Stay Charlottesville

Name: Stay Charlottesville
Address: 100 2nd Street NW, Suite F, Charlottesville, VA, 22902, US
Telephone: +14349770442
Price range: $

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Charlottesville, VA
Stay Charlottesville

Executive & Vacation Rental Homes in Charlottesville, VA Live Like a Local!

Nightly, weekly, and monthly rentals of Charlottesville's best carriage houses, condos, apartments, and historic homes.

05/01/2026

graduation is coming soon.
Plans change… and every now and then, graduation timelines do too.

There are individual room bookings at The 200 South Street—one of the most unique stays in Charlottesville.

Think a beautifully restored historic estate, pool access, and a location just steps from the Downtown Mall—close to everything, but still tucked away.

Book yours or send to someone still searching.

Link in bio → search The 200 South Street (individual room listings)

📸 aerowingva

https://www.staycharlottesville.com/uva-and-surrounding/

04/21/2026

Cabell Cottage 🤍

Tucked along scenic Garth Road and surrounded by forest views, this cozy guest house feels like a true retreat — quiet, comfortable, and full of charm. Skylights fill the space with natural light, while the wood-burning fireplace and screened-in porch make it easy to settle in and stay awhile.

Spring and summer here are especially beautiful, with lush greenery all around and peaceful mornings that feel a world away — yet you’re just 7 miles from UVA and downtown Charlottesville. Sleeps 5.

July availability is open if you’re planning a summer escape.

Learn more, or book your stay...
https://www.staycharlottesville.com/property/cabell-cottage/?adults=2

04/17/2026

As the weather warms up, downtown Charlottesville really comes alive — think Tom Tom Festival, Fridays After Five, concerts at the Pavilion, outdoor dining, and long evenings out. It’s one of the best times to be here.

If you’re planning a visit, the Jefferson Guest House is the perfect home base, and still has some weekend availability left in June and July. Just blocks from the Downtown Mall, this beautifully restored home blends historic charm with modern comfort — with space for up to 10 guests (bring your crew).

Enjoy a chef’s kitchen, private patio, and refined interiors, plus exclusive access to Common House for co-working, dining, and rooftop views. Part of The 100 Collection™, this home meets the highest standards for quality, care, and experience.

Learn more or book...

https://www.staycharlottesville.com/property/jefferson-guest-house/?adults=2

04/02/2026

Escape to the Cottage at Deer Ridge Farm 🤍

Tucked into a private clearing on 220 acres, this peaceful retreat is surrounded by forest and just minutes from Charlottesville’s wineries, history, and downtown charm. It’s the kind of place where you can truly slow down — quiet mornings, fresh air, and space to unwind.

Thoughtfully managed and selected to be included into The One Hundred Collection, this home reflects the level of care, quality, and consistency we’re proud to stand behind.

Learn more or book your stay...
https://www.staycharlottesville.com/property/cottage-at-deer-ridge-farm/?adults=2

03/12/2026

Escape to the Waterperry Farmhouse 🌿✨

Historic, luxurious, and set on 100 acres with sweeping Blue Ridge Mountain views. Spring is especially magical here — lush gardens, blooming flowers, and sparkling water all come alive. Lounge by the heated pool, stroll the grounds, hit the tennis or pickleball courts, or just soak in the serenity. Five bedrooms, a full kitchen, and chic Country French décor make it a dream getaway — part of the 100 Collection™ for top-tier stays.

Learn more, or book your stay...
https://www.staycharlottesville.com/property/waterperry-farm-farmhouse/?adults=2

02/07/2026

Did you know Stay Charlottesville offers more than just rental properties for individuals? ✨

Our properties are ideal for celebrations, meetings, and special weekends with loved ones.🥂 Whether you’re planning something intimate or gathering a larger group, we offer access to a curated list of trusted local partners - from catering and transportation to photography, offsite venues, and special hotel rates - making it easier to plan your gathering.

Learn more or fill out an inquiry...
https://www.staycharlottesville.com/meetings-events/

01/31/2026

Believe it or not, spring is around the corner 🌸🎶

�And with it comes one of the best times to visit Charlottesville — live music, festivals, and nights out on the Downtown Mall.

From shows at The Jefferson, Paramount, and Ting Pavilion to live music at favorites like The Southern, Whiskey Jar, and Miller’s, there’s always something happening. Add in warmer evenings and the energy of Tom Tom Festival, and it’s a great excuse to plan a visit.

🎤 A few spring shows on our radar:�

• Luke Combs — April 4 @ Scott Stadium�
• Billy Strings — April 17–18 @ JPJ Arena
• Lake Street Dive — April 19 @ Ting Pavilion
�• Old 97’s — April 10 @ Jefferson Theater
• Ole 60 — May 7 @ Ting Pavilion

Browse stays close to the action and start planning now. We have so many great options that are on the mall, or walking distance downtown.

Link to downtown properties...
https://www.staycharlottesville.com/charlottesville-downtown-vacation-rentals/

📸 Photo credits:
Upper left: Tristin Williams
Upper right: Tom Tom Festival
Lower left: Tristin Williams

01/13/2026

Just over 30 minutes north of downtown Charlottesville, River Ridge Overlook is a truly stunning retreat perched above the river—peaceful, private, and surrounded by 20 acres of countryside. 🪵🌿

Designed with beautiful architecture and modern finishes, this light-filled home is made for slowing down. Spend your days reading with a view, relaxing in the barrel sauna and hot tub overlooking the water, cooking a meal in the beautifully appointed kitchen, or gathering in the game room for a round of shuffleboard. This Stay property has been designated as part of , a curated group of homes and hospitality partners known for exceptional quality and service.

A perfect winter getaway for family or friends, with availability in late January and select dates in February and March.

Learn more, browse properties, or book your stay at the link in our bio!

01/05/2026

If you live here in Charlottesville, you’ve most likely seen this house at the end of High Street—and probably noticed how stunning it is. ✨ Just a reminder: it’s also a Stay Charlottesville property.

High Street Inn is a hidden gem steps from the Downtown Mall, blending historic charm with modern convenience. This beautifully preserved Mediterranean-style villa can be booked as a whole house for group stays, weddings, or corporate retreats—or individual rooms and suites for smaller visits.

🏡Lush gardens, private patios, walkable downtown access, and rare off-street parking make it an easy favorite. Plus, all Stay guests receive free access to Common House, just around the corner.

One to keep in mind for hosting out-of-town guests—or your next downtown stay!

Learn more, or book your stay...
https://www.staycharlottesville.com/property/high-street-inn/?adults=2

12/16/2025

The Jefferson Guest House is a beautifully restored property offering timeless elegance just blocks from downtown. Fully redesigned and renovated in 2025, it blends historic charm with modern luxury—spacious interiors, refined furnishings, a chef’s kitchen, and a private patio perfect for unwinding after a day in the city.

Sleeping up to 10 guests with off-street parking included, it’s ideal for family gatherings, group getaways, or a refined weekend in Charlottesville. This home has also been selected for inclusion in , a global designation reserved for top-tier vacation rentals known for exceptional quality and service.

As with all Stay Charlottesville properties, guests enjoy exclusive access to , including co-working space, a full-service restaurant, and a rooftop terrace with sweeping views of Charlottesville.

Book your stay...
https://www.staycharlottesville.com/property/jefferson-guest-house/?adults=2

Address

100 2nd Street NW, Suite F
Charlottesville, VA
22902

Telephone

+14349770442

Website

http://StayCharlottesville.com/

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