Holiday houses in Upper Shirley

4.9 out of 5 average rating, 41 reviews

Home in Hopewell

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.

4.76 out of 5 average rating, 62 reviews

Home in Charles City

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!

4.93 out of 5 average rating, 14 reviews

Home in Chester

Ellie's Beautiful, Spacious, River Home

Families and furry friends will love, Ms Ellie's River home nestled on the banks of the James River. Revel in the high-end interior and historical touches across the vacation rental's 4 bedrooms, 3 full bathrooms, and 2 half bathrooms. Or, step outside to enjoy the waterfront deck, park your boat at the dock, or set by the fire pit in the open yard. For adventure seekers, Chester boasts endless historic sites like Henricus Historical Park and plenty of scenic spots like Four Mile Creek Park!

4.82 out of 5 average rating, 123 reviews

Home in Hopewell

Refresh, cheerful home from home.

Relax with the whole family at this peaceful place to stay. A home you surely call home . Newly renovated, professionally decorated to give you the feeling of calmness and enjoyment. Located in the heart of the Tri-cities, near Fort Lee, Southpark Shopping Center, Hopewell marina, the Crossing Shopping Center, convenient store, fast food, gas stations movie theater are minutes away. The house has spacious front, back and left side views with no adjacent neighbors on these three sides.

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.

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.

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.

4.98 out of 5 average rating, 48 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!

4.89 out of 5 average rating, 46 reviews

Apartment in Hopewell

$ 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!

4.94 out of 5 average rating, 16 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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Other great holiday rentals in Upper Shirley

4.8 out of 5 average rating, 5 reviews

Private room in Hopewell

Hopewell Retreat, close to Fort Gregg-Adams

JahronRating, 5 stars2 weeks ago

This was my first Airbnb stay. Mrs. Janet is very kind and when I had a question she responded in a short time. The house is very clean and quiet. it almost felt like I was there by myself. If I could give a 10 stars I would!

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.

4.91 out of 5 average rating, 94 reviews

Hydrangea Room

AliceRating, 5 stars1 month ago

Absolutely loved my stay here. The house is beautiful and cozy, and Terri is very kind and welcoming. She was very communicative, and if I had any questions, she answered quickly. I am disabled and had medical equipment with me, she let me place things where I'd have easy access and it would be as accessible as possible.

Top Guest favourite

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!

5 out of 5 average rating, 6 reviews

Private room in Hopewell

Cozy Loft Retreat

BeckyRating, 5 stars4 weeks ago

perfect for the 2 days we needed. It was very clean and offered everything that was needed. We definitely would come back if available

4.9 out of 5 average rating, 10 reviews

Private room in Chester

Private Room #2 with Queen Bed + 55" Smart TV

JulieRating, 5 stars6 months ago

My husband said the mattress was very comfortable (firm and not saggy). He enjoyed the ambience. Daniel was VERY responsive on text, but more than responsive -- he processed 2 changes I made with competence, without delay, and with no hint of it being a hassle. He was kind. I really appreciated his communication skills.

4.82 out of 5 average rating, 11 reviews

CozySleepFull-Bed & FreeParking

Cesar ArturoRating, 5 stars3 weeks ago

All good. The house is just as described; they were very punctual and attentive in answering any questions. I would return without hesitation. ✅️🥇