Family-friendly holiday rentals in Lexington

4.94 out of 5 average rating, 240 reviews

A spacious living area features large windows allowing natural light to illuminate the space. Comfortable seating options include a traditional rocking chair and modern lounge chairs, arranged around a patterned area rug. A bookshelf filled with various titles is positioned along one wall.

Apartment in Lexington

"Greenery on the Hill" - near W&L and downtown

My spacious private ground-floor apartment is located close to campuses and restaurants. Modern well-equipped kitchen. Private entrance & parking. THE BASE PRICE IS FOR TWO GUESTS TO USE ONE BEDROOM. IF YOU REQUIRE TWO GUESTS TO USE TWO BEDROOMS (an additional $40), please REGISTER AS 3 GUESTS, even though there are only two of you. You may not bring in overnight guests that you did not include in your reservation. Long pickup trucks will have difficulty turning around in our driveway.

FamilyIndoor spacesBackyard

4.96 out of 5 average rating, 113 reviews

A charming cottage with a white exterior and a metal roof is surrounded by greenery and trees. Large windows allow natural light into the inviting front porch area, which is adorned with potted plants. A gravel pathway leads up to the welcoming entrance.

Cottage in Lexington

Solitude- A Tranquil Riverfront Experience

Come and enjoy the peace and beauty that Solitude has to offer. This newly renovated cottage sits on the beautiful Maury River offering relaxation for those looking for a getaway, while also boasting one of the most desirable spots on the Maury for a fun swim, fishing, or a nice float from Beans Bottom to Jordan's Point! Located just 5 minutes from Lexington, you can be in the heart of downtown in just minutes and enjoy all of the attractions that Lexington/Rockbridge County has to offer.

FamilyKitchenHiking

4.91 out of 5 average rating, 257 reviews

A clear creek flows through the property, showcasing gentle ripples and natural rock formations. The landscape is lined with bare trees and a hillside, where a cottage is visible in the background. The serene water reflects the surrounding scenery under a clear blue sky.

Farm stay in Lexington

Cottage on Buffalo Creek *Fishing *Pets *Bikes

Wilderness area farm five miles from VMI and W&L in Lexington, Virginia. A natural spring fed creek runs through the property about 1/2 mile frontage- great for fishing which is available to guests. Fronts route 76 national bike route (Plank Road) a bikers paradise. Four mountain bikes available for guests. Spectacular natural views- fields, mountains, river and cliffs. Property include use of large outdoor spaces, decks, porches, fire pit and picnic tables. Dogs welcome!!

FamilyKitchenCondition

4.92 out of 5 average rating, 210 reviews

Stay in Downtown Lex, Hot Tub, Walk to VMI, W&L

The Beebe House is a charming historic home on Main Street in downtown Lexington. Perfectly positioned for W&L and VMI events, both campuses are an easy walk away. Enjoy private parking—a rare find downtown—plus a relaxing hot tub and fire pit patio for gathering under the stars. With restaurants, shops, and culture right at your doorstep, you'll experience the best of downtown Lexington living in this inviting home. We happily welcome your four-legged friends with a pet fee!

Indoor spacesFamilyCleanliness

A charming farmhouse displays a metal roof and a welcoming front porch. The porch is lined with white railings and features potted plants. Two windows are adorned with shutters, framed by lush green grass and trees in the background.

4.92 out of 5 average rating, 104 reviews

Modern Farmhouse near vmi, w&l, svu & VA Horse Ctr

Escape to Michie Shire, a beautifully restored 1930’s farmhouse set on 17 rolling acres of pristine Virginia countryside. Located just 3 miles from historic downtown Lexington, this 1,800-square-foot retreat offers the perfect balance of rural tranquility and easy access to the campuses of Washington and Lee University and the Virginia Military Institute (VMI). With four spacious bedrooms and three full bathrooms, the farmhouse comfortably accommodates up to eight guests.

Indoor spacesFamilyNearby

4.96 out of 5 average rating, 175 reviews

The cottage is framed by lush greenery, with a smooth gravel driveway leading to its entrance. Lounge chairs are positioned nearby under the trees, inviting relaxation. The surrounding meadow features scattered trees and shrubs, enhancing the natural beauty of the property.

Cottage in Lexington

Creekside Cottage + Wi-Fi Near Vhc, W&L & VMI

Pleasant Valley Cottage is a fully detached, beautifully furnished guest cottage on our family property. This 1,100-square-foot home has three bedrooms, two full baths, dedicated high-speed Wi-Fi, and room for six. We personally care for every detail to make your stay comfortable and welcoming. Enjoy the creek, gardens, nature, and smokeless fire pit in a peaceful neighborhood minutes from Lexington—2.9 miles from VHC, 3.5 miles from VMI, and 4.2 miles from W&L.

Indoor spacesFamilyHiking

4.97 out of 5 average rating, 503 reviews

A cozy living area features a light-colored sofa with complimentary cushions, positioned on a geometric patterned rug. A wood coffee table adds warmth, while a large window invites natural light and offers views of the greenery outside.

Farm stay in Raphine

The Bread Barn

Welcome to Seasons' Yield Farm! Your retreat sits atop a working bakery amidst a family farm in the beautiful Shenandoah Valley. Minutes off highway 81, within 20 minutes of Lexington and Staunton. This getaway is perfect for the guest passing through or a family looking for a rural getaway. Enjoy the solitude of the country and the yield of a bakery! Custom made coffees delivered to your doorstep every morning! Check us out at Seasons' Yield Farm. Welcome!

KitchenFamilyBathroom

Cabin in Rockbridge Baths

A rustic log cabin is nestled among lush trees, showcasing its stone chimney and a welcoming porch. The natural setting offers a serene atmosphere, with dappled light filtering through the leaves, highlighting the cabin's historic log structure.

Little Cabin in the Woods is quiet and secluded!

Enjoy our rustic, cozy, historic log cabin in the woods on 21 acres with two streams and a little meadow. The logs, from the 1800's, were reconfigured 17 years ago combining a rich history with high speed internet and modern amenities. Sink into the luscious bed with totally organic sheets, mattress topper, and pillows. Take a walk on the original wagon train road down to a stream or bath your senses in the majestic view of Jump Mountain from the meadow.

KitchenFamilySolo travel

4.98 out of 5 average rating, 454 reviews

4.99 out of 5 average rating, 221 reviews

A log cabin is showcased with a sloped metal roof and a welcoming green door. Surrounding the entrance, colorful flowers and foliage enhance the natural setting. A small porch leads to a balcony above, providing an elevated view of the scenic landscape.

Cabin in Lexington

Lazy Acres Cabins, on farm close to campuses & VHC

Comfortable and cozy log cabin on a beautiful farm looking down the Shenandoah valley with stunning views of the Blue Ridge mtns. Dog friendly, Wi Fi, central heat/air. Peace and quiet yet only 2 miles to the Virginia Horse Center and 5 miles to downtown Lexington, Washington & Lee and VMI campuses. A covered porch with a gas grill and beautiful views. Fully equipped kitchen, laundry, everything you need, a home away from home. Dog Friendly. 2 dog max.

KitchenFamilyAccess

Cabin in Rockbridge Baths

The cabin is surrounded by trees, showcasing a wrap-around porch with a screened area. The two-story structure features a stone chimney and a metal roof. A grassy area is visible in front, enhancing the natural setting.

Maury River Cabin w/ Private Access near WLU & VMI

Welcome to Home Place on the Maury, a historic 1700s log cabin in Virginia’s Shenandoah Valley with direct Maury River access. This charming getaway blends rustic history with modern comfort, featuring screened porches, two fireplaces, and 15+ acres of grounds. Perfect for families, history lovers, and outdoor enthusiasts. Kayaks and river floats are provided for relaxing or adventurous days on the water.

Indoor spacesFamilyValue

4.99 out of 5 average rating, 154 reviews

4.98 out of 5 average rating, 221 reviews

A spacious living area features a spiral staircase leading to a loft, complemented by large glass doors that invite natural light. Comfortable seating arrangements include a leather sofa and two white chairs, set against a light wooden ceiling and neutral walls.

Cabin in Lexington

Cabin Retreat at Stillhouse Farm *Sunset *Private

The cabin at Stillhouse Farm offers a secluded getaway with Blue Ridge Mountain sunset views less than 5 miles from W&L, VMI, and Lexington. The expansive porches and wide glass feature the beauty of Rockbridge Co. No neighbors in sight or sound! Stars shine bright in the certified dark skies. Check out our guidebook for local hikes and our other listing *Stillhouse Farm Yurt*

KitchenIndoor spacesBreakfast

4.99 out of 5 average rating, 129 reviews

A bright studio space is presented with warm hardwood floors. A queen bed is paired with a wooden bedside table near a window. A comfortable sofa and armchair face a coffee table, with a kitchenette visible in the background. Natural light flows through the window.

Guest suite in Lexington

Charming Carriage House Loft, Steps from Downtown

This comfortable, light-filled, carriage house studio is located on a beautiful, quiet street within a 15-20 minute walk of downtown Lexington, W&L, and VMI. ***NEW*** The nightly rate includes everything except taxes — in addition to our longstanding policy of charging no cleaning fee, there are now no hidden platform service fees (thanks to Airbnb’s updated structure!)

Indoor spacesKitchenCheckout

Popular amenities for Lexington family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.96 out of 5 average rating, 136 reviews

Home in Vesuvius

Huge Countryside Lux Home w Epic Views-Lexington

KitchenFamilyAccess

4.94 out of 5 average rating, 159 reviews

A hot tub rests on a patio, surrounded by lush greenery and framed by mountains in the distance. Sunlight glistens on the water's surface, and the sky displays a few wispy clouds, enhancing the serene outdoor setting.

Home in Fairfield

Amazing Mountain Views + Hot Tub near WLU & VMI

FamilyIndoor spacesValue

4.96 out of 5 average rating, 353 reviews

A bright living area features a cozy cream couch and an inviting small sofa surrounded by a decorative area rug. A wood-burning stove stands against a yellow wall, while a skylight allows natural light to brighten the space. A dining area with a table is accessible through a doorway.

Guesthouse in Lexington

Entire Country Cottage guesthouse / Very Private

FamilyIndoor spacesHeating

4.99 out of 5 average rating, 139 reviews

An historic log cabin is framed by lush greenery, showcasing its rustic wooden exterior with large windows adorned with shutters. A pathway lined with stones leads to the entrance, while a vibrant garden flourishes in front, enhancing the tranquil mountain setting.

Cabin in Montebello

Pre-Civil War Log Cabin w Sauna, Hot tub & Firepit

FamilyIndoor spacesCleanliness

Superhost

An aerial view captures a cabin with a wraparound deck overlooking a serene river. The deck features a hot tub and outdoor seating, surrounded by green foliage. The river reflects the gentle flow of water, inviting relaxation amidst nature's tranquility.

Cabin in Goshen

River Cabin with Hot Tub, Fire Pit, Blue Ridge

KitchenFamilyAmenities

4.92 out of 5 average rating, 212 reviews

A bubbling hot tub is featured under a covered porch, surrounded by trees. Water cascades gracefully from the tub's jets, with a serene sunset visible in the background, illuminating the landscape.

4.95 out of 5 average rating, 116 reviews

Secluded Home with Private Hot Tub & CA King Beds

KitchenIndoor spacesBackyard

4.92 out of 5 average rating, 644 reviews

Farm stay in Nellysford

Spindle Hill Cottage: an Artist’s Farm, Hot Tub

KitchenFamilyBreakfast

4.99 out of 5 average rating, 294 reviews

The cabin is surrounded by lush greenery, prominently featuring a welcoming deck and a circular hot tub. A spacious lawn extends in front, bordered by trees, providing a serene mountain retreat.

Cabin in Amherst

Dee's Cozy Haven~Mountain Views, HOT tub

Indoor spacesKitchenNearby

Family- and pet-friendly home rentals

4.96 out of 5 average rating, 179 reviews

Cottage in Fairfield

Here It Is: Adesso Vineyards – Vintner’s Cottage WLU-VMI

KitchenFamilyPets

An aerial view of Oakridge Retreat showcases a charming home with a sloped roof and multiple gabled windows. Lush greenery surrounds the property, providing a serene backdrop of rolling hills and mountains in the distance.

4.88 out of 5 average rating, 229 reviews

Mountain Luxury: Hot Tub, Fire Pit, Views

Indoor spacesKitchenCondition

A pair of black wicker chairs are positioned on a patio, offering a comfortable spot to enjoy panoramic views of green hills and distant white houses. A bright sky with fluffy clouds enhances the serene landscape.

4.98 out of 5 average rating, 102 reviews

"Blue Ridge Hideaway" Private home. 2m to Lex'ton

FamilyKitchenComfort

4.91 out of 5 average rating, 106 reviews

A welcoming entrance is featured, showcasing a vibrant blue door framed by wooden logs. An American flag flutters beside a small bench and two Adirondack chairs placed on a wood-paneled porch. Lush greenery surrounds the base, providing a natural contrast.

Cabin in Lexington

The Marshall #82 - The Cabins at Lexington

Indoor spacesKitchenPets

4.97 out of 5 average rating, 148 reviews

A serene outdoor pool area is surrounded by lush greenery and tall trees. Lounge chairs and umbrellas provide seating, while a gazebo offers shaded space. The pool reflects the blue sky and sun rays, creating a bright and inviting atmosphere for relaxation.

Guest suite in Lexington

The Getaway

FamilyKitchenSleep quality

Superhost

Cottage in Lexington

Cozy Tiny Home w/ Mountain Views near W&L & VMI

Indoor spacesFamilyHiking

4.89 out of 5 average rating, 244 reviews

4.97 out of 5 average rating, 109 reviews

Farm stay in Eagle Rock

Unique & Cozy Gypsy Wagon on The Cowpasture River

Indoor spacesFamilyAccess

4.9 out of 5 average rating, 214 reviews

A bright living space is visible, featuring a well-equipped kitchen with white cabinets and a countertop. Soft natural light enters through multiple windows. A comfortable seating area includes a grey sofa and a ceiling fan, contributing to an inviting atmosphere.

Home in Buena Vista

A Blue Ridge Home

KitchenFamilyParking

Family-friendly home rentals with a pool

Home in Wintergreen Resort

Cliffs Edge - It’s Pumpkin Spice Time!

Indoor spacesFamilyAmenities

4.97 out of 5 average rating, 130 reviews

4.92 out of 5 average rating, 118 reviews

A serene heated saltwater pool is surrounded by a large natural stone patio, featuring lounge chairs and a shaded area under an umbrella. A waterfall feature enhances the pool's ambiance, while expansive green pastures and distant mountains create a picturesque backdrop.

Farm stay in Roseland

Huge Farmhouse, Heated Pool for Family Vacations

Indoor spacesFamilyWalkability

Home in Wintergreen Resort

A wooden walkway leads to the entrance of the house, framed by vibrant pink rhododendron flowers. Tall trees provide a natural backdrop, with dappled sunlight filtering through the leaves, creating a serene outdoor setting.

Bear's Mountain Escape

Indoor spacesKitchenComfort

4.95 out of 5 average rating, 170 reviews

Superhost

A private furnished patio features a cozy seating area with light-colored cushions on a dark frame sofa. A wooden coffee table sits in front, accented by a woven rug. The surrounding greenery adds a natural backdrop, creating a peaceful setting for relaxation.

Condo in Wintergreen Resort

1 bedroom condo, close to hikes & breweries & pool

FamilyIndoor spacesPool

4.92 out of 5 average rating, 216 reviews

Condo in Wintergreen Resort

A scenic view of rolling hills is captured at sunset, with soft hues of orange, pink, and purple coloring the sky. In the foreground, a glass of clear liquid rests on a wooden railing, enhancing the tranquil atmosphere.

3 BR 3 BA, 2 story condo in Highlands

FamilyKitchenHiking

4.99 out of 5 average rating, 185 reviews

4.98 out of 5 average rating, 233 reviews

A bright and airy living area is highlighted by large windows offering mountain views. A casual seating arrangement features a light-colored sofa and a wooden dining table surrounded by black chairs. Sliding glass doors provide access to an outdoor deck.

Apartment in Rockfish

Blue Ridge Bliss - For family & friends to enjoy!

FamilyKitchenCondition

Condo in Wintergreen Resort

A glass of white wine is positioned in the foreground, capturing the warm hues of a sunset. The sun's golden rays reflect off the wine, while silhouettes of trees and distant mountains create a tranquil backdrop in the evening sky.

Panoramic Sunsets Mountain Views Pool $99 Midweek

FamilyIndoor spacesLayout

4.99 out of 5 average rating, 276 reviews