Are pets allowed at Wayside Inn?

Sorry, pets aren't allowed, but service animals are welcome.

Is parking offered on site at Wayside Inn?

Yes, there's free self and extended parking. Parking spots may be limited. Free RV/bus/truck parking is available.

What are the check-in and check-out times at Wayside Inn?

Check-in start time: 3:00 PM; Check-in end time: 8:00 PM. There's a charge of USD 50.00 for early check-in (subject to availability). Check-out time is 11:00 AM. Late check-out is available for a charge of USD 50.00 (subject to availability). Express check-out is available.

What is there to do at Wayside Inn and nearby?

Wayside Inn has a picnic area and a garden.

What's the area around Wayside Inn like?

Wayside Inn is located a short 1-minute walk from Wayside Theater.

Wayside Inn, Middletown: Hotel Reviews, Rooms & Prices

8/10 Very good

Sep 19, 2025

Great, Historic Motor Coach

Very interesting place to stay. Lots of history.

Tim, 2-night trip

8/10 Very good

Jul 7, 2025

We stayed last year on July 4th. ...really liked it...decided to make it an annual event. I like the small town atmosphere.

jeffrey, 1-night trip

10/10 Exceptional

Jun 15, 2025

Friendly, helpful staff.

Louise, 1-night trip

8/10 Very good

Jun 29, 2025

We arrived very late but man from the bar was extremely helpful and walked us to our room. Was a nice place to sleep, wish we had more time to explore.

Alecia, 1-night trip

10/10 Exceptional

May 28, 2025

Friends were camping near by but I needed a haven away!

Judith C, 2-night trip

8/10 Very good

Jun 30, 2025

Old Inn with unique features great for those who don’t want the cookie cutter experience. Great history and furniture was amazing, the building itself was incredible. Lot of history in the building. The manager was very knowledgeable about the history and property. Staff was great. Enjoyed my visit.

Michael, 1-night trip

8/10 Very good

Jun 17, 2025

If your history buff exploring the area this is your ideal base of operations. Close to many local historical sites and the place itself is a piece of Americana. If the walls could talk in this place who knows what it would tell us about the past. The place is remarkably well kept given its age and the centuries old architecture lends to the quaintness of this landmark.

Dale, 1-night trip

10/10 Exceptional

Apr 26, 2025

Wayside Inn charming

Connecting with Family and Friends. Wanted to stay someplace interesting not a box/tel. Wayside was charming and interesting. An old, so expectations should be tailored accordingly.

Daniel, 1-night trip

10/10 Exceptional

Feb 2, 2025

Was a very fun atmosphere with and employees and also other guess very nice and friendly and excellent wings

Jennifer, 2-night trip

10/10 Exceptional

Jan 16, 2025

Very charming. I will stay there again.

Steven, 1-night trip

10/10 Exceptional

Jan 24, 2025

Absolutely Spectacular

This inn is absolutely amazing. Staff went above and beyond to ensure we were comfortable and our stay was memorable. We plan to come back very soon!

Priscilla, 2-night trip

10/10 Exceptional

Apr 18, 2024

Beautiful hotel!

JONATHAN, 1-night trip

8/10 Very good

May 26, 2024

Nice quiet inn in a historic setting.

Laszlo, 1-night trip

6/10 Good

May 19, 2025

It was quaint and interesting, but beware if you don’t like the smell of antiques. I had to track down staff to check in and call the manager who frankly seemed a bit miffed that I called her. Staff member was friendly upon arrival. Water pressure in the shower was not great, although the room was clean.

Marianne, 1-night trip

10/10 Exceptional

Oct 18, 2024

Historically decorated place…very unique

Celina, 1-night trip

8/10 Very good

Jul 7, 2024

The country’s oldest motor inn.

William, 2-night trip

10/10 Exceptional

Oct 2, 2024

Wonderful historic town and tavern. When you want to stay in something other than the usual hotel this is a fun alternative. Historic for sure - dining only on certain days but plenty of good choices around - don’t miss Shaffer’s barbecue further down road - incredible food!!!!!

anne, 1-night trip

8/10 Very good

May 23, 2024

Everyone was super nice! Beautiful place!

Sabrina, 1-night trip

10/10 Exceptional

Jul 24, 2024

i loved the history of the property

Carl, 2-night trip

10/10 Exceptional

Jan 4, 2025

P&W

What a gem! The place is fantastically kept, the decor (including Holiday) was beautiful. Our room was comfortable, drinks and dinner at the Tavern were excellent. The Service was exceptional. Our check-in clerk (Brittany) was so nice and knowledgeable about the Inn. She gave us a tour along with the history. We loved our stay and will definitely return!

Wayne Or Patti, 1-night trip

8/10 Very good

Sep 29, 2024

This historical property was very well kept and welcoming! I rebooked on checkout.

Rosanne, 1-night trip

10/10 Exceptional

Oct 24, 2022

If you like an old Inn with a lot of character and history, this is the place. we really enjoyed our two night stay.

Eric, 2-night trip

10/10 Exceptional

Jul 24, 2022

It was a pleasant stay in a unique inn.

Marianne, 2-night trip

10/10 Exceptional

Jul 20, 2024

I'd stay there again!

We were fortunate enough to stay in one of the original rooms. Beautifully decorated, comfortable,clean and quiet. Exceptionally nice staff which told us the history of the Inn. I look forward to returning and having brunch with them on a Sunday.

Kenneth, 2-night trip

10/10 Exceptional

May 21, 2024

A peek into the world of the past in a very comfortable environment!

Prashant, 1-night trip

Wayside Inn

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Popular amenities

Main amenities (11)

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01 - Jubal Early Stateroom

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03 - Cedar Creek Guest Room

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04 - Wilkenson Guest Room

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05 - Middletown Guest Room

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06 - Lincoln Stateroom

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07 - Jefferson Guest Room

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09 - Harrison Guest Room

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11 - Tyler Guest Room

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12 - Madison Stateroom

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14 - Rhodes Suite

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15 - Bernstein Suite

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16 - Washington Stateroom

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18 - Shenandoah Guest Room

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20 - Rutherford Stateroom

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21 - Hite Guest Room

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22 - Byrd Guest Room

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23 - Wilson Guest Room

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24 - Monroe Guest Room

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19 - Massanutten

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17 - Lee Guest Room

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