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Monday 9am - 5pm Tuesday 9am - 5pm Wednesday 9am - 5pm Thursday 9am - 5pm Friday 9am - 5pm

Guesthouses

Discover Charlottesville Your Way: Vacation Rentals for Every Stay. Since 1976. Book now and feel at home!

Discover the charm of Charlottesville with VA Guesthouses, your trusted local host since 1976. Our diverse portfolio includes vacation homes, urban lofts, and extended stay options. Find the perfect rental for your romantic getaway, family vacation, or business trip.

09/01/2026

There’s nothing quite like Fall in Virginia, especially at Ramsay Estate & Vineyard.

Discover this 78-acre vacation rental property at the base of the Blue Ridge Mountains:
🍇5 minutes to Chiswell Farm & Winery Septenary Winery and Pollak Vineyards
🥾8 minutes to Shenandoah National Park
🐎8 minutes to King Family Vineyards
🎓15 minutes to University of Virginia

Book one of our 4 houses on vaguesthouses.com

08/14/2026

One of our favorite kitchens: bright & airy; espresso, coffee, & cooking supplies included; and a built-in washer/dryer.

Experience it yourself at Fox Cottage in Afton, Virginia, just minutes to vineyards and Shenandoah National Park.

Book today with Virginia Guesthouses 🗝️

08/06/2026

That feeling when you see, “dogs welcome!”

Hotel Rose Jean is a boutique, locally owned 5-room hotel in a renovated historic building 1 block from Charlottesville’s downtown mall. Room 5 is dog friendly and has its own entrance.

📷: We were happy to host Caroline Jean Gray | Fine Art Photographer and her adorable pup recently. Thank you for sharing photos from your Charlottesville adventure!

07/10/2026

Introducing Blairbrook Farm, a countryside retreat set on a working peony farm in the heart of Crozet 🌸

Walkable to Chiles Peach Orchard, around the corner to King Family Vineyards, and suitable to sleep 13, this makes for the ideal family or wedding party retreat.

Book now at vaguesthouses.com
📷: John Bennett Fitts

07/01/2026

We’re excited to announce that Virginia Guesthouses is partnering with The Greencroft Club to provide swim, racquet, and dining amenities to our guests staying at select properties.

Just in time for peak summer travel, the whole family can enjoy the best of what our region has to offer.

Book your stay with us at vaguesthouses.com

05/22/2026

It’s a packed weekend in Charlottesville! The town is abuzz with visitors enjoying Memorial Day Weekend and the 2026 NCAA Men’s Lacrosse Championship at Scott Stadium.

We have one property available for tonight only- GreenLeaf! Give us a call to snag it 🧳 434-979-7264

05/18/2026

Stonemont Farm Cottage ✨ here’s a closer look into this special retreat in Keswick, VA. The cottage sits on a historic 170-acre farm and features 3 bedrooms, 2 bathrooms, a hot tub, fire pit, private pond, and more. It’s down the road from .wines and 🍾

Book a magical summer stay at Stonemont, or enter our giveaway to win an adventure-packed weekend here. Details in our recent post!

05/14/2026

Charlottesville’s Downtown Mall features three locally owned and operated boutique hotels just steps to the best restaurants, concert venues, and nightlife:

1. Hotel Rose Jean: inspired by European Inns and featuring local artwork, this hotel feels spacious and offers a lovely backyard retreat, welcome dining al fresco. Rooms have vaulted ceilings and lux en-suite bathrooms with heated floors.
2. The Jeff Hotel: sitting above the historic Jefferson Theater, this modern hotel offers sweeping views of the mall. Enjoy the large windows, daily maid service, and easy access to the city’s best nightlife.
3. The Townsman: nestled above downtown shops, you’ll find a retreat to intentionally styled rooms, each featuring amenities like balconies, work from home stations, and pull out sofas.

Hotel room blocks are available across these properties and more, bookable on vaguesthouses.com

05/12/2026

We’re pleased to announce that VA Guesthouses now manages The Inn at Stinson Vineyards, a luxury bed and breakfast on a vineyard in the heart of Virginia Wine Country.

This private inn offers four beautifully appointed guest rooms, a heated outdoor pool, a full kitchen, dining room, library, multiple outdoor living spaces, and more. Available for entire inn and individual room rentals.

Breakfast is included each morning of your stay, and wine may be purchased to enjoy on site. Stroll next door to the tasting room or take a hike at the nearby Sugar Hollow.

Whether you are local, a yearly visitor, or wine lover exploring new regions, this is surely a destination to add to your list.

05/05/2026

Find a vacation rental where the whole family to stay together 🏡 Browse our selection of homes for 6+ guests in the Charlottesville area.

Available now for UVA Graduation 2027:
Blue Mountain Haven
Chimney Corner
Downtown Penthouse
GreenLeaf
Park Street Retreat
Ramsay Estate Cottage
Piedmont Place Suites
Stockton Creek Farmhouse
Stonemont Retreat
The Inn at Stinson Vineyards

Address

Charlottesville, VA
22903

Opening Hours

Monday	9am - 5pm
Tuesday	9am - 5pm
Wednesday	9am - 5pm
Thursday	9am - 5pm
Friday	9am - 5pm

Website

http://www.vaguesthouses.com/

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