
Family-friendly holiday rentals in Jamestown
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Jamestown
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 Jamestown family-friendly rentals
Family-friendly home rentals with a hot tub

King Bed, Hot Tub, BBQ, Board Games, Allergy-Free
Very cozy, friendly neighbors and the perfect pit stop while waiting to move into my new home.

Luxury Hot Tub, King Beds & Showers, Sleeps 20+
Great place to stay in a wonderful neighborhood. Our group felt right at home with the many amenities, cleaniness, and spacious rooms. Host was very helpful & responsive! Would re-book if ever back in the area :)

Remodeled Oasis in the heart of Greensboro
Rebecca was the perfect host for our stay in Greensboro. The home was in the perfect location and totally exceeded our expectation. Rebecca was very flexible and always responded to my questions and request within 30 mins or less. This was a beautiful modern home as described with all the amenities. True Oasis for the weekend. I would definitely rent again when visiting the area.

Sedgefield Manor
This is a big House. It has one European style living room and traditional one. It is great. the House got everything. We have a team and everyone satisfied with this beautiful House. I think we will stay here if we have next year travel schedule. Farida is nice in communication.

Cozy King Bed, Hot Tub, Pet Friendly, Firepit
Great host and very nice house.

Pet Friendly Charming King Bed Ping Pong BBQ Grill
Perfect place for my family Thanksgiving. Host was very friendly, responsive and helpful. Loved it.

Ardmore Suite: King Bed & Jacuzzi Oasis
We loved our stay here! It was well beyond expectations we would definitely recommend anyone wanting a night away to book immediately you will not be let down in the least bit. We will certainly be booking here again soon! Thank you so much!
Family- and pet-friendly home rentals

Courtyard Cottage Safe Parking! No pet fees!
We loved staying in Jennifer's Airbnb. It was the perfect size for two people spending a weekend in Winston-Salem. Everything we wanted to do downtown (sights, restaurants, bars) was within walking distance from her house. The loft itself was clean and had all the amenities we needed.

Emerywood family home close to HPU and downtown
If you’re looking for the typical cookie-cutter, sterile Airbnb experience, this place is not for you. When you check into Austin’s home, expect to feel like a welcome guest at a good friend or family member’s beautiful home. It’s comfortable, charming, and full of character—clearly well-lived in and loved. Every corner has personality, and there’s a warmth that makes you feel right at home. We loved our stay!

The Homeplace at Idlewild.
We are incredibly grateful to have found this place and to have met Candy and Gary! Our two years here were nothing short of amazing, and we truly felt like part of the family. We look forward to visiting as often as possible!

2 Bedroom 1 Bathroom Entire Home
We stayed at David's place so we could be close to our daughter while she was giving birth to her first child and our 3rd grandchild at Atrium Health Baptist Hospital. The place was great and fit all of our needs. David was a great host and worked with us to ensure that both us and, indirectly, our daughter had a stress-free environment and experience. If you are looking for a great place to stay, with a host that is willing to go above and beyond, look no further. If I ever need to return to Winston-Salem, I will be looking this place up and booking it if it is open.

Cedar Shake Cottage
We loved our stay here! Susan and Jeff were very nice and responsive. The house and surroundings were beautiful!

"Kennarda" in Winston-Salem, North Carolina
Lovely home in a fantastic neighborhood. We had a great time staying here with our dog. It was very walkable with excellent restaurants and groceries nearby. The home was quite roomy and included a much appreciated washer and dryer. While the back yard was not fully fenced in, it was landscaped and had a comfortable patio. We enjoyed sitting out there with our pup.

Entire Home Greensboro, HP, W-S
Chris is a fantastic host and a great communicator. The home is perfect for a family stay in the Greensboro area as it is comfortable and very convenient to town. The kitchen is large and open, with an attached to a breakfast area and family room with a fireplace. We had everything we needed to prepare meals and enjoy our relaxing downtime. The backyard view and the attached deck are added bonuses. We would have enjoyed using the outside furniture and fire pit, but the weather did not cooperate since it rained when we arrived and even snowed while we were there. We had a great time making final preparations for our daughter's wedding while staying at Chris' home and being together as a family for this special weekend. Many thanks to Chris for his friendliness and local recommendations!

Mountain serenity 5 miles from downtown
This wonderful house sits well off the road in a beautiful wooded area of the City. Even though there are houses in the area we never saw or heard any neighbors making it the perfect place for long time friends to gather and catch up for a weekend of golf and good times. Our favorite part of the house was the huge covered outdoor space which is attached directly to the house. We spent pretty much every afternoon and evening out there - enjoying the company and the woods. Susan was so accommodating and did a fantastic job of communicating with us. I would highly recommend this house to anyone looking for a special place to get together with family and friends.
Family-friendly home rentals with a pool

2br King-Queen/2ba/Pool/ No cleaning fees!
Thaddeus was the best host I have had to date. Over delivered in every category!

Studio 1BR near WFU
Dave's place was great, just as described and the neighborhood is so pretty and peaceful. Great place to walk your dog. Dave is very responsive if you need anything but otherwise gives you your privacy. Wonderful place to spend the weekend. I'll definitely stay again when I'm in town.

Peace of Mind
House was great, pretty private, great pool. Lots of space for the family and there were snacks out for us which everyone really enjoyed. Had everything we needed for our stay. The only negative about the house was listed no pets. But there clearly were pets that lived there. Being highly allergic to animals with fur that probably would have not chosen that location. I needed to medicate the whole time. Other than that the home was what we needed.

Henry Connor Bost House
This house has a very historic and comfortable feel. Beautiful bedrooms. Well equipped kitchen and lots of dining space for a large group. It has quiet country charm. Our family loved coming together here for Thanksgiving.

Sanctuary – 1bedroom & 1bathroom
Super clean place🔥💯💯i enjoyed my stay, bro kinda hooked me up. had the huzz going crazy over it 10/10

The Cottage at Henry Connor Bost Farm
The cottage is a beautiful escape into an quieter and simpler way of life. Well equipped. Easy commute to the transportation museum, downtown shops and restaurants and wineries. Our second stay, and the whole family had another truly remarkable experience. Will be back 💕
Quick stats about holiday rentals that are family-friendly in Jamestown
Total rentals
30 properties
Nightly prices starting at
£54 before taxes and fees
Total number of reviews
1.5K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi
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