Name: Wayside Inn
Address: 7783 Main St, Middletown, Middletown, Middletown, 22645, United States of America
Rating: 9

Smoking areas

Garden

Terrace

Outdoor furniture

No elevators

Reception desk

General

Restaurant

Meals

Free Wi-Fi

Internet

Library

Picnic area

Recreation

Parking

Event facilities

Business

Pets Not Allowed

Pets

Extra decontamination measures

Additional measures against COVID-19

Health and Safety Measures

Location

At the hotel

Winchester Regional Airport

Wayside Inn

Middletown

child-bed

child-bed-fee

external-private-bathroom

private-bathroom

shared-bathroom

10-beds

11-beds

12-beds

13-beds

14-beds

15-beds

16-beds

17-beds

18-beds

19-beds

2-beds

20-beds

21-beds

22-beds

23-beds

24-beds

25-beds

26-beds

27-beds

28-beds

29-beds

3-beds

30-beds

31-beds

32-beds

33-beds

34-beds

35-beds

36-beds

37-beds

38-beds

39-beds

4-beds

40-beds

5-beds

6-beds

7-beds

8-beds

9-beds

king-bed

queen-bed

limited-time

lounge

treatment

no-window

bay-view

bosphorus-view

canal-view

city-view

courtyard-view

garden-view

golf-view

harbour-view

inland-view

lake-view

land-view

mountain-view

ocean-front

ocean-view

oceanside

panoramic-view

park-view

partial-ocean-view

partial-sea-view

partial-view

pool-view

river-view

sea-front

sea-view

street-view

sunrise-view

sunset-view

water-view

with-view

annex

basement

main-building

1-bedroom

2-bedrooms

3-bedrooms

4-bedrooms

5-bedrooms

6-bedrooms

not-guaranteed

wired-internet-access

smoking

sauna

duplex

safe

mini-bar

breakfast-for-1

breakfast-for-2

pets-allowed

wi-fi

kitchen

Great, Friendly, Knowledgeable, Willing to please, everything you want in hotel staff. The staff may be limited but at no time was there a need that wasn't met. The front desk clerk, Kat, was always smiling and full in information. Peirce provided a tour and history of not only the hotel/Inn/Tavern but also local history as well. The bar staff jumped in and helped the wait staff when our very large group (from Vermont to Florida to Illinois) all decided to have dinner in the restaurant at the same time.
I absolutely would stay here again and recommend this to others.

Perfect! Historic, helpful and friendly staff full of smiles.

I enjoyed the historic hotel. My room was comfortable.  I highly recommend staying when the tavern is open.  I did not.  The hotel was locked when I arrived.  I called a number on a sign at the door and was given a code to get into the hotel.  There were no employees on site until the next morning.

A fun, historic adventure

We went in for dinner, were greeted by a server who was brand new and, after an hour and ten minutes still did not have what we ordered .  All we got were apologies.  No free drinks or chips or bread or anything thing was offered except excuses and “just 10 minutes more” assurances that never delivered.  We got up and left and would never go back.  FYI, the drinks are way overpriced.

Would Never Go Back

The Location is very convenient to the I-81.
The parking was Big Rig friendly.
The community is Historic, quiet and safe.
We are at the Tavern and as our meal was being prepared, we got a private tour of this Historic landmark. Beautiful period furniture and decor.

The meal at the tavern was excellent.
Our server was attentive and friendly.
I had the best French Dip meal ever with home made chips and a frosty beer.
My wife ate a delicious Crab cake sandwich and enjoyed her freshest and flavorful meal.

Come visit and enjoy a meal in this Historic Inn.
You won’t be disappointed.

Cheers 
DJT

We stayed as a Harvest Host member.

We had a wonderful night here - ok so no ghosts or neighing horses, but the staff was wonderful, especially at the tavern. Met wonderful travelers and locals and had a great night. Try the peanut soup! We loved it all.

Great evening; fun place

Having gotten married in Winchester, VA 25 years ago, we decided to revisit the area to celebrate our anniversary. But we wanted something other than a chain hotel for this special occasion. We were intrigued with the idea of an historical inn, so we booked our stay at The Wayside Inn. Upon arrival, we were greeted by Monica and noticed the Christmas decorations throughout the common areas. Piers also popped in to be sure we were being attended to. Monica gave us a quick tour of the first floor, then took us to our room on the second floor. It's interesting imagining all the people, famous and regular folks, who have stayed at the Inn throughout its history. Descending the staircase from our second floor room, I told my husband, "This is like being on a Hallmark Christmas movie set!" That was fun thinking about! We ate several meals in Larrick's Tavern, and enjoyed each experience. We enjoyed chatting with Ricardo, who served us most of the time. We definitely plan to return and enjoy the area and hospitality at The Wayside Inn & Larrick's Tavern!!

25th Anniversary Celebration

Several friends and I booked the Wayside Inn to be close to a nearby trout fishing stream, but we were delighted by its welcoming staff and  fascinating historic 
hotel structure. Our bed was most comfortable, the inn spotless and the 
entire town of Middletown walkable and 
friendly. We look forward to returning to the Wayside Inn! 

Historic and welcoming

This is a very beautiful quaint inn.  The room was clean and comfortable.  We stayed in #3.  The staff was friendly and the check in/out is simple.  We had everything  we needed.  Dinner at the adjoining tavern was delicious, as well.  

Clean and Quiet

From the moment we walked into the front patio, we felt welcomed by this beautiful inn (the oldest continuously operated in the US). Rocking chairs and umbrella tables invite you to sit and take in the relaxing atmosphere. We were greeted by Terry and Monica who told us a little of the history and showed us the coffee station, which is always open and stocked with snacks. We stayed in the former Inn Keeper’s room, which is absolutely gorgeous, with a 4 poster bed and beautiful antiques throughout the 3 rooms. 
The biggest hi-light was Larrick’s tavern, located onsite. From unbelievably delicious meals (prime rib & short ribs for dinner, and perfectly prepared eggs Benedict for breakfast), to live music and hand crafted cocktails, the Tavern provides a unique experience that is hard to top. Sarah expertly makes each guest feel as if they are the only one and elevates the dining experience. 
I can’t recommend the Wayside Inn enough!  We will be back!

There’s a reason they’ve stayed in business over 200 years!

The Wayside Inn and Larrick Tavern is a beautiful historic Colonial Era Inn right out of the history books. This spectacular Inn & Tavern features room after room steeped in Virginia History, full of gorgeous period antiques and comfortable cozy private areas to relax with a good book. The bedroom I had featured two spacious areas: the large bedroom itself, and a generous sitting area filled with elegant and comfortable Federal period furnishings. A large private bathroom completed the 3-room suite; a total space far larger than any Holiday or Hampton Inn. And for less than half the bloated prices of these major hotel chains. 

Once down in the main public areas, I was transported to the 18th and 19th century in several elegant dining rooms and drawing rooms with pianos, grandfather clocks, shelves filled with old books, statuary, oil on canvas portraits of people long gone, and more gorgeous antiques than most shops can boast. It was like touring an antebellum mansion, except you get to stay the night too! And that’s not the best part. The restaurant’s many dining areas feature several sprawling rooms filled with more Virginia and American history pieces, from heart pine, and maple tables with cane chairs, to colonial portraiture and delightful faux gas lamps, to the low hand hewn beam ceilings.

The oldest room in the tavern is the “Summer Kitchen” dating to the 1740’s. While dining next to the massive hearth, stuffed with 18th century cooking implements, I fully expected Thomas Jefferson or George Washington to walk in and sit down beside me. The décor and atmosphere is truly THAT authentic. 

If you’re concerned about road noise from US 11, don’t let that deter you. My room overlooked the road, and after 9pm, the traffic never bothered me at all. Nor did the music from the onsite Larrick tavern, which was pleasant, and which also finished by 9pm. I had a dinner and a breakfast the next morning. Both meals were excellent, well presented, hearty, and reasonably priced. 

Having traveled the Shenandoah Valley corridor hundreds of times since the 1960’s, I wish I had known about this Inn many years before. As it is, I will stay here again and again every chance I get. For the American history buff and antique lover, this Inn is an absolute treasure.

   


Wayside Inn

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