Family-friendly vacation rentals in Winchester

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Winchester family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
A hot tub is situated on a wooden deck, framed by a railing. The surrounding trees display autumn foliage, with warm colors of orange and yellow contrasting against the clear sky. A trail can be seen in the background, hinting at nearby hiking opportunities.
Cabin in Berkeley Springs
4.91 out of 5 average rating, 147 reviews

Private Modern Log Cabin w/Hot Tub

RandallRating, 5 stars4 months ago
We enjoyed our time and the hot tub was great. Truly peace and quiet
Guest favorite
A hot tub is situated inside a gazebo with a wooden ceiling. Surrounding greenery provides a natural backdrop, while the tub features built-in seating and a clear view of the outdoors, promoting a serene relaxation experience.
Tiny home in Orrtanna
4.93 out of 5 average rating, 437 reviews

Apple Blossom Cottage HT is extra$

KarliRating, 5 stars2 weeks ago
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!
Guest favorite
Chalet in Great Cacapon
4.95 out of 5 average rating, 421 reviews

Fern Haven - Waterfront Chalet w/ WiFi & Hot tub!

DwayneRating, 5 stars1 week ago
Me and my family had a great stay felt right at home and the view is amazing
Superhost
A spacious hot tub is situated within a screened enclosure, surrounded by wooden beams and greenery. The tub is covered with a wooden lid, offering a serene atmosphere while allowing views of the outdoor natural surroundings.
Cabin in Luray
4.76 out of 5 average rating, 314 reviews

Foggy River Cabin Shenandoah River

MerissaRating, 5 stars2 weeks ago
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!
Guest favorite
Two wooden Adirondack chairs are positioned on a spacious deck, facing panoramic views of the blue sky and distant mountains. Lush trees and greenery fill the scene, creating a serene outdoor atmosphere.
Chalet in Rileyville
4.94 out of 5 average rating, 165 reviews

"The Chalet" Shenandoah Valley Getaway w/ Hot Tub

DavidRating, 5 stars3 weeks ago
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.
Superhost
A large wooden deck is surrounded by trees, featuring a hot tub and two black metal chairs. The sunlight filters through the foliage, creating a natural setting ideal for relaxation.
Tiny home in Mathias
4.85 out of 5 average rating, 412 reviews

Lost River Tiny House, dog-friendly + hot tub

AaronRating, 5 stars5 days ago
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.
Guest favorite
The cabin's exterior is characterized by natural wood siding and a green metal roof. A spacious porch extends along the front, featuring two rocking chairs and hanging plants. Lush greenery surrounds the cabin, creating a tranquil setting.
Cabin in Rileyville
4.92 out of 5 average rating, 238 reviews

Secluded Starry Sky, Near Luray, Hottub, FastWi-fi

RobertRating, 5 stars3 weeks ago
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!
Top guest favorite
The image shows three well-maintained tennis courts surrounded by greenery. A gazebo sits at one end of the courts, providing shade and seating. The courts feature a primarily maroon surface, divided by white lines, with fencing and lighting installed for play.
Home in Castleton
4.95 out of 5 average rating, 114 reviews

Romantic Cottage with Private Hot Tub

AnnRating, 5 stars1 week ago
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

Superhost
The historic home is situated on a spacious lawn, surrounded by a wooden fence. Its two-story façade features light-colored siding, a covered porch with a lattice detail, and several windows allowing natural light into the interior.
Home in Elkton
4.79 out of 5 average rating, 241 reviews

Historic River House-Riverfront!

JenniferRating, 5 stars1 month ago
Everything was great and we had a wonderful time!
Guest favorite
A treehouse is positioned amidst lush greenery, featuring a wooden deck that wraps around it. Large windows provide views of the surrounding forest. Two chairs are placed on the deck, inviting relaxation in a serene outdoor setting.
Cabin in Stanley
4.94 out of 5 average rating, 290 reviews

Shenandoah Treehouse & Mountain Lodge

AmyRating, 5 stars2 weeks ago
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.
Superhost
A light-filled seating area features a plush daybed with decorative pillows, positioned beside a stylish floor lamp. Natural wood floors reflect the afternoon sun, while large windows offer views of the outdoor space and allow for an inviting atmosphere.
Home in Chester Gap
4.95 out of 5 average rating, 223 reviews

The Nest

IrinaRating, 5 stars6 days ago
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.
Top guest favorite
The exterior of the cottage is captured from an angle, showcasing its charming two-story structure with a sloped metal roof. Lush green hills rise in the background, while a grassy area with trees surrounds the property, providing a serene natural setting.
Cottage in Mathias
4.93 out of 5 average rating, 190 reviews

Lost River Dog/Bike friendly 3BR/2BA-large deck

ChrisRating, 5 stars1 month ago
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!
Guest favorite
A cozy living area features a brown leather sofa, accompanied by two green armchairs and a black coffee table. A large TV is mounted on the wall, while warm lighting enhances the wood-paneled accent wall. Nearby, dining chairs are arranged around a kitchen counter. Plant accents add a touch of greenery.
Home in Strasburg
4.9 out of 5 average rating, 246 reviews

Shenandoah Siesta

ElizabethRating, 5 stars2 months ago
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!
Guest favorite
The exterior of a cozy brick building is framed by lush greenery and trees. A small patio area features two chairs, surrounded by freshly mulched beds with low shrubs. The building's porch is screened, offering a welcoming entrance.
Guesthouse in Front Royal
4.89 out of 5 average rating, 261 reviews

"Cabbin" at Mountain Home B&B

MatthewRating, 5 stars6 months ago
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!
Top guest favorite
The exterior of Acorn Hill features a welcoming red wooden cabin surrounded by trees. A spacious deck with a wooden railing offers seating options, creating a comfortable entrance to the home. The gravel driveway provides access, with a natural landscape enhancing the serene environment.
Home in Luray
4.96 out of 5 average rating, 269 reviews

Charming pet friendly home, 15 mins to caverns

MansiRating, 5 stars3 weeks ago
Spotless place, amazing hosts. Highly recommend. We’ll be coming back.
Top guest favorite
Farm stay in Hamilton
4.97 out of 5 average rating, 230 reviews

Ballenger Farm

KirbyRating, 5 stars2 months ago
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

Guest favorite
Loft in Bridgewater
4.93 out of 5 average rating, 547 reviews

Private Studio Apt Retreat

JeanneRating, 5 stars1 week ago
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.
Guest favorite
A cozy living area features a comfortable grey sofa facing a black television. A round ottoman sits in front of the sofa. Natural light streams through a large window, highlighting the vibrant green wall. In the corner, a colorful lamp adds a touch of warmth.
Home in Massanutten
4.88 out of 5 average rating, 119 reviews

Mid-Century Modern Cool: Hot Tub~Grill~Pool Access

KimRating, 5 stars3 months ago
Great mountain house! House was clean and had everything we needed. The host sent us local recommendations and checkin/out was easy!
Superhost
A hot tub is situated on a shaded deck, surrounded by trees. Soft bubbles rise in the water, creating a relaxing ambiance. A folded towel rests on the edge, complementing the inviting atmosphere of the outdoor space.
Cabin in Massanutten
4.91 out of 5 average rating, 127 reviews

Log Cabin Lodge That Has It All

TravisRating, 5 stars2 months ago
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!
Superhost
A charming cabin is nestled among trees, featuring a sloped roof and large glass windows that offer abundant natural light. A wraparound deck provides outdoor space, while a cylindrical chimney and air conditioning unit are visible on the exterior.
Cabin in Hedgesville
4.88 out of 5 average rating, 225 reviews

Deer Crossing at The Woods

LauraRating, 5 stars3 months ago
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.
Guest favorite
The exterior of the cabin is surrounded by well-maintained evergreen trees, offering privacy and a natural setting. The wooden deck extends from the front, featuring railing and steps leading to the entrance. Stone details highlight the foundation, while a steeply pitched roof enhances the rustic charm.
Cabin in McGaheysville
4.91 out of 5 average rating, 179 reviews

Gigi's Mountain Log Cabin with New luxury hot tub

VinceRating, 5 stars5 days ago
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.
Guest favorite
A seasonal saltwater pool features clear blue water surrounded by lush greenery. A gazebo nearby includes two pink chairs, providing a shaded area for relaxation. The pool area is designed for shared use among guests, inviting leisure and tranquility within nature.
Farm stay in Stanardsville
4.96 out of 5 average rating, 585 reviews

GreeneHouse*HotTub*MTN.views*farm*Hiking*POOL

DeborahRating, 5 stars5 days ago
Really nice place. Lovely and peaceful and just what we needed
Superhost
A spacious outdoor area features a blue swimming pool with clear water, surrounded by verdant grass. The backdrop showcases rolling mountains beneath a partly cloudy sky, adding to the serene landscape. The log cabin is visible nearby, enhancing the setting.
Cabin in Rileyville
4.77 out of 5 average rating, 105 reviews

Log Cabin, *Pool, Hot Tub* Views, Views, Log Fires

SiegfriedRating, 5 stars2 months ago
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.
Guest favorite
A pool area is framed by an arch covered in vibrant flowers. The inviting water reflects the clear blue sky, while lounge chairs line the deck. Lush greenery surrounds the space, and a gazebo is visible in the background, enhancing the serene landscape.
Guest suite in Purcellville
4.82 out of 5 average rating, 226 reviews

Monet Suite, elegnt lrg 2rm suite/blcny in villa

ChadRating, 5 stars6 months ago
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

Destinations to explore