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Middletown · Hotel shortlist

The best hotels in the city centre, Middletown

Peter Halvorsen

Peter Halvorsen The Nordics

Updated 1 September 2026 · 53 Middletown hotels assessed

These are my five favourites in Middletown, out of the 53 that qualified. I read what other travellers scored them before I picked, so the order follows the guests, 4.894393 down to 4.6.

Pet Friendly Trails Head Cabin is the one I would book myself.

Pet Friendly Trails Head Cabin

Highest rated of the five

Pet Friendly Trails Head Cabin

★★★★★4.894393 from 799 reviews

Pet Friendly Trails Head Cabin comes out on top of this list, and not narrowly: 4.894393 from 799 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 $208 a night on the dates we checked.

53 hotels in Middletown qualified for this list and five made it. Glenmere Mansion Hotel Restaurant and Spa is the one I would book if the first is full.

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All five, ranked

  1. Pet Friendly Trails Head Cabin1

    Pet Friendly Trails Head Cabin

    ★★★★★4.894393 from 799 reviews

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    • Glenmere Mansion Hotel Restaurant and Spa2

      Glenmere Mansion Hotel Restaurant and Spa

      ★★★★★4.7 from 350 reviews

      • Pool
      • Spa
      • Gym
      • Restaurant
      • Bar
      • Parking

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    • Relaxing Farm Cottage Escape, 10 Min from LEGOLAND3

      Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

      ★★★★★4.8950725 from 414 reviews

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      • Beautiful, remote Catskills cabin over waterfall with amazing views & hot tub4

        Beautiful, remote Catskills cabin over waterfall with amazing views & hot tub

        ★★★★★5 from 253 reviews

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        • Stagecoach Inn, Goshen NY5

          Stagecoach Inn, Goshen NY

          ★★★★★4.6 from 343 reviews

          • Restaurant
          • Bar
          • Parking
          • Air conditioning
          • Accessible

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        How this list was put together

        53 Middletown 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.

        Peter Halvorsen

        Peter Halvorsen The Nordics

        Twenty-six years of teaching means 26 long summers. Trains and driving through most of Europe, now further afield, usually alone with a tent. Keeps every train ticket since 1994.

        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.