Holiday rentals in Chesterfield

Guest house in Church Road

5 out of 5 average rating, 210 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.

4.91 out of 5 average rating, 197 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!

Guest house in Chesterfield

4.98 out of 5 average rating, 53 reviews

Lulu's Peaceful Cottage

Enjoy a relaxing stay at this great located cottage. Lulu's Peaceful cottage is brand new, stylishly decorated for comfort. Private little cottage in a park like setting amongst trees & nature. Inside is an equipped kitchenette, coffee/tea bar, & is meal prep friendly. Relax in the soaking tub, or shower if you prefer. Lulu's is close to everything. Shopping, gyms, parks, & recs, hospitals, museums, & airport, and just a few miles from all major highways. Easy driveway parking & keyless entry.

4.93 out of 5 average rating, 44 reviews

Nala's Place

Bring the whole family or a group of friends to this great place with lots of room for fun, located between Richmond, VA and Washington, DC: Spacious retreat in prime location. This roomy home offers comfort and convenience, featuring: • Fully equipped kitchen • Multiple bedrooms to accommodate large groups • Less than hour from attractions Busch Gardens, Richmond Convention Center, DC Area Perfect for families, friends, or business travelers seeking a comfortable base to explore the city.

4.94 out of 5 average rating, 272 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, 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.

4.85 out of 5 average rating, 323 reviews

Flat in Chesterfield

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.

Guest house in Chesterfield

4.95 out of 5 average rating, 252 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.

4.76 out of 5 average rating, 34 reviews

Wood Fireplace & Private Master

Comfort and charm in one space! The living room has a cozy fireplace, perfect for relaxing evenings. The master suite has a king-size bed and a private bathroom with a luxurious double-headed shower. With additional bedrooms for privacy, our house is perfect for families or friends. Situated in a peaceful neighborhood, you'll enjoy tranquility and be just minutes away from local attractions. Experience the ideal combination of relaxation and adventure!

4.89 out of 5 average rating, 186 reviews

Treehouse in Richmond

Romantic Treehouse for 2 (No Kids) in Farm

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. Only adults allowed. Cabin is 10 X 12" of cuteness with all the amenities you might need to feel comfortable, electricity, Smart TV, wifi, coffee maker, memory foam bed, and an awesome outdoor bathroom to shower under the stars!

4.96 out of 5 average rating, 267 reviews

Guest house in Richmond

Funky & colorful private guesthouse with parking!

This unique place has a style all its own with carefully curated touches of yellow! A private guesthouse tucked away and at the top of a spiral staircase. This space is a five minute drive from Richmond's most popular neighborhoods. Fully equipped with a mid-century modern kitchenette, private patio, and A/C! This space is an experience in itself. Explore Richmond's best kept secret; the Yellow Tiger's Den.

4.84 out of 5 average rating, 124 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!

Holiday rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodation 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 holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Chesterfield

Home in Creighton

4.81 out of 5 average rating, 453 reviews

Pool/Hot tub/Entire House 2100 Sq ft

EliRating, 5 stars3 days ago

Comfortable home that was exactly what my family needed. The rooms were spacious and beds comfortable. Shower on the first floor is my favorite of any place I’ve stayed. Maria was always responsible and was flexible my with requests.

Private room in Colonial Heights

4.99 out of 5 average rating, 364 reviews

Travel and Explore, enjoy this home with Heart

DeborahRating, 5 stars1 week ago

My mom and I stayed with Don and Jane, and we cannot express enough how great the experience was. This was the first time traveling and staying in an Airbnb with my mom, so I made this selection with my mom in mind, and it was the best decision! Don and Jane were welcoming and kind, while simultaneously providing a space that was beautiful, comfortable, and felt totally private. Having the extra bedroom was a bonus. Don and Jane take care to provide EVERYTHING you could possibly need for your stay. The morning muffins were very much appreciated. My mom and I THOROUGHLY enjoyed our stay and hope to have the opportunity to return in the future. Thank you, Don and Jane! You were a blessing to Mom and me.

Private room in Montrose Heights

4.88 out of 5 average rating, 224 reviews

Cape Cod's Attic

DonnaRating, 5 stars2 weeks ago

I enjoyed my two nights at Stacey's. The dogs are big and love attention, but they don't jump up, they don't keep after you and they aren't allowed in the upstairs space. They were sweet and a joy to have around. I was worried about them getting out when I opened the gate, but as long as I was interacting with them they stayed right by me. Stacey's communication was great. We coincided a couple of times as I was heading in or out, and she was very friendly. It's a nice neighborhood--quiet and safe. The space was clean and comfortable. A chair and small desk would be a great addition, but it was a great stay at a reasonable price.

Private room in Brookland Park

4.98 out of 5 average rating, 201 reviews

“Captain’s Quarters” in 1920’s Craftsman Home

RuiwenRating, 5 stars2 weeks ago

The place is so beautiful and clean and all the furniture are very unique and have the vintage vibe. It is also close to everything. I highly recommend!

4.98 out of 5 average rating, 254 reviews

Private room in Richmond

Charming - 9 mins to downtown

MadisonRating, 5 starstoday

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!

Private room in Glen Allen

4.94 out of 5 average rating, 174 reviews

Charming Upstairs Retreat with Workspace

JeremyRating, 5 stars2 weeks ago

My stay at Justina's place was absolutely charming! Every detail was thoughtfully curated, making the space feel incredibly welcoming and cozy. The apartment was spotless, beautifully decorated, and had everything we needed for a comfortable and relaxing getaway. Justina was a fantastic host – communication was seamless, and she was so friendly and helpful, providing great local recommendations. We truly enjoyed our time and would highly recommend Justina's place to anyone looking for a delightful and memorable stay!

5 out of 5 average rating, 187 reviews

Private room in Powhatan

Luxury and Private Entrance Suite-No Shared Spaces

KylieRating, 5 stars5 days ago

Our stay at Karen’s was amazing. She was very responsive and generous throughout our stay. Her Airbnb gave us everything we needed. I highly recommend Karen’s place!