Vacation rentals in Upper Shirley

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Top-rated vacation rentals in Upper Shirley

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Top guest favorite

The image captures a serene sunset over Lake Chesdin, with vibrant hues of orange and purple reflecting on the water's surface. A wooden dock extends into the lake, accompanied by a flag gently fluttering in the breeze. The scene embodies tranquility and natural beauty.

Guesthouse in Church Road

5 out of 5 average rating, 224 reviews

Heron Rock: Lakefront Cottage on Lake Chesdin

Enjoy peaceful lakefront living at Heron Rock Cottage, where you can stroll through the woods, swim or fish off the dock, paddle the lake in kayaks, or simply relax and enjoy the wildlife and beautiful sunsets. Situated on 6 acres in Dinwiddie County, this newly renovated cottage includes 2 bedrooms, full bath, full kitchen, living room with fireplace and private patio with dining area. Your stay includes full access to the grounds and dock and you are welcome to tie up a boat if you bring one.

Superhost

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

4.87 out of 5 average rating, 47 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, 106 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, 115 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, 32 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.

Superhost

The living room showcases a cozy atmosphere with a light-colored carpet and a fireplace beneath a mounted television. Two armchairs are positioned around a white coffee table, which holds a checkers game. Natural light filters through the windows, creating a bright and inviting space.

Home in Charles City

4.74 out of 5 average rating, 74 reviews

The Bike Path House! Cozy 2 BR w/ Fireplace

Welcome to the "Bike Path" house! Whether you come to ride, walk, tour nearby plantations & vineyard, or are just looking for some quiet relaxation, this is the spot for you! Located conveniently across from the enchanting Capital Trail that connects Richmond to Williamsburg, on historic Route 5! Have an adventure & explore the 12 acres of woods behind the house! Easy and very scenic drive to Richmond or Williamsburg! The house is stocked w/ games for you to enjoy after a day of outdoor fun!

Top guest favorite

The exterior of a tiny home features rustic wooden siding, framed by a well-maintained white picket fence. A single window allows natural light inside, with trees and blue skies visible in the background. The surrounding grassy area provides space for outdoor activities.

Tiny home in Richmond

4.98 out of 5 average rating, 105 reviews

The Barkin’ B & B

Just five minutes from the airport and downtown, this cozy tiny home offers rustic charm and modern comfort. Fully equipped with kitchen essentials, books, games, and even coloring books, it’s perfect for relaxing. Pet-friendly, it comes stocked with dog treats, chews, toys, and a large fenced-in backyard for furry companions to enjoy. Conveniently located for travelers, it provides a peaceful retreat while keeping you close to city attractions. A perfect home away from home!

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, 494 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

The living area features natural wood paneling with high ceilings. A comfortable sofa is arranged facing a wall-mounted TV, alongside a wooden coffee table. A staircase leads to the loft, visible above, while a doorway opens to the kitchen area.

Guesthouse in Petersburgh

4.95 out of 5 average rating, 183 reviews

"Lofty Cottage" Adorable 1-Bedroom Guest House

Enjoy this quaint Cozy Cottage with bedroom loft! This adorable 1-bedroom unique place has a style all its own. Built in the 1960’s behind the main house, it has floor to ceiling pine paneling, pine floors and fireplace. It has been recently remodeled with new tiled bathroom , newly remodeled kitchen and stainless steel appliances. A new Heating and Air unit was installed summer 2021. The pine paneling and 16 foot high ceilings gives it that "cottagey" feel.

Guest favorite

The spacious living room is furnished with reclining loveseats and features a 50-inch Roku TV. A patterned rug covers the floor, while natural light filters in through a window. Wall art adds a touch of personality to the neutral walls.

Bungalow in Hopewell

4.93 out of 5 average rating, 43 reviews

Spacious, Clean & Comfy, 2 BR & 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

Top 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, 60 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 covered outdoor entertaining area features comfortable seating arranged around a fire pit. Soft lighting strung above creates a warm ambiance. The space is complemented by decorative plants and cushioned sofas, providing a cozy environment for gatherings.

Home in Colonial Heights

4.93 out of 5 average rating, 162 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!