Stone statues and a brick wall.

Photo by Beth Hughes

Chesterfield Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Packages with flights are ATOL protected

  • Your Chesterfield Holiday

    With all the details organised before you take off, our Chesterfield holiday packages mean you can simply focus on having a great time. Whether you stay in the neighbourhood of Yorktown, which is great for golfing, or someplace else in town, this exciting city promises a wealth of discoveries. If your trip to Chesterfield includes a little sightseeing, don't miss much-loved attractions like Hoosier Park, Anderson Roll Arena and Mounds State Park. Expedia is here to help you escape your daily routine. Tailor your holiday to Chesterfield to suit your style of travel, whatever that may be!

    Discover the most popular places to visit in Chesterfield

    Labyrinth

    Enjoy an outing to Labyrinth during your stay in Chesterfield. While you're in the area, stroll along the riverfront.

    See properties

    Chesterfield Hotel Deals

    Anderson Chesterfield Travel Inn

    A hotel hallway with a fire extinguisher sign, an exit sign, and a vending machine.
    • Address: 15701 W Commerce Rd, Daleville, IN, 47334, US
    • Location: 1.3 mi from Chesterfield
    • Star rating: 2/5
    • Guest rating: 7.8/10 (Good, 294 reviews)
    • Price: £59, includes taxes & fees, 15 Nov - 16 Nov
    • Review: Kind owners and quiet property. I've stayed here a few times now and have enjoyed both stays.

    Tru By Hilton Anderson

    A modern hotel building with a prominent 'tru by Hilton' sign, multiple floors, and a well-lit entrance area.
    • Address: 2410 E 64th St, Anderson, IN, 46013, US
    • Location: 5 mi from Chesterfield
    • Star rating: 2.5/5
    • Guest rating: 8.8/10 (Excellent, 386 reviews)
    • Price: £64, includes taxes & fees, 6 Dec - 7 Dec

    Fairfield Inn & Suites by Marriott Anderson

    A modern hotel lobby with a stone fireplace, a blue sofa, a round table, and a reception desk.
    • Address: 2400 East 64th Street, Anderson, IN, 46013, US
    • Location: 5.3 mi from Chesterfield
    • Star rating: 3/5
    • Guest rating: 8.8/10 (Excellent, 576 reviews)
    • Price: £97, includes taxes & fees, 27 Nov - 28 Nov

    Best Western Plus Anderson

    A restaurant with a fire feature, dining tables, chairs, and a view through a mesh screen.
    • Address: 2114 E 59th St, Anderson, IN, 46013, US
    • Location: 4.8 mi from Chesterfield
    • Star rating: 2.5/5
    • Guest rating: 8.8/10 (Excellent, 1000 reviews)
    • Price: £86, includes taxes & fees, 24 Nov - 25 Nov

    Quality Inn & Suites Anderson I-69

    A spacious lobby with a staircase, a dining area with chairs and a table, and a reception desk.
    • Address: 1836 East 64th Street, Anderson, IN, 46013, US
    • Location: 5.2 mi from Chesterfield
    • Star rating: 2.5/5
    • Guest rating: 8.2/10 (Very good, 1001 reviews)
    • Price: £53, includes taxes & fees, 6 Dec - 7 Dec

    Baymont by Wyndham Anderson

    A hotel room with a large bathtub, a bed with a red and black patterned bedspread, two bedside lamps, and a wooden headboard.
    • Address: 2215 East 59th St, Anderson, IN, 46013, US
    • Location: 4.8 mi from Chesterfield
    • Star rating: 2.5/5
    • Guest rating: 8/10 (Very good, 834 reviews)
    • Price: £62, includes taxes & fees, 6 Dec - 7 Dec

    Comfort Inn Anderson South

    A covered swimming pool with a hot tub, seating area, and a view of the surrounding greenery.
    • Address: 2229 East 59th Street, Anderson, IN, 46013, US
    • Location: 4.8 mi from Chesterfield
    • Star rating: 2.5/5
    • Guest rating: 8/10 (Very good, 1000 reviews)
    • Price: £58, includes taxes & fees, 6 Dec - 7 Dec

    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.

    See all properties in Chesterfield

    Frequently Asked Questions

    How much does a Chesterfield travel package cost?

    Less than you might think — from just , in fact! By combining flights, hotels and car rentals into a customized travel package, your Chesterfield escape is only clicks away.

    If I'm not able to travel, can I cancel my Chesterfield travel package?

    Yes you can, and we'll help you every step of the way. You may be able to amend or cancel your Chesterfield travel package at no cost within 24 hours of booking. But you may incur a fee from your hotel, airline or car rental company for older bookings. If your travel plans suddenly change, look up our Customer Service Portal for further information.

    How do I get a cheap travel package to Chesterfield?

    You'll save a ton of money if you bundle your flights, hotels and car rentals into a Chesterfield holiday package. Sometimes cheap packages mean fewer options. But that's not the case with Expedia. We offer more than 550 air carriers and 1,000,000 hotels throughout the world, so you'll always have plenty of variety to choose from. Want to save even more? Add some popular activities to your package deal to unlock even bigger discounts! After all, travel is about more than just getting to your destination.

    Does Expedia offer Book Now, Pay Later Chesterfield holidays?

    Expedia has teamed up with online lender Klarna to make booking your next break a bit easier on the wallet. Paying by instalment means you can spread the costs of your next big holiday, leaving you with more cash to splash while you're away. Klarna has several payment plans to pick from, so you're sure to find something that falls within your budget. Consider these flexible payment options:

    • Pay monthly holidays: Make your holiday dreams come true sooner with Klarna's easy monthly instalment plans. If paying just a small amount each month sounds right for you, pick this option during the checkout process.
    • Pay in instalments holidays: If you'd prefer to pay for your escape across multiple transactions, holidays paid in instalments might be right for your Book Now, Pay Later holiday through Klarna.
    • Low deposit holidays: When you come across an awesome deal but your budget doesn't quite cover it yet, Klarna's low deposit holiday plan will help you lock in your getaway.

    Where should I stay in Chesterfield?

    There's so much to do in Chesterfield, so spend your nights near its attractions and allow yourself more time sightseeing. Mounds State Park is one place to add to your itinerary.

    What are the top hotels in Chesterfield?

    Holiday Inn Express Hotel & Suites ANDERSON NORTH, an IHG Hotel and Quality Inn & Suites Anderson I-69 are a couple of the most well-known hotels in Chesterfield. Why not look up the facilities and rates at each and then make a decision?

    How far in advance should I book my Chesterfield holiday?

    Travellers are usually able to browse international airfares on Expedia up to a year in advance of departure. Booking at the last minute? With a bit of luck, it's still possible to score a cheaper ticket only weeks before your journey.

    What does an Expedia Chesterfield travel package include?

    Packages include flights, rental cars and hotels, but you can mix and match them to create your ideal Chesterfield holiday. You can also add on some activities and tours once you've made your booking. You're the boss! When you bundle your bookings with Expedia, you'll enjoy deals you won't find anywhere else.

    What should I know before booking a Chesterfield travel package?

    Get set to save with an Expedia travel package. Bundle your flights, rental cars and hotels and pick up fantastic discounts. Hotels aren't your only option, though. Book with us and take your pick of beachside villas, rural cottages and even treehouses and ranches!

    Can I choose my airline with a Chesterfield Expedia travel package?

    Yes, you sure can. We have more than 550 airline partners across the globe, so pick the carrier that best fits your travel needs.

    * Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.