Family-friendly holiday rentals in Charlottesville

5.0 out of 5 average rating, 165 reviews

A charming cottage is nestled among lush green grass and surrounded by trees. Its metal roof and white siding are complemented by well-maintained shrubbery. Dappled sunlight filters through the tree branches, creating a serene outdoor ambiance.

Cottage in Covesville

Historic cottage with stunning mountain views

Welcome to Rose Cottage in picturesque Albemarle County, where you'll enjoy expansive 360-degree views of the mountains surrounding historic Cove Lawn Farm. Relax in the tranquil rural setting or stroll more than two miles of comfortable walking paths that wind through 25 acres of stream-lined hayfields. From Rose Cottage, you're just minutes from the best local cideries, distilleries, and wineries including Pippin Hill Farm & Vineyards. Easy 20-minute drive to UVa and 22 minutes to Monticello.

FamilyIndoor spacesLocation

Townhouse in Charlottesville

The exterior of a modern two-story home is presented, featuring a light color palette. A set of stairs leads to the front door, flanked by greenery and landscaped areas. The home includes a small balcony with glass railings and multiple windows that allow natural light.

4.96 out of 5 average rating, 242 reviews

Belmont Home with Hot Tub - steps from Downtown

The perfect destination for your Charlottesville visit in the hip neighborhood of Belmont, where you can read on the loggia with great views or in the hot tub on the patio. From this modern home, you can walk to the best restaurants the city has to offer as well as the popular Downtown Mall and IX Art Park. The University of Virginia and Monticello are each just a short drive, and the home is convenient to the Monticello Wine Trail and Skyline Drive. See below for link to basement apt. listing.

FamilyKitchenAmenities

5.0 out of 5 average rating, 255 reviews

A cozy cottage, named the 'Sugah Shack,' is nestled amidst the rolling hills of the Blue Ridge Mountains. The white exterior contrasts with the vibrant greenery surrounding the property, while the majestic mountains form a picturesque backdrop against a bright, partly cloudy sky.

Cottage in Afton

Cozy Mountain Cottage on Brew/Wine Trail-King Bed

Welcome to the Sugah Shack, a cozy, beautifully appointed new construction cottage nestled in the foothills of the Blue Ridge Mountains! Located midway on the Brew Ridge Trail, but 500 yards off the byway, so guests have a quiet retreat. Perfect for romantic getaways, destination telework space, or families exploring this outdoor paradise community. Stunning property boasts beautiful vistas with sweeping 300-degree mountain and a year-round calendar of outdoor activities. GAS FIREPLACE/FIREPIT

Indoor spacesKitchenAccuracy

4.89 out of 5 average rating, 258 reviews

A charming cottage exterior showcases a green facade with textured wood siding, complemented by a welcoming porch. Outdoor seating is provided by rustic chairs around a fire pit on the lawn. A table nearby offers an inviting spot for dining, set against a backdrop of distant mountains.

Cottage in Crozet

Idyllic Cottage Retreat

⭐️ Condé Nast Traveler Approved ⭐️ Cozy cottage nestled on a historic 400-acre Blue Ridge Mountain farm abutting Shenandoah National Park. Every space inside this cozy cottage is creatively styled, with tons of perfectly imperfect charm. Outside, a hammock beneath the elm trees, fire pit and grill, all allow for enjoying the splendor of this peaceful enclave. Excellent day-tripping to many of central Virginia's celebrated wineries and breweries, as well as scenic drives and hiking trails.

FamilyKitchenBarbecue

4.99 out of 5 average rating, 108 reviews

The unique octagonal house is framed by lush greenery, showcasing its distinctive architecture. A spacious deck offers a vantage point for enjoying unobstructed views of the surrounding landscape. Panoramic windows reflect the natural beauty of the Blue Ridge Mountains, inviting light into the living space.

Home in Afton

Mountain Overlook House - Blue Ridge Parkway

Unique octagonal house with stunning views of the Blue Ridge Mountains of Virginia. Located 2 miles from I-64, 15 minutes to downtown Waynesboro and an easy 25 min drive to Charlottesville and UVA. Open floor plan, perfect for gathering, and long-range 180 degree views from nearly every room. Fully equipped renovated kitchen. Quality linens and bedding. Rustic, yet modern decor. Home features large fireplace, outside fire pit, wifi, and board games galore. Stargazing and birdwatching heaven.

KitchenFamilyWalkability

4.99 out of 5 average rating, 347 reviews

Four horses graze on a lush green lawn, with a charming two-story building in the background. The house features a balcony and is surrounded by blooming shrubs and trees, creating a serene atmosphere on the farm.

Farm stay in Afton

Afton, Mountain View Mini Farm

Welcome to Mountain View Mini Farm! We are located in the Rockfish Valley(Afton, VA)with amazing views of the Blue Ridge Mountains. Our farm is just minutes to wineries, breweries, cideries, Shenandoah National Park and more! There is so much to do close by, but once you get on the farm, you won't want to leave! We have a total of 5 horses, with 3 being mini rescue horses. There's a fire pit area where you can roast S'mores while you watch the sunset. Be sure to look at bedrm 2 description.

FamilyIndoor spacesOutdoor spaces

4.95 out of 5 average rating, 280 reviews

The interior of the tiny house features an open kitchen layout with modern appliances and a central island. A geometric area rug extends across the floor, while light wood accents create a warm feel. Shelving holds books and decor, enhancing the cozy atmosphere.

Cabin in Nellysford

Tiny Luxury Retreat: Lake, Hikes, Brews & Vines

Welcome to our luxurious tiny house nestled in the heart of Nelson County, Virginia. This enchanting retreat, surrounded by the majestic Blue Ridge Mountains, offers an unparalleled experience in a landscape dotted with wineries, breweries, distilleries, and sprawling farmland. This luxury tiny house was built in 2022 and is available for couples, solo travelers, or a small family wanting to explore this beautiful stretch of the Blue Ridge Mountains. FREE Electric Vehicle Charger on-site.

Indoor spacesFamilyCheckout

4.99 out of 5 average rating, 239 reviews

The dark wooden cabin, framed by lush greenery, sits at a hillside location with panoramic mountain views. A deck extends from the cabin, featuring a hanging basket chair. A warm sunset casts a golden hue across the sky, enhancing the serene atmosphere.

Cabin in Free Union

Shenandoah Stargazer with Sauna

Stargazer is the perfect place to get away from it all! The stillness and serenity of being nestled in a bird and wildlife sanctuary is so good for your soul. Watch the sunrise from a hanging basket chair at 2700 feet of elevation, or wait for moonrise and toast spectacular star views! Relax in the sauna after a day filled with hiking and an al fresco meal on the deck. Roast s’mores at the deck fire table or over the side yard fire pit. There's magic in the air at this mountaintop retreat!

KitchenIndoor spacesComfort

4.99 out of 5 average rating, 251 reviews

Bungalow in Afton

The Bungalow at Afton Mountain Retreat by Veritas

Welcome to The Bungalow at Afton Mountain Retreat in the heart of Brewery Trail/Route 151, Vineyard country and the foothills of the Blue Ridge Mountains. The Bungalow is located 1/4th mile from Veritas Vineyard. It is within 10 minutes to every brewery, vineyard, distillery and cidery along Route 151 Crozet, 1 mile from the newly opened Blue Ridge Tunnel and 20 minutes to Wintergreen Resort for winter fun! Completely remodeled and ready to spoil the best guests who simply want to unwind.

Indoor spacesFamilyBathroom

Cottage in Charlottesville

The exterior of a charming cottage is featured, showcasing white brick walls and a sloped gray roof. Two dormer windows enhance the appearance, while a welcoming red door serves as a focal point. Well-maintained green grass and manicured shrubs surround the house, creating a friendly environment.

4.91 out of 5 average rating, 455 reviews

Adorable cottage steps from Grounds

A cozy Milton Grigg designed cottage and detached carriage house three minutes walk to the Lawn and ten minutes walk to the Stadium. Nestled in a wooded neighborhood. Perfect for visiting parents, UVA chapel weddings, med student rotations, and football games. NOTE: The cottage sleeps five adults and the carriage house two adults. There is one bathroom in the cottage and one in the carriage house. Please read through all the information in the 'Description' section below before booking.

Indoor spacesKitchenLong stay

4.96 out of 5 average rating, 135 reviews

Cabin in Charlottesville

Ivy Rose Cottage nestled b/t Cville & Vineyards

The Ivy Rose Cottage bestows an exceptional ambiance that will captivate your heart. Whisk yourself away to this two bedroom cottage located in Ivy halfway between the Shenandoah Park/Brewery Trail and Charlottesville, home of UVA. The Ivy Rose Cottage, designed and handbuilt by the hosts, is an enchanting mix of cypress, timber frame, copper trellis work, pergolas and other architectural treasures. Fully equipped kitchen and a washer/dryer for those lengthier stay conveniences.

KitchenIndoor spacesAccuracy

4.99 out of 5 average rating, 164 reviews

An outdoor tub is positioned on a stone patio, surrounded by wooden fencing. Glass doors reveal a cozy bedroom with warm textiles. Soft lighting enhances the space, while a small table nearby holds two glasses and a bucket, inviting relaxation.

Cottage in Faber

Luxury Cottage | Outdoor Tub + Mountain Views

Soak in a private outdoor bathtub beneath the stars, wake to mountain views from your king bed, and open an entire wall of glass to bring the Blue Ridge Mountains inside. Welcome to The Cottage at Perkins Hollow Retreat! Located in Nelson County, just minutes from the Nelson 151 Brew Trail, award-winning wineries, breweries, hiking, and only 25 minutes from Charlottesville, The Cottage is the perfect destination for a romantic getaway, anniversary, honeymoon, or peaceful retreat.

KitchenFamilySolo travel

Popular amenities for Charlottesville family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.99 out of 5 average rating, 221 reviews

The entrance features double wooden doors that open to a welcoming interior. A 'hello' mat is placed on the threshold, and two stylish chairs are positioned on the balcony above, inviting guests to enjoy the view. Lush plants accentuate both sides of the entrance.

Apartment in Somerset

Cozy Farm Apt near Cville•hot tub, sauna, mt views

Indoor spacesFamilyAccess

4.95 out of 5 average rating, 183 reviews

The exterior of a lakeside log cabin showcases a large, sloped roof with wooden beams and expansive windows. A spacious deck is visible, featuring various seating options. The structure combines natural stone and wood elements, reflecting a rustic yet modern aesthetic.

Cabin in Faber

Lakefront Cabin w Stunning Curated Decor & Hot Tub

FamilyIndoor spacesHospitality

Holiday home in Lovingston

The cabin's exterior is surrounded by lush greenery, featuring a spacious porch with seating and a hot tub nearby. The two-story structure is constructed of wood, with large windows allowing natural light to fill the interior. A picnic table is located in the yard.

4.96 out of 5 average rating, 274 reviews

Ultimate cabin in the mountains

FamilyIndoor spacesBarbecue

4.93 out of 5 average rating, 311 reviews

A charming cottage with a metal roof features a welcoming front porch, surrounded by greenery. Rocking chairs offer a cozy spot, while stone pathways lead to a landscaped yard. Light spills onto the deck from nearby trees, blending indoor and outdoor spaces harmoniously.

Home in Barboursville

Spaniel Hill; cozy hilltop home w privacy & views

Indoor spacesKitchenRiver

4.98 out of 5 average rating, 130 reviews

A serene view of the Blue Ridge Mountains is presented, showcasing rolling hills blanketed in mist during sunrise. The sky is painted with soft pastel shades of orange and pink, highlighting the natural beauty of the surrounding landscape.

Home in Afton

Mountain Mama- Amazing Views! + Hot Tub!

Indoor spacesFamilyHiking

4.99 out of 5 average rating, 155 reviews

An inviting outdoor space features a hot tub surrounded by a spacious deck, with mountain views in the background. A large dining table with wooden chairs is positioned indoors, complemented by a fully-equipped kitchen visible in the adjacent area. A cozy fire pit with adirondack chairs provides a warm setting.

Home in Afton

Hot Tub, Firepit, Mtn Views, Walk to Coffee & Park

KitchenIndoor spacesComfort

4.95 out of 5 average rating, 507 reviews

An aerial view captures the guest house and the surrounding property, showcasing a spacious grass area and a 30,000-gallon in-ground pool. The pool area features several blue lounge chairs and is framed by mature trees and landscaped pathways.

Cottage in Madison

THE PERFECT HIKING & WINERY COUNTRY RETREAT

FamilyIndoor spacesGetting around

Earthen home in Stanardsville

The hobbit house features a distinctive curved roof covered with greenery, enhancing its natural appearance. Large windows framed by wooden arches provide ample light, while the stone exterior blends seamlessly with the surrounding landscape of trees and grass.

4.85 out of 5 average rating, 302 reviews

Hobbithouse at White Lotus Eco Spa Retreat

KitchenIndoor spacesAir conditioning

Family- and pet-friendly home rentals

4.96 out of 5 average rating, 357 reviews

A spacious, two-story house with white siding and large porches is featured. Lush green grass surrounds the structure, and the landscape includes open pastures and trees. The setting is serene, with plenty of natural light illuminating the exterior.

Home in Dyke

Living Water Farm, Blue Ridge

KitchenIndoor spacesAir conditioning

4.94 out of 5 average rating, 461 reviews

Walk DT | Pets | Soaking Tub | Parking

Indoor spacesFamilyAccess

4.97 out of 5 average rating, 395 reviews

The image features a charming two-story home surrounded by lush greenery and flowering trees. A circular driveway leads to the entrance, with manicured lawns enhancing the exterior. The backdrop includes rolling hills and bright blue skies, creating a serene and inviting setting.

Home in North Garden

Lux Country Retreat minutes from Charlottesville!

Indoor spacesFamilyHospitality

A single-story home with light blue siding is set against a clear sky. A vibrant door adds a pop of color to the entrance, which is framed by landscaped flower beds. A paved walkway leads up from the driveway, inviting visitors towards the front entrance.

4.98 out of 5 average rating, 154 reviews

3BR / Pets Welcome / Fenced Yard / Fiber Internet

Indoor spacesFamilyParks

Cottage in Charlottesville

The exterior of a renovated home is visible, featuring a covered front porch with seating and a white front door. Lush greenery surrounds the house, enhancing the view of the neatly landscaped lawn and paved pathway leading to the entrance.

4.93 out of 5 average rating, 255 reviews

Woolen Mills Cottage- 2 Beds, 1 Bath, Full Kitchen

Indoor spacesKitchenHospitality

4.99 out of 5 average rating, 162 reviews

A firepit area features several Adirondack chairs arranged around a sandy circle. Natural rock formations and a lush tree line create a serene backdrop, framed by expansive mountain views in the distance.

Chalet in Afton

Elk Mountain Overlook: Breathtaking Views

KitchenIndoor spacesTV

Apartment in Charlottesville

A cozy sleeping area is highlighted by a queen size bed with a floral-patterned quilt. Natural light filters through the large windows, framed by white trim, offering views of lush greenery. A television is positioned on a wooden stand, with decorative plants and artwork adorning the walls.

4.98 out of 5 average rating, 387 reviews

Sunny private studio, walk to the University

Indoor spacesKitchenPets

4.98 out of 5 average rating, 134 reviews

A compact living area features a cozy seating arrangement with a sofa and a daybed adorned with vibrant cushions. Large windows provide ample natural light and views of the surrounding greenery. A well-equipped kitchenette is visible, complete with a sink and modern appliances.

Tiny home in Afton

Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat

Indoor spacesKitchenCondition

Family-friendly home rentals with a pool

Apartment in North Downtown

The image showcases a grand brick Victorian house surrounded by lush greenery. A well-maintained pathway leads to the entrance, flanked by dense shrubs. The sky is bright, with a few clouds visible above the distinctive architectural features of the home's multiple gables and turrets.

4.96 out of 5 average rating, 112 reviews

Private Apt in Historic C'ville Home (Lane Side)

FamilyKitchenShared spaces

The exterior of Pine Lake Lodge is displayed, featuring a stone chimney and a covered porch with several chairs. Lush green grass surrounds the lodge, complemented by trees and colorful foliage in the background, creating a serene outdoor setting.

4.92 out of 5 average rating, 239 reviews

Pine Lake Lodge

FamilyIndoor spacesQuiet

4.96 out of 5 average rating, 1295 reviews

A round green yurt stands surrounded by a grassy area, accented by a flower bed of daffodils in bloom. A wooden deck leads to the entrance, while a fire pit with log seating is positioned nearby. Bare trees provide a serene mountain backdrop.

Yurt in Stanardsville

Yurt*FARM*horses*goats*woods*STARS*Hotub*Hiking

FamilyIndoor spacesPets

Guest suite in Charlottesville

4.74 out of 5 average rating, 116 reviews

Affordable Private Lower-Level 2BR Suite

FamilyIndoor spacesBeach

A historic two-story estate is visible beyond a cobblestone driveway, framed by lush green trees. In the foreground, a stone statue of a dog holds a basket of fruit, adding charm to the property entrance against a clear blue sky.

4.98 out of 5 average rating, 123 reviews

Rivanna Farm Estate North I Pickleball I Pool

Indoor spacesKitchenShared spaces

4.93 out of 5 average rating, 255 reviews

An open living area features high wooden ceilings with exposed beams, creating a spacious atmosphere. A large kitchen island with bar seating is situated near a dining table. Two spiral staircases lead to upper levels, while large windows frame views of the surrounding nature.

Home in Robertson

One Of A Kind Home in VA Wine Country on 50 acres

KitchenIndoor spacesWalkability

4.99 out of 5 average rating, 146 reviews

The exterior of the converted barn and silo is softly illuminated by string lights at dusk. A serene pond, framed by smooth stones, reflects the warm glow of light. The porch invites relaxation with its spacious seating and rustic charm, creating a peaceful outdoor setting.

Barn in Louisa

Unique OASIS - Silo Barn - Swim Pond- 5 Miles Trai

FamilyIndoor spacesOutdoor spaces