Holiday rentals in Upper Shirley

City Point Cottage

This tiny cottage is a uniquely charming, one of a kind getaway in a breathtaking location. Located directly across the street from Appomattox Manor Park and the rivers, this newly renovated home was designed with guest experience in mind. Every inch of this decorator-grade, 500 square foot 1910 house is fresh, whimsical and filled with charming vintage character. Excellent bedding, a plush Winndom mattress, and a fully equipped kitchen and bathroom will make you comfortable and right at home.

The Henry Lofts Unit 1 - 'Chloros Lux Collection'

The Henry Lofts studio provides style, convenience, exposed brick & an open floor plan with 800 sq. ft. You will find a fully fenced pet friendly yard to go along with your private parking, & accommodated apartment with all new everything. This historic building was built in the 1800's but completely renovated with all new appliances and systems in 2024! Walk to all of the local breweries, restaurants, museums, galleries, and boutiques in downtown Old Towne Petersburg, VA. Private Deck/Patio

$75 (Sun-Thur 1 nights) $125 (Fri-Sat) Pets.

Farmstay on a 14 acre farm Queen bed loft upstairs. Down stairs has a bathroom, kitchen with sink, stove, oven, microwave, and complimentary kitchen-cups . There is a twin sleeper sofa in living room. Front and back porch, wireless internet and RukuTv. 14 acre farm with walking trails, old mill and creek. There is a shared hot tub for guests. Pet fee $50. No aggressive breeds including Pitbulls. All monies go toward our Horse sanctuary 501c nonprofit. Cleaning Fee is $50.

Private guest apt on creek w/ patio & fire feature

“The Nest” is a completely private, ground level “basement” apartment. 15 minutes from downtown Richmond & 18 minutes to Pocahontas State Park, this space offers a peaceful, conveniently located, retreat. Private entrance, cozy patio, & large yard- all creek side and professionally designed. Laundry in unit, high speed internet, Smart TV. Yard is wooded and private. Many restaurants and tons of shopping within 5 min of the house, and 2.5 miles from highway access.

Spacious, Clean & Comfy, 2 Full baths!

Welcome to the Travel Vibes Bungalow! - Centrally located between the vibrant cities of Richmond and Williamsburg - 3-minute walk to the Appomattox River (Hopewell City Marina - fishing, park, kayak and boat launch) - Less than 6 miles to Fort Gregg-Adams - 2 miles from Petersburg National Battlefield Park Trailhead - approximately 20 mins to Richmond - Approximately 45 mins to Historic Williamsburg - 40' driveway to accommodate truck/smaller boat combos

Parkside Log Cabin

This 1930s log cabin is a peaceful getaway nestled inside the rural National Battlefield Park system while only 20 minutes from all that downtown Richmond has to offer. Overlooking a private pond for canoeing, fishing or stargazing, this property has all the charm of a vintage log cabin but with modern amenities like a fully stocked kitchen, cozy loft for sleeping, and a luxurious bathroom with an oversized shower, complete with plush robes for two.

$ Cozy 1BR 1BA Apartment: Near Fort Gregg-Adams $

Welcome to our newly remodeled private apartment with 2 separate entrances. Enjoy a dedicated workspace, 2 smart TVs with free Roku, and proximity to Fort Gregg Adams, dining, and shopping. Stay secure with keyless entry and exterior cameras. Fully equipped kitchen, off-street parking, and adjustable thermostat included. Rest peacefully with blackout curtains and a Queen-size bed. Welcome to your home away from home!

Brand new, beautiful home.

This new built home, with 1570 sf , fresh from driveway to kitchen, welcomes you. Come, Relax with the whole family at this brand new elegant, peaceful place to stay. The house is in a quiet, peaceful Chester neighborhood, minutes from Amazon warehouse, Capital One, Lego Land. Cinema Cafe, Fort Greg-Adam, Richmond downtown, Richmond Airport are less than 30’. You’ll love it.

River Edge Cottage

🌿 Escape to River Edge Cottage! 🏡✨ Welcome to our cozy and historic riverside retreat in Charles City — the perfect getaway for families, couples, or solo travelers. Located right on the Capital Bike Trail and just minutes from local attractions, wineries, and wedding venues, you’ll enjoy the best of adventure and relaxation.