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Chesterfield · Hotel shortlist

High end hotels near the station in Chesterfield

Tobias Lang

Tobias Lang Germany, Austria and Switzerland

Updated 1 September 2026 · 23 Chesterfield hotels assessed

These are my five favourites in Chesterfield, out of the 23 that qualified. I read what other travellers scored them before I picked, so the order follows the guests, 4.899319 down to 4.5.

Main Street 2BR Apartment with Garage and Deck is the one I would book myself.

Main Street 2BR Apartment with Garage and Deck

Highest rated of the five

Main Street 2BR Apartment with Garage and Deck

★★★★★4.899319 from 294 reviews

Main Street 2BR Apartment with Garage and Deck comes out on top of this list, and not narrowly: 4.899319 from 294 guest reviews is a score that holds up at that volume, which is the whole test here. A perfect ten from nine people does not beat it.

It is found under city centre and around $249 a night on the dates we checked.

23 hotels in Chesterfield qualified for this list and five made it. 334 N Main Street Unit A is the one I would book if the first is full.

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All five, ranked

  1. Main Street 2BR Apartment with Garage and Deck1

    Main Street 2BR Apartment with Garage and Deck

    ★★★★★4.899319 from 294 reviews

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    • 334 N Main Street Unit A2

      334 N Main Street Unit A

      ★★★★★4.714957 from 234 reviews

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      • 1107 S. Main3

        1107 S. Main

        ★★★★★4.879752 from 121 reviews

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        • Fairfield by Marriott Inn & Suites St. Louis Westport4

          Fairfield by Marriott Inn & Suites St. Louis Westport

          ★★★★★4.5 from 463 reviews

          • Pool
          • Spa
          • Gym
          • Restaurant
          • Parking
          • Kid friendly

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        • 4BR Game Room Pet-Friendly 9 min Airport5

          4BR Game Room Pet-Friendly 9 min Airport

          ★★★★★4.804167 from 96 reviews

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          How this list was put together

          23 Chesterfield hotels qualify for this list. We ranked them on guest rating, then on class, and took the top five.

          Two things decide these lists. The first is my own time in the city: every hotel on this page is one I have stayed in, walked into and looked at, or gone back to check. That is where the shortlist starts, and it is why some well reviewed places are not on it.

          The second is the numbers, and those are what set the order. The rating and review count come from the big travel sites, pooled through Google, so a score here reflects Expedia, Booking, Hotels.com and the rest together rather than any one of them. I also read the review breakdown by topic, which is where the figures on service, breakfast and location come from. Hotels with fewer than forty reviews are left out altogether, because a rating that thin is not a rating. No more than two come from one neighbourhood.

          What I do not do is move anyone up the order. The ranking is the guest score, highest first, and nobody pays to be on the list.

          Distances are straight lines from published coordinates, so the real walk is a little longer. Amenities are as recorded by Google Hotels and can change without notice. Rates are an indicative nightly figure for a midweek autumn stay, not a quote. Check the booking page before you commit.

          Tobias Lang

          Tobias Lang Germany, Austria and Switzerland

          Touring already moves him around Europe nine months a year, so he stays on three or four extra days at his own cost whenever a tour hits somewhere new. He calls it stealing time.

          Trip Grapevine earns a commission on bookings made through the links on this page. It costs you nothing, and it does not change the order of the list, which is set by the measurements above.