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Ashland · Hotel shortlist

Ashland hotels with a bar

Yuna Park

Yuna Park Korea, Taiwan and Hong Kong

Updated 1 September 2026 · 16 Ashland hotels assessed

These are my five favourites in Ashland, out of the 16 that qualified. I read what other travellers scored them before I picked, so the order follows the guests, 4.6 down to 4.4.

Winchester Inn is the one I would book myself.

Winchester Inn

Highest rated of the five

Winchester Inn

★★★★★4.6 from 216 reviews

Winchester Inn comes out on top of this list, and not narrowly: 4.6 from 216 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 a 5 star property, found under city centre and around $503 a night on the dates we checked.

16 hotels in Ashland qualified for this list and five made it. Green Springs Inn & Cabins is the one I would book if the first is full.

Why it works for this trip

  • Air conditioningthe one that decides a summer trip
  • Restaurantdinner downstairs on the night you land
  • Bara drink without going back out
  • Family roomscots and larger rooms rather than a squeeze
  • Parkinga real consideration if you are driving in

Check rates Read more

All five, ranked

  1. Winchester Inn1

    Winchester Inn

    ★★★★★4.6 from 216 reviews

    • Restaurant
    • Bar
    • Parking
    • Pet friendly
    • Kid friendly
    • Air conditioning

    Check rates Read more

  2. Green Springs Inn & Cabins2

    Green Springs Inn & Cabins

    ★★★★★4.8 from 898 reviews

    • Spa
    • Restaurant
    • Bar
    • Parking
    • Kitchen
    • Pet friendly

    Check rates Read more

  3. Bayberry Inn Bed and Breakfast and Retreat3

    Bayberry Inn Bed and Breakfast and Retreat

    ★★★★★4.9 from 130 reviews

    • Restaurant
    • Bar
    • Parking
    • Kitchen
    • Pet friendly
    • Kid friendly

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  4. Compass Hotel Medford by Margaritaville4

    Compass Hotel Medford by Margaritaville

    ★★★★★4.5 from 589 reviews

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

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  5. Ashland Springs Hotel5

    Ashland Springs Hotel

    ★★★★★4.4 from 777 reviews

    • Spa
    • Restaurant
    • Bar
    • Parking
    • Pet friendly
    • Kid friendly

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How this list was put together

16 Ashland 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.

Yuna Park

Yuna Park Korea, Taiwan and Hong Kong

Negotiated a fully remote contract and works a month at a time from a different city on home-office hours. Eleven cities in two years. Likes the routine in new places more than sightseeing.

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.