Photo by Nick Pagano

Search Holiday Homes in Chesterfield

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Browse Select Chesterfield Holiday Homes

5 bedrooms, desk, iron/ironing board, free WiFi
In the Village Of Powhatan- walking distance to owners restaurant
10.0 out of 10, Exceptional, (23)
"Just what we needed while in Powhatan for a wedding. Tracy was very helpful and the house was perfect for us."
In the Village Of Powhatan- walking distance to owners restaurant
Dining
Beautiful Three Bedroom one story house on quiet street
10.0 out of 10, Exceptional, (7)
"We stayed at this house for our daughter’s graduation from the University of Richmond. Campus was 10 to 15 minutes away. Grocery store is minutes away. Great to have 2-1/2 baths with six adults in the house getting ready. Plenty of space for all of us to hang out together. Christian was very responsive to any communication I had with him. Great place to stay."
Beautiful Three Bedroom one story house on quiet street
Property grounds
The Bike Path House! Cozy 2 BR w/ Fireplace
9.4 out of 10, Exceptional, (9)
"We loved the central location & proximity to the Bike Path. Very clean & cozy."
The Bike Path House! Cozy 2 BR w/ Fireplace
Save an average of 15% on thousands of hotels when you're signed in
Smart TV
Cozy Cape Cod Home!
10.0 out of 10, Exceptional, (24)
"We stayed at the house for a long weekend for our son’s lacrosse game at The University of Richmond. The house was clean and was exactly as pictured. The fire pit in the back was a nice plus and we really liked the lights above it. The house was close to many stores and an easy ride to other locations in Richmond."
Cozy Cape Cod Home!
Fridge, microwave, oven, stovetop
The Bamboo House! Dog-Friendly Home n RVA Sleeps 8
10.0 out of 10, Exceptional, (6)
"We were very happy with our stay."
The Bamboo House! Dog-Friendly Home n RVA Sleeps 8
Interior
Cozy retreat just 1 mile from the Fine Creek Brewery & eclectic wedding venue.
10.0 out of 10, Exceptional, (2)
"This cottage was straight out of Country Living Magazine. All you could want with a bottle of wine awaiting arrival. Coffee creamers, pods, eggs, make up remover pads etc. It was immaculate and comfy. We highly recommend and would definitely stay there again."
Cozy retreat just 1 mile from the Fine Creek Brewery & eclectic wedding venue.
Property grounds
3-Bed Grace Street Getaway in Museum District
10.0 out of 10, Exceptional, (2)
"Lovely place, close to everything! Great for our family while visiting our VCU students."
3-Bed Grace Street Getaway in Museum District
Fridge, microwave, oven, stovetop
Serenity in the Suburbs: Your Gorgeous RVA Getaway
9.6 out of 10, Exceptional, (11)
"We are grateful to have found this hideaway! It was really exactly what we needed in space and close to every event we had scheduled for that weekend. We have no complaints and we would definitely book again! Our host, James Divine, was so communicative and responsive to our questions and concerns. I recommended this home for group or family outings."
Serenity in the Suburbs: Your Gorgeous RVA Getaway
Exterior
Modern, Lovely and Spacious Home
10.0 out of 10, Exceptional, (9)
"This is a lovely home with the charm of years gone by and located in historic Jackson Ward. It is in easy walking distance from numerous restaurants, shops, and the contemporary art museum. The hostess was in regular communication with us to ensure we had a great stay."
Modern, Lovely and Spacious Home
Terrace/patio
Central location w/ large fenced yard FIRE-PIT
10.0 out of 10, Exceptional, (22)
"Great stay the dogs really enjoyed the backyard. The coaches enjoyed the other houses well, not sure which houses says, but both houses were really well."
The price is £257
per night
28 May - 29 May
Central location w/ large fenced yard FIRE-PIT
Dining
Modern 4 Bedroom Home, 6 mins away from Downtown
10.0 out of 10, Exceptional, (6)
"The house is beautiful inside the yard is decent. Not the prettiest neighborhood, but not bad according to my coaches.. We would definitely stay again."
Modern 4 Bedroom Home, 6 mins away from Downtown
Fridge, microwave, oven, stovetop
Fresh 3BR Near Minutes to James River, VCU, and VA Capitol
8.0 out of 10, Very good, (1)
"Hamid was very attentive and helpful. The kitchen was well stocked. The house was a bit out dated but certainly worked. I would stay at any of the host’s properties due to how attentive he was to our needs. The Vrbo app was confusing and did not have all the info it said it would have about the property but that is a Vrbo thing and not related to this host or house"
Fresh 3BR Near Minutes to James River, VCU, and VA Capitol
Exterior
Welcome to suburbia! 3bedroom townhome in Midlothian - close to 288 & Powhite!
4.0 out of 10, (2)
"This house has a good layout, hardwood floors in the main area, and is in a quiet neighborhood. It reminds me of a rental house for college students that the landlord decided didn’t need maintenance. There are screws, nails, and marks on the walls throughout the house. There is a definite dog smell, especially in the stairwell, and some dog hair, but I can tell there was an effort made since the last review. The house had been cleaned, but only spackling, paint, and ripping up the carpet will...
Welcome to suburbia! 3bedroom townhome in Midlothian - close to 288 & Powhite!
Fridge, microwave, stovetop, dishwasher
Terre Haute Manor Farmhouse w/ Gardens & Deck!
10.0 out of 10, Exceptional, (19)
"I took two teams (UMASS & JMU) to the college super regional Pickleball tournament. The house was fantastic because it was affordable for college kids (though one needed to be 30 years of age to book it…I exceed that age), it had lots of beds and enough bathrooms and a kitchen. I recommend getting there in the daylight hours because it is a little off the beaten path and dark when you arrive but it was perfect fit for our needs - great hospitality! Beautiful animals in the property too (donkeys...
Terre Haute Manor Farmhouse w/ Gardens & Deck!
Property grounds
Great Location. Close to about everywhere .Can't beat the value. Check reviews!
10.0 out of 10, Exceptional, (168)
"Perfect location for attending our son's graduation from University of Richmond. Pleasant, walkable neighborhood. Short distance to a grocery, the University, and restaurants. Lots of space, including a formal dining room. Although we didn't cook, the kitchen was well stocked. Check in & out was easy. Would stay again."
Great Location. Close to about everywhere .Can't beat the value. Check reviews!
Property grounds
The Black Pot - Dog friendly & Free parking
9.4 out of 10, Exceptional, (29)
"we enjoyed our accommodations' and Delores was very nice and easy to connect with. would stay there again."
The Black Pot - Dog friendly & Free parking
Exterior
Beautiful and Spacious home w/Outdoor Kitchen
10.0 out of 10, Exceptional, (15)
"We had a great stay at Tina's property. Her house was immaculate and had everything you would need on a visit. Plenty of sheet, towels, shampoo and condiments. The beds were very comfortable as well and the backyard was beautiful."
Beautiful and Spacious home w/Outdoor Kitchen
4 bedrooms, iron/ironing board, free WiFi, bed sheets
The Cozy Rancher | Petersburg | King Bed
10.0 out of 10, Exceptional, (21)
"We loved this property it was truly a home away from home. This house was clean, decorative, nice clean smell, and located in a quite neighborhood. It was truly relaxing and made us feel right at home."
The price is £280
per night
23 May - 24 May
The Cozy Rancher | Petersburg | King Bed
Exterior
Amazing Private House Rental w/ pool! Richmond, VA
9.2 out of 10, Wonderful, (52)
"The space was wonderful for the way I wanted to celebrate my birthday with family and friends! We played group games with up to 12 people in the living room and a playlist from YouTube in the background. The kitchen is impressive. My friends who came who are parents didn’t bring their children this time but appreciated knowing the space can accommodate them. There is ample parking on the pavement next to the house and on the street in front. My fave feature was the shower in the master bedroom!...
The price is £262
per night
3 Jun - 4 Jun
Amazing Private House Rental w/ pool! Richmond, VA
Fridge, microwave, oven, stovetop
Recline at Timberline! Family friendly!
9.4 out of 10, Exceptional, (23)
"The house was neat and clean, and very comfortable for me and my two sisters. Better than we hoped for. Would definitely stay here again."
The price is £261
per night
8 Jun - 9 Jun
Recline at Timberline! Family friendly!
Don't see what you're looking for?
See all available properties in Chesterfield
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.

Other property types in Chesterfield

Exterior
Magnolias, a chill out place.
10.0 out of 10, Exceptional, (7)
"Magnolias is exactly what it is advertising. A great place to stay for a few nights when visiting RVA. Super close to the RIC. Easy to get to and from downtown. Very comfortable. Well worth the price."
The price is £101
per night
3 Jun - 4 Jun
Magnolias, a chill out place.
Fridge, microwave, oven, stovetop
Downtown Living in Historic Richmond Loft
8.4 out of 10, Very good, (41)
"Wonderful apartment, plenty of room for us and located near many things to do!"
The price is £258
per night
3 Jun - 4 Jun
Downtown Living in Historic Richmond Loft
Property grounds
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
9.6 out of 10, Exceptional, (191)
"We had an enjoyable stay on the houseboat. The bed was comfortable, and the accommodations had everything we needed. We even made spaghetti the first night for dinner since we arrived later than planned. The area is private, we only saw a few people and those we did see gave a friendly hello if they didn't stop to chat with us. For anyone wondering about the movement of the boat, it is very stable. The boat is docked in a channel off the main river so not a lot of boat traffic and the currents...
The price is £158
per night
2 Jun - 3 Jun
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
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.

Chesterfield Holiday Homes information

Number of reviews
420
Accommodation
267 Holiday Homes
Lowest Price
£257
Highest Price
£280

Chesterfield Hotel Reviews
Expedia verified reviews