Vacation rentals in Upper Shirley

Guesthouse in Church Road

A wooden dock extends over the calm water, featuring a round table surrounded by four blue chairs. A swinging hammock chair hangs nearby, with an American flag gently waving. String lights are suspended overhead, adding a touch of ambiance to the scenery.

5 out of 5 average rating, 211 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

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!

5 out of 5 average rating, 25 reviews

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

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.

4.97 out of 5 average rating, 124 reviews

An open living space features wooden walls and beams, creating a warm and inviting environment. A gray sectional sofa is placed near a dining table, paired with modern gray cabinetry in the kitchen area. Natural light streams through multiple windows, enhancing the cozy atmosphere.

Cottage in Lanexa

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.

4.98 out of 5 average rating, 211 reviews

Cottage in Quinton

Luxury countryside cottage, IVY, near Richmond, 1

Two peaceful luxury cottages on a farm. Book one or both (Separate listings). Tranquility close to downtown Richmond and Richmond Int. Airport (15 min). Wineries, craft breweries, wedding venues, Busch Gardens, and more! We are 30mins from Williamsburg and 25min from downtown Richmond. Cities not your thing? We are less than an hour from beaches, national parks, golf courses, and fishing spots. So come and relax on your private deck overlooking a horse farm and enjoy the sunset.

4.89 out of 5 average rating, 488 reviews

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

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.

4.92 out of 5 average rating, 38 reviews

Bungalow in Hopewell

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

4.98 out of 5 average rating, 48 reviews

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

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.

4.93 out of 5 average rating, 149 reviews

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

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!

4.98 out of 5 average rating, 45 reviews

A modern kitchen is showcased, featuring white cabinetry and stainless-steel appliances. A central island with two light gray stools is present. The space is illuminated by pendant lighting, and a large window allows natural light to enter, enhancing the bright atmosphere.

Home in Chester

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.

4.93 out of 5 average rating, 15 reviews

Home in Charles City

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.

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Popular amenities for Upper Shirley vacation rentals

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Other great vacation rentals in Upper Shirley

5 out of 5 average rating, 11 reviews

A bright, airy space is captured, featuring a staircase leading to an upper level. Natural wood beams stretch across the ceiling, enhancing the room's openness. A modern white table with a wire chair is positioned next to a kitchenette, where minimal cabinetry and decor complement the simplicity.

Apartment in Ashland

Luminous Architectural Gem

ChristianRating, 5 stars3 days ago

I've been on 10 total airBnb trips & this one was the best! This space was private, quiet, and gorgeous. Very roomy for 2 people. It made for the perfect getaway for a birthday trip. Shoshannah is a helpful & friendly host. Do not hesitate to book this place! Also, the retro fridge is so cute & it is a lot bigger in person!

4.94 out of 5 average rating, 17 reviews

A collection of four guest reviews is displayed against a bright red background featuring the phrase 'See What Guests Are Saying' in bold. Each review highlights positive experiences with the home's amenities and host communication.

Home in Richmond

Steps to Pool, Pickleball + Patio Movie Nights!

KatrinaRating, 5 stars1 week ago

Very modern, big, and comfortable home! It’s easy to find and easy to find parking. Felt right at home very spacious. The host was very helpful and proactive. Highly recommend!

A front porch is featured, showcasing a dark front door and two blue chairs positioned on a wooden deck. A small table is placed between the chairs, with a decorative lantern sitting atop it. Windows beside the door provide natural light.

4.9 out of 5 average rating, 31 reviews

• Private Room in Charming Cottage 5 mins from RVA

RachaelRating, 5 stars1 week ago

Such a great stay to explore Richmond as a possible place to live. Good amount of space, cotton crisp sheets, en suite clean bathroom, soooo quiet and plenty of parking. Sarah & Michel & Blue (kitty) are so friendly and welcoming (not to worry, blue isn't in the room). Easy all around, and even my Oura (sleep data) was wondering what I did for so many good night's rest. The location is up and coming, neighbors were friendly and access to all great restaurants, biscuit havens, park walks, museums, etc are within 5 - 15 mins.

Private room in Colonial Heights

A front porch is shown with a welcoming entrance, featuring white columns and a heart-shaped decoration on the door. Steps lead up to the entrance, bordered by a manicured pathway. Lush greenery and colorful flowers enhance the outdoor space, creating an inviting atmosphere.

4.99 out of 5 average rating, 365 reviews

Travel and Explore, enjoy this home with Heart

EugeneRating, 5 stars4 days ago

Jane seems to rent to rent out the room for the purpose of serving and pleasing her guests. She saw us looking at deer and brought bread so Heidi could feed them. She knew when a cloud burst dumped rain on our walk and met us at the door with large towels for each of us, like a doting mother would do. And she literally gets up so early that she made muffins for us by 6:30 AM each morning! We have been to many Airbnbs and find this one to be tops for our personal enjoyment.

4.91 out of 5 average rating, 738 reviews

Charming Suite in little Farm with Goats & Alpacas

AshishRating, 5 stars3 weeks ago

We had a lovely overnight stay at the farm — peaceful, comfortable, and a perfect break in our journey. Maria and Ed were wonderful hosts. We especially enjoyed the morning farm tour where we got to meet the goats, chickens, and alpacas — such a fun experience! Ed also gave us some great brunch spots and local recommendations. Highly recommend if you’re looking for a unique and relaxing stopover.

4.98 out of 5 average rating, 202 reviews

“Captain’s Quarters” in 1920’s Craftsman Home

RuiwenRating, 5 stars3 weeks ago

The place is so beautiful and clean and all the furniture are very unique and have the vintage vibe. It is also close to everything. I highly recommend!

A kitchen counter features a coffee maker next to a basket labeled 'for Guests.' The basket contains coffee, sweeteners, and condiments. The backsplash consists of white tiles, complemented by a speckled granite countertop.

4.98 out of 5 average rating, 254 reviews

Charming - 9 mins to downtown

MadisonRating, 5 stars3 days ago

Easy same day booking, decided to take a last minute 1 night trip. Got booked right away, Nancy is super sweet and met me when I got there. She also made me coffee the morning I was leaving. I had no issue with sharing the bathroom or noise. Cute little home that is perfect for a short and sweet stay!