Vacation rentals in Chesterfield

Guesthouse in Church Road

5 out of 5 average rating, 212 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.

4.9 out of 5 average rating, 198 reviews

Luxury BOHO upper unit

Relax in this calm, stylish 3 bedroom/2 full bath upper level unit. Another Airbnb is in the finished basement unit. The space is completely yours and no access to the other basement unit. Only shared area is the back deck. Unit has a completely updated kitchen with stainless steal and granite. Master bedroom has a super comfy queen bed and a master bath that has a beautiful walk in shower. Guest room has another queen bed and office area has a futon. Elegance and romantic boho style throughout!

5 out of 5 average rating, 102 reviews

Cabin in Dinwiddie

Dinwiddie Couples Getaway- Wells Cabin @WeldanPond

Wells Cabin @Weldan Pond is a beautiful new space designed for couples who love to relax, enjoy the outdoors (hike, fish, trail bike, & more), & marvel over beautiful views. The Cottage has a full kitchen, a large king bedroom, a bright, window filled sitting area, and a new deck overlooking Upper Weldan Pond and acres of healthy, natural hardwood forest with nearly 4 miles of trails to explore. You'll also love just enjoying the deck and the beauty of the Virginia countryside.

Guest suite in Midlothian

4.96 out of 5 average rating, 141 reviews

Chateau Midlothian Retreat Suite

The perfect guest suite waiting to great you to relax in this cozy retreat. Full renovation completed in 2022, including all new furnishings. As an Airbnb traveler, I focused on a clean, comfortable space that guests enjoy and recommend to others. The Chateau Midlothian Suite Retreat is limited to two adult guests with reservations. No other outside guests are permitted. All guests must have their identity verified through Airbnb with at least two reviews to make reservations.

4.94 out of 5 average rating, 275 reviews

Cottage in Powhatan

$75 (Sun-Thur 1 nights) $125 (Fri-Sat) Pets.

Farmstay on a 14 acre farm Queen bed loft upstairs. Down stairs has a bathroom, kitchen with sink, stove, oven, microwave, and complimentary kitchen-cups . There is a twin sleeper sofa in living room. Front and back porch, wireless internet and RukuTv. 14 acre farm with walking trails, old mill and creek. There is a shared hot tub for guests. Pet fee $50. No aggressive breeds including Pitbulls. All monies go toward our Horse sanctuary 501c nonprofit. Cleaning Fee is $50.

4.89 out of 5 average rating, 489 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.

Farm stay in Chesterfield

4.97 out of 5 average rating, 104 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.

Apartment in Chesterfield

4.85 out of 5 average rating, 325 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.

Guesthouse in Chesterfield

4.95 out of 5 average rating, 255 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.

4.99 out of 5 average rating, 103 reviews

Apartment in Church Hill

Classy, Spacious Apt Near Esteemed Restaurants

Welcome to Eileen East! The new gateway to exploring Richmond, where boutique style meets 5-star hospitality. You’ll find a little bit of everything in this historic, charming neighborhood just outside downtown proper -- from award-winning restaurants to parks with scintillating views of the city’s skyline, come make yourself at home in the heart of Church Hill. Booking now for vacations, staycations, and everything in between.

4.83 out of 5 average rating, 127 reviews

Cozy Cape Close to the City!

Enjoy a relaxing experience in a quiet neighborhood conveniently located less than a 10 minute drive to the city! This location is perfect for any traveling nurses who are going to McGuire VA hospital or anyone looking to experience all that the city of Richmond has to offer! Located right outside of the city and close to several highways it is a great location for everyone looking to stay in the area!

4.89 out of 5 average rating, 200 reviews

GALLERIA SOUTH minutes away from Downtown RVA!

Welcome to our stylish Galleria inspired home, in South Side Richmond VA. You will experience a true essence of local artists and how they inspire our community! Galleria South is centrally located for everything in Richmond Virginia. We are only 5 minutes away from the James River and Forest Hill. And located about 10 minutes from Church Hill, Downtown, Carytown, The Fan, & Museum District!

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Chesterfield vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Chesterfield

4.93 out of 5 average rating, 58 reviews

Guesthouse in Richmond

The Carriage House

AshleyRating, 5 stars3 weeks ago

A very beautiful place that’s so close to so many things around! Patricia was wonderful and very attentive and helpful. Everything was so comfortable and homey. Even the kitchen was stocked with basic necessities if you’d like to utilize it! 10/10 would recommend staying here. Even for a lengthy stay, everything is perfect!

Apartment in Chesterfield

4.95 out of 5 average rating, 22 reviews

Stonewall Manor at Keystone

LeeRating, 5 stars2 weeks ago

We stayed 3 nights at Stonewall Manor and it was perfect while we were visiting family in the area. We loved the serenity and openness of the property and enjoyed the horses as well. Our dog Alfred loved being able to run in the large front yard. Our host Tina was friendly and quick to respond from the booking process to checking out. We would definitely stay here again.

4.78 out of 5 average rating, 36 reviews

Wood Fireplace & Private Master

JustinRating, 5 stars2 weeks ago

Nice place and worked well for our needs, great master bedroom shower!

4.91 out of 5 average rating, 46 reviews

Nala's Place

CarolynRating, 5 stars3 weeks ago

The house was perfect for a family gathering. Lots of bedrooms and space to hang out. The neighborhood was nice and quiet.

4.98 out of 5 average rating, 48 reviews

Cabin in Henrico

Parkside Log Cabin

BenjaminRating, 5 stars1 month ago

Much needed peaceful, private getaway!! Fun unique setting. Nice newly updated bathroom and kitchen were a great addition to the otherwise rustic ambience.