Holiday rentals in Upper Shirley

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Upper Shirley

Guests agree: these stays are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Top guest favourite

Guest house in Church Road

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!

Top guest favourite

Home in Hopewell

5 out of 5 average rating, 25 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 favourite

Cottage in Lanexa

4.97 out of 5 average rating, 124 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.

Top guest favourite

Cottage in Quinton

4.98 out of 5 average rating, 211 reviews

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.

Guest favourite

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

Flat 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 favourite

Bungalow in Hopewell

4.92 out of 5 average rating, 38 reviews

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

Guest favourite

Cabin in Henrico

4.98 out of 5 average rating, 47 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 favourite

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 favourite

Home in Chester

4.98 out of 5 average rating, 45 reviews

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.

Guest favourite

Home in Charles City

4.93 out of 5 average rating, 15 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.