Search Vacation Homes in Chesterfield

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
6 Mar - 8 Mar
In two months
17 Apr - 19 Apr
In three months
15 May - 17 May
In four months
12 Jun - 14 Jun

Our top choices for Chesterfield vacation homes

3 bedrooms, desk, iron/ironing board, free WiFi

3 BR Colonial Revival in 2 Acres, 5 min to State Park. Family & Pet Friendly!

3 BR Colonial Revival in 2 Acres, 5 min to State Park. Family & Pet Friendly!
Chesterfield County
3 BR Colonial Revival in 2 Acres, 5 min to State Park. Family & Pet Friendly!
Terrace/patio

🦢Swanhaven Offers Serene, Corporate Style Waterfront Luxury Living

🦢Swanhaven Offers Serene, Corporate Style Waterfront Luxury Living
Richmond
8.8 out of 10, Excellent, (3 reviews)
"Great Hosts"
United States
Yamiya N.
The price is AED 1,308
AED 2,164 total
includes taxes & fees
24 Feb - 25 Feb
🦢Swanhaven Offers Serene, Corporate Style Waterfront Luxury Living
Exterior detail

PRIVATE 2 BEDROOM w/ BATH/SHOWER COMBO - Chesterfield, VA

PRIVATE 2 BEDROOM w/ BATH/SHOWER COMBO - Chesterfield, VA
Hampton Park
2.0 out of 10, (2 reviews)
"We did not end up staying there. The listing was for the entire home. When we arrived, a white vehicle was parked in the driveway. When we went in, the foyer was not picked up-see photo. The kitchen was not usable because the countertop contained dirty dishes, 3 ears of freshly cooked corn, and a large helping of shredded meat-see photo. There was a small pile of shredded meat beside the stove-see photo. The sink was full of unwashed pots and pans-see photo. Also, the listing was for two...
United States
Theresa H.
The price is AED 212
AED 328 total
includes taxes & fees
28 Feb - 1 Mar
PRIVATE 2 BEDROOM w/ BATH/SHOWER COMBO - Chesterfield, VA
Exterior

Steel Magnolias Cozy Main Home in Amelia County

Steel Magnolias Cozy Main Home in Amelia County
Amelia Court House
10.0 out of 10, Exceptional, (12 reviews)
"I would highly recommend Jenny’s VRBO- the house was beautiful, clean, and she was incredibly welcoming and communicative! "
United States
Marissa H.
The price is AED 533
AED 1,071 total
includes taxes & fees
23 Feb - 24 Feb
Steel Magnolias Cozy Main Home in Amelia County
Exterior

Private bedroom and bath!

Private bedroom and bath!
Midlothian
10.0 out of 10, Exceptional, (1 review)
"We had a lacrosse tournament at River city sports plex. This was perfect location to stay for us. Friendly and amazing combination with host. Extremely pleased with our stay"
United States
Ridge W.
The price is AED 477
AED 867 total
includes taxes & fees
23 Feb - 24 Feb
Private bedroom and bath!
Fridge, microwave, oven, stovetop

Cupid's Hideout

Cupid's Hideout
Fan District
The price is AED 380
AED 1,203 total
includes taxes & fees
23 Feb - 24 Feb
Cupid's Hideout
Terrace/patio

Backyard Fire-Pit, Modern, Roomy, 7 Min Downtown

Backyard Fire-Pit, Modern, Roomy, 7 Min Downtown
Northern Barton Heights
9.4 out of 10, Exceptional, (13 reviews)
"Loved it. Plenty of room for grandkids, their parents & I to have fun."
United States
Jane B.
The price is AED 393
AED 1,478 total
includes taxes & fees
3 Mar - 4 Mar
Backyard Fire-Pit, Modern, Roomy, 7 Min Downtown
Terrace/patio

Newly finished basement suite in Midlothian. Very clean and spacious.

Newly finished basement suite in Midlothian. Very clean and spacious.
Midlothian
10.0 out of 10, Exceptional, (2 reviews)
"Great spot to spend the evening while traveling through! Comfortable space.Host was very helpful through the check in process and my stay.Thanks Pamela!"
United States
Shawn P.
The price is AED 264
AED 600 total
includes taxes & fees
1 Mar - 2 Mar
Newly finished basement suite in Midlothian. Very clean and spacious.
Fridge, microwave, oven, stovetop

Luxury Stay! 10 min away from Fort Lee.

Luxury Stay! 10 min away from Fort Lee.
Prince George
8.2 out of 10, Very Good, (13 reviews)
"The location was excellent as it was central to a lot of places. Raymond was very quick to respond whenever I reached out. Accessing the house was easy. Very quiet neighborhood, besides the fact that everyone speeds on the street that runs along side of the house in case you have children with you. "
United States
Cindy M.
The price is AED 579
AED 1,062 total
includes taxes & fees
3 Mar - 4 Mar
Luxury Stay! 10 min away from Fort Lee.
TV, books, offices

The Sweet Family retreat/Fenced & Free Parking

The Sweet Family retreat/Fenced & Free Parking
Sauer's Gardens
9.8 out of 10, Exceptional, (62 reviews)
"Wonderful Host & great amenities. Everything we needed for a wonderful and peaceful stay. "
United States
Rosemary S.
The price is AED 757
AED 1,401 total
includes taxes & fees
5 Mar - 6 Mar
The Sweet Family retreat/Fenced & Free Parking
Dining

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

Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!
Downtown Richmond
9.8 out of 10, Exceptional, (73 reviews)
"Loved the apartment, great setup in a historic building in RVA with great restaurants in walking distance. "
United States
David Y.
The price is AED 337
AED 721 total
includes taxes & fees
1 Mar - 2 Mar
Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!
Smart TV, fireplace, computer monitors

Charming 1-bedroom suite with WiFi and AC in Bon Air

Charming 1-bedroom suite with WiFi and AC in Bon Air
Bon Air
10.0 out of 10, Exceptional, (8 reviews)
"The host was very responsive to any questions I had, responding within a few minutes each time. The space was as advertised with all needed amenities. "
United States
David W.
The price is AED 359
AED 1,064 total
includes taxes & fees
23 Feb - 24 Feb
Charming 1-bedroom suite with WiFi and AC in Bon Air
Exterior detail

Vintage Charm in Lakeside | A Timeless RVA Retreat

Vintage Charm in Lakeside | A Timeless RVA Retreat
Lakeside
10.0 out of 10, Exceptional, (4 reviews)
"The house was clean and very nice in a great location. The stay was great and Anna provided clear, consistent communication. She answered any questions I had quickly and often provided information prior to me asking. I would definitely stay there again. "
United States
Katie A.
The price is AED 640
AED 1,811 total
includes taxes & fees
24 Mar - 25 Mar
Vintage Charm in Lakeside | A Timeless RVA Retreat
Interior

Carytown Home/Free Parking/Fenced Yard/Family-Friendly/4TVs

Carytown Home/Free Parking/Fenced Yard/Family-Friendly/4TVs
Byrd Park
8.8 out of 10, Excellent, (16 reviews)
"Perfect location within walking distance to lots of eateries and shops. All other essential Richmond spots within quick drive. Great for short weekend with the girls."
United States
Amber V.
The price is AED 415
AED 942 total
includes taxes & fees
5 Mar - 6 Mar
Carytown Home/Free Parking/Fenced Yard/Family-Friendly/4TVs
Interior

Superb 3BR W/Balcony Near Capitol Center

Superb 3BR W/Balcony Near Capitol Center
Chimborazo
9.6 out of 10, Exceptional, (15 reviews)
"My stay was amazing. I love the property! "
United States
Donte M.
Superb 3BR W/Balcony Near Capitol Center
Interior

Superb 3-bedroom house. Minutes away from major hospitals. Close to VUU and VCU.

Superb 3-bedroom house. Minutes away from major hospitals. Close to VUU and VCU.
Richmond
10.0 out of 10, Exceptional, (2 reviews)
"Host was amazing and the house was excellent. Would book again for sure"
United States
Jon K.
The price is AED 588
AED 1,226 total
includes taxes & fees
5 Mar - 6 Mar
Superb 3-bedroom house. Minutes away from major hospitals. Close to VUU and VCU.
Private kitchen

Historic Modern Walkable to to VCU

Historic Modern Walkable to to VCU
Downtown Richmond
8.8 out of 10, Excellent, (11 reviews)
"Big clean home with lots of room!"
United States
Judy S.
The price is AED 400
AED 1,485 total
includes taxes & fees
24 Feb - 25 Feb
Historic Modern Walkable to to VCU
Outdoor dining

A Clean, Safe, House full of steel balls & vintage game consoles

A Clean, Safe, House full of steel balls & vintage game consoles
Dumbarton
9.8 out of 10, Exceptional, (28 reviews)
"The host was an excellent communicator and house was quite unique and fun."
United States
Paul N.
The price is AED 1,735
AED 2,378 total
includes taxes & fees
23 Feb - 24 Feb
A Clean, Safe, House full of steel balls & vintage game consoles
TV, offices

Charming Ranch Home/pet friendly/fenced yard/4TVs

Charming Ranch Home/pet friendly/fenced yard/4TVs
Sherwood Park
The price is AED 665
AED 1,415 total
includes taxes & fees
5 Mar - 6 Mar
Charming Ranch Home/pet friendly/fenced yard/4TVs
Exterior detail

Charming Fan District Getaway

Charming Fan District Getaway
Fan District
9.8 out of 10, Exceptional, (30 reviews)
"We had a wonderful stay at this Fan district home- great location, beautiful home and very responsive owner. Everything was as pictured, would definitely recommend for a Richmond stay!"
United States
Laura W.
The price is AED 889
AED 1,906 total
includes taxes & fees
23 Feb - 24 Feb
Charming Fan District Getaway
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.
View all properties

Eid al-Fitr Sale

Members save up to 40% on hotels. Plan this year’s big trip and save.
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chesterfield Hotel Reviews

Graduate by Hilton Richmond

Graduate by Hilton Richmond

10/10 Excellent
"Nice rooms and staff"
Jon 1-night trip
Posted 3 days ago
Graduate by Hilton Richmond

Explore a world of travel with Expedia