resort. While not part of the resort, the amenities and surrounding Breweries offered plenty to do while not relaxing in the hot tub or on the private deck. Beds were comfortable, and there was plenty of space for our family to spread out. Access to WiFi and movie channels were convenient and supplemented the secluded feel for a well balanced vacation. Highly recommend this rental for families and groups looking to get away for a relaxing and enjoyable time in the mountains. Bring your cameras and charge your phones to take pictures of the breathtaking views at and around the house!
Destinations to explore
- Rentals with a patio Highland County
- House rentals Highland County
- Family-friendly rentals Highland County
- Rentals with outdoor seating Highland County
- Rentals with a washing machine and dryer Highland County
- Rentals with a firepit Highland County
- Cabin rentals Highland County
- Pet-friendly rentals Highland County
- Rentals with a fireplace Highland County
- Family-friendly rentals Virginia
- Family-friendly rentals United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom