Vacation rentals in Upper Shirley

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Top-rated vacation rentals in Upper Shirley

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Superhost

Home in Hopewell

4.9 out of 5 average rating, 41 reviews

Charming, Private Abode: Serenity in Hopewell, VA!

Welcome to our private 1 bedroom, 1 bathroom abode! Our charming home is the perfect place for your stay in the heart of Hopewell, VA. Ideal for a couple’s retreat, a couple of friends or a solo traveler. Conveniently located near popular attractions, dining options & shops. With its cozy & cool atmosphere, you'll feel right at home during your stay. We look forward to hosting you at our home, where comfort & convenience await. Book your stay today & enjoy a memorable experience in Hopewell, VA!

Top guest favorite

A charming pink cottage showcases a welcoming porch with white railings. Dual windows on either side of the entrance allow natural light to fill the space. Lush green plants surround the base, complementing the serene outdoor setting with trees and blue skies in the background.

Home in Hopewell

5 out of 5 average rating, 26 reviews

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.

Guest favorite

Four light grey Adirondack chairs are arranged on lush green grass, facing a wooden deck overlooking the river. A large umbrella shades a dining area on the deck, surrounded by dense foliage and trees under a partly cloudy sky.

Home in Chester

4.93 out of 5 average rating, 14 reviews

Ellie's Beautiful, Spacious, River Home

Families and furry friends will love, Ms Ellie's River home nestled on the banks of the James River. Revel in the high-end interior and historical touches across the vacation rental's 4 bedrooms, 3 full bathrooms, and 2 half bathrooms. Or, step outside to enjoy the waterfront deck, park your boat at the dock, or set by the fire pit in the open yard. For adventure seekers, Chester boasts endless historic sites like Henricus Historical Park and plenty of scenic spots like Four Mile Creek Park!

Top guest favorite

The spacious interior features vaulted ceilings with exposed wooden beams. Natural light floods through large arched windows, highlighting rustic wooden tables and a bar area. Guests are seen enjoying meals at various tables, creating a lively atmosphere within the historic setting.

Apartment in Petersburgh

5 out of 5 average rating, 21 reviews

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

Superhost

Home in Hopewell

4.82 out of 5 average rating, 123 reviews

Refresh, cheerful home from home.

Relax with the whole family at this peaceful place to stay. A home you surely call home . Newly renovated, professionally decorated to give you the feeling of calmness and enjoyment. Located in the heart of the Tri-cities, near Fort Lee, Southpark Shopping Center, Hopewell marina, the Crossing Shopping Center, convenient store, fast food, gas stations movie theater are minutes away. The house has spacious front, back and left side views with no adjacent neighbors on these three sides.

Top guest favorite

A friendly pony with a blonde and white mane gazes curiously through a wooden fence, showcasing its soft facial features and striking brown eyes. The natural setting surrounds the pony, adding a rustic charm to the scene.

Cottage in Powhatan

4.94 out of 5 average rating, 272 reviews

$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.

Guest favorite

A houseboat, painted in blue and white, is docked next to a wooden marina. Surrounding greenery provides a natural backdrop, while a wooden structure with a red roof is visible in the background, showcasing a peaceful riverside setting.

Boat in Richmond

4.89 out of 5 average rating, 488 reviews

Warm, Cozy and Comfortable Houseboat, Gated Marina

Note: Dates taken? I have one other boat online-- The Cookie B with beautiful river views. We offer no contact boarding if desired and we understand the need for a clean place to stay. Therefore we go beyond the recommended guidelines concerning sanitation by fogging the entire boat after each guests departure. And for dining, you can cook aboard or enjoy the Lily Pad Cafe, an outdoor covered and heated restaurant on the river, and it is only two miles from the marina.

Superhost

A view down a well-lit hallway leads to a cozy bedroom, with a bright window providing natural light. Neutral-toned walls offset the soft carpeting. To the right, the inviting living area is visible, featuring a green plant and tasteful decor.

Apartment in Chesterfield

4.85 out of 5 average rating, 324 reviews

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.

Guest favorite

An inviting loft area features a spacious bed topped with a soft blanket, surrounded by wooden beams and rustic log walls. A window provides natural light, while a plush throw is draped across the bed for added comfort.

Cabin in Henrico

4.98 out of 5 average rating, 48 reviews

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.

Guest favorite

A spacious covered outdoor lounge is presented, featuring comfortable seating with neutral cushions and vibrant accents. A central fire pit adds warmth, surrounded by stylish wicker furniture. String lights overhead create a cozy ambiance, enhancing the inviting atmosphere for relaxation or gatherings.

Home in Colonial Heights

4.93 out of 5 average rating, 149 reviews

HideawayOasis/VSU/95/FortGreggAdams/FirePT/PoolTBL

Welcome to Our Hidden Oasis! 🌿✨ This cozy retreat is designed with love and thoughtfulness, perfect for small families and intimate connections. Enjoy year-round outdoor fun—roast s’mores by the fire pit, relax on the patio, or challenge friends to a game of pool. Sleep soundly in our comfy beds and wake up refreshed for new adventures. Whether unwinding or making memories, this home is your perfect getaway. We can't wait to host you!

Guest favorite

A bright and spacious kitchen area is visible, featuring modern gray cabinets and stainless steel appliances. A dining table with four chairs is positioned near a window, while a clean, tiled bathroom can be seen through an open door, highlighting the apartment's functional layout.

Apartment in Hopewell

4.89 out of 5 average rating, 46 reviews

$ 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!

Guest favorite

Home in Charles City

4.94 out of 5 average rating, 16 reviews

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.