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Search Holiday Rentals in Chesterfield

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Top Holiday Rentals in Chesterfield

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
22 May - 23 May
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
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.
Downtown Living in Historic Richmond Loft
8.6 out of 10, Excellent, (40)
"Wonderful apartment, plenty of room for us and located near many things to do!"
The price is £260
per night
15 May - 16 May
Downtown Living in Historic Richmond Loft
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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
13 May - 14 May
Downtown Living in Richmond's Amazing Shockoe Bottom
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
Lovely 2 Bedroom in the Heart of The Fan
9.4 out of 10, Exceptional, (33)
"The apartment was just as described. It was clean and had everything we needed. It’s in a great neighborhood and it’s a short walk to many restaurants and shops."
The price is £246
per night
22 May - 23 May
Lovely 2 Bedroom in the Heart of The Fan
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!
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
Cozy Cape Cod Home!
10.0 out of 10, Exceptional, (23)
"We came to Richmond for my friends 70 and over Senior Softball Tournament . The house was clean and well equipped. The beds were comfortable. We were able to cook our meals and had everything we needed in the Kitchen. The only thing ,we had more than 3 cars for the driveway and did not know you could not park on the street. There were no signs. We had 4 cars from 4 different areas staying at the house. We would definitely stay again, but would make that adjustment for parking our cars. Thank you...
Cozy Cape Cod Home!
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!
Cozy and Family-Sized RVA Haven located near Short Pump Mall
8.0 out of 10, Very good, (1)
"Property and stay was great. Had issues with access to check in and communication with owner. Getting code to gain access and checking in took 2 hours. Owner did reimburse $68 for dinner. Overall positive experience."
The price is £286
per night
27 May - 28 May
Cozy and Family-Sized RVA Haven located near Short Pump Mall
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
Brand New, Gorgeous Studio Close to Everything!
10.0 out of 10, Exceptional, (24)
"Emily was awesome in keeping communications with us. Our our outgoing flight was delayed by several hours, and Emily was able to accommodate us for an extra couple of hours so we didn't have to wait at the airport. Highly recommend!!!"
Brand New, Gorgeous Studio Close to Everything!
Serenity in the Suburbs: Your Gorgeous RVA Getaway
9.4 out of 10, Exceptional, (9)
"The house was very convenient to Pocahontas State park. Tucked into a secluded area, we didn't feel like we were in the suburbs at all. Large yard, common spaces, and amenities made this a nice house for bigger groups."
Serenity in the Suburbs: Your Gorgeous RVA Getaway
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!
Bright & Cozy Downtown Apartment - Free Parking - Dogs Welcome - Fast Wi-Fi
9.6 out of 10, Exceptional, (7)
"This location was a short walk to the convention center which was perfect for us. So much more spacious than a hotel. The beds were comfortable. The white noise alarm clocks in the bedrooms were perfect for blocking out the street noise. The only thing we would have liked to have that we didn’t was a toaster in the kitchen. We will stay again if attending events at the convention center."
The price is £275
per night
28 May - 29 May
Bright & Cozy Downtown Apartment - Free Parking - Dogs Welcome - Fast Wi-Fi
Great Location. Close to about everywhere .Can't beat the value. Check reviews!
10.0 out of 10, Exceptional, (167)
"This is our go to in Richmond. Always great. Thanks Josh."
Great Location. Close to about everywhere .Can't beat the value. Check reviews!
Modern, Lovely and Spacious Home
10.0 out of 10, Exceptional, (8)
"We stay in a number of rentals on our vacations, and this one was top notch with all the small things provided, paper towels/toilet paper/dish soap etc. Proximity to VCU Medical Center, and all the wonderful downtown areas is incredible. The host reached out a number of times checking in to see if we needed anything and hoping we were having a good stay. He was wonderful! The house had an incredible coziness to it and we all felt at home. The beds were comfortable. The towels were great. The...
Modern, Lovely and Spacious Home
The Black Pot - Dog friendly & Free parking
9.4 out of 10, Exceptional, (28)
"we enjoyed our accommodations' and Delores was very nice and easy to connect with. would stay there again."
The price is £144
per night
10 Jun - 11 Jun
The Black Pot - Dog friendly & Free parking
Beautiful and Spacious home w/Outdoor Kitchen
10.0 out of 10, Exceptional, (14)
"We enjoyed Tina’s home so much and it was very well appointed. She had fresh flowers, a welcome basket of snacks, and wine upon arrival. The home is very spacious and perfect for gatherings. Tina thinks of everything and is very responsive if needed. The backyard is like a meditation zen garden. I would definitely recommend staying here."
Beautiful and Spacious home w/Outdoor Kitchen
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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

Drury Plaza Hotel Richmond
3.0 star property
9.6 out of 10, Exceptional, (2278)
"This was a quick overnight stay. The staff were friendly and welcoming. The room was clean was clean and comfortable. Very enjoyable "
The price is £109
per night
27 May - 28 May
Drury Plaza Hotel Richmond
Graduate Richmond
4.0 star property
8.4 out of 10, Very good, (1119)
"Nice place. "
The price is £148
per night
19 May - 20 May
Graduate Richmond
Omni Richmond Hotel
4.0 star property
8.6 out of 10, Excellent, (1166)
"Omni was great convenient and clean."
The price is £141
per night
2 Jun - 3 Jun
Omni Richmond Hotel
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.

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 Magnolia Grange 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.

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