Pet-friendly holiday rentals in Chesterfield County

Contemporary Living in the Historic Fan District

Built in 1911, this spacious home has been renovated to blend contemporary design and traditional architecture. Notice the bold feature walls and expressive artwork and head to the patio to enjoy a drink while cooking with the BBQ. The house features three bedrooms, two full baths, updated kitchen and basement with a washer / dryer, as well as a large front porch and backyard that features a outdoor TV, grill and table and chairs for six. Fully stocked kitchen features everything you'd need to cook. Super fast fios internet, Sonos sound system througout the house, 60 inch TV with AppleTV in family room, 60 inch TV w/AppleTV outside. The house is mere blocks from great restaurants like Kuba Kuba, Joe's Inn (my favorite) and Flora - just to name a few. Best coffee in town can be found at Lamplighter (5 blocks) and the best drinks are at Heritgage (2 blocks). About a 15 minute walked to The VMFA, Carytown shopping and The Museum District. Guests have full access to the house. I'm happy to assist you throughout your stay if you have any questions. Call or text. The Fan District is a superb location with tree-lined streets and historic homes. Head to the unique boutique shops, try some local cuisine in an independently-owned restaurant, and have fun exploring the Museum District. Walking or biking are your best bet. Everything is close and there's a bikeshare just down the street. Easy to use and lots of places to return.

Walkability · Outdoor spaces · Location

Urban Farmhouse w/ Swings, FirePit & Putting Green

Welcome to your charming Richmond retreat 🏡💛! 🌳 Just a short walk to James River Park & Floodwall Park for nature lovers 🍺 Steps away from Bolos Rooftop Bar & Legend Brewery 🍩 Walking distance to Sharolina's Cakes, Croaker's Spot & Brewer’s Café 🚗 2 min drive to Downtown Richmond, I-95 & I-195 The highlight? A fenced backyard oasis with a dreamy pergola, cozy fire pit🪵🔥, playful swings, and even a mini golf putting green ⛳ — perfect for sipping, chatting, and making memories outdoors.

Walkability · Pets · Check-in

Hot Tub Oasis, Minutes from Downtown Richmond

Find the best of both worlds here, a tranquil getaway while only 12 minutes from Downtown, Carytown, Scott's Addition, the VMFA, and more. Enjoy the James River by Tubing, Kayaking, Rafting or Swimming, Hiking, Award Winning Restaurants, all within a 5 minute drive. Our home includes amenities such an 8 person hot tub, a pond dock with beautiful views, outdoor fire pit, patio, essential oil bath, and tea/ coffee on us! Our kitchen is stocked with cookware, spices, & dishes. STR-135430-2024 is

Pets · Outdoor spaces · Layout

Private Garden Home w/ Large Fenced Yard + Gazebo

Experience Casa Terra, a one-of-a-kind historic home in the urban heart of Richmond, Virginia. Tucked away on a sprawling 1/3 acre property just ten minutes from downtown, this thoughtfully restored 1928 Craftsman bungalow blends timeless character with natural calm. Designed for couples, small families and furry companions, Casa Terra features a 6ft fully fenced backyard where dogs can play beneath the branches of a 100-year-old willow oak while guests unwind in the gazebo or around the fire.

Outdoor spaces · Walkability · Check-in

4 beds/3 Private parking/2 mins to I-64 & I-95

Your family will be close to everything when you stay at this centrally-located place with a 92 walk score. 3 minutes to VCU, 7 minutes to Scott’s Addition Historical District and 2 minutes to I-64/95. New house built in 2016. Hosts up to 8-9 people comfortably Dripping coffee & Keurige coffee machine and coffee pods are provided! Pet friendly! Crib& high chair and kids dishes are provided for kids! This place is great for families with kids,couples,solo adventures,business travelers.

Outdoor spaces · Walkability · Comfort

Contemporary 3-Bedroom Home with Balcony in RVA

We welcome you to vacation at our beautifully decorated & modern 3-bed, 2 bath home! Our home is located just a bridge away from many adventurous spots on the James River such as Brown's Island & Texas Beach, along with numerous walking trails & much more. Our property is perfect for friends & family looking to explore the city, enjoy a nature getaway or simply relax on a staycation! Lots of delicious, local restaurants & artsy, historic attractions nearby like the VA Museum of Fine Arts.

Walkability · Pets · Nearby

Keystone Acres Farm *Enclosed Heated Pool*

Keystone Acres is located in Chesterfield, VA at a beautiful 1000 acre horse farm. On property we have roughly 60 horses owned by different tenants. The brick farm house in which you will be staying in overlooks one of our ponds & multiple horse barns. We have many "internal" roads here and hope you enjoy the farm views. Our 5 bedroom house is perfect for families or friends who want to have a getaway to "unplug" and experience the country life and each other's time.

Outdoor spaces · Pets · Condition

Renovated Modern Home Minutes to Downtown Richmond

Welcome to your bright, peaceful, spacious retreat, while only 15 minutes from Downtown, Carytown, Scott's Addition, the VMFA, and more. And only a 4 minute drive to Trader Joe's! Local hikes, restaurants and Chesterfield mall, all within a 7 minute drive. Your kitchen boasts all brand new appliances and plenty of new cookware. Local sightseeing, brewery & eatery guides provided. *Note: Carbon monoxide alarm not present because the house runs entirely on electric*

Pets · Walkability · Laundry

Private Eyrie - Gorgeous View!

Enjoy a relaxing view of Falling Creek from the second floor apartment with a private entrance and balcony. The wall of windows overlooks a secluded backyard with visiting deer, heron, owls, and other wildlife. Sit by the pond, creek or fire pit. The property offers off street parking in a safe neighborhood which is located 20 minutes from downtown Richmond, 10 mins to Midlothian and Chesterfield, 3 mins to Swim RVA. 15 mins to the airport or train station.

Walkability · Pets · Solo travel

Spacious unit in Arts District

Tucked away in the heart of The Arts District, you'll be able to walk to all the best restaurants and activities the city has to offer. A few blocks away from The National and a few minutes away from Cary Town, The Fan, Shockoe Bottom, Manchester, and Scott's Addition, you'll have easy access to anything the city has to offer! Just blocks away from the convention center, this unit is perfect for Richmond guests who are in town for work related events.

Pets · Walkability · Air conditioning

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!

Walkability · Outdoor spaces · Family

The Cottage in the City -Private Yard and Fire Pit

Your family will be close to everything when you stay at this peaceful, centrally-located home. This home is equipped with anything you may need during your stay! Enjoy the beautiful naturally lit living room throughout the day, or stargaze in the back yard while enjoying gentle heat from the firepit. The best part? We are a quick drive to anything you may be looking to do in Richmond and only 12 minutes to downtown center city.

Walkability · Outdoor spaces · TV