Chesterfield Holidays from £1,053

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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.

Top Chesterfield Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Club Wyndham Kingsgate

Club Wyndham Kingsgate

3 out of 5
per person
14 Sept - 19 Sept
found 9 hours ago
Return direct flight included
Manchester (MAN) to Richmond (RIC)
8.8/10 Excellent! (1,004 reviews)
Nice place to stay with a lot to do. Unfortunately, our vehicle was hit by someone in the activities center parking lot while we were at the pool. We came out to see the damage with no note. There’s no security cameras in that area either so whomever did it will likely get away. Also, the smoke alarm in the bedroom kept randomly going off while our kids were sleeping. Spent a substantial amount of time on that.

Reviewed on 3 Aug 2025

The Colonies at Williamsburg

The Colonies at Williamsburg

3 out of 5
per person
14 Sept - 19 Sept
found 9 hours ago
Return direct flight included
Manchester (MAN) to Richmond (RIC)
9/10 Wonderful! (1,012 reviews)
No food options on site but king bed was hard and queen bed was just right.

Reviewed on 11 Aug 2025

Griffin Hotel, an official Colonial Williamsburg Hotel

Griffin Hotel, an official Colonial Williamsburg Hotel

3 out of 5
Colonial Williamsburg
per person
14 Sept - 19 Sept
found 9 hours ago
Return direct flight included
Manchester (MAN) to Richmond (RIC)
8.8/10 Excellent! (731 reviews)
Beautiful setting in Colonial Williamsburg - if you are fairly mobile, this is great spot within the Colonial area so you can walkl everywhere. The spa gym building is separate but it is a pretty walk behind the sister hotel Williamsburg Inn where you check inn. The place itself was a good sized room and we slept 5 of us for this last minute stay and we normally get separate roomed suites, but this worked fine and was more budget friendly. The room itself was not super modernly updated, but it was fine, big, quiet, and peaceful. Great job!

Reviewed on 5 Aug 2025

Wedmore Place

Wedmore Place

3.5 out of 5
per person
14 Sept - 19 Sept
found 9 hours ago
Return direct flight included
Manchester (MAN) to Richmond (RIC)
9.6/10 Exceptional! (1,000 reviews)
Rooms were all decorated different, beds comfortable. Staff, especially housekeeping were very friendly and helpful

Reviewed on 11 Aug 2025

Kingsmill Resort

Kingsmill Resort

4 out of 5
Kingsmill
per person
14 Sept - 19 Sept
found 9 hours ago
Return direct flight included
Manchester (MAN) to Richmond (RIC)
8.8/10 Excellent! (1,001 reviews)
A very nice place family oriented to relax.

Reviewed on 11 Aug 2025

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

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 £247 per night from 24 Aug to 25 Aug
£247
24 Aug - 25 Aug
includes taxes & fees
9.8/10 Exceptional! (1,004 reviews)
"Bed very comfortable, spacious bathroom, soft and large bath towels"

Reviewed on 10 Aug 2025

The Jefferson Hotel
Studio 6 Richmond, VA - Airport

Studio 6 Richmond, VA - Airport

2 out of 5
580 Trampton Road, Sandston, VA
Fully refundableReserve now, pay when you stay
The price is £66 per night from 4 Sept to 5 Sept
£66
4 Sept - 5 Sept
includes taxes & fees
8.8/10 Excellent! (210 reviews)
"1"

Reviewed on 10 Aug 2025

Studio 6 Richmond, VA - Airport
Omni Richmond Hotel

Omni Richmond Hotel

4 out of 5
100 S 12th St, Richmond, VA
Fully refundableReserve now, pay when you stay
The price is £131 per night from 24 Aug to 25 Aug
£131
24 Aug - 25 Aug
includes taxes & fees
8.8/10 Excellent! (1,159 reviews)
"It was a beautiful site inside and out"

Reviewed on 9 Aug 2025

Omni Richmond Hotel
See all 957 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.
All Inclusive Holidays
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Beach Holidays
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Family Friendly Holidays

Popular places to visit

Pocahontas State Park Museum

You can spend an afternoon exploring the galleries in Pocahontas State Park Museum during your travels in Chesterfield. Take in the live music in this family-friendly area.

Pocahontas State Park Museum

What to do in Chesterfield

Historic Trolley Tour

Historic Trolley Tour

£31
per adult
100% of travellers recommend
Historic Trolley Tour
Group Shot at the Virginia State Capitol!

Richmond Landmark Segway Tour

£41
per adult
Richmond Landmark Segway 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 £1,053, 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.