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27 Winchester hotels with suites or connecting rooms

Every hotel below has suites. The ones with confirmed connecting rooms come first, but a hotel does not need them to be here.

1–20 of 27 hotels in Winchester, KY
SortMost connectingLowest rateHighest ratedA–Z
Best Western Inn★★WinchesterRated 4.4 by 752 Expedia reviewers. Rated 4.5 by 250 Tripadvisor reviewers.33 suitesSleeps up to 10View suitesCountry Inn & Suites by Radisson, Winchester, VA★★★WinchesterRated 4.4 by 1,002 Expedia reviewers. Rated 4.5 by 1,329 Tripadvisor reviewers.19 suitesSleeps up to 5View suitesSleep Inn & Suites Winchester near University★★WinchesterRated 3.8 by 1,005 Expedia reviewers. Rated 4.0 by 561 Tripadvisor reviewers.17 suitesSleeps up to 10View suitesDays Inn by Wyndham Winchester★★WinchesterRated 3.3 by 572 Expedia reviewers.12 suitesSleeps up to 10View suitesTownePlace Suites by Marriott Lexington South/Hamburg Place★★★LexingtonRated 4.6 by 955 Expedia reviewers. Rated 4.5 by 184 Tripadvisor reviewers.12 suitesSleeps up to 6View suitesCandlewood Suites Winchester by IHG★★WinchesterRated 4.4 by 644 Expedia reviewers. Rated 4.0 by 154 Tripadvisor reviewers.10 suitesSleeps up to 4View suitesHoliday Inn Express Hotel & Suites Winchester by IHG★★WinchesterRated 4.5 by 868 Expedia reviewers. Rated 4.0 by 301 Tripadvisor reviewers.10 suitesSleeps up to 6View suitesComfort Inn & Suites Winchester★★WinchesterRated 4.7 by 1,137 Expedia reviewers.8 suitesSleeps up to 4View suitesHoliday Inn Express Lexington East - Winchester by IHG★★WinchesterRated 4.7 by 605 Expedia reviewers.8 suitesSleeps up to 4View suitesHoliday Inn Winchester Se-Historic Gateway by IHG★★★WinchesterRated 4.5 by 1,001 Expedia reviewers.8 suitesSleeps up to 4View suitesMicrotel Inn & Suites by Wyndham Winchester★★WinchesterRated 4.6 by 1,458 Expedia reviewers.8 suitesSleeps up to 4View suitesTRU By Hilton Winchester★★WinchesterRated 4.6 by 1,003 Expedia reviewers.8 suitesSleeps up to 4View suitesHampton Inn Winchester N/Conference Center, VA★★WinchesterRated 4.6 by 941 Expedia reviewers.7 suitesSleeps up to 4View suitesBest Western Winchester Hotel★★WinchesterRated 4.3 by 1,003 Expedia reviewers.6 suitesSleeps up to 4View suitesQuality Inn Winchester★★WinchesterRated 4.7 by 1,009 Expedia reviewers.6 suitesSleeps up to 10View suitesLa Quinta Inn & Suites by Wyndham Winchester★★★WinchesterRated 4.6 by 2,272 Expedia reviewers.5 suitesSleeps up to 5View suitesBaymont by Wyndham Winchester★★WinchesterRated 3.6 by 850 Expedia reviewers.4 suitesSleeps up to 4View suitesHampton Inn Winchester-University/Mall Area★★WinchesterRated 4.5 by 1,001 Expedia reviewers.4 suitesSleeps up to 4View suitesRed Roof Inn Winchester, VA★★WinchesterRated 3.7 by 1,000 Expedia reviewers.4 suitesSleeps up to 4View suitesComfort Inn Winchester★★WinchesterRated 3.5 by 388 Expedia reviewers.3 suitesSleeps up to 4View suites

Choosing between them

Does a bigger hotel mean a better chance of a connecting room?

Usually, but the count matters more than the size. A 5,000-room resort with 40 connecting pairs is a worse bet than a 700-room property with 90. That is why this list sorts by connecting rooms rather than by rooms — the number in gold is the one that decides whether you get the door.

Are these prices per room or for the whole booking?

For the whole thing. A connecting pair at $212 means both rooms, one reservation, one card. Two-bedroom suite prices are for the entire suite. Taxes and resort fees appear as one line at checkout before you pay.

Why does a hotel I know is here not appear?

It is here if we have details of its suites. A few more appear once you search real dates, because their rooms are only priced when we ask the hotel.