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House holiday rentals in Chesterfield County

Find and book unique houses on Airbnb

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Popular amenities for house rentals in Chesterfield County

House rentals with a pool

Home in Richmond
4.81 out of 5 average rating, 456 reviews

Pool/Hot tub/Entire House 2100 Sq ft

EliRating, 5 stars1 week 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.
Top guest favourite
Home in Richmond
5 out of 5 average rating, 25 reviews

Historic Blanton Getaway

SarahRating, 5 stars3 weeks ago
This place was great! The location makes it easy to get to many places in Richmond quickly and it was a perfect location for a family wedding in nearby Maymont. The house is beautiful and the furnishings very comfortable. The pool was a special bonus - lovely and relaxing with incredible plantings. Clearly a lot of time was spent considering what guests might want. I just wish we'd had more time to enjoy it.
Guest favourite
Home in Midlothian
5 out of 5 average rating, 9 reviews

A house you wish you called home

RebeccaRating, 5 stars12 months ago
Good communication, great value, and flexible with a small adjustment that was needed. I would definitely stay there again.
Home in Sandston
4.86 out of 5 average rating, 14 reviews

Sandston Home w/ Private Pool ~ 9 Mi to Richmond!

WarrenRating, 5 stars6 months ago
As described and exactly what we needed.
Home in Chesterfield
4.83 out of 5 average rating, 35 reviews

Lakefront Resort

TeresaRating, 5 stars2 weeks ago
It is an incredible property, pictures and words don’t do it justice. The home, grounds and neighborhood are very well appointed with a wonderful layout. There are multiple outdoor gathering areas, we saw swans daily, the bird and frog songs were enchanting. We walked the neighborhood every day. The pool and landscaping were amazing. The master wing is exceptional. We were there for a family wedding and the “princess” dressing room was very well used. The master bath/ shower room has a steam feature that we enjoyed and the” sparkly” bath and shower were magical for our grandkids ( and the adults.). The art and collections were exotic and everyone, not just the grandchildren were enchanted. We entertained 10-25 guests comfortably each evening. As to previous reviews about cleanliness-it was fine, as per linens, everything was available, clean, folded. PS if you want the St. Regis this property has much more to offer than fluffy robes and slippers. We will be back!

Weekly house rentals

Guest favourite
Home in Chesterfield
5 out of 5 average rating, 5 reviews

Pennwood Place - The Place to Stay!

AmandaRating, 5 stars3 weeks ago
Really enjoyed staying at James’s place. Very clean, comfortable and spacious.
Guest favourite
Home in Chester
4.93 out of 5 average rating, 14 reviews

Ellie's Beautiful, Spacious, River Home

BenjaminRating, 5 stars1 month ago
This house was terrific for family to stay at during our son's graduation place. Beautiful, spacious home in a beautiful setting right on the river. The indoor and outdoor amenities were many and very comfortable. The dock on the river was beautiful. Very clean, comfortable and with everything we needed for a nice stay.
Top guest favourite
Home in Richmond
5 out of 5 average rating, 33 reviews

Brand-New Boho Family Getaway!

TrenaRating, 5 stars3 weeks ago
Perfect Haven! Loved the home. It was exactly what we needed. Lot's of space for a large family. All the amenities we needed and close to everywhere we needed to go. We truly enjoyed our stay.
Superhost
Home in Hopewell
4.79 out of 5 average rating, 29 reviews

4 Bedrooms House

AngeliqueRating, 5 stars1 week ago
Our family recently enjoyed a wonderful stay in your spacious and comfortable home. It was perfectly sized for our needs, providing ample room for everyone. We were particularly impressed by the thoughtful provision of all necessary amenities, making our stay incredibly convenient and relaxing. The peaceful location was a welcome respite, offering a tranquil atmosphere we thoroughly appreciated. The cleanliness of the property was exceptional, contributing significantly to our overall positive experience. Thank you for providing such a welcoming and well-maintained home for our family weekend. We would highly recommend your property to others.
Top guest favourite
Home in Richmond
4.98 out of 5 average rating, 97 reviews

Private 2 acres. Huge yard/drive. 8 min to Airport

KellyRating, 5 stars3 days ago
Great location right off the interstate. House had a great set up and was as described!
Top guest favourite
Home in Richmond
5 out of 5 average rating, 38 reviews

Cupid's Hideout

IsabellaRating, 5 stars6 days ago
Alexander was a wonderful host. Very responsive and helpful. Check in was a breeze. This was located in a prime location. Tons to do within walking distance. Many excellent restaurants in the area. I highly recommend El Pope, Beauvine, Abi’s Books & Brews, and Little Mexico! The home was beautiful!!! Absolutely stunning in person. Very clean. Great amenities! It is a hidden gem! There’s tons to do if you want to drive as well. Very cute area. Well worth it!! Thank you!!
Top guest favourite
Home in Richmond
5 out of 5 average rating, 78 reviews

Hot Tub Oasis, Minutes from Downtown Richmond

HollyRating, 5 stars1 week ago
Clean home, safe quiet neighborhood, wonderful back yard to relax very peaceful. Had everything you can possibly need. Huge kitchen. Close to restaurants and planet fitness right down the street. Any question I had the host (Elizabeth) responded right away, very kind. We loved our stay. Thank you!
Guest favourite
Home in Richmond
4.93 out of 5 average rating, 14 reviews

Entire Cozy Home in Richmond

ByrdRating, 5 stars2 weeks ago
"I loved my stay! The place was cozy and well-kept, with everything I needed. My host was super helpful and provided great recommendations for local attractions and activities. I felt right at home. Highly recommend!"

Private house rentals

Guest favourite
Home in Richmond
4.83 out of 5 average rating, 75 reviews

House full of peace, with a parking patio for 4 cars

JeanneRating, 5 stars2 weeks ago
We had a very comfortable and enjoyable stay. This older home in a quiet older neighborhood is well-maintained, thoughtfully updated, cozy, and comfortable. It was spotlessly clean, and the check-in process was a breeze. We appreciated the ample off-street parking and the layout, which easily accommodated the multiple generations of our family during our gathering in Richmond. Plus, the location was ideal—less than 15 minutes to downtown. Mayra, our host, made us feel very welcome and was quick to respond to any questions. The home was well stocked with everything we needed. (including a crib and bassinet) There is a large private fenced backyard and a nice office area. I would certainly stay here again.
Top guest favourite
Home in Hopewell
5 out of 5 average rating, 26 reviews

City Point Cottage

DestinyRating, 5 stars2 weeks ago
This Airbnb is one of the best I’ve ever stayed at we lost power due to a storm that passed through and Caroline the host was super responsive and helpful through the whole process we were able to spend time in Richmond and sight see around Hopewell I would recommend the boathouse restaurant and then the city point boardwalk. I would definitely visit again!!
Guest favourite
Home in Petersburgh
5 out of 5 average rating, 23 reviews

2-Bedroom oasis in Chesterfield

MicheleRating, 5 stars7 months ago
Ashley was amazing! When I told some issues she came and looked into it and fixed it ASAP. (Issue was very minor). The layout was great, sofas comfortable enough that you could sleep on them! Backyard was great for my two large dogs! Ashley was great! This is a perfect place for temporary housing or for like me for in between houses where I sold and had to wait a couple weeks until I could get into my new place!
Guest favourite
Home in Richmond
4.89 out of 5 average rating, 80 reviews

Spacious Home w/Large Deck near Downtown Richmond

PaigeRating, 5 stars3 weeks ago
We had plenty of room between the two living rooms, dining room and spacious back deck. The place was clean and beds were comfy. Conveniently located.
Top guest favourite
Home in Richmond
5 out of 5 average rating, 23 reviews

The Green House: A 1 BR boho city retreat

KarenRating, 5 stars1 week ago
Amazing stay that allowed us to have a perfect Richmond weekend. We loved the neighborhood and sitting in the front porch as well as frequenting the local restaurants and coffee shops. Comfy bed and it was nice to have the space to relax or use the kitchen.
Top guest favourite
Home in Richmond
5 out of 5 average rating, 13 reviews

RVA Getaway!

KimoneRating, 5 stars6 days ago
I had such a wonderful stay at this Airbnb! The space was clean, cozy, and exactly as pictured. You can tell the host put thought into the little details that make guests feel at home. The neighborhood was peaceful and felt safe, and everything I needed was just a short drive away. Communication with the host was smooth and friendly from start to finish. I would absolutely stay here again and highly recommend it to anyone looking for a comfortable and relaxing getaway.
Guest favourite
Home in Richmond
4.96 out of 5 average rating, 53 reviews

Peaceful apartment near the James River

DariaRating, 5 stars3 weeks ago
Usually I am a little apprehensive about sharing a space with the owners but my mind changed with this air bnb. Felt private, everything was clean amd very chic. In a secluded peaceful area but still driving distance from Richmond city center. A great place!
Top guest favourite
Home in Powhatan
5 out of 5 average rating, 23 reviews

Equine Country Living 'n Powhatan, VA: Rusmar Farm

FeliciaRating, 5 stars3 weeks ago
The property and house were stunning. The house was super clean, beautifully decorated and stocked with everything we needed. Everything about the home was comfortable. We enjoyed our mornings outside with coffee and feeding the horses. The property is stunning and quiet. Gail and Randy were kind and gave us riding lessons and a historical tour around the property. We will be back and we recommend the home! it's a gem!

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