Family-friendly holiday rentals in Surry County

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Surry County family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
Train in Fancy Gap
4.87 out of 5 average rating, 77 reviews

#Depot - Grassy Creek Cabooses

KayRating, 5 stars3 months ago
This is the second time that we have stayed with Donnie. The first time was in one of the cabooses. This time we stayed in The Depot. Both of these places were as described and pictured! I had good enough phone service that we did not miss having WiFi and there was cable for television. I had two children with me, an eight year old and a twelve year old, and they were both fine there! And we could look out the front door and see Buffalo Mountain. Because of Hurricane Helene damage, we did not get to go there but it was not for lack of trying! Sunday morning before we left, I got to see a deer in the pasture behind the depot! And some beautiful sunrises!
Superhost
Train in Fancy Gap
4.9 out of 5 average rating, 300 reviews

#407 Grassy Creek Cabooses

D.H.Rating, 5 stars5 months ago
Beautiful location, place as described. Jacuzzi was great. Lots of hot water. Good water pressure, good shower. Bed was comfortable. Donnie was helpful and responsive.
Superhost
Train in Fancy Gap
4.9 out of 5 average rating, 172 reviews

#042 - Grassy Creek Cabooses

MistyRating, 5 stars3 months ago
We wanted to do something unique & different for our anniversary & this did NOT disappoint. From the “main” road you can see the 3 red cabooses up on the hill & our hearts smiled. They recently had storms & we could see where the flood waters deteriorated the sides of the driveway but it was still wide enough for us to pass another small vehicle if needed. Office Check in was a breeze and took less than five mins before we were standing in our getaway train(caboose) which is on a real track! We were the only ones staying this weekend but if others were present, there was plenty of room. Our furbabies throughly enjoyed having a large field in front of the cabooses to run in. The views from the swings were breathtaking especially during the sunsets. Once Inside, we enjoyed the comforts of home (except for a stove). The hotness of the water & the relaxing hot tub added to our experience. Some things were dated but that is to come with the territory. We hope to visit again in the fall.
Guest favourite
Cabin in Floyd
4.93 out of 5 average rating, 254 reviews

Stylish Cabin near wineries & parkway

JoshuaRating, 5 stars2 weeks ago
May be one of my favorite mountain stays I’ve had! Definitely will be back!
Top Guest favourite
Cabin in Elkin
5 out of 5 average rating, 45 reviews

Papa John's: Private Cabin in the Woods

LisaRating, 5 stars4 months ago
Had a great stay at “papa Johns” cabin. Perfect getaway with the hubby for his birthday. The cabin was well equipped with essential supplies and very clean. I’m a housekeeper myself so I’m very particular! The hot tub was perfect, very relaxing. And we highly recommend “Southern on Main” restaurant, it was fantastic!
Guest favourite
Cabin in Crumpler
4.9 out of 5 average rating, 115 reviews

Huckleberry Hideaway

KarenRating, 5 stars9 months ago
Very cool and interesting house in a beautiful setting, We loved the porch and hot tub and being able to let the dogs wander around the huge fenced yard. It was nice being out in the country watching and listening to the sheep next door and the cows across the street. We enjoyed hiking at New River state park (very close by) and letting the dogs wade in the river there, we also hiked Mount Jefferson (beautiful views) and played disc golf at Ashe county park disc golf course, which is a really nice course. We enjoyed the breweries in West Jefferson and loved the Outhouse Goods restaurant, great food and you can sit outside with a gorgeous view. Our only warning is don't walk your dogs in the woods behind the house, the neighbors dog running loose almost attacked our dogs. Overall, a great place to stay!
Top Guest favourite
Cabin in Elkin
4.93 out of 5 average rating, 56 reviews

The Mill House: Dog Friendly Cabin

MelodyRating, 5 stars2 months ago
We had a wonderful time at this little cabin in the woods. It's on a beautiful piece of property and even though there were a few other buildings around, it felt very private. You could hear the stream in the background which was just lovely. The cabin itself was extremely clean and very welcoming. The decor was nice without being too cluttered feeling. Just the perfect amount of stuff. I don't think more than 2 people could stay here comfortably as it's basically just one big room, but for us, it was absolutely perfect! The back deck overlooked the stream and had a hot tub. We didn't use the hot tub and it was a bit loud which drowned out the sound of the stream. Teresa said that in the future, we can ask that it be turned off if we're not going to use it, so that's a great option for next time. Overall, a great place to spend a lovely, restful weekend in Elkin. We definitely plan to come back!
Top Guest favourite
Cabin in Ararat
4.92 out of 5 average rating, 405 reviews

A great place on Blue Ridge Parkway for a getaway

JennyRating, 5 stars4 weeks ago
We really enjoyed our visit! The house was perfect. We were so happy just relaxing on the deck and in the hot tub. We lost power only briefly but the generator kicked on so no real interruption. We found it hard to leave and head back home. Thank you for the wine as well as such a beautiful place to spend our vacation.

Family- and pet-friendly home rentals

Superhost
Home in Fancy Gap
4.86 out of 5 average rating, 132 reviews

Fancy Gap Mountain Escape

TimothyRating, 5 stars8 months ago
The place was beautiful and private with great views and not too far away. Linda & Michael were wonderful. They were very nice, helpful and ready to meet any need to make our stay relaxing and memorable. We look forward to going back in the future.
Top Guest favourite
Cabin in Pilot Mountain
4.93 out of 5 average rating, 199 reviews

2 bedr 2 baths Custom Log Cabin on Pilot Mtn Farm

TriciaRating, 5 stars1 month ago
This was the most relaxing, peaceful and carefree weekend we have ever had. My husband and our 2 kids and 2 dogs had the most fun, and we didn’t even feel the need to be on our phones or watch tv! The cabin felt like home; so much so, that we didn’t want to leave. My husband and I are already planning a trip back. Carey was an amazing hostess and we are so appreciative that she opened her home to us. The views were breathtaking. We literally sat outside all weekend. We only went inside to cook and sleep. Oh! And we got to enjoy a meteor shower Saturday night! Super awesome!! And, even cooler, there’s a dollar general market at the end of the main road! Coolest thing I’ve ever seen! So you don’t need to bring a bunch of food! We drove 5 hours to come stay here, and honestly, I would drive 10 just to come back. This cabin was every bit of home and we can’t wait to come back!
Superhost
Home in Winston-Salem
4.81 out of 5 average rating, 207 reviews

Winston posh bungalow near Wake

CharisseRating, 5 stars2 weeks ago
I was here with my daughter n grand daughter n twin cousins and this was exactly what was needed for our stay. Grateful am I! The toilet paper roll was priceless thank you! If back n WS will book here if available.
Top Guest favourite
Cabin in Fries
4.95 out of 5 average rating, 603 reviews

Remote Mountain Cabin in the Woods

KaysiaRating, 5 stars2 weeks ago
We had an excellent stay in this cabin. It was quiet and private but still close to things we wanted to do. The little walking trail on the property was great. 10/10 would stay here again.
Superhost
Home in Laurel Springs
4.82 out of 5 average rating, 135 reviews

Sadie's Place on the Blue Ridge Parkway

TessaRating, 5 stars2 weeks ago
Wonderful, peaceful location. Fully stocked and easy access. The country setting is a perfect way to relax.
Top Guest favourite
Cabin in Grassy Creek
4.95 out of 5 average rating, 436 reviews

Grove Cabin 20 acres of privacy (no extra fees)

DierdreRating, 5 stars1 week ago
If you have a chance to stay at Scott’s place I would absolutely recommend you do so. This is a beautiful, peaceful very unique place - everything you need in a lovely, simple package. Also close to Grayson Highlands and Doughton State Park.
Guest favourite
Home in Hillsville
4.89 out of 5 average rating, 219 reviews

Mark of Design Farmhouse Retreat

ChalonRating, 5 stars1 month ago
We’ve stayed at Mark of Design many times! We enjoy the beautiful & peaceful setting of the horse farm. In addition to watching the horses in the fields, we saw deer, wild turkeys & rabbits. It is also very convenient for restaurants in downtown Hillsville, as well as nearby Galax & Mt Airy.
Top Guest favourite
Cottage in Elk Creek
4.96 out of 5 average rating, 232 reviews

Granny's - no extra cleaning fees

NicholasRating, 5 stars1 week ago
This is a perfect beautiful little cottage. The gardens and play place were amazing little spots to spend time with our family. We were in town for a family reunion so the location for us was absolutely perfect. Amelia’s place is clean and cozy and it was a great choice for our needs. We’re going to book for our trips back to Elk Creek going forward! Thank you :)

Family-friendly home rentals with a pool

Condo in Clemmons
4.92 out of 5 average rating, 169 reviews

2br King-Queen/2ba/Pool/ No cleaning fees!

KevinRating, 5 stars20 months ago
Thaddeus was the best host I have had to date. Over delivered in every category!
Top Guest favourite
Guesthouse in Winston-Salem
4.95 out of 5 average rating, 383 reviews

Studio 1BR near WFU

DougRating, 5 stars1 week ago
Absolutely loved the rustic yet extremely comfortable feeling of the room. The West End Café as recommended was phenomenal. Without Dave letting me know that Google maps takes you somewhere wrong I would’ve been lost. However, he was proactive and told me that and I ended up right at the door very easily. Beautiful area quiet felt at home. He actually came and checked on me this morning after I texted and told him I was leaving he came out of the house just to make sure everything was OK. If I have the opportunity to be back there and spend the night again, I will definitely stay at Dave’s place if it’s available. Not sure if it was on purpose or if someone else had left it, but there was even Bud Light in the fridge if I had wanted! Thank you for your hospitality!
Guest favourite
Condo in Winston-Salem
4.91 out of 5 average rating, 445 reviews

Sanctuary – 1bedroom & 1bathroom

MollieRating, 5 stars2 weeks ago
I had a great stay at this Airbnb! The space was clean, comfortable, and exactly as described in the listing. Check-in was easy, and the host was super friendly and quick to respond to any questions I had. The location was perfect—close to restaurants, shops, and public transportation, but still nice and quiet at night. Would definitely stay here again next time I'm in the area. Highly recommended!
Farm stay in Ararat
4.88 out of 5 average rating, 17 reviews

Laurel Glen Cottage at Wolf Creek Farm

KhanRating, 5 stars24 months ago
Our kids had a great time! Very private location with no ongoing traffic. They played in the front of the cabin all day with no worries from us about vehicles. Great spot to getaway and relax with outdoor activities (fishing, hiking, doing smores).

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