Pet-friendly vacation rentals in Chesterfield County

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Chesterfield County

Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

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Superhost

A sitting area features a two-tone black sofa and matching armchair, complemented by a textured orange rug. Natural light filters through sheer curtains, illuminating the space and highlighting the subtle details of the room's design.

Home in Richmond

4.8 out of 5 average rating, 491 reviews

Cozy Carver Accommodations

You've found a rare unicorn! This ultra-cozy row home is perfectly placed just blocks from VCU, and a short walk to the Fan, Jackson Ward & downtown. It's also less than 2 miles from "Richmond's Playground": Scott's Addition. This 540 sq. ft. home is filled with midcentury accents, local art, granite countertops, stainless steal appliances & pine floors. It has everything you need to cook and do laundry. You can also park for free with our street parking pass. We welcome your well-trained pets!

Outdoor spacesPetsCondition

Top guest favorite

Home in Richmond

4.96 out of 5 average rating, 268 reviews

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.

PetsWalkabilityIndoor spaces

Guest favorite

An outdoor hot tub is situated next to wooden steps in a yard adorned with autumn leaves. Surrounding trees display vibrant red foliage, while the house stands to the side, illuminated by soft afternoon sunlight.

Home in Richmond

4.96 out of 5 average rating, 162 reviews

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

PetsWalkabilityFamily

Top guest favorite

A bedside table is shown beside a spacious bed, topped with a vase of colorful flowers and a magazine. Soft white bedding and multiple pillows are arranged on the bed, complemented by a lamp casting a warm glow against a softly colored wall.

Home in Colonial Heights

4.97 out of 5 average rating, 110 reviews

The Spruce House

The Spruce House is a cozy 1960's rancher, ideal for tourists who loves to explore historic places, traveling health workers, business and workers on special projects, sports tour for local tournaments. The simplicity of this house will welcome you during your stay. Nestled at the heart of the city, but when you look out in the windows, you will enjoy the tranquility of the countryside, the twitting of the birds in the rain forest and the backyard designed to look like a campsite.

Outdoor spacesPetsRiver

Top guest favorite

Tiny home in Richmond

4.99 out of 5 average rating, 209 reviews

The Barkin’ B & B

Just five minutes from the airport and downtown, this cozy tiny home offers rustic charm and modern comfort. Fully equipped with kitchen essentials, books, games, and even coloring books, it’s perfect for relaxing. Pet-friendly, it comes stocked with dog treats, chews, toys, and a large fenced-in backyard for furry companions to enjoy. Conveniently located for travelers, it provides a peaceful retreat while keeping you close to city attractions. A perfect home away from home!

PetsWalkabilityTV

Superhost

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

4.88 out of 5 average rating, 522 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.

WalkabilityOutdoor spacesAccuracy

Guest favorite

A compact kitchen is featured with a gas stove and ample counter space, complemented by natural wood cabinetry. A stylish patterned wall adds character, while large windows allow for natural light to fill the area. The sleeping area is visible in the background, adding to the cozy ambiance.

Bus in Chesterfield

4.93 out of 5 average rating, 181 reviews

Creekside Cool Bus - skoolie near Pocahontas SP

Experience a cozy, rustic stay in our converted school bus, nestled on 5 acres of woods including a private creek. Thoughtfully designed for a simple, comfortable getaway, it's packed with charm and everything you need for a unique glamping experience. Visit the friendly chickens, spot the gnomes on our private woodland trail, relax by the fire pit, and enjoy nature all around you. Just 5 minutes from Pocahontas State Park (pass included) and 30 minutes from Richmond.

Outdoor spacesPetsCondition

Guest favorite

An enclosed pool area features a turquoise swimming pool, surrounded by large glass panels that provide views of the outdoor landscape. Two blue lounge chairs are positioned near the pool, creating a calming space for relaxation.

Farm stay in Chesterfield

4.95 out of 5 average rating, 130 reviews

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.

PetsOutdoor spacesNearby

Superhost

A warm living area features a dark wooden accent wall and a decorative fireplace framed by built-in bookshelves. A large television is mounted above the mantelpiece. A cozy rug lies on the hardwood floor, complemented by stylish seating and soft throw blankets.

Home in Richmond

4.89 out of 5 average rating, 138 reviews

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*

WalkabilityOutdoor spacesAmenities

Top guest favorite

Guesthouse in Chesterfield

4.95 out of 5 average rating, 324 reviews

Gorgeous Creek View from your Private Eyrie

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.

Outdoor spacesWalkabilityQuiet

Guest favorite

The spacious living area features a green couch, a reclining chair, and a wooden coffee table, arranged on a soft area rug. Light streams in from the high ceiling, highlighting framed plant artwork on the wall and a glimpse of the kitchen in the background.

Apartment in Richmond

4.94 out of 5 average rating, 155 reviews

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.

PetsWalkabilityHospitality

Top guest favorite

A covered outdoor entertaining area features comfortable seating arranged around a fire pit. Soft lighting strung above creates a warm ambiance. The space is complemented by decorative plants and cushioned sofas, providing a cozy environment for gatherings.

Home in Colonial Heights

4.93 out of 5 average rating, 198 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!

WalkabilityOutdoor spacesGetting around