Holiday houses in Charlottesville

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Top-rated holiday rentals in Charlottesville

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Top Guest favourite
A bright living area features a striped sofa adorned with green and gold cushions. A wooden coffee table sits in the center, complemented by a soft armchair nearby. Natural light filters through two windows, casting a warm glow on the decor, including framed artwork and a large flat-screen TV.
Apartment in Belmont
4.97 out of 5 average rating, 239 reviews

Belmont BnB ~ 2BR/1BA ~ Comfort & Convenience

Welcome to our well-appointed, centrally located 2 BR/1BA apartment! This cozy spot, with comfy queen beds, full kitchen, and cottage garden is a perfect homebase to relax in after a day of exploring. Set out on foot to: • Belmont Park (2 blocks) • Belmont Restaurants (15 min) • The Rivanna Trail (5 min) • The Downtown Mall (20 min) Short drives to Monticello (< 4 mi), grocery stores (1-2 mi), and UVA (2 mi). Your hosts are readily available in the above apartment should you need anything!

Top Guest favourite
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
4.91 out of 5 average rating, 214 reviews

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.

Top Guest favourite
A modern structure is nestled among tall trees, surrounded by lush greenery. The building features a dark exterior with large windows, allowing natural light to highlight the inviting entrance. Vibrant plants and foliage are visible in the foreground, enhancing the serene landscape.
Guesthouse in Charlottesville
4.98 out of 5 average rating, 301 reviews

Renew @ Coniferidge.

Constructed in 2017 “ Renew” offers a peaceful, clean and simple space furnished with a comfortable modern mix style. It is situated a short distance from the main home and offers just the privacy you are looking for. This property, located outside beautiful Charlottesville Va. is an easy drive to restaurants, shopping, art, culture, wineries, history, parks and the Uva . Flat Screen Smart TV (use your logins to access your favorite sites ) NO pets - out of consideration of future guests

Guest favourite
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.
Cottage in Jefferson Park Avenue
4.91 out of 5 average rating, 442 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.

Top Guest favourite
The outdoor firepit area is surrounded by wooden seating and log stump tables. Two wooden structures flank the space, providing a unique aesthetic. The treehouse sits elevated in the background, with trees displaying autumn foliage creating a vibrant backdrop.
Treehouse in Verona
4.99 out of 5 average rating, 224 reviews

The Laurel Hill Treehouse

Fully immerse yourself in nature in this serene Scandinavian-inspired woodland retreat, perfect for a couple's getaway. The treehouse is perfectly nestled amongst the trees, offering a chance to unwind while enjoying the beautiful views of nature. Just imagine yourself relaxing on the wrap around porch, soaking in the hot tub, cooling off in the creek, & cozying up to a crackling fire. We invite you to unwind, reconnect with nature & create cherished memories in this tranquil hideaway.

Top Guest favourite
A serene patio area features a small round table surrounded by two black chairs. Lush greenery and a pathway visible in the background enhance the tranquil setting, with garden views inviting relaxation.
Cottage in Charlottesville
5 out of 5 average rating, 176 reviews

Honey B - Beautiful loft near UVA, Monticello

Best of both worlds! In beautiful nature but close to UVA, Monticello and downtown. Honey B (Honey House 2) has a lofty feel with the footprint of a small house. High ceilings and several skylights allow for light and privacy in the quiet neighborhood, Located on the southwest side of Charlottesville, just 7 minutes to Scott Stadium, UVA campus, and restaurants, 10 minutes to historic downtown mall, Thomas Jefferson’s Monticello and central to many major wineries and breweries.

Top Guest favourite
A grassy open area is depicted, with a black and white dog lying comfortably on the ground. In the background, several canoes are visible on a trailer, positioned under trees that provide partial shade.
Guest suite in Charlottesville
4.92 out of 5 average rating, 155 reviews

The Brothers Great Room

Your private guest suite is located in Northern Albemarle County Virginia. We cannot allow cats(due to family members with allergies and the extra cleaning required) We are just off of Route 29 with easy access to local venues. The suite is up one flight of stairs. Albemarle County is central to the University of Virginia, Monticello, Montpelier, wineries, craft beer breweries, and wedding venues in the area. Your dogs may run the open areas. Please clean up after your pet.

Top Guest favourite
The cabin exterior features a wooden facade complemented by metal accents. A screened-in porch with a white door opens into the entryway, surrounded by potted plants and greenery. Stone steps lead to the porch, creating an inviting entrance.
Tiny home in Scottsville
4.92 out of 5 average rating, 267 reviews

Convenient Rustic Cabin near Wineries

I’m located 6 miles from Scottsville, 15 miles from Charlottesville, 25-30 minute drive. A pasture of cattle is not too far away you can hear the mooing at times and see sightings of deer quite often. It’s a private and quiet location. Two large rivers, James and Rivanna offer recreational activities. Rustic cabin, country located. Clean and cozy with a well stocked kitchen with all your cooking needs. If not, leave suggestions on what is missed. Thank you.

Top Guest favourite
A cozy dining area features a wooden table with dark chairs and a decorative plate holding small vases of blossoms. In the background, a spacious bed is framed by bright natural light, complemented by a wreath on the wall above.
Guest suite in Crozet
4.98 out of 5 average rating, 218 reviews

Guesthouse at Hamilton Oaks

Escape to our guesthouse on a little farmette. This peaceful setting tucked away on several acres along a creek with nature trails is the perfect mountain getaway. We are conveniently situated near quaint wineries, breweries along with hiking and the Blue Ridge Parkway that is a short hop, jump and a skip away. Every effort has been made to keep this a green haven, chemical and synthetic scent free, so you can leave recharged and rested. Non-smoking

Guest favourite
The exterior of the cottage features a welcoming entrance with large glass doors flanked by tall windows. A small set of steps leads to a grassy area, where two white chairs and two adirondack chairs are situated among lush greenery.
Tiny home in Charlottesville
4.94 out of 5 average rating, 732 reviews

Oxford Cottage: Cville’s favorite tiny home!

Tiny living done right! Discover 350 sq ft of stylish simplicity in this thoughtfully designed mini cottage. With an airy entry, cozy living area, smart kitchenette, full bath, lofted sleeping nook, and clever storage, it’s perfect for 1–4 guests seeking a relaxed stay—whether for a romantic retreat, work escape, quick stopover, or lively Charlottesville event like weddings, concerts, or triathlons.

Top Guest favourite
A bright dining space is showcased, featuring a white table surrounded by wooden chairs. Natural light filters through large windows, highlighting the modern decor. A stylish pendant light hangs above the table, complemented by a decorative centerpiece of fresh flowers.
Guesthouse in Fry's Spring
5 out of 5 average rating, 186 reviews

Luxury tiny house 3 min from UVA

La Casita is a new tiny home combining modern luxury with central location adjacent to UVA, central to wineries, and 10 minutes from Monticello. La Casita is design built to offer custom furnishings and luxurious touches. We are in the residential pedestrian-friendly neighborhood of Fry's Spring, near I 64. Walk to restaurants and Scott Stadium. Enjoy all amenities including a high-speed internet.

Guest favourite
A spacious living area is illuminated by natural light, featuring a modern sectional couch in blue. The room showcases exposed wooden beams along the ceiling and a round area rug with intricate patterns. A small coffee table and vibrant accent pillows add inviting touches.
Apartment in Charlottesville
4.93 out of 5 average rating, 119 reviews

Beautiful, Cozy, Downtown Apt!

Enjoy a stylish experience at this centrally-located place. Beautifully curated apartment with luxury kitchen, tiled bathroom and wonderful deck. It has two split units to keep the place as cool or as warm as you desire. Semi-firm Queen mattress for a perfect nights sleep. A short walk to the Historic Downtown Malls shops and restaurants and The Rivanna River for tubing, swimming, biking, picnics.

Popular amenities for Charlottesville holiday rentals

When is the best time to visit Charlottesville?

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Avg. price$243 NZD$248 NZD$257 NZD$282 NZD$327 NZD$258 NZD$250 NZD$265 NZD$282 NZD$301 NZD$277 NZD$257 NZD
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Frequently Asked Questions

  • What are the best places to stay in Charlottesville?

    Charlottesville has distinct neighborhoods like Downtown, Belmont, and Locust Grove, each known for a mix of walkable streets, culture, and dining options. Some stays near the University area are frequently suggested for quick access to parks, galleries, and local eateries.

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

    Families often explore the Virginia Discovery Museum, walk gardens at local parks, and enjoy hands-on activities at Carter Mountain Orchard. Outdoor adventures, history, and interactive exhibits are frequently suggested for younger travelers.

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

    Charlottesville has historic estates like Monticello, locally rooted food markets, and vibrant arts venues around Downtown. Hiking at local parks and exploring wine country are also often recommended experiences.

  • How is the weather in Charlottesville?

    Charlottesville has chilly winters around 28–44°F (-2–6°C), and warm summers near 68–84°F (20–29°C), with rainfall spread through the year. Spring and fall bring milder temperatures and changing leaves.

  • What are the best places to visit in Charlottesville?

    Monticello, the Downtown Mall, and the University of Virginia area are among the most popular stops in Charlottesville. Some sites interpret local history and culture, while gardens and galleries offer art and outdoor experiences.

  • What are some hiking trails in Charlottesville?

    Explore wooded trails at Saunders-Monticello Trail, or hike paths around Ragged Mountain Natural Area. Local parks frequently suggested for nature walks also feature family-friendly routes and varied terrain.

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

    Families can pick fruit and enjoy views at Carter Mountain Orchard, discover interactive science at the Virginia Discovery Museum, or explore parks for picnics and playgrounds. Locally rooted festivals and outdoor concerts are enjoyed by all ages.

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

    Many visitors explore Shenandoah National Park for mountain vistas, wander historic sites in nearby towns, or sample regional wines at local vineyards. River kayaking and apple picking are also frequently suggested experiences just outside Charlottesville.

  • Are there any pet friendly accommodations available in Charlottesville?

    Charlottesville has pet-friendly vacation rentals across neighborhoods such as Belmont and Rugby Road. Green spaces and walking paths throughout the city make it convenient for guests traveling with pets.

  • What are some local tips for visiting Charlottesville?

    Locals suggest exploring early in the day for quieter experiences at markets and trails, and checking out seasonal produce at roadside stands. Bring layers for changing weather, and look out for murals and public art throughout central neighborhoods.

  • What is Charlottesville known for?

    Charlottesville is known for its historic estates like Monticello, vibrant arts culture, and a strong food and wine scene. The area has locally rooted traditions linked to the University of Virginia and natural surroundings.

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

    Some locally loved spots include Ivy Creek Natural Area, tucked-away bookshops around Midtown, and small art galleries showcasing regional artists. Community gardens and food trails also invite quiet exploration.

  • What are the best foods to try in Charlottesville?

    Regional dishes often feature farm-fresh produce, apple cider donuts, and Virginia ham. Locally made cheeses, artisan breads, and barbecue styles are frequently suggested, along with wines produced nearby.

  • What should I bring for a trip to Charlottesville?

    Pack comfortable walking shoes, layers for shifting temperatures, and a rain jacket, especially if exploring outdoors. A reusable water bottle is handy for market visits and hikes, and bring sunscreen for summer days.

  • What is the nightlife in Charlottesville like?

    Charlottesville has lively music venues, cozy breweries, and dance lounges concentrated around the Downtown Mall and Belmont. Smaller bars and cafes often host local performers, creating a vibrant nighttime atmosphere.

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

    Charlottesville has events such as the Virginia Film Festival, Tom Tom Festival, and spring wine celebrations. Local music gatherings and farmers markets keep the city active throughout the year.

  • Are there family friendly vacation rentals in Charlottesville?

    Family-friendly vacation rentals are available in neighborhoods like Locust Grove, Downtown, and on quiet residential streets near parks. Many homes have amenities for children and offer easy access to outdoor spaces.

  • When is the best time to visit Charlottesville?

    Late spring and early fall are often recommended for pleasant temperatures and colorful scenery. Seasonal festivals, blooming gardens, and outdoor markets create lively atmospheres during these months.

Quick stats about holiday rentals in Charlottesville

  • Total holiday rentals

    Explore 950 holiday rentals in Charlottesville

  • Nightly prices starting at

    Charlottesville holiday rentals start at $17 NZD per night before taxes and fees

  • Verified guest reviews

    Over 63,180 verified reviews to help you choose

  • Family-friendly holiday rentals

    510 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 280 rentals that welcome pets

  • Holiday rentals with a pool

    60 properties feature pools

  • Rentals with dedicated workspaces

    530 properties have a dedicated workspace

  • Wi-Fi availability

    940 of Charlottesville holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Monthly stays, Self check-in and Gym across Charlottesville rentals

  • 4.9 Average rating

    Charlottesville stays are highly rated by guests—averaging 4.9 out of 5!

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