Vacation rentals in Upper Shirley

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Top-rated vacation rentals in Upper Shirley

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A well-appointed bedroom features a spacious bed with layered bedding and decorative pillows. Natural light streams through two windows, complemented by light curtains. A small desk with a chair is positioned beside the bed, offering a dedicated workspace. A light fixture adds warmth to the room.
Home in Hopewell
4.88 out of 5 average rating, 51 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
The dining area features a wooden table surrounded by metal chairs, set near a sliding glass door leading to a deck. A centerpiece of purple flowers adds a touch of color. Modern light fixtures hang above, providing ample illumination.
Home in Charles City
4.98 out of 5 average rating, 113 reviews

Cap 2 Cap Cottage VA Capital Trail Charles City

Cap 2 Cap Cottage - Rural oasis awaits in a NEWLY RENOVATED COTTAGE on 6 acres. 52 mile Virginia Capital Trail (Jamestown - Richmond) is only 3/10 of a mile away.Primary suite w/ 1 King bed. Add'l bedroom w/ 1 Queen bed. 2 full baths. Great Wifi, Smart TV, fully equipped kitchen, private deck. Fantastic restaurant/brewery Indian Fields Tavern is 3 miles away. Perfect stay for cyclists ,history lovers or just unwinding. NO Smoking or parties. Colonial Williamsburg 24 miles, Richmond is 30 miles .

Top guest favorite
A view through a multi-pane window reveals a serene landscape with trees and a winding gravel path. Scattered leaves cover the ground, while a lamp gently illuminates the outdoor space, enhancing the natural surroundings.
Barn in Providence Forge
4.97 out of 5 average rating, 119 reviews

Unique 2 BR. Barn Apt. with Incredible views

Want a quiet apt. getaway in the woods? Views from every room overlooking fields with woods, deer and wildlife, 2 day min. stay, 3 day holidays, or extended stays permitted if available. A luxurious 2 BR apt., located upstairs in a unique barn, loaded with amenities nestled 1/2 mile down a gravel drive, with scenic woods and wildlife. This accommodation sleeps up to 4 people + child Bedrooms have ceiling fans, new king bed in bedroom furnished in antiques Washer dryer * Low cleaning fee

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, 35 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.

Top guest favorite
A cozy treehouse cabin is illuminated by warm light, set among tall trees in a wooded area. A wooden bridge leads to the entrance, with a fire pit nearby surrounded by chairs. Soft string lights hang, adding a gentle glow to the space.
Treehouse in Sandston
4.99 out of 5 average rating, 281 reviews

Treehouse in the woods w/AC & heat (bath at house)

Cozy "treehouse" cabin with AC and heat tucked in the woods, with bridge for easy entry. Large windows overlook stream. Site has picnic table and fire ring. Full-size Purple mattress in loft. 80 Mb WiFi, 4KTV. Outdoor hot tub is on the deck of our home and open to guests 24/7. Trails are closed at treehouse, but many trails available nearby. Fridge, microwave, Keurig. No bathroom at treehouse, but guests have exclusive use of our guest bathroom in our main house anytime - just a short walk.

Top guest favorite
The exterior of a large black barn is shown under a clear blue sky. Two wooden doors are open, revealing a welcoming entrance. Flower pots are arranged along the path, while two wooden chairs are positioned in front, inviting relaxation amidst a tranquil rural setting.
Farm stay in Charles City
4.99 out of 5 average rating, 133 reviews

Lovely space above barn on a working farm!

Getaway to the country!! Suitable for a 4 adults or families of 5. Wake up to beautiful sunrises. Spend a peaceful day surrounded by farm and wild animals. Enjoy the dark night sky lit with millions of stars after watching the sunset. Above our barn is a two bedroom, one bath living space with a living area open to a kitchen fit for every cook!! Located near Williamsburg, Jamestown and Yorktown, Busch Gardens and Water Country, the Virginia Capitol Trail and 5,217 acre wildlife refuge.

Guest favorite
A red kayak rests at the edge of the serene reservoir, surrounded by trees that frame the waterway. The calm surface reflects the clear blue sky and soft ripples created by a gentle breeze, ensuring a tranquil outdoor experience.
Cottage in Lanexa
4.97 out of 5 average rating, 140 reviews

TooFine Lakehouse, pet friendly waterfront cottage

Cute & cozy (tiny) waterfront cottage nestled in a pine forest. Situated on an almost 3 acre point on the Diascund Reservoir this is THE perfect spot to get away from it all & still be in the middle of everything! Options abound - fishing from the dock, bird watching, canoeing, roasting marshmallows around the fire pit, swinging in the hammocks, napping on the screened in porch, grilling on the patio, reading in the loft, playing games (inside & out), or just chill & feel the vibe.

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, 499 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.

Top guest favorite
An aerial view captures the riverfront A-Frame home surrounded by lush greenery. The spacious deck extends toward the water, showcasing a blend of natural beauty and modern architecture under a soft, early evening sky.
Home in Charles City
4.99 out of 5 average rating, 310 reviews

Hutch's Bluff - Waterfront near Williamsburg

Charming riverfront A-Frame home on 2 acres overlooking the Chickahominy River. Completely updated interior, including all furnishings and appliances. Wake in a King bed loft space with a majestic view of the river, or choose one of the two Queen bedrooms below. First floor all tile bathroom with a walk in shower. Stainless appliances and granite countertops. Bring your fishing gear, relax at the end of the pier, or enjoy the views from the large deck and fire pit.

Guest favorite
Bungalow in Hopewell
4.94 out of 5 average rating, 47 reviews

Clean, Comfy & Spacious with 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

Guest favorite
A cozy living area features a plush, green sofa adorned with textured cushions. A round wooden coffee table displays decorative bottles and a stack of books. Sunlight filters through a partially draped window, creating a warm ambiance against the rustic log walls.
Cabin in Henrico
4.98 out of 5 average rating, 64 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 bright bedroom features a spacious bed with white bedding centered on a dark wood floor. Two windows with light beige curtains let in natural light. A desk with a chair and a television are positioned to the side, while decorative wall art adds subtle accents.
Apartment in Hopewell
4.9 out of 5 average rating, 52 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!

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