Vacation rentals in Chester

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!

Historic Meets Hip: Modern Basement Retreat

Welcome to Historic Meets Hip, a stylish 1-bed, 1-bath basement retreat near Battery Park, just 5 minutes from downtown Richmond with a private entrance. Important Before Booking: This suite includes a kitchenette for light meal prep (microwave, mini fridge, sink, coffee maker) but does not have a stove/oven. Guests selecting the non-refundable discounted rate receive a reduced price and acknowledge the reservation is final; travel insurance is strongly recommended when selecting this option.

Private guest apt on creek w/ patio & fire feature

“The Nest” is a private, ground level “basement” apartment. 15 min from downtown Richmond & 18 min to Pocahontas State Park, this space offers a peaceful, conveniently located, retreat. Private entrance, cozy patio, & large yard- all creek side. Laundry, high speed internet, Smart TV. Yard is wooded and private. Restaurants and tons of shopping within 5 min of the house, and 2.5 miles from highway access. A friend rents the upstairs of the home, which is completely separate- no shared space.

Eclectic Designer Retreat Near UofR + Peloton Bike

Modern design, impeccable lighting, and high-end finishes with a cozy wood burning fireplace. PELOTON exercise bike here, bring your cycling shoes! This charming private home is nestled in the heart of Westhampton just one mile from the University of Richmond and Libbie and Grove AVE. Surrounded by some of Richmond’s best shopping and dining and designed specifically for Airbnb guests to have a comfortable stay. Westhampton is one of Richmond’s most sought after neighborhoods. Welcome home!

Snug in Carver

Right in the heart of Carver, we're just blocks from VCU, the Altria Theater, and Monroe Park. We're also THE closest Airbnb to the interstate in the city of Richmond. If you're getting off 95/64 in the evening, you can slip right back on in the morning in about 90 seconds flat! We're just a hop-skip from downtown and all that has to offer. Stroll down through the First Friday gallery walk, or enjoy all the delicious restaurants and bars Jackson Ward and Broad St. have to offer.

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!

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.

Chic Downtown Hideaway

Located in the heart of the Arts District, this historic gem offers comforting amenities and charming details. Carefully restored to preserve its elegance, this beautiful house is perfect for large groups looking to explore Richmond. Dozens of popular restaurants, museums, and music venues are all within walking distance, not to mention fun nightlife, amazing thrift shops, and the James River trails. VCU and the convention center are less than a few blocks away.

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.

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.

Romantic Treehouse for 2 in Farm (no kids)

Surrounded by trees and peace in our small farm in a neighborhood, this cozy little cabin is made for secluded romantic stays and to enjoy a relaxing and restful night. Not suitable for children. Cabin is 10 X 12" of cuteness with all the amenities you might need to feel comfortable, electricity, heater, Smart TV, wifi, coffee maker, memory foam bed, and an awesome outdoor bathroom to shower under the stars!

The Creekside Cool Bus

Experience the ultimate glamping adventure in our converted school bus! Nestled on 5 acres of land, the campsite features lush woods and a creek. Enjoy the peace and quiet of nature with the comfort of a home away from home. Our skoolie is the perfect basecamp for outdoor adventures-just 30 minutes to Richmond and 5 minutes from the nearest trailhead at Pocahontas State Park with pass included.