Chesterfield Holidays

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Your Chesterfield Holiday

Lock in a Chesterfield holiday package that includes everything you need and no unnecessary extras. Great for nightlife, cafes and festivals, think about basing yourself in the neighbourhood of Downtown Richmond. A trip to Chesterfield is a wonderful opportunity to see the sights. Be sure to stop by big-name attractions such as Pocahontas State Park, Castlewood and Magnolia Grange. Expedia has what you need to escape your daily routine. Tailor your holiday to Chesterfield to suit your style of travel, whatever that may look like.

Chesterfield Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Richmond Intl. Airport (RIC)
Population
3,800
Max Temp Winter
10ºC
Max Temp Summer
32ºC
Top Sights
Pocahontas State Park, Uptown Alley and Pocahontas State Park Museum

Top hotels in Chesterfield

Comfort Suites At Virginia Center Commons

Comfort Suites At Virginia Center Commons

2.5 out of 5
10601 Telegraph Rd Glen Allen VA
Fully refundable
The price is £73 per night from 1 Dec to 2 Dec
£73
1 Dec - 2 Dec
includes taxes & fees
8.2/10 Very good! (1,683 reviews)
"The room was clean. The towels was clean."

Reviewed on 10 Nov 2026

Comfort Suites At Virginia Center Commons
Holiday Inn & Suites Richmond West End

Holiday Inn & Suites Richmond West End

3 out of 5
8008 W. Broad St Richmond VA
Fully refundable
The price is £95 per night from 15 Nov to 16 Nov
£95
15 Nov - 16 Nov
includes taxes & fees
8.8/10 Excellent! (793 reviews)
"The stay was great, and clean. My only issue is the club next door really loud people drunk and everywhere in the parking lot"

Reviewed on 10 Nov 2026

Holiday Inn & Suites Richmond West End
The Jefferson Hotel

The Jefferson Hotel

5 out of 5
101 West Franklin Street Richmond VA
Fully refundableReserve now, pay when you stay
The price is £273 per night from 15 Nov to 16 Nov
£273
15 Nov - 16 Nov
includes taxes & fees
9.8/10 Exceptional! (1,011 reviews)
"Outstanding hotel and staff."

Reviewed on 10 Nov 2026

The Jefferson Hotel
See all 1,080 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.
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Family Friendly Holidays

Stay near popular Chesterfield attractions

Pocahontas State Park

8.4/10 (31 reviews)
Virginia's largest state park offers 90+ miles of trails through lush forests and three serene lakes. Explore world-class mountain biking routes or cool off at the seasonal Aquatic Centre after a day of adventure.
See properties

What to do in Chesterfield

Downtown Richmond Must-See Landmarks with Self-Guided Audio Tour

Downtown Richmond Must-See Landmarks with Self-Guided Audio Tour

£8
per traveller
80% of travellers recommend
Downtown Richmond Must-See Landmarks with Self-Guided Audio Tour
Down in the Shokoe Bottom, the most haunted neighborhood with 350+ years of history and hauntings!

The Haunted History of Richmond tour

£23
per adult
The Haunted History of Richmond tour
Historic Trolley Tour

Historic Trolley Tour

£34
per adult
100% of travellers recommend
Historic Trolley Tour
See all activities in Chesterfield

Frequently asked questions

How much does a Chesterfield travel package cost?
Our Chesterfield packages, which start from as low as , are the best way to save money. Choose your preferred hotels, flights and more to create your perfect itinerary.
If I'm not able to travel, can I cancel my Chesterfield travel package?
Whether it's your hotel, flight or rental car, yes, you can cancel or amend it. Locked in your Chesterfield travel package in the last 24 hours? You may be able to make changes or cancellations at no cost. For older bookings, you may incur a charge from your hotel, airline or car rental company. For more details, browse our Customer Service Portal. We're here to help you every step of the way.
How do I get a cheap travel package to Chesterfield?
One of the simplest ways to save cash (and time) is to bundle your bookings with Expedia. Hotels, flights, activities and rental cars — we've got them all. Choose a combination that best suits you and see your savings grow. We know a package deal is never a one-size-fits-all. That's why Expedia offers over 550 partner airlines and 1,000,000 hotel options around the globe, which lets you customize your Chesterfield adventure.
Does Expedia offer Book Now, Pay Later Chesterfield holidays?
Good news! We do. Expedia has teamed up with online lender Klarna to help you conveniently pay for your trip in instalments. Simply pick the payment plan that works for you during the checkout process and take the stress out of budgeting for your next trip. Make sure you bundle your accommodation, flights and car hire with Expedia to get the biggest bang for your travel buck. Take a look at our flexible payment options below:

  • Pay monthly holidays: Klarna offers easy monthly payment plans that work for all types of budgets, so you can take that well-deserved holiday now.
  • Pay in instalments holidays: Like the idea of paying for your holiday in multiple transactions? Consider this Book Now, Pay Later option with Klarna.
  • Low deposit holidays: If paying a small percentage of your trip (rather than all of it upfront) makes it easier to hit that "book now" button, consider a low deposit holiday payment plan with Klarna.

Where should I stay in Chesterfield?
With so much to do in Chesterfield, we suggest you book a room in a hotel close to its attractions. Pocahontas State Park, Castlewood and Pocahontas State Park Museum are some top ones to put on your must-see list.
What are the top hotels in Chesterfield?
Suburban Extended Stay Hotel Chester I-95 and La Quinta Inn & Suites by Wyndham Richmond-Midlothian are two of the most popular hotels in Chesterfield. Why not have a look at the amenities and facilities at each and then make up your mind?
How far in advance should I book my Chesterfield holiday?
To score discount prices, book as early as you can. Airlines typically release flights, along with some of the lowest fares, nearly 12 months ahead of time. Hotels, activities and car rental should also be booked well in advance so you can have the pick of the bunch. If you were hoping for a last-minute getaway in Chesterfield, there are always lots of great deals on Expedia. Book something in today!
What does an Expedia Chesterfield travel package include?
From hotels and flights to rental cars, Expedia can help you shape a Chesterfield package that's ideal for you. Heading off for a week or two? Give some thought to a flight, rental car and hotel bundle. If your break is short, a hotel and flight deal could be more your style. Activities can also be added after you've booked. Our travel packages make it easy to plan and save.
What should I know before booking a Chesterfield travel package?
Booking all the parts of your escape together is a great way to save. Combine your flights, car rentals and hotels into a tidy package. But you're not limited to hotels. Expedia features all types of properties, including holiday rentals such as mountain cabins and spacious residences. The list goes on!
Can I choose my airline with a Chesterfield Expedia travel package?
Yes — that's one of the best things about an Expedia travel package. You get to choose. We have access to more than 550 partner airlines around the world, so you have options galore when planning your Chesterfield trip.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.