Holiday rentals in Lexington

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Top-rated holiday rentals in Lexington

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Top guest favourite
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.
Guest house in Lexington
4.96 out of 5 average rating, 314 reviews

Entire Country Cottage guesthouse / Very Private

Gloriously private without feeling secluded, this charming guesthouse was totally updated in 2019. Enjoy the peace and quiet. Go for a walk or bike ride on the 28 plus acres or pretty rural lanes. 2.5 miles away is Lake Robertson for activities . Sit on the porch too! On a snowy night, enjoy the wd-burning fireplace . (We will often leave fireplace prepared to light. Gas heating also). Get cozy with the full kitchen, washer/dryer, games and books. DirecTv in the living room and bedroom. too!

Top guest favourite
A scenic landscape features a herd of cattle grazing in a lush green field, framed by rolling hills and distant mountains. A rancher is seen overseeing the cattle near a water trough, with a partly cloudy sky providing a backdrop of natural beauty.
Guest house in Lexington
5 out of 5 average rating, 255 reviews

Spectacular Mountain views

Enjoy the breathtaking scenery when you stay in this beautiful, brand new space. A transformed outbuilding has become a quaint guest cottage with all of the amenities of home. Full kitchen w/all cooking essentials, K-cup coffee machine, new appliances, granite counter tops, full bath w/private shower and a jacuzzi tub with mountain views. Wake up in your master bedroom to spectacular mountain views. Living room w/electric fireplace, large screen TV. Your own private deck/pergola/gas grill.

Guest favourite
A comfortable living area features a dark leather sofa adorned with patterned throw pillows, accompanied by a recliner. A light wooden side table stands beside the recliner. Natural light filters through two windows covered with light curtains, complementing the soft area rug.
Home in Buena Vista
4.96 out of 5 average rating, 138 reviews

“Be Our Guest” House

Kick back and relax in this calm, classy, newly renovated space. Enjoy the quiet neighborhood and private location. You won’t want to leave! It feels like home, only better. There is no stress when you stay here. Come put your feet up and enjoy the cozy. Popular Locations Nearby Southern Virginia University 1 mi Virginia Military Institure 8.5 mi Washington & Lee University 8.5 mi Safari Park & Zoo 14 mi Natural Bridge State Park 16 mi

Guest favourite
Cottage in Lexington
4.92 out of 5 average rating, 227 reviews

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

Welcome to our charming pet-friendly Irish farmhouse, set on three picturesque acres just outside Lexington. This 500-square-foot retreat features a clawfoot tub, propane fire pit, and screened-in porch with mountain views. Enjoy the cozy feel of a tiny home with plenty of space for a memorable stay. You’ll enjoy the perfect mix of country relaxation and easy access to downtown Lexington. Whether relaxing on the porch or dining on Main Street, the farmhouse offers the best of both worlds.

Top guest favourite
Home in Lexington
4.92 out of 5 average rating, 195 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!

Top guest favourite
The living area features rugged timber beams that create a warm ambiance. Large windows provide a view of the surrounding landscape, while a stone fireplace adds a focal point. Comfortable seating arrangements include a pair of chairs and a sofa, complemented by a decorative rug.
Cottage in Rockbridge Baths
5 out of 5 average rating, 416 reviews

The Maury River Treehouse

Welcome to The Maury River Treehouse. This luxury timber frame cabin sits on the banks of the Maury River. The Treehouse was built almost entirely by local craftsmen making it a true showstopper! Located 9 miles from Lexington, Washington & Lee and Virginia Military Institute. It's a fisherman's dream, paddlers paradise or just a relaxing retreat! The true timber frame construction, stone fireplace, gourmet kitchen and park like setting will take your breath away!!

Guest favourite
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
4.94 out of 5 average rating, 134 reviews

Spring Mountain Views + Hot Tub near WLU & VMI

Amazing contemporary home features a stunning mountain view from the hot tub patio and a spacious open layout filled with vintage furniture. This piece of paradise located on 6 private acres is the perfect weekend mountain escape! 15 minutes to downtown Lexington, W&L, VMI. 10 minutes to the Virginia Horse Center. Minutes from Ecco Adesso Vineyard and Rockbridge Winery. Sunrise Ridge is a pet-friendly property, we warmly welcome your pets with a pet fee of $150.

Guest favourite
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
4.98 out of 5 average rating, 489 reviews

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!

Top guest favourite
The exterior of a newly renovated farmhouse is displayed, featuring a metal roof, stone accents, and wooden shutters. A spacious porch is furnished with rocking chairs, and a gravel pathway leads to the house. Lush green grass surrounds the property, with rolling hills visible in the background.
Home in Lexington
4.98 out of 5 average rating, 238 reviews

Julian's Place-Modern Farmhouse with Amazing Views

Only 5 miles from downtown Lexington and both VMI and Washington and Lee Universities. Come feel at home and relax in this newly renovated farmhouse with beautiful views and cozy charm! Enjoy the views of the Blue Ridge and Alleghany Mountains from the outdoor shower, screen porch, sunroom or outdoor fire pit. This house has your scenic views in mind, while also providing the convenience to downtown Lexington and Rockbridge County!

Top guest favourite
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
4.98 out of 5 average rating, 178 reviews

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! We are a working farm and primarily raise sheep. Stars shine bright in the certified dark skies. Check out our guidebook for local hikes and our other listing *Stillhouse Farm Yurt*

Guest favourite
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.
Farm stay in Lexington
4.96 out of 5 average rating, 165 reviews

Cottage, creek, gardens, wifi. Near VHC, W&L, VMI.

Pleasant Valley Cottage is a 1100 sq ft, beautifully furnished, 3 bedroom, 2 full bath home, with new high speed, dedicated, wired and wireless internet connection. It sleeps up to six guests and is located on a lovely property, with a sparkling creek, smokeless fire pit, gardens and nature, yet in a neighborhood only five minutes from Lexington, 2.8 miles to Horse Center, 3.5 miles W&L, 3 miles to VMI.

Top guest favourite
The entryway of the home is surrounded by lush greenery and vibrant foliage. A brick facade complements the inviting front door, which is framed by soft lighting. A stone pathway guides visitors through the manicured lawn toward the entrance.
Home in Lexington
4.96 out of 5 average rating, 208 reviews

Charming Brick Cottage, walk to W&L and VMI

Our home is close to Washington & Lee University and VMI in Lexington VA. On the edge of downtown, it's a short walk to the University, restaurants, and historic attractions. Southern Virginia University is just 8-10 minutes away. Our home is yours to enjoy, and is less expensive than 2 hotel rooms while providing the true personalized Lexington experience in a private home!

Popular amenities for Lexington holiday rentals

When is the best time to visit Lexington?

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Avg. price$215 SGD$221 SGD$235 SGD$258 SGD$288 SGD$238 SGD$217 SGD$230 SGD$258 SGD$288 SGD$249 SGD$230 SGD
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Frequently Asked Questions

  • What are the best places to stay in Lexington?

    Lexington has a mix of options, from stays in the historic downtown area to homes near Washington and Lee University. Many visitors enjoy accommodations with scenic views of the surrounding Blue Ridge foothills.

  • What are the best things to do in Lexington with kids?

    Kids can explore museums, engage with animals at local farms, or enjoy interactive exhibits at small discovery centers. Parks and walking trails around Lexington often provide open space for play and picnics.

  • What are some of the best things to do in Lexington?

    Explore historic campuses like Virginia Military Institute, stroll downtown’s shops and galleries, or visit museums with regional stories. Nearby trails and scenic overlooks around Lexington are frequently suggested for nature enthusiasts.

  • How is the weather in Lexington?

    Lexington’s winters are chilly, with highs near 46°F (8°C) in January and some snowfall. Summers bring warm temperatures, often reaching 87°F (31°C) in July, with autumn known for mild, crisp days and colorful foliage.

  • When is the best time to visit Lexington?

    Late spring and early autumn are often recommended for milder temperatures and vibrant natural scenery. Many visitors enjoy the pleasant weather for walking tours and outdoor activities during these seasons.

  • What are the best places to visit in Lexington?

    The campuses of Washington and Lee University and Virginia Military Institute are frequently suggested for their architecture and history. Museums, art galleries, and the nearby Natural Bridge also draw many visitors.

  • What are some hiking trails in Lexington?

    Lexington has access to several scenic hiking trails with views of the Blue Ridge Mountains. Visitors often explore paths near the Chessie Nature Trail or trails in natural areas just outside town.

  • What are some family activities we can do in Lexington?

    Families can enjoy educational visits to museums, hands-on learning at discovery centers, or lively time at local farms. Parks and outdoor picnic spots around Lexington also invite relaxed gatherings.

  • What are some of the best day trip ideas from Lexington?

    Discover stunning rock formations at Natural Bridge, explore mountain trails in surrounding parks, or visit historic sites in neighboring towns. Wine tastings and river activities are also frequently suggested.

  • Are there any pet friendly accommodations available in Lexington?

    Many accommodations in Lexington welcome pets, especially in homes around downtown or on the outskirts. Local parks and green spaces make it convenient for travelers exploring with animals.

  • What are some local tips for visiting Lexington?

    Comfortable shoes are helpful for exploring Lexington’s hilly streets and campus grounds. Locals often suggest trying regional foods at small eateries and allotting time for both downtown strolls and surrounding natural areas.

  • What is Lexington known for?

    Lexington is known for its historic college campuses, Civil War-era sites, and preserved downtown with characterful buildings. The area has connections to complex histories, including those of notable military leaders and interpretations of past eras.

  • What are the best hidden gems to explore in Lexington?

    Smaller art galleries, tucked-away bookshops, and quiet walking trails draw those seeking less crowded experiences. Historic cemeteries and local shops downtown are also frequently mentioned by returning visitors.

  • What are the best foods to try in Lexington?

    Visitors often try Appalachian-inspired dishes, regional barbecue, or locally made cheeses and baked goods. Markets and restaurants showcase seasonal produce and traditional Southern flavors.

  • What should I bring for a trip to Lexington?

    Layers are useful as temperatures can vary, especially in spring and autumn. Comfortable walking shoes and a light rain jacket are helpful for campus tours or exploring nearby trails.

  • What is the nightlife in Lexington like?

    Lexington has a relaxed nightlife scene centered on casual pubs, cozy wine bars, and occasional live music in local venues. Downtown’s gathering spots invite conversation and a taste of regional brews.

  • What are the most popular events or festivals in Lexington?

    Parades, arts festivals, and seasonal celebrations around local colleges are among the most popular events in Lexington. Annual horse-related events and community fairs are also frequently suggested, especially during spring and autumn.

  • Are there family friendly vacation rentals in Lexington?

    Lexington has family-friendly vacation rentals, including larger homes and properties with kitchens and outdoor areas. Staying near parks or in residential neighborhoods is often suggested for families seeking more space.

Quick stats about holiday rentals in Lexington

  • Total holiday rentals

    Explore 50 holiday rentals in Lexington

  • Nightly prices starting at

    Lexington holiday rentals start at $77 SGD per night before taxes and fees

  • Verified guest reviews

    Over 2,620 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    50 of Lexington holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Self check-in, Gym and BBQ grill across Lexington rentals

  • 4.9 Average rating

    Lexington stays are highly rated by guests – averaging 4.9 out of 5!

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