Chesterfield Holidays from £714

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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.

The Latest Chesterfield Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Wingate by Wyndham Richmond Short Pump

Wingate by Wyndham Richmond Short Pump

2.5 out of 5
Short Pump
per person
1 Sept - 8 Sept
found 21 hours ago
Return flight included
London (LON) to Richmond (RIC)
8.6/10 Excellent! (1,783 reviews)
Kisia was very professional Room was great

Reviewed on 22 Jun 2025

Westgate Historic Williamsburg Resort

Westgate Historic Williamsburg Resort

3.5 out of 5
per person
1 Sept - 8 Sept
found 21 hours ago
Return flight included
London (LON) to Richmond (RIC)
8.4/10 Very Good! (1,009 reviews)
Surprisingly comfortable place to stay

Reviewed on 22 Jun 2025

The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
per person
1 Sept - 8 Sept
found 21 hours ago
Return flight included
London (LON) to Richmond (RIC)
9/10 Wonderful! (1,246 reviews)
Unique art, love the size of the rooms. Perfect location. Didn’t like that I had to valet my truck. No room service and limit staff All the staff was very pleasant and helpful.

Reviewed on 22 Jun 2025

Country Inn & Suites by Radisson, Ashland - Hanover, VA

Country Inn & Suites by Radisson, Ashland - Hanover, VA

3 out of 5
per person
1 Sept - 8 Sept
found 21 hours ago
Return flight included
London (LON) to Richmond (RIC)
8.8/10 Excellent! (1,011 reviews)
Great area that felt much safer than most interstate hotels

Reviewed on 22 Jun 2025

La Quinta Inn & Suites by Wyndham Richmond-Midlothian

La Quinta Inn & Suites by Wyndham Richmond-Midlothian

3 out of 5
North Chesterfield
per person
1 Sept - 8 Sept
found 21 hours ago
Return flight included
London (LON) to Richmond (RIC)
8.2/10 Very Good! (1,356 reviews)
Property is well kept. Location was convenient. The staff was friendly. The stay was pretty much spoiled by the excessively loud ice machine that was in constant use from 6:00 am until we checked out at 8:00 am on Sunday morning. That combined with a text message at 7:30 am telling us that late checkout requests would not be honored which was immediate followed by the housekeeping staff knocking on doors and loudly yelling "Housekeeping" while speaking loudly in the hallway would cause me to stay somewhere else next time where they actually allow you to sleep.

Reviewed on 22 Jun 2025

Stay-Over Suites

Stay-Over Suites

3 out of 5
per person
1 Sept - 8 Sept
found 21 hours ago
Return flight included
London (LON) to Richmond (RIC)
9/10 Wonderful! (735 reviews)
I absolutely loved it! I will definitely be staying again. The front desk staff is incredible!

Reviewed on 21 Jun 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

Our pick of the best Chesterfield Hotel Deals

Regency Inn Richmond
Regency Inn Richmond
2 out of 5
1500 Eastridge Road, Richmond, VA
Stay at this business-friendly hotel in Richmond. Enjoy free Wi-Fi, free parking and room service. Our guests praise the helpful staff in their reviews. Popular ...
7/10 Good! (1,002 reviews)
"I love staying here and it’s quiet and peaceful"

Reviewed on 16 Jun 2025

Regency Inn Richmond
Omni Richmond Hotel
Omni Richmond Hotel
4 out of 5
100 S 12th St, Richmond, VA
Stay at this 4-star business-friendly hotel in Richmond. Enjoy breakfast (surcharge), room service and a 24-hour fitness centre. Our guests praise the helpful ...
8.8/10 Excellent! (1,124 reviews)
"cool ."

Reviewed on 17 Jun 2025

Omni Richmond Hotel
Red Roof Inn Richmond South
Red Roof Inn Richmond South
2 out of 5
4350 Commerce Rd, Richmond, VA
Stay at this hotel in Richmond. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in their reviews. ...
6.4/10 (1,000 reviews)
"Great hotel, good service, my only issue is they need to change the air conditioner filters in certain rooms."

Reviewed on 19 Jun 2025

Red Roof Inn Richmond South
See all 955 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

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

How much does a Chesterfield travel package cost?
Our Chesterfield packages, which start from as low as £714, 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.

Discover the most popular places to visit in Chesterfield

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

Unmissable things to do in Chesterfield

Historic Trolley Tour

Historic Trolley Tour

£31
per adult
Historic Trolley Tour
Richmond: Guided Hike in James River Park

Richmond: Guided Hike in James River Park

£21
per adult
Richmond: Guided Hike in James River Park
“Our guide was awesome, kind and very knowledgeable about the area and each restaurant. I highly recommend this company and we will be taking the other tours they offer.” - River City Food Tours guest

Arts District Food Tour in Richmond with Discover Richmond

£69
per adult
Arts District Food Tour in Richmond with Discover Richmond
See all activities in Chesterfield

* 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.