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Wayside Inn

3-star hotel Excellent 7783 Main St, Middletown, VA, 22645, US
Wayside Inn
Wayside Inn – Middletown, VA
Wayside Inn – Middletown, VA
(540) 869-6038
Check in 3:00 PM
Check out 11:00 AM
9+ rooms? Request a group quote

About Wayside Inn

With a stay at Wayside Inn in Middletown, you'll be within a 5-minute drive of Cedar Creek Battlefield Foundation and Belle Grove Plantation. This hotel is 5. 1 mi (8. 1 km) from Valerie Hill Winery and 5. 8 mi (9. 3 km) from Strasburg Theater. Take advantage of recreation opportunities such as karaoke or take in the view from a terrace and a garden. This Colonial hotel also features complimentary wireless Internet access, wedding services, and a fireplace in the lobby. The front desk is staffed during limited hours. Free self parking is available onsite. At Wayside Inn, enjoy a satisfying meal at the restaurant. Wrap up your day with a drink at the bar/lounge. A complimentary full breakfast is served daily from 8:00 AM to 9:00 AM. Make yourself at home in one of the 22 individually decorated guestrooms. Complimentary wired and wireless Internet access keeps you connected, and cable programming provides entertainment. Private bathrooms with bathtubs or showers feature complimentary toiletries and hair dryers. Housekeeping is provided on request, and rollaway/extra beds (surcharge) can be requested.

Amenities

  • Meeting space
  • On-site dining
  • Bar / lounge
  • Café / coffee shop
  • Breakfast available
  • Express check-in / check-out

Reviews

4.6 / 5
Excellent 453 reviews
  • Engine customer Oct 2026

    Nothing to add.

  • Engine customer Oct 2026

    Wonderful staff and vibe . If you enjoy history then this is a place for you . The rooms are “old school ;so, don’t be prepared for the “newest” amenities . Thus is a place for people who like to “feel” the historic vibe

  • Engine customer Oct 2026

    This is the oldest hotel in the US. An exceptionally unique property from the mid 1700’s.

  • Engine customer Oct 2026

    There wasn’t really a staff or amenities… the young lady that gave me my key also showed me my room…. But there wasn’t anyone there when I left so I just left my key on the desk… never say anyone else that worked there. There was a coffee maker in the central area. No actual amenities in the rooms. I didn’t use the A/C unit so I don’t know about that… I think if you truly love and appreciate experiencing the historic era first hand this location is for you but if you’re like me and appreciate it but not want to live it probably not the location for you

  • Engine customer Sep 2026

    Charmingly beautiful hotel. Like staying in a Civil War museum. Comfortable mattress. Slightly creaky bed. Got to hear the haunted boots on the wooden floor footsteps! Cute coffee shop next door. Will gladly be back!

  • Engine customer Sep 2026

    We love staying at Wayside Inn. This is our third or fourth stay. The place is such a treasure! The food in the restaurant is good and the bar is fun. The only thing we noticed this time is that the bar closed at 9 p.m. on a Saturday night. We came in from dinner at 9:15 and planned to have a night cap and were told the bar closed at 9:00! The previous times we stayed there the bar was open until 10 or 11 on Saturday. We though such an early closing time was odd for the weekend.

  • Engine customer Sep 2026

    This is a quaint, historical place to stay with lots of antiques and interesting furnishings. We enjoyed the patio, pub and live music on the night we stayed. We would stay again if we find ourselves in the area.

  • Engine customer Aug 2026

    It was a very nice room with very comfortable bed. We misplaced the key and they were very helpful getting a replacement after hours. Fortunately, we found the lost key. Staff bwas very pleasant. Air conditioner was a little loud but effective. Did not prevent from sleeping. Would stay again.

  • Engine customer Aug 2026

    Clean room at a reasonable price. Interesting old inn.

  • Engine customer Aug 2026

    Nice place

  • Engine customer Aug 2026

    There was not an elevator. We were not able to stay at the Wayside Inn. We were taken aback when we were informed that the front door would be locked at 9pm. While there is a pad with a code for access, there is no staff on site. It was not what we expected, that is not the fault of staff or management. However, the exterior image posted on Expedia is not accurate. Wayside Inn is a wooden structure. The image on Expedia shows an impressive brick facade as a front elevation. That is a significant disconnect from reality.

  • Engine customer Jul 2026

    Full of character

  • Engine customer Jul 2026

    Historic, charming, relaxing.

  • Engine customer Jun 2026

    Quaint and quiet. Love historic places like this.

  • Engine customer Jun 2026

    I was given a room on the third floor without elevators. I think I was the only person staying at the hotel so I decided since I was a solo traveler I was given a room for one person and maybe because I booked thru Expedia, I don’t know. The room was very comfortable. Restaurant and bar were closed until later in the week. I was there on a Monday so beware of limited places to eat and drink on a Monday evening. The desk clerk goes home at 9 pm but there is a number to call after hours for a problem. Since I was leaving at 7:30 I had to search around how to get out as the office didn’t open until 9 am and I hadn’t been given info on how to exit it I was leaving early. But, I found a back door I could unlock and open and it would lock after me. The antiques were amazing! WIFI spoty. The evening hit or miss but good in the morning. I have Xfinity as a cell service and I had mostly 1 bar with an occasionl 2bars - so be aware of that.

  • Engine customer Jun 2026

    A historical inn with charming features and friendly, helpful staff.

  • Engine customer Jun 2026

    Clean, well-maintained, delicious food, hot shower!

  • Engine customer Jun 2026

    Nice historic place

  • Engine customer May 2026

    Everything and everyone were great. The extra roll out bed was not.

  • Engine customer May 2026

    was nice and my gf enjoyed it

Frequently asked questions about Wayside Inn

Does Wayside Inn have free Wi-Fi?
Yes, Wayside Inn offers free Wi-Fi for all guests.
Does Wayside Inn offer parking?
Yes, Wayside Inn offers free parking on-site.
Does Wayside Inn have meeting spaces, conference centers, or conference rooms?
Yes. Wayside Inn offers banquet and reception facilities for events and group gatherings.
Does Wayside Inn have a fitness center?
Wayside Inn does not list an on-site fitness center. Some properties partner with nearby gyms — check directly with the hotel.
Where is Wayside Inn located, and how walkable is the area?
Wayside Inn is located at 7783 Main St, Middletown, VA 22645. With a Walk Score of 32, the area is rated Car-Dependent. A car or rideshare is recommended for most trips in this area.
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