Photo by Jocey Hurt

Holiday Rentals in Chesterfield County

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Featured Holiday Rentals in Chesterfield County

Recline at Timberline! Family friendly!

9.4 out of 10, Exceptional, (33)
"This is such a cosy house! I adore the floor plan, the huge backyard, the front porch! I personally love hearing the far away trains passing by, definitely not an obnoxious sound just peaceful. The neighborhood is quiet and feels very safe! We were able to bake my 4 year olds cake and celebrate his birthday! It's right between richmond and Fort Lee/Fort Gregg-Adams so its a very minimal commute whicever direction. We qould definitely stay here again!"
Recline at Timberline! Family friendly!

Beautiful and Spacious home w/Outdoor Kitchen

10.0 out of 10, Exceptional, (23)
"Tina's home was so clean, so well equipped and just super comfortable! My family enjoyed it immensely, cooked a wonderful meals for elderly relatives who we were visiting and loved the screened in porch. Would stay here again in a minute!!!"
Beautiful and Spacious home w/Outdoor Kitchen

🦢Swanhaven Offers Serene, Corporate Style Waterfront Luxury Living

8.8 out of 10, Excellent, (3)
"My teenage son and I stayed here for a 4 day swim meet at SwimRva which was conveniently about 5 minutes away. The basement apartment was very clean and extremely well put put together!. The apartment was comfortable and my son certainly enjoyed the video games on the giant tv! Sharon was extremely communicative and even left out snacks for us every morning! I would highly recommend this property!"
The price is €317
includes taxes & fees
28 Nov - 29 Nov
🦢Swanhaven Offers Serene, Corporate Style Waterfront Luxury Living

Luxe Cottage - South Chesterfield Stylishly renovated, w/ large master suite

10.0 out of 10, Exceptional, (3)
"Perfect location for my family & I attending my niece college grad from VSU. Lovely home, very clean & comfortable. If I ever need to come back to this area, I will seek out this home & host."
Luxe Cottage - South Chesterfield Stylishly renovated, w/ large master suite

Lovely 1-Bedroom Loft with Free Parking and Wifi

8.8 out of 10, Excellent, (10)
"We were in town for a tournament at the convention center and looking for something walking distance. This was perfect! Less than 5 min walk. The loft had everything we could have asked for and was immaculate. Instructions for entering the loft were clear and easy to follow, as well as communication before, during and after was A+! My only suggestion is that the outside of the place was difficult to find - possibly a photo of the entrance would help! But once we found it, the rest of the stay...
The price is €251
includes taxes & fees
2 Dec - 3 Dec
Lovely 1-Bedroom Loft with Free Parking and Wifi

A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city

9.6 out of 10, Exceptional, (203)
"Captain Ron is my favorite host so far! He met me at the dock on the cold dark pouring rain, to make sure I got aboard and was comfortable. And the next day, kept me posted on the tide situation. He was helpful in every way possible. The boat is comfortable and welcoming. It is quiet and the water is calm. It is close enough to go do things, but secluded enough to feel like you’re a million miles away from every day life. I definitely will stay again, and I’ve already recommended it to...
The price is €200
includes taxes & fees
1 Dec - 2 Dec
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city

Cozy Cabin @James River; Live/Work/Play Experience

10.0 out of 10, Exceptional, (6)
"This was the perfect place for us and the kids to get away to! The house and surrounding property were absolutely beautiful. Tons of space for the kids to run and play, a huge porch to relax on, and the beds were all so comfortable nobody had any issue sleeping. Will absolutely be back!"
Cozy Cabin @James River; Live/Work/Play Experience

Lovely 2 Bedroom in the Heart of The Fan

9.4 out of 10, Exceptional, (45)
"We stayed in the cottage for 4 nights while in town for a family event with our daughter’s family. Great little place. It does have two bedrooms but only sleeping for 3 adults as the second bedroom has only a daybed. Main bedroom does have a queen size bed. Apartment has a large kitchen but not many utensils. It would be nice if more spoons,forks and cooking utensils were provided to be able to cook eggs etc. Also all pillows were as flat as pancakes. Maybe some new ones would be nice. Also...
The price is €294
includes taxes & fees
2 Dec - 3 Dec
Lovely 2 Bedroom in the Heart of The Fan

Cozy Get-A-Way in Neighborhood On 3 Lakes, With Fishing Docks, Firepit, Kayaks

9.6 out of 10, Exceptional, (25)
"Great spot to spend the weekend for a family wedding in Va. Close to the venue and a beautiful lake to walk around before heading to the wedding "
The price is €404
includes taxes & fees
1 Dec - 2 Dec
Cozy Get-A-Way in Neighborhood On 3 Lakes, With Fishing Docks, Firepit, Kayaks

Great Location. Close to about everywhere .Can't beat the value. Check reviews!

10.0 out of 10, Exceptional, (188)
"Beautiful neighborhood and host! House was comfortable, clean and had everything we needed! "
Great Location. Close to about everywhere .Can't beat the value. Check reviews!

Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!

10.0 out of 10, Exceptional, (51)
"The property was great with incredible views! The apartment was comfortable & has a lot of walkable options for food/drinks! "
Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!

Idlewood Hive, the Heart of Richmond

9.8 out of 10, Exceptional, (37)
"This place had everything we needed and was in a great location. The host was incredibly responsive and we’d stay there again for sure! Neighbors were a bit loud at night but nothing a sound machine can’t block out. "
Idlewood Hive, the Heart of Richmond

Downtown Living in Richmond's Amazing Shockoe Bottom

9.0 out of 10, Wonderful, (20)
"My biggest complaints would be that there were dirty dishes in the cupboards so I ended up washing most of them before using them. There were several lights out or not working in the apartment. The kitchen is very small which is okay but not well pictured in the listing. No extra toilet paper just the single half roll you get when arriving. The ‘free’ parking is at max two spaces in front of the building. Which were always full. The parking lot next to it is very dirty, broken glass and full of...
The price is €249
includes taxes & fees
15 Dec - 16 Dec
Downtown Living in Richmond's Amazing Shockoe Bottom

Downtown Living in Historic Richmond Loft

8.4 out of 10, Very good, (48)
"Good place."
The price is €308
includes taxes & fees
30 Nov - 1 Dec
Downtown Living in Historic Richmond Loft

Garden Penthouse in RVA! 3 Bedroom, 3 Bath!

9.8 out of 10, Exceptional, (18)
"Property was as described in a nice neighborhood for a weekend visit to the Richmond area."
Garden Penthouse in RVA! 3 Bedroom, 3 Bath!

Brand New, Gorgeous Studio Close to Everything!

10.0 out of 10, Exceptional, (29)
"Beautiful, newly renovated studio apartment very close to everything and with restaurants, bakeries and pubs few steps away. The owner was very responsive and courteous. I loved my stay and will certainly return. I highly recommend this place!"
Brand New, Gorgeous Studio Close to Everything!

Quiet & Cozy Ashland Home

9.8 out of 10, Exceptional, (29)
"Our family of 6 stayed one night in this lovely home. We had everything we needed for our overnight stay. Check-in and check-out was seemless. Beds are comfy, linens are soft. We cooked breakfast and had all cookware and utensils that we needed. needed."
The price is €332
includes taxes & fees
1 Dec - 2 Dec
Quiet & Cozy Ashland Home

Stunning! River-Front Log Cabin Near Williamsburg

10.0 out of 10, Exceptional, (37)
"Great location from the wedding venue! Gorgeous log cabin with all amenities. Responsive owner. Our family throughly enjoyed our stay. I would highly recommend. "
Stunning! River-Front Log Cabin Near Williamsburg

Tranquil Retreat: Woodland Views & Peaceful Vibes!

8.4 out of 10, Very good, (5)
"The space was so very nice, comfortable and clean. We had everything we needed! "
Tranquil Retreat: Woodland Views & Peaceful Vibes!

Industrial Chic Loft in the Heart of Downtown Richmond!

8.8 out of 10, Excellent, (9)
"The property was as listed, however the key wasn't in the lockbox when we arrived and it took several calls from myself and VRBO customer service to reach the host to inform them of this. We waited an hour for someone to arrive with a key. Parking isnt convenient unless you pay the $15 daily for the lot across the street from the building. The unit was fine, but the bathroom wasn't at the level of cleanliness that I was expecting. There was dust along the floor boards, hair on the tub and sink...
Industrial Chic Loft in the Heart of Downtown Richmond!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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