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Top Holiday Rentals in Chesterfield

Exterior
Magnolias, a chill out place.
10.0 out of 10, Exceptional, (6)
"Pleasant host"
The price is £102
per night
14 May - 15 May
Magnolias, a chill out place.
Exterior
Beautiful and Spacious home w/Outdoor Kitchen
10.0 out of 10, Exceptional, (14)
"The property was perfect for the 6 of us adults. The rooms were and beds were large and comfortable, the screened in porch was a huge hit and we spent a large amount of time out on it. Tina was a perfect host, providing personalized touches and accommodating our scheduling needs for flights in and out. Highly recommend and will definitely be a repeat renter for our future visits with our grandkids!!"
Beautiful and Spacious home w/Outdoor Kitchen
Smart TV
Cozy Cape Cod Home!
10.0 out of 10, Exceptional, (21)
"The house and property was very clean. The beds were all comfortable. The house had all the smenities we needed for five adults and two toddlers. We used this house for a visit with my other duaghter who lives near by"
Cozy Cape Cod Home!
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Fridge, microwave, oven, stovetop
Garden Penthouse in RVA! 3 Bedroom, 3 Bath!
10.0 out of 10, Exceptional, (9)
"This is the place for you and yours! We came to Richmond to see the sites and tour civil war era places. It was always so nice to come "home""
Garden Penthouse in RVA! 3 Bedroom, 3 Bath!
Interior
Gorgeously Renovated 3500 square foot Oxford home in Richmond!!
10.0 out of 10, Exceptional, (21)
"My family of three stayed here for a long weekend. The house is exactly as described. The home was clean and well stocked with the essentials. Ryan was a great host. The community is quiet and we felt very safe. We loved the basement entertainment area for a long weekend of movies and watching football. Thank you so much for a great stay. We hope to visit again soon."
Gorgeously Renovated 3500 square foot Oxford home in Richmond!!
Interior
The Bike Path House! Cozy 2 BR w/ Fireplace
10.0 out of 10, Exceptional, (8)
"We loved the central location & proximity to the Bike Path. Very clean & cozy."
The Bike Path House! Cozy 2 BR w/ Fireplace
Property grounds
Great Location. Close to about everywhere .Can't beat the value. Check reviews!
10.0 out of 10, Exceptional, (166)
"The house was great and just like described. The beds were a little hard but manageable. More instructions on how things work (like the gas stove top) would be helpful. Overall a great house in a great location!"
Great Location. Close to about everywhere .Can't beat the value. Check reviews!
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!
Interior
Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!
10.0 out of 10, Exceptional, (43)
"We went to Richmond for a play at the Altria Theater and this location was within walking distance to the theater and some great restaurants. We only stayed one night, parking was right behind building. Host was excellent with great info."
Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!
Fridge, microwave, oven, stovetop
Stunning Modern Studio Will Take Your Breath Away
10.0 out of 10, Exceptional, (25)
"Sub Rosa Bakery, Pizza Bones, Union Market all within 5 minutes by foot; Computer Cave a half hour walk away to fix your electronics. Jefferson Park a 10-minute walk away. The state capitol is 30 minutes walk distant, same for the Virginia Commonwealth University Medical Center. Memorial of the notorious triangle trade (Liverpool-West Africa-Richmond) is in Shockoe Valley, 25 minutes by foot from your room. Thanks to the year 2020 protests, very few of the monuments can be found anymore that...
Stunning Modern Studio Will Take Your Breath Away
Property grounds
Cozy walkable downtown retreat, 3 minutes to VCU
10.0 out of 10, Exceptional, (5)
"Home was spotless. Each of the three couples had their own bedroom and bathroom. Kitchen well equipped. Nice areas to hang out and eat meals. We were issued parking passes as promised however discovered they were expired after being ticketed. The property manager has already reimbursed us for this. Excellent care taken to correct this. Would recommend this for a conveniently located home in an unpretentious historical neighborhood."
The price is £377
per night
14 May - 15 May
Cozy walkable downtown retreat, 3 minutes to VCU
Interior
🦢Swanhaven Offers Serene, Corporate Style Waterfront Luxury Living
10.0 out of 10, Exceptional, (1)
"Great Hosts"
The price is £252
per night
6 May - 7 May
🦢Swanhaven Offers Serene, Corporate Style Waterfront Luxury Living
Fridge, microwave, stovetop, dishwasher
Colonial Heights Home w/ Large Yard & BBQ Grill!
10.0 out of 10, Exceptional, (1)
"Quiet location on a nice street. Plenty of space and amenities. Great host. Will come back again."
Colonial Heights Home w/ Large Yard & BBQ Grill!
Private kitchen
Cozy Cabin @James River; Live/Work/Play Experience
10.0 out of 10, Exceptional, (2)
"We celebrated Christmas here and it was very nice and quiet"
Cozy Cabin @James River; Live/Work/Play Experience
Private kitchen | Fridge, microwave, oven, stovetop
City Life Richmond, Escape and Relax, Free Parking
10.0 out of 10, Exceptional, (14)
"The space was clean. Couches and beds were comfortable. The outdoor space was nice too. Was a little loud at night but overall great stay"
The price is £410
per night
14 May - 15 May
City Life Richmond, Escape and Relax, Free Parking
Fridge, microwave, oven, stovetop
Downtown Living in Richmond's Amazing Shockoe Bottom
9.8 out of 10, Exceptional, (12)
"Clean loft. Walkable location to restaurants and things to do."
The price is £212
per night
14 May - 15 May
Downtown Living in Richmond's Amazing Shockoe Bottom
Exterior
Industrial Chic Loft in the Heart of Downtown Richmond!
9.8 out of 10, Exceptional, (7)
"I loved it was so close to everything history this place was amazing and will be back in the future "
Industrial Chic Loft in the Heart of Downtown Richmond!
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 £159
per night
8 May - 9 May
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
Property grounds
The Black Pot - Dog friendly & Free parking
9.6 out of 10, Exceptional, (27)
"In transit, stayed one night overnight. Easy location to find right off I95. Excellent communication with Host; quiet location, easy check in. Close to amenities such as take out foods and corner store. House is also wheelchair/ Walker accessible as it is a bungalow with a ramp up to the front door. Highly recommend this rental."
The price is £159
per night
13 May - 14 May
The Black Pot - Dog friendly & Free parking
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 £246
per night
6 May - 7 May
Recline at Timberline! Family friendly!
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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 Rental Travel Info

Other types of properties in Chesterfield you may be interested in

Lobby
Drury Plaza Hotel Richmond
3.0 star property
9.6 out of 10, Exceptional, (2266)
"Clean and very spacious rooms. Friendly, helpful staff. Great breakfast"
The price is £109
per night
7 May - 8 May
Drury Plaza Hotel Richmond
Exterior
Omni Richmond Hotel
4.0 star property
8.6 out of 10, Excellent, (1171)
"Great facilities, easy access, friendly staff. Three issues: periodic noises coming from the HVAC vent/facilities. Confusion about lack of housekeeping (including replenishing coffee) associated with tag on the door. Suggest you separate that from the tag for do not disturb. Extra payments disguise the price. WiFi should be built into the room price. Overnight parking and valet service is too expensive. "
The price is £141
per night
2 Jun - 3 Jun
Omni Richmond Hotel
Rooftop terrace
Graduate Richmond
4.0 star property
8.4 out of 10, Very good, (1124)
"Great overnight stay! Very clean with excellent front desk service. Love all the details that make this property unique. "
The price is £155
per night
13 May - 14 May
Graduate 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.

Everything you need to know about Chesterfield holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chesterfield holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesterfield holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chesterfield holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesterfield. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesterfield holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesterfield holiday rentals we have selected for you start as low as £102 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chesterfield rentals

At Expedia, we put the best Chesterfield holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chesterfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesterfield holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesterfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Chesterfield?

Yes, there are holiday rentals close to the most popular sights in Chesterfield, or you can select a more secluded option if you're looking for a relaxing stay. Chesterfield is known for its shopping and golf courses. Make sure you have time to check out the parks and museums during your trip.

What are some of the best holiday rentals that Chesterfield has to offer?

Spacious Home Close To Downtown, VCU, MCV, The Fan: This holiday home rental outside of Chesterfield is located in the city centre, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Chesterfield?

Expedia has 8 holiday rentals for your stay in Chesterfield.

What can I see and do in Chesterfield?

Pocahontas State Park and Appomattox River are a couple of lovely local spots to get outside and enjoy nature. Castlewood and Chesterfield Historical Society of Virginia are other places to visit while you're in town.

What are holiday rentals like in Chesterfield?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chesterfield. Holiday rentals offer extras such as patios, hot tubs and fire pits so you'll have all the conveniences of home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from shared hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for families.

Recent reviews of Chesterfield properties
Expedia verified reviews