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Choose from 620 Middletown Hotel Deals
Wayside Inn
Cozy and quaint. Felt like being in a home filled with lots of history! The people were very friendly in the restaurant and bar. Would definitely stay again.
Reviewed on May 10, 2026
Spark by Hilton Winchester
Breakfast menu was simple but fresh.
Reviewed on May 16, 2026
The George Washington Hotel, A Wyndham Grand Hotel
The staff was helpful and kind. The architecture was incredible.
Reviewed on May 12, 2026
Travelodge by Wyndham Winchester
The room was clean, and the staff was very welcoming and friendly. The location is especially convenient for truckers or anyone needing a quick overnight stop. The rooms have been partially updated with new flooring and a more modern look, but the walls still need some attention, which made the updates ...
Reviewed on May 16, 2026
Microtel Inn & Suites by Wyndham Winchester
The hotel was clean and the bed was comfortable. However, there were no cups in the room for coffee, yet there was a coffee machine and lids for cups. I called down to the front desk and was told they don't supply cups in the room and if I wanted a cup I had to go down to the coffee bar to get one. ...
Reviewed on May 13, 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
You have to pay 8.00 for breakfast, but it was very good. Room was clean, safe location.
Reviewed on May 16, 2026
La Quinta Inn & Suites by Wyndham Winchester
Be Aware!! Parking was a bit hard( we were pulling an enclosed trailer) had to back out from around the building because it did not circle all the way around . Room was clean and comfortable bed was soft, breakfast was the usually continental hot breakfast nothing special but ok. Would stay ...
Reviewed on May 15, 2026
TRU By Hilton Winchester
The front desk employee was very helpful, professional and pleasant. She was very friendly and greeted all of the hotel guests in a pleasant manner. She is a great asset to your organization.
Reviewed on May 15, 2026
Comfort Inn & Suites Winchester
Would highly recommend
Reviewed on May 16, 2026
Ramada by Wyndham Strasburg/Shenandoah Valley
Nice stay no issues, and front desk person very pleasant.
Reviewed on May 15, 2026
Courtyard by Marriott Winchester
Great hotel but missing the inclusive buffet breakfast for us travelers. :)
Reviewed on May 11, 2026
Holiday Inn Express Woodstock-Shenandoah Valley by IHG
Checked in and discovered toilet didnt work. Evan at the front desk checked it out and quickly moved us to another room. Great customer service!
Reviewed on May 15, 2026
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