
Family-friendly vacation rentals in Winchester
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Top-rated family-friendly rentals in Winchester
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Winchester family-friendly rentals
Family-friendly home rentals with a hot tub

Private Modern Log Cabin w/Hot Tub
We enjoyed our time and the hot tub was great. Truly peace and quiet

Apple Blossom Cottage HT is extra$
I rented this Air BNB for my parents for a gift to them. I couldn’t have asked for a more responsive host and they had nothing but phenomenal things to say once arriving home!

Fern Haven - Waterfront Chalet w/ WiFi & Hot tub!
Me and my family had a great stay felt right at home and the view is amazing

Foggy River Cabin Shenandoah River
Patricia was a great host. We absolutely recommend booking with her. The cabin was clean when we arrived. Hot tub was amazing. The area is private and we will be booking again!

"The Chalet" Shenandoah Valley Getaway w/ Hot Tub
The chalet was a perfect home base for our stay in the valley over a birthday weekend. Derek gave us clear instructions ahead of time, we had no trouble getting in. We were able to just crash and watch TV the first night in front of the electric fireplace. Second night we hit the hot tub which we needed after a long hike. We found good restaurants in Front Royal and Luray (Osteria Maria, Chop House Bistro) and for coffee in the morning Broad Porch. Check out was also easy, we just needed to strip the beds and take out the trash. And of course we loved being able to bring our doggo. My fiancee had previously been hosted by Derek and we would definitely stay here again.

Lost River Tiny House, dog-friendly + hot tub
Rick and Brittany’s place was perfect for what I was looking for a long weekend away from the noise with the pup. It was quiet and private. Everything was just as described. Clean and easy to use. I do not mind driving a little further so took a venture over to Shenandoah for hiking but also got experience the local the lost river state park for hiking as well another day. Enjoyed grilling out for every meal too.

Secluded Starry Sky, Near Luray, Hottub, FastWi-fi
The only part of the stay that didn't get 5 stars was that it wasn't quite as secluded as I'd hoped for. There are a number of homes on the road to the cabin, and a thin line of trees breaks the view. Admittedly unless you're looking for the other houses you don't notice them, so I got past that quickly enough. That said, the cabin was perfect, clean, cozy and everything worked as stated. Having grown up in the country, but living in a city now, I felt the stress melt away as soon as I stepped into the massive yard where my son and I spent a lot of time playing soccer and other sports. My son and wife really enjoyed the hot tub. The location is 15 minutes away from Luray which meant that the stars were amazing for the brief break in the clouds we got, but that it was close enough to get groceries and take out as needed. Plus it's about 20 minutes away from Front Royal so there are places to go and enjoy like Skyline or Luray Caverns. Jackie was a great and responsive host!

Romantic Cottage with Private Hot Tub
Connie's Rock Cottage was amazing! much thought was put into this cottage. Firewood and fire starter for the wood stove on chilly nights, robes we used for getting to and from the private hot tub just steps outside the back door,map of entire 550 acres of land including the wonderful paved walkway which meanders through the property. This was the mosr exceptionally prepared kitchen we have seen in out travels. Tons of utensils, a full set of potsand pans, dish towels, trivets, cutting boards and cooking sheets! We love to cook together when we travel and this kitchen was big enough for 2! We got some amazing pictures all over the farm. The lack of light pollution allowed us to enjoy the stars and Pink Full Moon in all their glory! We will be back to enjoy this cottage again!
Family- and pet-friendly home rentals

Historic River House-Riverfront!
Everything was great and we had a wonderful time!

Shenandoah Treehouse & Mountain Lodge
Had a great stay with our dogs. We loved the privacy with no neighbors in sight. There were lots of bees so it was a bit hard to enjoy sitting out on the deck but otherwise was great! Nice to be able to walk into Shenandoah right from the house.

The Nest
My family of 4 plus our 2 fur babies had the best time at Julie’s home. The house is beautiful and unique with all the original remnants of wood and brick. It’s clean and very well maintained. The kitchen is well equipped with all the necessities. The pictures don’t do this house justice, honestly. The property is very private. We hardly saw any neighbors. We enjoyed everything the house had to offer, hot tub, couches outside, bathrobes, etc. we appreciated the tea, chocolate, wine and flowers left for us, too. Such a pleasant surprise, really! There are plenty of things to do around in the area. We had a great time. Thank you, Julie, for allowing us to enjoy your beautiful home with our entire family.

Lost River Dog/Bike friendly 3BR/2BA-large deck
The cottage/house was as described and wonderful. The location was perfect to explore the many nearby hiking and outdoors options. The property itself has an excellent view. The fenced in yard was convenient for our dog. Inside everything was clean and well-maintained. There were a number of nice touches to make you feel at home. There was everything one would need and more. I needed to work remotely one day and the WiFi was very reliable. Great stay!

Shenandoah Siesta
We had a very nice 3 day weekend at Elizabeth's place. The house was really cozy and we felt relaxed and at home there. It was a great location to reconnect with family as my brother and his wife only had to drive an hour from DC area to spend time with us. We enjoyed being able to walk from the house to downtown for lunch at the Box Office Brewery and antiquing at Strasburg Emporium. On a sunnier day, we had a great hike at nearby Elizabeth Furnace Recreation Area. Something for everyone in the area!

"Cabbin" at Mountain Home B&B
This place was our best choice even before we realized there would be a freshly-prepared, multi-course gourmet breakfast. House is as advertised, clean, and well-located. Scott and Lisa are friendly, responsive, and fantastic cooks. Enjoy!

Charming pet friendly home, 15 mins to caverns
Spotless place, amazing hosts. Highly recommend. We’ll be coming back.

Ballenger Farm
Perfect for our girls weekend and we loved getting a chance to see the animals. What a charming place!
Family-friendly home rentals with a pool

Private Studio Apt Retreat
Brad and Stacey‘s loft was exactly as described. The loft was extremely squeaky clean. The bed and pillows were over the top comfy. My daughter will be going to James Madison University and I have a feeling that I will be using this loft many times in the future. Thank you to Stacey and Brad for hosting us.

Mid-Century Modern Cool: Hot Tub~Grill~Pool Access
Great mountain house! House was clean and had everything we needed. The host sent us local recommendations and checkin/out was easy!

Log Cabin Lodge That Has It All
This was an amazing and beautiful cabin! The cabin was very spacious and was perfect for what we needed. Owners were very proactive and responsive and communicative. I appreciated that there were no surprises and if anything came up, they would be able to respond in a timely manner. Would definitely stay here again!

Deer Crossing at The Woods
This was our second stay at Janel's place and it was just as enjoyable as the first time. We loved the fireplace and views from the A frame windows. The hot tub wasn't working unfortunately, but things happen and Janel was communicative about it. Had a great weekend regardless. Also love that Janel is accommodating of dogs. Our fur babies were happy to join us on our getaway.

Gigi's Mountain Log Cabin with New luxury hot tub
Comfortable beds, super clean hot tub and such a nice place to spend spring break. Excellent communication and very pleasant hosts. Will definitely keep this place in mind for future trips.

GreeneHouse*HotTub*MTN.views*farm*Hiking*POOL
Really nice place. Lovely and peaceful and just what we needed

Log Cabin, *Pool, Hot Tub* Views, Views, Log Fires
Very private location. The house was a nice cabin with spectacular views and comfortable furnishings. Very spotty Verizon cell service, but wifi worked very well for calling and internet. Would recommend for a private get-away.

Monet Suite, elegnt lrg 2rm suite/blcny in villa
Lovely place. Tons of space in the suite, beautiful views and Maud is a great host.
Quick stats about vacation rentals that are family-friendly in Winchester
Total rentals
40 properties
Nightly prices starting at
$60 before taxes and fees
Total number of reviews
2.7K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi
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- Bryce Resort
- Whitetail Resort
- Luray Caverns
- Cacapon Resort State Park
- Gambrill State Park
- Stone Tower Winery
- Cunningham Falls State Park
- South Mountain State Park
- Robert Trent Jones Golf Club
- Twin Lakes Golf Course
- Whiskey Creek Golf Club
- Shenandoah Valley Golf Club
- River Creek Club
- JayDee's Family Fun Center
- Berkeley Springs State Park
- Notaviva Vineyards
- Sly Fox Golf Club
- Bowling Green Country Club
- Car and Carriage Caravan Museum
- Herndon Centennial Golf Course
- Creighton Farms
- Dinosaur Land
- The Golf Club at Lansdowne
- Reston National Golf Course
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