Holiday rentals in Upper Shirley

Guest house in Church Road

5 out of 5 average rating, 210 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

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

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

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

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.

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, 47 reviews

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

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

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 holiday rentals

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Other great holiday rentals in Upper Shirley

5 out of 5 average rating, 11 reviews

Flat in Ashland

Luminous Architectural Gem

ChristianRating, 5 stars1 day 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, 16 reviews

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!

4.9 out of 5 average rating, 31 reviews

• Private Room in Charming Cottage 5 mins from RVA

RachaelRating, 5 stars5 days 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

4.99 out of 5 average rating, 364 reviews

Travel and Explore, enjoy this home with Heart

DeborahRating, 5 stars1 week ago

My mom and I stayed with Don and Jane, and we cannot express enough how great the experience was. This was the first time traveling and staying in an Airbnb with my mom, so I made this selection with my mom in mind, and it was the best decision! Don and Jane were welcoming and kind, while simultaneously providing a space that was beautiful, comfortable, and felt totally private. Having the extra bedroom was a bonus. Don and Jane take care to provide EVERYTHING you could possibly need for your stay. The morning muffins were very much appreciated. My mom and I THOROUGHLY enjoyed our stay and hope to have the opportunity to return in the future. Thank you, Don and Jane! You were a blessing to Mom and me.

4.91 out of 5 average rating, 738 reviews

Charming Suite in little Farm with Goats & Alpacas

AshishRating, 5 stars2 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, 201 reviews

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

RuiwenRating, 5 stars2 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!

4.98 out of 5 average rating, 254 reviews

Charming - 9 mins to downtown

MadisonRating, 5 stars1 day 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!